Organic compound, mixture, composition, organic electronic device, and display panel

Abstract

The invention relates to an organic compound, a mixture, a composition, an organic electronic device and a display panel, the structural formula of the organic compound is shown in the specification, and the organic compound provided by the invention can be applied to the organic electronic device as a blue light host material so as to prolong the service life of the device and reduce the voltage of the device.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of display, in particular to an organic compound, mixture, composition, organic electronic device and display panel. BACKGROUND

[0002] As a revolutionary breakthrough of self-luminous display technology, the organic light-emitting diode (OLED) has rapidly penetrated from smart phones, wearable devices to vehicle display and augmented reality (AR) / virtual reality (VR) fields due to its core advantages of ultra-thin flexibility, high contrast and low power consumption. The realization of full-color display of OLEDs highly depends on blue light technology, but the blue OLED often causes material degradation due to high exciton energy, resulting in low efficiency, which greatly limits the application.

[0003] Generally speaking, the traditional fluorescent material can only utilize 25% of the exciton and lacks color purity, while the phosphorescent material can achieve 100% exciton capture but faces the fatal defect of insufficient lifetime. To solve this contradiction, the current blue OLEDs all adopt host-guest doping systems. Among them, the host material undertakes the functions of carrier transmission and exciton energy transfer, which not only can effectively disperse the guest material to avoid concentration quenching, but also can convert triplet excitons into singlet excitons through the triplet-triplet annihilation (TTA) effect and transfer them to the fluorescent guest material through the Forster energy transfer pathway, so that the theoretical exciton utilization rate is improved to 62.5%. Therefore, reasonable control of the exciton energy of the blue light emitting layer is the key to improving the efficiency and lifetime of OLEDs.

[0004] At present, the commercial host materials generally have the following shortcomings or risks: poor film-forming property in the evaporation process caused by low glass transition temperature; serious intermolecular π-π stacking caused by small steric hindrance of the host material, which easily causes serious fluorescence quenching; excessive accumulation of holes or electrons between interfaces caused by mismatched energy levels, which easily causes direct capture of holes or polaron quenching; insufficient carrier mobility of the material molecules, causing transmission loss of holes or electrons. In summary, the development of suitable blue host materials plays an important role in improving the performance of OLED devices. SUMMARY

[0005] The present application provides an organic compound, mixture, composition, organic electronic device and display panel, the organic compound can be applied as a blue host material in an organic electronic device to improve the service life of the device and reduce the voltage of the device.

[0006] To achieve the above object, according to a first aspect of the present application, there is provided an organic compound, the structural formula of which is shown as formula (1):

[0007]

[0008] wherein Ar is selected from any one or a combination of multiple of substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0009] R 1 and R 2 are selected from any one or a combination of multiple of hydrogen, deuterium, straight-chain alkyl groups having 1 to 16 carbon atoms, branched-chain alkyl groups having 3 to 16 carbon atoms, cyclic alkyl groups having 3 to 16 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 16 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 16 carbon atoms;

[0010] L 1 and L 2 are selected from any one or a combination of multiple of single bonds, substituted or unsubstituted aromatic groups having 6 to 16 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 16 carbon atoms;

[0011] n1 is selected from any one integer from 1 to 10;

[0012] n2 is selected from any one integer from 1 to 9.

[0013] According to a second aspect of the present application, there is provided a mixture comprising at least one of the above-mentioned organic compounds and at least one organic functional material selected from at least one of hole injection materials, hole transport materials, electron injection materials, electron transport materials, light-emitting auxiliary materials, hole blocking materials, guest materials, and host materials.

[0014] According to a third aspect of the present application, there is further provided a composition comprising at least one organic solvent and at least one of the above-mentioned organic compounds, or comprising at least one of the organic solvents and the above-mentioned mixture.

[0015] According to a fourth aspect of the present application, there is further provided an organic electronic device comprising:

[0016] a first electrode;

[0017] a second electrode disposed opposite to the first electrode;

[0018] an organic functional layer between the first electrode and the second electrode, a material of the organic functional layer comprising at least one of the above-mentioned organic compounds, or a material of the organic functional layer comprising the above-mentioned mixture, or the organic functional layer being made of the above-mentioned composition.

[0019] According to a fifth aspect of the present application, a display panel is also provided, which comprises the above-mentioned organic electronic device.

[0020] In the organic compound, the mixture, the composition, the organic electronic device and the display panel of the embodiments of the present application, the molecular structure of the organic compound shown in formula (1) is composed of pyrene and The two pure carbon-hydrogen fused rings are combined with aromatic groups or heteroaromatic groups Ar, so that the organic compound has high excited state energy level and strong stability. When the organic compound is applied as a host material in a light-emitting layer (especially a blue light-emitting layer), efficient energy transmission can be achieved by π electron delocalization, which is conducive to fully transferring the excited state energy to the guest material of the light-emitting layer, thereby improving the service life of the organic electroluminescent device. At the same time, when the organic compound shown in formula (1) is used as a host material of a light-emitting layer and is combined with another light-emitting layer to participate in light emission, efficient utilization of excitons and reduction of carrier accumulation can be achieved, so that the stability of the light-emitting layer film formed by the organic compound shown in formula (1) as a host material is further improved, and the driving voltage of the device is reduced. Therefore, the service life of the organic electronic device using the organic compound of the present application can be improved, and the driving voltage can be reduced.

[0021] Other features and advantages of the present application will be described in detail in the following specific embodiments. BRIEF DESCRIPTION OF DRAWINGS

[0022] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings needed in the embodiment description will be briefly introduced below. Obviously, the drawings in the following description are only some embodiments of the present application, and other drawings can also be obtained by those skilled in the art without creative labor.

[0023] In order to more completely understand the present application and its beneficial effects, the following will be described in conjunction with the drawings, wherein the same reference numerals in the following description represent the same parts.

[0024] Figure 1 is a structural schematic diagram of an organic electronic device provided by the embodiments of the present application;

[0025] Figure 2 is a structural schematic diagram of another organic electronic device provided by the embodiments of the present application;

[0026] Figure 3 is a mass spectrum of an organic compound prepared in Synthetic Example 1 of the present application;

[0027] Figure 4 is a photoluminescence spectrum of an organic compound prepared in Synthetic Example 1 of the present application.

[0028] BRIEF DESCRIPTION OF DRAWINGS 100, organic electronic device; 1, substrate; 2, first electrode; 3, second electrode; 4, organic functional layer; 5, hole injection layer; 6, hole transport layer; 7, light-emitting auxiliary layer; 8, light-emitting layer; 8a, first light-emitting layer; 8b, second light-emitting layer; 9, electron transport layer; 10, electron injection layer. DETAILED DESCRIPTION

[0029] The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application.

[0030] In the present application, aromatic group, aromatic and aromatic ring system have the same meaning and can be interchangeable.

[0031] In the present application, heteroaromatic group, heteroaromatic and heteroaromatic ring system have the same meaning and can be interchangeable.

[0032] In the present application, "substituted" means that the hydrogen atom in the substituent is replaced by the substituent.

[0033] In the present application, the same substituent appears multiple times can be independently selected from different groups. For example, if the general formula contains multiple R, R can be independently selected from different groups.

[0034] In the present application, "substituted or unsubstituted" means that the defined group can be substituted or unsubstituted. When the defined group is substituted, it is understood that the defined group can be substituted with one or more substituents R selected from, but not limited to, a deuterium atom, an isocyano group, a nitro group, a halogen, an alkyl group having 1 to 20 carbon atoms, a heterocyclic group having 3 to 20 ring atoms, an aromatic group having 6 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, -NR'R", a silyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a halogen carboxyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, and the above groups can be further substituted with an acceptable substituent in the art; it is understood that R' and R" in -NR'R" are each independently selected from, but not limited to, H, a deuterium atom, an isocyano group, a nitro group, a halogen, an alkyl group having 1 to 10 carbon atoms, a heterocyclic group having 3 to 20 ring atoms, an aromatic group having 6 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms. Preferably, R is selected from, but not limited to, a deuterium atom, an isocyano group, a nitro group, a halogen, an alkyl group having 1 to 10 carbon atoms, a heterocyclic group having 3 to 10 ring atoms, an aromatic group having 6 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, a silyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a halogen carboxyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, and the above groups can be further substituted with an acceptable substituent in the art.

[0035] It is to be noted that the substituent R in the organic compound provided in the present application does not include a cyano group and an anthracene group.

[0036] In the present application, the "number of ring atoms" means the number of atoms among the atoms constituting the ring itself of a structural compound obtained by bonding atoms into a ring (e.g., a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted with a substituent, the atoms included in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thiophene group is 5.

[0037] In the present application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived by removing a hydrogen atom from a aromatic ring compound, which can be a monocyclic aryl group, or a fused ring aryl group, or a polycyclic aryl group, and at least one of the rings in the polycyclic ring is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" refers to an aryl group having 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, naphthacene, fluorenyl, rylene, and derivatives thereof. It can be understood that multiple aryl groups can also be interrupted by short non-aromatic units (e.g. <10% non-H atoms such as C, N or O atoms), in particular as in acenaphthene, fluorene, or 9,9'-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl.

[0038] In the present application, "heteroaryl or heteroaromatic group" refers to a group in which at least one carbon atom in an aryl group is replaced by a non-carbon atom, which can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted; suitable examples include, but are not limited to: thienyl, furanyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, perylenyl, phenanthridinyl, perimidinyl, quinazolinonyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, and derivatives thereof.

[0039] In the present application, "alkyl" can represent a straight chain, branched chain, and / or cyclic alkyl group. The number of carbons in the alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, for example, "C 1-9"Alkyl" refers to an alkyl group containing from 1 to 9 carbon atoms, which can be Ci alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl, each occurrence of which is independent of the other and is optionally substituted. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyl-octyl, 2-hexyl-octyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyl-dodecyl, 2-hexyl-dodecyl, 2-octyl-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 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, and the like.

[0040] In the present application, "amine group" refers to derivatives of amines, having the structural feature of the formula -N(X)2, wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, and the like. Non-limiting types of amine groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclyl)2, -NH(heterocyclyl), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), and the like.

[0041] In the present application, unless specifically defined, hydroxy refers to -OH, carboxy refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, halogenformyl refers to -C(=O)Z (wherein Z represents halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0042] In the present application, the term "alkoxy" refers to a group of structure "-O-alkyl", i.e. an alkyl group as defined above attached to another group via an oxygen atom. Suitable examples of the phrase comprising this term include, but are not limited to: methoxy (-O-CH3or -OMe), ethoxy (-O-CH2CH3or -OEt) and tert-butoxy (-O-C(CH3)3or -OtBu).

[0043] In the present application, "*" attached to a single bond indicates a connection or a fused site.

[0044] In the present application, when the connection site is not specified in a group, it means that any optional connection site in the group is the connection site.

[0045] In the present application, when the fused site is not specified in a group, it means that any optional fused site in the group is the fused site, preferably two or more sites in the group in ortho position are the fused sites.

[0046] In the present application, when there are multiple substituents with the same symbol on the same group, each substituent can be the same as or different from each other, for example The six R on the benzene ring can be the same as or different from each other.

[0047] In the present application, a single bond to which a substituent is attached is throughout the corresponding ring, which means that the substituent can be connected to any optional position of the ring, for example R is connected to any substitutable site of the benzene ring; for example means can be connected to to form a naphthyl ring at any optional position of the benzene ring.

[0048] The cyclic alkyl or cycloalkyl according to the present application have the same meaning and can be interchangeable.

[0049] The embodiment of the present application provides an organic compound, and a structural formula of the organic compound is as shown in the following formula (1):

[0050]

[0051] wherein Ar is selected from any one or a combination of multiple of substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms;

[0052] R 1 and R 2It is selected from any one or more combinations of hydrogen, deuterium, straight-chain alkyl groups having 1 to 16 carbon atoms, branched alkyl groups having 3 to 16 carbon atoms, cyclic alkyl groups having 3 to 16 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 16 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 16 carbon atoms.

[0053] L 1 and L 2 Selected from any one or more combinations of single bonds, substituted or unsubstituted aromatic groups having 6 to 16 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 16 carbon atoms;

[0054] n1 is any integer from 1 to 10;

[0055] n2 is any integer from 1 to 9.

[0056] It should be noted that the substituents in the organic compounds shown in formula (1) do not include cyano and anthracene groups, and general formula (1) does not include the structure shown in formula (2) below:

[0057]

[0058] It is understood that in the organic compounds provided in the embodiments of this application, L 1 Groups and Connect to any connectable site on the group, L 2 The group is attached to any connectable site on the pyrene group, and L 2 Groups and Specific linking sites on the group are used for connection.

[0059] In the embodiments of this application, the molecular structure of the organic compound represented by formula (1) consists of pyrene and The organic compound is composed of two pure carbon-hydrogen fused rings combined with aromatic or heteroaromatic Ar groups, giving it high excited-state energy levels and strong stability. When this organic compound is used as the host material in the light-emitting layer (especially the blue light-emitting layer), it can achieve efficient energy transfer by utilizing π electron delocalization, which is beneficial for transferring the excited-state energy to the guest material of the light-emitting layer, thereby improving the lifespan of the organic electroluminescent device. At the same time, when the organic compound shown in formula (1) is used as the host material of one light-emitting layer and is combined with another light-emitting layer to participate in light emission, the efficient utilization of excitons and the reduction of carrier accumulation can be achieved, which further improves the stability of the light-emitting layer film formed by the organic compound shown in formula (1) as the host material and reduces the driving voltage of the device. Therefore, the lifespan of organic electronic devices using the organic compound of this application can be improved and the driving voltage can be reduced.

[0060] In some embodiments, in equation (1), Choose any one of the following structures:

[0061]

[0062] In this context, "*" indicates a connection site.

[0063] In a preferred embodiment, in formula (1), Selected from the following structures:

[0064] It should be noted that when pyrene and... When two rigid pure hydrocarbon groups are connected in a near-orthogonal manner, the molecular structure is more stable, making the excited state energy levels and distribution of the organic compound more conducive to energy transfer to the guest. The lifespan of organic electronic devices using the organic compound of this application can be further improved.

[0065] In some embodiments, Ar is selected from any one or a combination of the following groups, either substituted or unsubstituted:

[0066]

[0067] In this context, "*" indicates a connection site.

[0068] In some embodiments, L 1 and L 2 It is selected from at least one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuran group, and a substituted or unsubstituted benzonaphthofuran group; wherein the substituted or unsubstituted substituent group includes, but is not limited to, deuterium and methyl.

[0069] In some embodiments, R 1 and R 2 It is selected from any one of hydrogen, deuterium, deuterated or unsubstituted phenyl, deuterated or unsubstituted naphthyl, and dibenzofuran group.

[0070] In one specific embodiment, the organic compound is selected from any one of the compounds shown in formulas P-1 to P-214:

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080] The organic compounds provided in this application embodiment can be used as functional materials in the organic functional layers of organic electronic devices. The organic functional layers include at least one of the following: a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), an electron injection layer (EIL), a hole blocking layer (HBL), a prime layer, and an emission material layer (EML).

[0081] In some embodiments, the organic compounds provided in this application are applied to the light-emitting layer.

[0082] In one specific embodiment, the organic compound provided in this application is used as the main material of the light-emitting layer.

[0083] Accordingly, this application also provides a mixture comprising at least one organic compound described in the above embodiments and at least one organic functional material, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron injection materials, electron transport materials, light-emitting auxiliary materials, hole blocking materials, guest materials, host materials and inorganic quantum dots.

[0084] This application further provides a composition comprising at least one organic solvent and at least one of the organic compounds, or the composition comprising at least one of the organic solvents and the mixture thereof.

[0085] The organic solvent is selected from at least one of aromatic, heteroaromatic, ester, aromatic ketone, aromatic ether, aliphatic ketone, aliphatic ether, alicyclic, olefinic, borate ester or phosphate ester compounds.

[0086] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic organic solvents.

[0087] Examples of aromatic or heteroaromatic organic solvents suitable for this application include, but are not limited to: p-diisopropylbenzene, pentobenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentylene, 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 Benzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 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, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furanoate, ethyl 2-furanoate, etc.

[0088] Examples of suitable aromatic ketone-based organic solvents for this application include, but are not limited to: 1-tetrahydronaphthone, 2-tetrahydronaphthone, 2-(phenylepoxy)tetrahydronaphthone, 6-(methoxy)tetrahydronaphthone, acetophenone, phenylacetone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, 2-methylphenylacetone, etc.

[0089] Examples of aromatic ether-based organic solvents suitable for this application include, but are not limited to: 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-ethylbenzene, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl 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.

[0090] Examples of aliphatic ketone-based organic solvents suitable for this application include, but are not limited to: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, frankinc, phorone, isophorone, di-n-pentyl ketone, etc.; or 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.

[0091] Examples of ester-based organic solvents suitable for this application include, but are not limited to: alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0092] In some embodiments, the composition further comprises another organic solvent selected from at least one of methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, 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, tetrahydronaphthalene, naphthane, and indene.

[0093] Optionally, in some embodiments, organic solvents particularly suitable for this application are those with Hansen solubility parameters within the following ranges:

[0094] δd (dispersion force) is in the range of 17.0–23.2 MPa. 1 / 2 The range, especially in the range of 18.5–21.0 MPa 1 / 2 Scope;

[0095] δp (polar force) is in the range of 0.2–12.5 MPa. 1 / 2 The range, especially 2.0–6.0 MPa 1 / 2 Scope;

[0096] δh (hydrogen bond strength) ranges from 0.9 to 14.2 MPa. 1 / 2 The range, especially 2.0–6.0 MPa 1 / 2 The range.

[0097] In the compositions provided in this application, the boiling point of the organic solvent must be considered when selecting it. In this application, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; even more preferably ≥250°C; and most preferably ≥275°C or ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet printhead. The organic solvent can evaporate from the solvent system to form a thin film containing functional materials.

[0098] In some embodiments, the composition provided in this application is a solution.

[0099] In a preferred embodiment, the composition provided in this application is a solution.

[0100] In a preferred embodiment, the composition provided in this application is a suspension.

[0101] In this embodiment, the composition may include 0.01 wt% to 20 wt% of the organic compound or the mixture. Further, the mass fraction of the organic compound or the mixture in the composition may be 0.1 wt% to 15 wt%. Preferably, the mass fraction of the organic compound or the mixture in the composition may be 0.2 wt% to 10 wt%.

[0102] In some embodiments, the organic compound or the mixture in the composition has a mass fraction of 0.01%, 0.05%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3%, 0.35%, 0.4%, 0.45%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1%, 3%, 5%, 8%, 10%, 12%, 15%, 18%, or 20%.

[0103] This application also provides an example of the use of the composition as a coating or printing ink in the preparation of organic electronic devices. A particularly preferred use is to use the composition as a coating or printing ink to prepare organic electronic devices by printing or coating methods.

[0104] Suitable printing or coating technologies include (but are not limited to) inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing or pad printing, and slot-type extrusion coating. Gravure printing, inkjet printing, and gravure printing are preferred. The solution or suspension may additionally include one or more components such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and binders to adjust viscosity, improve film-forming properties, and enhance adhesion.

[0105] This application also provides an organic electronic device, which comprises the organic compounds, mixtures, or compositions described above.

[0106] Please refer to Figure 1 and Figure 2 The organic electronic device 100 includes a substrate 1, a first electrode 2, an organic functional layer 4, and a second electrode 3; the first electrode 2 and the second electrode 3 are disposed opposite to each other, and the organic functional layer 4 is located between the first electrode 2 and the second electrode 3.

[0107] In some embodiments, the material of the organic functional layer 4 includes at least one organic compound of formula (1), or the material of the organic functional layer includes the mixtures described above, or the organic functional layer is made of the composition described above.

[0108] In some embodiments, the light-emitting layer of the organic electronic device 100 is a single-layer structure, for example, as shown in the figure. Figure 1 As shown, the organic functional layer 4 includes a hole injection layer 5, a hole transport layer 6, a light-emitting auxiliary layer 7, a light-emitting layer 8, an electron transport layer 9, and an electron injection layer 10 stacked between the first electrode 2 and the second electrode 3. The light-emitting layer 8 is made of a host material and a guest material, and the host material includes at least one of the organic compounds described above.

[0109] In other embodiments, the light-emitting layer of the organic electronic device 100 has a double-layer structure, for example, as shown in the figure. Figure 2 As shown, the organic functional layer 4 includes a hole injection layer 5, a hole transport layer 6, a light-emitting auxiliary layer 7, a first light-emitting layer 8a, a second light-emitting layer 8b, an electron transport layer 9, and an electron injection layer 10 stacked between the first electrode 2 and the second electrode 3. The first light-emitting layer 8a is made of a first host material and a first guest material, and the second light-emitting layer 8b is made of a second host material and a second guest material. The first host material or the second host material includes at least one of the aforementioned organic compounds.

[0110] In some embodiments, the first host material and the second host material are different; the first object material and the second object material may be the same or different.

[0111] In some embodiments, the first electrode 2 may be an anode layer and the second electrode 3 may be a cathode layer.

[0112] In some embodiments, the organic electronic device 100 emits any one of blue light, red light, and green light.

[0113] In a preferred embodiment, the organic electronic device 100 emits blue light. That is, the organic compound is preferably used as the host material of the blue light-emitting layer.

[0114] In some embodiments, the organic electronic device 100 includes, but is 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 (OLEFETs), organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes, with organic electroluminescent devices such as OLEDs, OLEECs, and OLEFETs being particularly preferred.

[0115] In the aforementioned organic electronic device 100, particularly in an OLED, a substrate 1, a first electrode 2, at least one light-emitting layer, and a second electrode 3 are included.

[0116] Substrate 1 can be opaque or transparent. A transparent substrate 1 can be used to fabricate a transparent light-emitting device. See, for example, Bulovic et al., Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. Substrate 1 can be rigid or flexible. Substrate 1 can be plastic, metal, semiconductor wafer, or glass. Preferably, substrate 1 has a smooth surface, and a substrate 1 without surface defects is particularly desirable. In a preferred example, substrate 1 is flexible and can be selected from polymer films or plastics with a glass transition temperature Tg of 150°C or higher, preferably 200°C or higher, more preferably 250°C or higher, and most preferably 300°C or higher. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0117] The first electrode 2 may comprise a conductive metal, metal oxide, or conductive polymer. Holes can be readily injected into the HIL, HTL, or EML. In one example, the absolute value of the difference between the work function of the first electrode 2 and the HOMO level or valence band level of the light emitter in the light-emitting layer or the p-type semiconductor material of the HIL, HTL, or EBL is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of materials for the first electrode 2 include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide, etc. Other suitable materials for the first electrode 2 are known and can be readily selected by those skilled in the art. The material of the first electrode 2 can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam deposition, etc.

[0118] In some embodiments, the first electrode 2 is patterned. Patterned ITO conductive substrates are commercially available and can be used to fabricate the organic electronic devices of this application.

[0119] The second electrode 3 may comprise a conductive metal or metal oxide. The second electrode 3 can readily inject electrons into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the second electrode 3 and the LUMO level or conduction band level of the light-emitting element or the n-type semiconductor material serving as the EIL, ETL, or HBL in the light-emitting layer is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials suitable for use as cathodes in OLEDs can potentially serve as materials for the second electrode 3 of the organic electronic device in this application. Examples of materials for the second electrode 3 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 material of the second electrode 3 can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam deposition, etc.

[0120] In some embodiments, the light-emitting layer 8, the first light-emitting layer 8a, or the second light-emitting layer 8b in the organic electronic device 100 provided in this application are prepared using the composition provided in the above embodiments.

[0121] In some embodiments, the emission wavelength of the organic electronic device 100 is between 300 nm and 1000 nm, preferably between 350 nm and 900 nm, and more preferably between 400 nm and 800 nm.

[0122] In some embodiments, the organic electronic device 100 is used in various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.

[0123] In some embodiments, an electronic device including the organic electronic device 100 includes, but is not limited to, a display device, a lighting device, a light source, a sensor, etc.

[0124] This application embodiment also provides a display panel, which includes the organic electronic device 100 described above.

[0125] The organic compounds provided in this application will be described below with reference to preferred embodiments. However, the organic compounds provided in this application are not limited to the following embodiments. It should be understood that the appended claims summarize the scope of this application. Those skilled in the art should realize under the guidance of the concept of this application that any changes made to the various embodiments of this application will be covered by the spirit and scope of the claims of this application.

[0126] (I) Specific Synthesis Examples

[0127] Example 1

[0128] The synthetic route for compound P-1 is shown below:

[0129]

[0130] Synthesis of intermediate I-3:

[0131] Weigh reactants I-1 (40 mmol) and I-2 (30 mmol) into a clean three-necked flask, add tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.6 mmol), potassium carbonate (0.12 mol), tetrahydrofuran (120 mL), and deionized water (40 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere, and reflux for 6 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and obtain intermediate I-3 by column chromatography with a yield of 86%. The electrospray ionization mass spectrometry (ESI-MS) result of the product is [H] + =383.

[0132] Synthesis of compound P-1:

[0133] Weigh intermediate I-3 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction solution to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction solution cools naturally, wash with water and separate the liquid, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-1, with a yield of 58%.

[0134] The mass spectrum of the obtained product is as follows Figure 3 As shown, the mass spectrometry result is m / z[H + The concentration of carbon in the sample was 504.76, and the elemental analysis results of the product by inductively coupled plasma (ICP) testing were C, 95.2; H, 4.8, thus proving that the obtained product is compound P-1. Furthermore, the photoluminescence spectrum (PL spectrum) of the product is shown below. Figure 4 As shown. By Figure 4 It can be seen that the prepared compound P-1 mainly emits blue-violet light at 433 nm after being excited.

[0135] Example 2

[0136] The synthetic route for compound P-6 is shown below:

[0137]

[0138] Synthesis of intermediate I-6:

[0139] Weigh reactants I-1 (40 mmol) and I-5 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (0.12 mol), tetrahydrofuran (120 mL), and deionized water (40 mL), purge with nitrogen three times, and reflux at 70 °C for 6 h under a nitrogen atmosphere. After the reaction solution cools naturally, wash with water and separate the layers. Dry the organic phase and evaporate to dryness. Column chromatography yields intermediate I-6 in 85% yield. The m / z of the product [H + =536.

[0140] Synthesis of compound P-6:

[0141] Weigh intermediate I-6 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and obtain compound P-6 by column chromatography, with a yield of 55%, m / z [H + =657, ICP results are C, 95.1; H, 4.9.

[0142] Example 3

[0143] The synthetic route for compound P-12 is shown below:

[0144]

[0145] Synthesis of intermediate I-8:

[0146] Weigh reactants I-1 (40 mmol) and I-7 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-8, with a yield of 81%. The m / z of the product [H + =509.

[0147] Synthesis of compound P-12:

[0148] Weigh intermediate I-8 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-12 in a yield of 46%. The m / z of the product [H + =631, ICP results are C, 95.2; H, 4.8.

[0149] Example 4

[0150] The synthetic route for compound P-19 is shown below:

[0151]

[0152] Synthesis of intermediate I-10:

[0153] Weigh reactants I-1 (40 mmol) and I-9 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-10, with a yield of 74%. The m / z of the product [H + =483.

[0154] Synthesis of compound P-19:

[0155] Weigh intermediate I-10 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-19, with a yield of 49%. The m / z of the product [H + =605, ICP results are C, 95.3; H, 4.7.

[0156] Example 5

[0157] The synthetic route for compound P-22 is shown below:

[0158]

[0159] Synthesis of intermediate I-12:

[0160] Weigh reactants I-1 (40 mmol) and I-11 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-12 with a yield of 88%. The m / z of the product [H + =473.

[0161] Synthesis of compound P-22:

[0162] Weigh intermediate I-12 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-22 in 48% yield. The m / z of the product [H + =595, ICP results are C, 92.9; H, 4.4; O, 2.7.

[0163] Example 6

[0164] The synthetic route for compound P-28 is shown below:

[0165]

[0166] Synthesis of intermediate I-14:

[0167] Weigh reactants I-1 (40 mmol) and I-13 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, then column chromatography to obtain intermediate I-14, with a yield of 83%. The m / z of the product [H + =523.

[0168] Synthesis of compound P-28:

[0169] Weigh reactants I-14 (20 mmol) and I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-28 in 51% yield. The m / z of the product [H + =645, ICP results are C, 93.1; H, 4.4; O, 2.5.

[0170] Example 7

[0171] The synthetic route for compound P-32 is shown below:

[0172]

[0173] Synthesis of intermediate I-16:

[0174] Weigh reactants I-1 (40 mmol) and I-15 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-16, with a yield of 85%. The m / z of the product [H + =523.

[0175] Synthesis of compound P-32:

[0176] Weigh intermediate I-16 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-32 in 58% yield. The m / z of the product [H + =645, ICP results are C, 93.1; H, 4.4; O, 2.5.

[0177] Example 8

[0178] The synthetic route for compound P-40 is shown below:

[0179]

[0180] Synthesis of intermediate I-18:

[0181] Weigh reactants I-1 (40 mmol) and I-17 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-18, with a yield of 81%. The m / z of the product [H+ =489.

[0182] Synthesis of compound P-40:

[0183] Weigh intermediate I-18 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-40 in 50% yield. The m / z of the product [H + =611, ICP results are C, 90.5; H, 4.3; S, 5.2.

[0184] Example 9

[0185] The synthetic route for compound P-42 is as follows:

[0186]

[0187] Synthesis of intermediate I-20:

[0188] Weigh reactants I-1 (40 mmol) and I-19 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-20, with a yield of 79%. The m / z of the product [H + =536.

[0189] Synthesis of compound P-42:

[0190] Weigh intermediate I-20 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-42 in 48% yield. The m / z of the product [H + =658, ICP results are C,84.0; H,4.0; Se,12.

[0191] Example 10

[0192] The synthetic route for compound P-54 is shown below:

[0193]

[0194] Synthesis of intermediate I-22:

[0195] Weigh reactants I-1 (40 mmol) and I-21 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-22 with a yield of 82%. The m / z of the product [H + =550.

[0196] Synthesis of compound P-54:

[0197] Weigh intermediate I-22 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-54 in 38% yield. The m / z of the product [H + =671, ICP results are C, 93.1; H, 4.5; O, 2.4.

[0198] Example 11

[0199] The synthetic route for compound P-63 is shown below:

[0200]

[0201] Synthesis of intermediate I-24:

[0202] Weigh reactants I-1 (40 mmol) and I-23 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, then column chromatography to obtain intermediate I-24, with a yield of 87%. The m / z of the product [H + =550.

[0203] Synthesis of compound P-63:

[0204] Weigh intermediate I-24 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-63 in 56% yield. The m / z of the product [H + =671, ICP results are C, 93.1; H, 4.5; O, 2.4.

[0205] Example 12

[0206] The synthetic route for compound P-73 is shown below:

[0207]

[0208] Synthesis of intermediate I-26:

[0209] Weigh reactant I-1 (40 mmol) and reactant I-25 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-26 with a yield of 80%. The m / z of the product [H + =383.

[0210] Synthesis of compound P-73:

[0211] Weigh intermediate I-26 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-73, with a yield of 59%. The m / z of the product [H + =510, ICP results are C, 94.3; H, 5.7.

[0212] Example 13

[0213] The synthetic route for compound P-77 is shown below:

[0214]

[0215] Synthesis of intermediate I-28:

[0216] Weigh reactant I-1 (40 mmol) and reactant I-27 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-28, with a yield of 73%. The m / z of the product [H + =440.

[0217] Synthesis of compound P-77:

[0218] Weigh intermediate I-28 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, column chromatography to obtain compound P-77 in 57% yield, m / z of the product [H + =562, ICP results are C,94.1; H,5.9.

[0219] Example 14

[0220] The synthetic route for compound P-87 is shown below:

[0221]

[0222] Synthesis of intermediate I-30:

[0223] Weigh reactants I-1 (40 mmol) and I-29 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-30, with a yield of 81%. The m / z of the product [H + =480.

[0224] Synthesis of compound P-87:

[0225] Weigh intermediate I-30 (20 mmol) and reactant I-31 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-87 in a yield of 47%. The m / z of the product [H + =611, ICP results are C, 90.5; H, 6.9; O, 2.6.

[0226] Example 15

[0227] The synthetic route for compound P-97 is shown below:

[0228]

[0229] The synthesis of intermediate I-3 is described in Example 1 and will not be repeated here.

[0230] Synthesis of compound P-97:

[0231] Weigh intermediate I-3 (20 mmol) and reactant I-32 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-97 in 55% yield. The m / z of the product [H + =505, ICP results are C, 95.2; H, 4.8.

[0232] Example 16

[0233] The synthetic route for compound P-109 is shown below:

[0234]

[0235] The synthesis of intermediate I-12 is described in Example 5 and will not be repeated here.

[0236] Synthesis of compound P-109:

[0237] Weigh intermediate I-12 (20 mmol) and reactant I-33 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-109, with a yield of 39%. The m / z of the product [H + =671, ICP results are C, 93.1; H, 4.5; O, 2.4.

[0238] Example 17

[0239] The synthetic route for compound P-119 is shown below:

[0240]

[0241] Synthesis of intermediate I-35:

[0242] Weigh reactants I-34 (40 mmol) and I-11 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-35, with a yield of 81%. The m / z of the product [H + =550.

[0243] Synthesis of compound P-119:

[0244] Weigh intermediate I-35 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-119, with a yield of 43%. The m / z of the product [H + =671, ICP results are C, 93.1; H, 4.5; O, 2.4.

[0245] Example 18

[0246] The synthetic route for compound P-139 is shown below:

[0247]

[0248] Synthesis of intermediate I-37:

[0249] Weigh reactant I-1 (40 mmol) and reactant I-36 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-37, with a yield of 77%. The m / z of the product [H + =433.

[0250] Synthesis of compound P-139:

[0251] Intermediate I-37 (20 mmol) and reactant I-38 (20 mmol) were weighed and placed in a clean three-necked flask. Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL) were added. The mixture was purged with nitrogen three times. The reaction mixture was heated to 100 °C and refluxed for 12 h under a nitrogen atmosphere. After the reaction mixture cooled naturally, it was washed with water and separated. The organic phase was dried and evaporated to dryness. Column chromatography was used to obtain compound P-139, with a yield of 49%. The m / z of the product [H] + =631, ICP results are C, 95.2; H, 4.8.

[0252] Example 19

[0253] The synthetic route for compound P-144 is shown below:

[0254]

[0255] Synthesis of intermediate I-40:

[0256] Weigh reactants I-39 (20 mmol) and I-4 (24 mmol) into a clean three-necked flask, add palladium catalyst Pd132 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 8 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-40, with a yield of 71%. The m / z of the product [H + =453.

[0257] Synthesis of intermediate I-41:

[0258] Weigh 10 mmol of intermediate I-40 and 12 mmol of pinacol diborate into a clean three-necked flask. Add 0.2 mmol of 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride (Pd(dppf)Cl2) and 40 mmol of potassium acetate dissolved in 1,4-dioxane. Replace the solution with nitrogen three times. Heat the reaction solution to 100 °C and reflux for 6 h under a nitrogen atmosphere. After the reaction solution cools naturally, wash with water and separate the layers. Dry the organic phase and evaporate to dryness. Column chromatography yields intermediate I-41 in 87% yield. The m / z of the product [H + =545.

[0259] Synthesis of compound P-144:

[0260] Weigh 10 mmol of intermediate I-41 and 10 mmol of reactant I-3 into a clean three-necked flask, add 0.1 mmol of Pd(PPh3)4, 20 mmol of potassium carbonate, 100 mL of toluene, 50 mL of ethanol, and 50 mL of deionized water, purge with nitrogen three times, and heat the reaction mixture to 100 °C under a nitrogen atmosphere and reflux for 12 h. After the reaction mixture cools naturally, wash with water and separate the layers. Dry the organic phase and evaporate to dryness. Column chromatography yields compound P-144 in 80% yield. The m / z of the product [H + =721, ICP results are C, 93.3; H, 4.5; O, 2.2.

[0261] Example 20

[0262] The synthetic route for compound P-152 is shown below:

[0263]

[0264] Synthesis of intermediate I-43:

[0265] Weigh reactants I-1 (40 mmol) and I-42 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, then column chromatography to obtain intermediate I-43, with a yield of 86%. The m / z of the product [H + =624.

[0266] Synthesis of compound P-152:

[0267] Weigh intermediate I-43 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-152 in 56% yield. The m / z of the product [H + =745, ICP results are C, 95.1; H, 4.9.

[0268] Example 21

[0269] The synthetic route for compound P-160 is shown below:

[0270]

[0271] Synthesis of intermediate I-46:

[0272] Weigh reactants I-44 (40 mmol) and I-45 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-46, with a yield of 89%. The m / z of the product [H + =632.

[0273] Synthesis of compound P-160:

[0274] Weigh intermediate I-46 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-160, with a yield of 52%. The m / z of the product [H + =753, ICP results are C,94.1; H,5.9.

[0275] Example 22

[0276] The synthetic route for compound P-161 is shown below:

[0277]

[0278] Synthesis of intermediate I-48:

[0279] Weigh reactants I-1 (40 mmol) and I-47 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-48 with a yield of 85%. The m / z of the product [H + =642.

[0280] Synthesis of compound P-161:

[0281] Weigh intermediate I-48 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-161, with a yield of 51%. The m / z of the product [H + =763, ICP results are C, 91.3; H, 5.0; Si, 3.7.

[0282] Example 23

[0283] The synthetic route for compound P-182 is shown below:

[0284]

[0285] Synthesis of intermediate I-50:

[0286] Weigh reactants I-49 (40 mmol) and I-11 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, then perform column chromatography to obtain intermediate I-50, with a yield of 88%. The m / z of the product [H + =473.

[0287] Synthesis of compound P-182:

[0288] Weigh intermediate I-50 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-182 in 60% yield. The m / z of the product [H + =595, ICP results are C, 92.9; H, 4.4; O, 2.7.

[0289] Example 24

[0290] The synthetic route for compound P-195 is shown below:

[0291]

[0292] Synthesis of intermediate I-52:

[0293] Weigh reactants I-51 (40 mmol) and I-25 (30 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-52 with a yield of 84%. The m / z of the product [H + =388.

[0294] Synthesis of compound P-195:

[0295] Weigh intermediate I-52 (20 mmol) and reactant I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to give compound P-195, with a yield of 61%. The m / z of the product [H + =510, ICP results are C, 94.3; H, 5.7.

[0296] Example 25

[0297] The synthetic route for compound P-207 is shown below:

[0298]

[0299] Synthesis of intermediate I-54:

[0300] Weigh reactant I-1 (40 mmol) and reactant I-53 (35 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.6 mmol), potassium carbonate (80 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 70 °C under nitrogen atmosphere and reflux for 10 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain intermediate I-54, with a yield of 67%. The m / z of the product [H + =507.

[0301] Synthesis of compound P-207:

[0302] Weigh reactants I-54 (20 mmol) and I-4 (20 mmol) into a clean three-necked flask, add Pd(PPh3)4 (0.3 mmol), potassium carbonate (40 mmol), toluene (100 mL), ethanol (50 mL), and deionized water (50 mL), purge with nitrogen three times, heat the reaction mixture to 100 °C under nitrogen atmosphere and reflux for 12 h; after the reaction mixture cools naturally, wash with water and separate the layers, dry the organic phase and evaporate to dryness, and column chromatography to obtain compound P-207 in a yield of 43%. The m / z of the product [H + =629, ICP results are C, 95.5; H, 4.5.

[0303] Comparative Example

[0304] This application also provides Comparative Examples 1 to 4, wherein the comparative compounds provided in Comparative Examples 1 to 4 are respectively designated as "Comparative Compound REF01, Comparative Compound REF02, Comparative Compound REF03 and Comparative Compound REF04", and their chemical structural formulas are shown below:

[0305]

[0306] (II) Fabrication and Characterization of OLED Devices

[0307] The organic electronic device 100 provided in this application embodiment can be an OLED device, and is based on... Figure 2 Taking the fabrication of the organic electronic device shown as an example, the following detailed description of the fabrication method of OLED device using the organic compound provided in the embodiments of this application will be provided through specific device examples.

[0308] In the following method for fabricating OLED devices, an ITO conductive glass substrate is used as the anode substrate, PD as the hole injection material, HT as the hole transport material, BP as the light-emitting auxiliary material, BD as the guest material of the first and second light-emitting layers, BH-2 as the host material of the second light-emitting layer, ET and Liq as electron transport materials, Liq as the electron injection material, and Al as the cathode material. Furthermore, OLED devices are fabricated using the compounds provided in the aforementioned synthesis examples 1 to 25 as the host materials of the first light-emitting layer.

[0309] The chemical structural formulas of PD, HT, BP, BD, BH-2, ET, and Liq are shown below:

[0310] The following specific examples illustrate the fabrication process of OLED devices using the above-mentioned materials.

[0311] Taking the fabrication method of OLED device using compound P-1 as the host material of the first light-emitting layer as an example, the resulting OLED device is denoted as "OLED-1 device". The fabrication method of OLED-1 device includes the following steps a to j.

[0312] Step a: ITO conductive glass substrate (i.e., attached) Figure 2 Cleaning of the first electrode 2). An ITO conductive glass substrate is provided and ultrasonically cleaned using one or more cleaning agents such as deionized water, acetone, isopropanol, or chloroform to improve the work function of the anode.

[0313] Step b: Form a hole injection layer 5 on the first electrode 2. Hole injection materials PD and HT are deposited on the first electrode 2 at a deposition rate of 3:97, resulting in a hole injection layer 5 with a thickness of 30 nm.

[0314] Step c: Form a hole transport layer 6 on the hole injection layer 5. At a certain evaporation rate, hole transport material HT is deposited on hole injection layer 5 to obtain hole transport layer 6 with a thickness of 60 nm.

[0315] Step d: Form a light-emitting auxiliary layer 7 on top of the hole transport layer 6. The evaporation rate was used to deposit the light-emitting auxiliary material BP on the hole transport layer 6 to obtain a light-emitting auxiliary layer 7 with a thickness of 10 nm.

[0316] Step e: Form a first light-emitting layer 8a on the light-emitting auxiliary layer 7. The evaporation rate of compounds P-1 and BD provided in Example 1 was used to evaporate on the light-emitting auxiliary layer 7, wherein the evaporation rate ratio of compounds P-1 and BD was 98:2, to obtain a first light-emitting layer 8a with a thickness of 10 nm.

[0317] Step f: Form a second light-emitting layer 8b on the first light-emitting layer 8a. BH-2 and BD are deposited on the first light-emitting layer 8a at a deposition rate of 98:2, resulting in a second light-emitting layer 8b with a thickness of 10 nm.

[0318] Step g: Form an electron transport layer 9 on the second luminescent layer 8b. In a vacuum chamber, electron transport materials ET and Liq are placed in different evaporation crucibles and subjected to high vacuum (1×10⁻⁶) conditions. -6 Under millibars, ET and Liq were co-deposited at a weight ratio of 5:5 to form an electron transport layer 9 with a thickness of 30 nm on the second luminescent layer 8b.

[0319] Step h: An electron injection layer 10 is formed on the electron transport layer 9. The electron injection material Liq was deposited on the electron transport layer 9 at a certain evaporation rate to obtain an electron injection layer 10 with a thickness of 1 nm.

[0320] Step i: Form a cathode (i.e., the second electrode 3) on the electron injection layer 10. The cathode material Al was deposited on the electron injection layer 10 at a certain evaporation rate to obtain a second electrode 3 with a thickness of 100 nm.

[0321] Step j: The device obtained by layer-by-layer deposition is placed in a nitrogen atmosphere glove box and encapsulated with ultraviolet curing resin to finally obtain the OLED-1 device.

[0322] The structure of the fabricated OLED-1 device is as follows: ITO / PD:HT(3:97,30nm) / HT(60nm) / BP(10nm) / compound P-1:BD(2%,10nm) / BH-2:BD(2%,10nm) / ET:Liq(5:5,30nm) / Liq(1nm) / Al(100nm).

[0323] The fabrication of OLED-2 to OLED-25 devices followed the fabrication method of OLED-1, using the organic compounds synthesized in Examples 2 to 25 as the host material for the first light-emitting layer of the OLED devices, respectively, to prepare OLED-2 to OLED-25 devices. It is understood that, in the above fabrication methods for OLED-1 to OLED-25 devices, all experimental conditions are the same except for the host material of the first light-emitting layer.

[0324] Furthermore, referring to the fabrication method of the device embodiments, comparative compounds REF01 to REF04 were used as the host materials of the first light-emitting layer to prepare comparative OLED-REF01 to OLED-REF04 devices respectively. Compared with the fabrication method of OLED-1 device, the experimental conditions are the same in the fabrication methods of OLED-REF01 to OLED-REF04 devices except for the host material of the first light-emitting layer.

[0325] In this embodiment, the current-voltage (JV) characteristics of OLED-1 to OLED-25 devices and OLED-REF01 to OLED-REF04 devices were characterized, and important parameters such as voltage, color coordinates, and lifetime were recorded. The results are shown in Table 1. The lifetime (LT95) is defined as the time taken at a constant current density of 10 mA / cm². 2 The time it takes for the device brightness to drop from the initial 1 knit to 95%.

[0326] Table 1

[0327]

[0328]

[0329] As shown in Table 1, the OLED devices prepared in the embodiments of this application all emit blue light, and the OLED devices prepared when the organic compounds provided in Embodiments 1 to 25 of this application are used as the main blue light material in the first light-emitting layer show better performance in terms of voltage and lifespan.

[0330] Compared to the comparative compounds REF01-REF04 provided in the comparative examples, the organic compounds provided in this application, when applied to the first light-emitting layer between the light-emitting auxiliary layer and the second light-emitting layer, better improve exciton utilization and avoid quenching problems caused by long-lived exciton accumulation. Therefore, using the organic compounds provided in this application as the main material of the first light-emitting layer can effectively improve the driving voltage and lifespan of organic light-emitting devices.

[0331] In summary, the molecular structure of the organic compound represented by formula (1) provided in the embodiments of this application consists of pyrene and The organic compound is composed of two pure carbon-hydrogen fused rings combined with aromatic or heteroaromatic Ar groups, giving it high excited-state energy levels and strong stability. When this organic compound is used as the host material in the light-emitting layer (especially the blue light-emitting layer), it can achieve efficient energy transfer by utilizing π electron delocalization, which is beneficial for transferring the excited-state energy to the guest material of the light-emitting layer, thereby improving the lifespan of the organic electroluminescent device. At the same time, when the organic compound shown in formula (1) is used as the host material of one light-emitting layer and is combined with another light-emitting layer to participate in light emission, the efficient utilization of excitons and the reduction of carrier accumulation can be achieved, which further improves the stability of the light-emitting layer film formed by the organic compound shown in formula (1) as the host material and reduces the driving voltage of the device. Therefore, the lifespan of organic electronic devices using the organic compound of this application can be improved and the driving voltage can be reduced.

[0332] In the description of this application, the terms "first" and "second" are used for descriptive purposes only and should not be construed as indicating or implying relative importance or implicitly specifying the number of technical features indicated. Therefore, a feature defined as "first" or "second" may explicitly or implicitly include one or more features. In the description of this application, "multiple" means two or more, unless otherwise explicitly specified.

[0333] In the above embodiments, the descriptions of each embodiment have different focuses. For parts not described in detail in a certain embodiment, please refer to the relevant descriptions in other embodiments.

[0334] The embodiments, implementation methods, and related technical features of this application can be combined and substituted for each other without conflict.

[0335] The above are merely preferred embodiments of this application and are not intended to limit this application in any way. Any simple modifications, equivalent changes, and alterations made to the above embodiments based on the technical essence of this application without departing from the scope of the technical solution of this application shall still fall within the scope of the technical solution of this application.

Claims

1. An organic compound, characterized in that, The structural formula of the organic compound is shown in formula (1): Ar is selected from any one or more combinations of substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms. R 1 and R 2 It is selected from any one or more combinations of hydrogen, deuterium, straight-chain alkyl groups having 1 to 16 carbon atoms, branched alkyl groups having 3 to 16 carbon atoms, cyclic alkyl groups having 3 to 16 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 16 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 16 carbon atoms. L 1 and L 2 Selected from any one or more combinations of single bonds, substituted or unsubstituted aromatic groups having 6 to 16 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 16 carbon atoms; n1 is any integer from 1 to 10; n2 is any integer from 1 to 9.

2. The organic compound according to claim 1, characterized in that, In equation (1), Choose any one of the following structures: In this context, "*" represents a connection site.

3. The organic compound according to claim 1 or 2, characterized in that, Ar is selected from any one or a combination of the following groups, whether substituted or unsubstituted: In this context, "*" represents a connection site.

4. The organic compound according to claim 1 or 2, characterized in that, L 1 and L 2 It is selected from at least one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted benzonaphthofuran group.

5. The organic compound according to claim 1, characterized in that, The organic compound is selected from any one of the compounds shown in formulas P-1 to P-214:

6. A mixture, characterized in that, The mixture includes at least one organic compound as described in any one of claims 1 to 5 and at least one organic functional material, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron injection materials, electron transport materials, light-emitting auxiliary materials, hole blocking materials, guest materials, and host materials.

7. A composition, characterized in that, The composition comprises at least one organic solvent and at least one organic compound as claimed in any one of claims 1 to 5, or the composition comprises at least one of the organic solvents and a mixture as claimed in claim 6.

8. An organic electronic device, characterized in that, The organic electronic device includes: First electrode; The second electrode is disposed opposite to the first electrode; An organic functional layer is located between the first electrode and the second electrode, wherein the material of the organic functional layer comprises at least one organic compound as described in any one of claims 1 to 5, or the material of the organic functional layer comprises a mixture as described in claim 6, or the organic functional layer is made of a composition as described in claim 7.

9. The organic electronic device according to claim 8, 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, wherein the host material includes at least one of the organic compounds.

10. A display panel, characterized in that, The display panel includes the organic electronic device as described in claim 8 or 9.

Images