Organic compound, mixture, composition, organic light-emitting device and display panel

Abstract

The invention discloses an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. Ar2 is selected from a structure represented by a formula (2). The organic compound provided by the invention is formed by combining two fused ring groups, namely anthracene and benzophenanthrene-furan, has proper excited state energy level and energy transmission efficiency, can improve the exciton utilization rate, reduces quenching, and can be applied to the field of organic light emitting devices, such as organic light emitting devices, organic light emitting devices, organic light emitting devices, organic light emitting devices, organic light emitting devices, organic light emitting devices, organic light emitting devices and organic light emitting devices. Therefore, the driving voltage of the organic light-emitting device is reduced and the service life of the organic light-emitting device is prolonged.

Description

TECHNICAL FIELD

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

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

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

[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 π-π stacking between molecules caused by small steric hindrance of the host material, which easily causes serious fluorescence quenching; too much accumulation of holes or electrons between interfaces caused by energy level mismatch, which easily causes direct capture of holes or polaron quenching; insufficient carrier mobility of material molecules, causing transmission loss of holes or electrons. In summary, developing suitable blue light 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 light emitting device and display panel, the organic compound can be applied as a blue light host material in an organic light emitting device to improve the lifetime of the device and reduce the voltage of the device.

[0006] In a first aspect, the present application provides an organic compound, the chemical structural formula of the organic compound is shown in general formula (1):

[0007] ​

[0008] wherein,

[0009] Ar 1 at least one selected from a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms;

[0010] Ar 2 selected from a structure represented by formula (2):

[0011]

[0012] Ar 3 selected from a structure represented by formula (3):

[0013]

[0014] wherein * represents a bonding site or a fused site;

[0015] R 1 and R 2 at least one selected from hydrogen, deuterium, a linear alkyl group having 1 to 16 carbon atoms, a branched alkyl group having 3 to 16 carbon atoms, a cyclic alkyl group having 3 to 16 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 16 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 16 carbon atoms;

[0016] L 1 and L 2 at least one selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 16 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 16 carbon atoms;

[0017] n1 is an integer selected from any one of 1 to 8;

[0018] n2 is an integer selected from any one of 1 to 11.

[0019] In a second aspect, the present application provides a mixture including at least one organic functional material selected from at least one of a hole injection material, a hole transport material, an electron injection material, an electron transport material, a light-emitting auxiliary material, a hole blocking material, a guest material, a host material, and a quantum dot material, and at least one organic compound as described above.

[0020] In a third aspect, the present application provides a composition including at least one organic solvent and at least one organic compound as described above, or the composition including at least one organic solvent and the mixture as described above.

[0021] In a fourth aspect, the present application provides an organic light-emitting device, comprising:

[0022] a first electrode;

[0023] a second electrode, disposed opposite to the first electrode; and

[0024] an organic functional layer, located between the first electrode and the second electrode;

[0025] wherein the material of the organic functional layer comprises at least one organic compound as described above, or the material of the organic functional layer comprises a mixture as described above, or the organic functional layer is made of a composition as described above.

[0026] In a fifth aspect, the present application provides a display panel, comprising an organic light-emitting device as described above.

[0027] The present application provides an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. The molecular structure of the organic compound provided by the present application is combined by anthracene and benzophenanthrene furan two kinds of fused ring groups. The combination of the two makes the organic compound have the triplet-triplet annihilation (TTA) effect brought by the electron delocalization and certain electron transport property, and has strong stability, high excited state energy level. When the organic compound is used as a host material or is used in a blue light-emitting layer in combination with other blue light host materials, the triplet state energy can be fully utilized through the TTA effect, realizing efficient energy transfer between multiple hosts and guests, reducing carrier accumulation, and fully transferring the excited state energy to the doped guest light-emitting material, thereby further improving the stability of the organic compound film, reducing the driving voltage, and improving the service life of the organic light-emitting device. Therefore, the voltage of the organic light-emitting device using the organic compound of the present application can be further reduced, and the service life can be further improved.

[0028] Other features and advantages of the present application will be described in detail in the following specific embodiments. BRIEF DESCRIPTION OF DRAWINGS

[0029] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following will briefly introduce the drawings needed in the embodiment description. Obviously, the drawings in the following description are only some embodiments of the present application, and other drawings can also be obtained according to these drawings without creative labor for those skilled in the art.

[0030] 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.

[0031] Figure 1is a structural schematic diagram of an organic light-emitting device provided by an embodiment of the present application;

[0032] Figure 2 is a structural schematic diagram of another organic light-emitting device provided by an embodiment of the present application;

[0033] Figure 3 is a UV-Vis spectrum of an organic compound P-33 in toluene provided by an embodiment of the present application;

[0034] Figure 4 is a PL spectrum of an organic compound P-33 in toluene provided by an embodiment of the present application;

[0035] Figure 5 is a UV-Vis spectrum of an organic compound P-204 in toluene provided by an embodiment of the present application;

[0036] Figure 6 is a PL spectrum of an organic compound P-204 in toluene provided by an embodiment of the present application;

[0037] Figure 7 is a ground state configuration of an organic compound P-33 provided by an embodiment of the present application;

[0038] Figure 8 is a ground state configuration of a comparative compound REF05 provided by the present application.

[0039] BRIEF DESCRIPTION OF DRAWINGS

[0040] 100, organic light-emitting device; 110, substrate; 120, first electrode; 130, organic functional layer; 131, hole injection layer; 132, hole transport layer; 133, light-emitting auxiliary layer; 134, light-emitting layer; 1341, first light-emitting layer; 1342, second light-emitting layer; 135, electron transport layer; 136, electron injection layer; 140, second electrode. DETAILED DESCRIPTION

[0041] The technical solutions in the embodiments of the present application will be described clearly and completely below with reference to the drawings in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, rather than all the embodiments of the present application. Based on the embodiments in the present application, all the other embodiments obtained by a person of ordinary skill in the art without creative work fall within the scope of protection of the present application. In addition, it should be understood that the specific implementation described herein is only used to illustrate and explain the present application, and is not used to limit the present application. In the present application, the orientation words such as "upper" and "lower" generally refer to the upper and lower in the actual use or working state of the device, and specifically refer to the direction of the drawing surface in the drawings; and "inner" and "outer" refer to the contour of the device. In the present application, "optionally", "optional" and "optionally" mean optional, that is, selected from "yes" or "no" two parallel schemes. If there are multiple "optionally" in a technical solution, if there is no special description, and there is no contradictory relationship or mutual restriction, each "optionally" is independent. In the present application, the technical features described in an open manner include closed technical solutions composed of listed features, and also include open technical solutions containing listed features.

[0042] In the present application, the aromatic group, aromatic, aromatic ring system have the same meaning and can be interchangeable.

[0043] In the present application, the heteroaromatic group, heteroaromatic, heteroaromatic ring system have the same meaning and can be interchangeable.

[0044] In the present application, "substituted" means that the hydrogen atom in the substituent is replaced by the substituent.

[0045] In the present application, the same substituent can be independently selected from different groups when it appears multiple times. For example, if the general formula contains multiple R, R can be independently selected from different groups.

[0046] 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, a cyano group, an isocyano group, a nitro group, or 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, a cyano group, an isocyano group, a nitro group, or 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, a cyano group, an isocyano group, a nitro group, or 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.

[0047] In the present application, "ring atom number" means the number of atoms constituting a ring itself in 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 is true for the "ring atom number" described below, unless otherwise specified. For example, the ring atom number of a benzene ring is 6, the ring atom number of a naphthalene ring is 10, and the ring atom number of a thiophene group is 5.

[0048] In the present application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived by removal of 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 for the rings in the polycyclic aryl group, at least one 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, anthryl, phenanthryl, fluoranthenyl, fluoranthene, pyrenyl, perylenyl, naphthacene, fluorenyl, rylenyl, 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.

[0049] 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.

[0050] 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, C2alkyl, C3alkyl, C4alkyl, C5alkyl, C6alkyl, C7alkyl, C8alkyl, or C9alkyl, 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.

[0051] 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.

[0052] 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.

[0053] 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 through an oxygen atom. Suitable examples of the phrase including this term include, but are not limited to: methoxy (-O-CH3or -OMe), ethoxy (-O-CH2CH3or -OEt), and tert-butoxy (-O-C(CH3)3or -OtBu).

[0054] In the present application, "*" attached to a single bond indicates a connection or a fused site.

[0055] In the present application, when the connection site is not specified in a group, it means that any optional connectable site in the group is the connection site.

[0056] 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, and preferably two or more sites in the group in ortho position are the fused sites.

[0057] In the present application, when a plurality of substituents of the same symbol are contained on the same group, each substituent can be the same as or different from each other, for example The six R's on the benzene ring can be the same as or different from each other.

[0058] In the present application, a single bond to which a substituent is attached is through the corresponding ring, which means that the substituent can be attached to any optional position of the ring, for example R is attached to any substitutable site of the benzene ring; for example means can form a naphthyl ring with any optional position of the benzene ring.

[0059] The cyclic alkyl group or the cycloalkyl group according to the present application have the same meaning and can be interchanged.

[0060] The present application provides an organic compound, the chemical structure of which is represented by the general formula (1):

[0061]

[0062] wherein,

[0063] Ar 1 at least one selected from a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms;

[0064] Ar 2 is selected from a structure represented by formula (2):

[0065]

[0066] Ar 3 is selected from the structure represented by formula (3):

[0067]

[0068] wherein * represents a connecting site or a fused site;

[0069] R 1 and R 2 is selected from at least one of hydrogen, deuterium, a linear alkyl group having 1 to 16 carbon atoms, a branched alkyl group having 3 to 16 carbon atoms, a cyclic alkyl group having 3 to 16 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 16 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 16 carbon atoms;

[0070] L 1 and L 2 is selected from at least one of a single bond, a substituted or unsubstituted aromatic group having 6 to 16 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 16 carbon atoms;

[0071] n1 is selected from any one integer from 1 to 8;

[0072] n2 is selected from any one integer from 1 to 11.

[0073] In the present application, the structure of the organic compound represented by formula (1) includes groups anthracene and benzo[ghi]periflanthene, and the combination of the two fused ring groups of anthracene and benzo[ghi]periflanthene makes the organic compound have the triplet-triplet annihilation (TTA) effect brought by electron delocalization and better electron transport property, and has strong stability and high excited state energy level. When the organic compound is used as a host material or is combined with other blue light host materials and applied to a blue light emitting layer, the triplet state energy can be fully utilized through the TTA effect, efficient energy transfer between the host and the guest is achieved, the carrier accumulation is reduced, and the excited state energy is fully transferred to the doped guest light emitting material, thereby further improving the stability of the organic compound thin film, reducing the driving voltage, and improving the service life of the organic light emitting device. Therefore, the voltage of the organic light emitting device using the organic compound of the present application can be further reduced, and the service life can be further improved.

[0074] wherein the group Ar 3 and Ar 2 The combination of the connecting sites can improve the steric hindrance of the organic compound, more easily construct a large steric hindrance orthogonal configuration, improve the stacking between molecules, construct the energy transfer channel between the host and the guest by widening the intermolecular distance, more easily adjust the excited state energy level, improve the energy transfer efficiency, and further reduce the driving voltage and improve the service life of the organic light emitting device.

[0075] In some embodiments, Ar 2 is selected from any one of the following groups, which are substituted or unsubstituted:

[0076]

[0077] wherein any H in Ar 2 is substituted to form a connection site to L 2 ; and any H in Ar 2 is unsubstituted or substituted with R 2 .

[0078] In some embodiments, Ar 2 is selected from any one of the following groups:

[0079]

[0080] In some embodiments, Ar 1 is selected from any one or combination of any of the following groups, which are substituted or unsubstituted:

[0081]

[0082] wherein any H in Ar 1 is substituted to form a connection site to L 1 .

[0083] In some embodiments, L 1 and L 2 are selected from at least one of a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted dibenzofurane.

[0084] In some embodiments, R 1 and R 2 are selected from at least one of hydrogen, deuterium, substituted or unsubstituted phenylene, and substituted or unsubstituted naphthylene.

[0085] In some embodiments, R 1 and R 2 are selected from hydrogen or deuterium.

[0086] In some embodiments, the organic compound is selected from any one of the following compounds represented by Formula P-1 to Formula P-520:

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] The organic compound of the present application can be applied to an organic functional layer of an organic light-emitting device as a functional material. The organic functional layer includes at least one of a hole injection layer (HIL), a hole transport layer (HTL), an electronic transport layer (ETL), an electron injection layer (EIL), a hole blocking layer (HBL), a prime layer, and an emission material layer (EML).

[0106] In some embodiments, the organic compound of the present application can be used in an emission layer. The organic compound can be applied to the emission layer as a host material, especially as a blue light host material, or applied to the emission layer by blending with other blue light host materials.

[0107] The present application also provides a mixture comprising at least one organic functional material selected from at least one of hole injection material, hole transport material, electron injection material, electron transport material, light-emitting auxiliary material, hole blocking material, guest material, host material, and quantum dot material, and at least one organic compound described in the above embodiments.

[0108] The present application further provides a composition comprising at least one organic solvent and at least one organic compound described in the above embodiments, or the composition comprising at least one organic solvent and the mixture.

[0109] In some embodiments, the organic solvent is selected from at least one of aromatic or heteroaromatic, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, alicyclic or olefinic compound, borate or phosphate ester compound.

[0110] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic based organic solvent.

[0111] Suitable aromatic or heteroaromatic based organic solvents for the present application include, but are not limited to, p-diisopropylbenzene, amylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-cymene, diamylbenzene, triamylbenzene, pentyltoluene, 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-cymene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorobenzophenone, 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-isopropyl naphthalene, quinoline, isoquinoline, 2-furancarboxylic acid methyl ester, or 2-furancarboxylic acid ethyl ester, and the like.

[0112] Suitable aromatic ketone based organic solvents for the present application include, but are not limited to, 1-tetralone, 2-tetralone, 2-(phenyloxy)tetralone, 6-(methyloxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, or 2-methylpropiophenone, and the like.

[0113] Suitable aromatic ether-based organic solvents for the present 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-ethyl ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butyl anisole, trans-p-allylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxy methyl ether, 2-phenoxytetrahydrofuran, or ethyl-2-naphthyl ether.

[0114] Suitable aliphatic ketone-based organic solvents for the present application include, but are not limited to, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, p-methylphenylacetone, isophorone, di-n-pentyl ketone, and the like; 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, or tetraethylene glycol dimethyl ether, and the like.

[0115] Suitable ester-based organic solvents for the present application include, but are not limited to, alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkyl lactones, alkyl oleates, and the like. Particularly preferred are octyl octanoate, diethyl sebacate, diallyl phthalate, or isononyl isononanoate.

[0116] 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, tetralin, naphthene, or indene.

[0117] In some embodiments, the organic solvent of the present application can be a solvent having a Hansen solubility parameter in the following ranges:

[0118] δ d in the range of 17.0 to 23.2 MPa 1 / 2 , especially 18.5 to 21.0 MPa 1 / 2in the range of 0.2-12.5 MPa, especially in the range of 2.0-6.0 MPa

[0119] δ p in the range of 0.2-12.5 MPa, especially in the range of 2.0-6.0 MPa 1 / 2 in the range of 0.2-12.5 MPa, especially in the range of 2.0-6.0 MPa 1 / 2 in the range of 0.2-12.5 MPa, especially in the range of 2.0-6.0 MPa

[0120] δ h in the range of 0.2-12.5 MPa, especially in the range of 2.0-6.0 MPa 1 / 2 in the range of 0.2-12.5 MPa, especially in the range of 2.0-6.0 MPa 1 / 2 in the range of 0.2-12.5 MPa, especially in the range of 2.0-6.0 MPa

[0121] In some embodiments, the organic solvent is selected considering its boiling point parameter. In the present application, the boiling point of the organic solvent is ≥ 150 °C; preferably ≥ 180 °C; more preferably ≥ 200 °C; even more preferably ≥ 250 °C; most preferably ≥ 275 °C or ≥ 300 °C. The boiling point in these ranges is beneficial to prevent clogging of the nozzles of the inkjet printing head.

[0122] It is to be noted that the organic solvent can be evaporated from the solvent system to form a thin film comprising the functional material.

[0123] In some embodiments, the composition provided by the embodiments of the present application can be a solution.

[0124] In some embodiments, the composition provided by the embodiments of the present application can be a suspension.

[0125] In some embodiments, the composition can comprise 0.01 wt% to 20 wt% of the organic compound or the mixture. Further, the content of the organic compound or the mixture in the composition can be 0.1 wt% to 15 wt%. Preferably, the content of the organic compound or the mixture in the composition can be 0.2 wt% to 10 wt%.

[0126] In some embodiments, the composition can be applied to the preparation of an organic light-emitting device as a coating or printing ink, for example, the organic light-emitting device can be prepared by a printing or coating method.

[0127] The printing or coating method includes, but is not limited to, inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, reverse-roller printing, offset lithography printing, flexographic printing, rotogravure printing, spray coating, brush coating or pad printing, slot-die coating, etc. Preferably, gravure printing, nozzle printing and inkjet printing. Further, the composition can further comprise one or more components, such as a surface-active compound, a lubricant, a wetting agent, a dispersant, a hydrophobic agent, an adhesive, etc., for adjusting the viscosity, improving the film-forming properties, improving the adhesion, etc.

[0128] This application also provides an organic light-emitting device 100, please refer to... Figure 1 The organic light-emitting device 100 includes: a first electrode 120, an organic functional layer 130, and a second electrode 140, wherein the organic functional layer 130 is located between the first electrode 120 and the second electrode 140; wherein the material of the organic functional layer 130 includes at least one organic compound as described above, or the material of the organic functional layer 130 includes a mixture as described above, or the organic functional layer 130 is made of a composition as described above.

[0129] Furthermore, the organic light-emitting device 100 also includes a substrate 110. The substrate 110 can be opaque or transparent. Transparent substrates can be used to fabricate transparent light-emitting devices, for example, see Bulovic et al., Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate 110 can be rigid or flexible, and the material of the substrate 110 can be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate 110 has a smooth surface; a substrate without surface defects is particularly desirable. Preferably, the substrate 110 can be flexible, including polymer films or plastics, such as polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN). The glass transition temperature T of the substrate 110... g The ideal temperature is above 150°C, preferably above 200°C, even better than above 250°C, and most preferably above 300°C.

[0130] In some embodiments, one of the first electrode 120 and the second electrode 140 is an anode and the other is a cathode. For example, the first electrode 120 can be an anode and the second electrode 140 can be a cathode.

[0131] The anode is the hole-injecting electrode and can inject holes into the organic functional layers, such as the hole-injecting layer, the hole-transporting layer, or the light-emitting layer. The anode can comprise at least one of a conductive metal, a conductive metal oxide, or a conductive polymer. Preferably, the absolute value of the difference between the work function of the anode and the HOMO (Highest Occupied Molecular Orbital) level or the valence band level of the light-emitting material in the light-emitting layer, or the p-type semiconductor material as a hole-injecting layer or a hole-transporting layer or an electron-blocking layer, is less than 0.5 eV, preferably less than 0.3 eV, more preferably less than 0.2 eV. The material of the anode includes, but is not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO (Indium Tin Oxide), aluminum-doped zinc oxide (AZO), and the like, or other suitable and known anode materials, which can be readily selected by one of ordinary skill in the art. The material of the anode can be deposited using any suitable technique, such as suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, e-beam, and the like. In some embodiments, the anode is patternable, such as a patterned ITO conductive substrate, which is commercially available and can be used to fabricate the organic light-emitting device of the present application.

[0132] The cathode is the electron-injecting electrode and can inject electrons into the organic functional layers, such as the electron-injecting layer, the electron-transporting layer, or the light-emitting layer. The cathode can comprise at least one of a conductive metal or a conductive metal oxide. Preferably, the absolute value of the difference between the work function of the cathode and the LUMO (Lowest Unoccupied Molecular Orbital) level or the conduction band level of the light-emitting material in the light-emitting layer, or the n-type semiconductor material as an electron-injecting layer or an electron-transporting layer or a hole-blocking layer, is less than 0.5 eV, preferably less than 0.3 eV, more preferably less than 0.2 eV. All materials that can be used as a cathode of an organic electronic device can be used as the cathode material of the device of the present application. The material of the cathode includes, but is not limited to, at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like. The material of the cathode can be deposited using any suitable technique, such as suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, e-beam, and the like.

[0133] In embodiments of the present application, the organic functional layer 130 can include one or more functional film layers. For example, the organic functional layer 130 can include one or more of a hole injection layer 131, a hole transport layer 132, a light-emitting auxiliary layer 133, a light-emitting layer 134, an electron transport layer 135, and an electron injection layer 136.

[0134] In some embodiments, the organic functional layer 130 includes a light-emitting layer 134. The material of the light-emitting layer 134 includes at least one organic compound as described above, or the material of the light-emitting layer 134 includes a mixture as described above, or the light-emitting layer 134 is made of a composition as described above.

[0135] In some embodiments, the organic functional layer 130 can include a plurality of light-emitting layers. For example, the organic functional layer 130 can include a first light-emitting layer 1341 and a second light-emitting layer 1342, the material of the first light-emitting layer 1341 and / or the second light-emitting layer 1342 includes at least one organic compound as described above, or the material of the first light-emitting layer 1341 and / or the second light-emitting layer 1342 includes a mixture as described above, or the first light-emitting layer 1341 and / or the second light-emitting layer 1342 is made of a composition as described above.

[0136] Further, the organic functional layer 130 further includes at least one of a hole injection layer 131, a hole transport layer 132, a light-emitting auxiliary layer 133, an electron transport layer 135, and an electron injection layer 136.

[0137] In an embodiment, referring to Figure 1 , the organic light-emitting device 100 includes a substrate 110, a first electrode (anode) 120, an organic functional layer 130, and a second electrode (cathode) 140, the organic functional layer 130 includes a hole injection layer 131, a hole transport layer 132, a light-emitting layer 134, an electron transport layer 135, and an electron injection layer 136. Among them, the hole injection layer 131 is located on the side of the first electrode 120 away from the substrate 110, the hole transport layer 132 is located on the side of the hole injection layer 131 away from the first electrode 120, the light-emitting layer 134 is located on the side of the hole transport layer 132 away from the hole injection layer 131, the electron transport layer 135 is located on the side of the light-emitting layer 134 away from the hole transport layer 132, and the electron injection layer 136 is located between the electron transport layer 135 and the second electrode 140.

[0138] In an embodiment, referring to Figure 2The organic light-emitting device 100 includes a substrate 110, a first electrode (anode) 120, an organic functional layer 130, and a second electrode (cathode) 140. The organic functional layer 130 includes a hole injection layer 131, a hole transport layer 132, a light-emitting auxiliary layer 133, a first light-emitting layer 1341, a second light-emitting layer 1342, an electron transport layer 135, and an electron injection layer 136. The hole injection layer 131 is located on the side of the first electrode 120 away from the substrate 110. The hole transport layer 132 is located on the side of the hole injection layer 131 away from the first electrode 120. The light-emitting auxiliary layer 133 is located on the side of the hole transport layer 132 away from the hole injection layer 131. The first light-emitting layer 1341 is located on the side of the light-emitting auxiliary layer 133 away from the hole transport layer 132. The second light-emitting layer 1342 is located on the side of the first light-emitting layer 1341 away from the light-emitting auxiliary layer 133. The electron transport layer 135 is located on the side of the second light-emitting layer 1342 away from the first light-emitting layer 1341. The electron injection layer 136 is located between the electron transport layer 135 and the second electrode 140.

[0139] In some embodiments, the organic light-emitting device 100 has an emission wavelength between 300 nm and 1000 nm, preferably between 350 nm and 900 nm, and more preferably between 400 nm and 800 nm.

[0140] In some embodiments, the organic light-emitting device can be, but is not limited to, an organic light-emitting diode (OLED), an organic photovoltaics (OPV), an organic light-emitting electrochemical cell (OLEEC), an organic field effect transistor (OFET), an organic light-emitting field-effect transistor (OLEFET), an organic laser, an organic spintronics device, an organic sensor, and an organic plasmon emitting diode, etc. Preferably, the organic light-emitting device is an organic light-emitting diode, an organic light-emitting electrochemical cell, or an organic light-emitting field-effect transistor.

[0141] In some embodiments, the organic light-emitting device can be applied to various electronic devices, such as display panels, lighting devices, light sources, sensors, etc.

[0142] The application also provides a display panel comprising the organic light-emitting device as described in the above embodiments. The display panel can be used in the fields of smart phones, tablet computers, smart wearable devices, televisions, virtual reality (VR), micro displays, and car central screens, but is not limited thereto.

[0143] The organic compounds provided by the application will be described below in conjunction with preferred embodiments, but the organic compounds provided by the application are not limited to the following embodiments. It should be understood that the appended claims generalize the scope of the application. Those skilled in the art should realize that certain changes made to the embodiments of the application will be covered by the spirit and scope of the claims of the application.

[0144] I. Synthesis of organic compounds

[0145] 1. Synthesis of intermediates

[0146] The synthesis route of the intermediate 1 is as follows:

[0147]

[0148] The reactant A (0.1 mol) and the reactant B (0.1 mol) were weighed into a clean three-necked flask, Pd(dppf)Cl2(2.0 mmol), potassium acetate (0.4 mol) were dissolved in 1,4-dioxane, and the three-necked flask was replaced with nitrogen three times. The reaction was heated to 100°C under a nitrogen atmosphere and refluxed for 6 h. After natural cooling, the organic phase was washed with water, dried, and rotary evaporated to obtain the intermediate 1 with a yield of 77%. The electrospray ionization mass spectrometry (ESI-MS) result of the intermediate 1 was m / z [H + ] = 394.

[0149] Synthesis of intermediates 2-23:

[0150] Referring to the preparation method of the intermediate 1, the reactant A raw material shown in Table 1 was selected to prepare the corresponding intermediates 2-23. The reactants, products, and corresponding parameter information of the intermediates 1-23 are shown in Table 1.

[0151] Table 1. Reactants, products, and corresponding parameter information of intermediates 1-23

[0152]

[0153]

[0154]

[0155] 2. Synthesis of organic compounds

[0156] Example 1

[0157]

[0158] Synthesis of compound P-1:

[0159] The reactant C (20 mmol) and the reactant D (20 mmol) were weighed into 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, and the reaction was replaced with nitrogen three times, and then heated to 100°C under nitrogen atmosphere and refluxed for 12 h. After natural cooling, water washing and separation, the organic phase was dried and rotary evaporated, and column chromatography was performed to obtain compound P-1 with a yield of 83%, m / z [H + ] = 521.

[0160] Examples 2-41

[0161] Referring to the preparation method of compound P-1 in Example 1, the reactant raw materials shown in Table 2 were selected to prepare the corresponding organic compounds of Examples 21-41. The reactants, products and corresponding parameter information of Examples 1-41 are shown in Table 2.

[0162] Table 2 Reactants, products and corresponding parameter information of Examples 1-41

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169] Comparative Examples 1-5

[0170] The present application also provides comparative examples, and the organic compounds of the comparative examples are denoted as "Comparative Compound REF01, Comparative Compound REF02, Comparative Compound REF03, Comparative Compound REF04 and Comparative Compound REF05", and the chemical structural formulae are as follows:

[0171]

[0172] II. Preparation and characterization of OLED devices

[0173] The organic light-emitting device provided in this embodiment is an OLED device. Figure 2 Taking the structure of the organic light-emitting device 100 shown as an example, the following detailed description of the preparation method of OLED device using the organic compound provided in the embodiments of this application will be carried out through specific device embodiments.

[0174] In the following method for fabricating OLED devices, ITO conductive glass 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 dopant material for the first and second light-emitting layers, BH-1 as the host material for the second light-emitting layer, ET-1 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 from the aforementioned synthesis examples as the host material for the first light-emitting layer. The chemical structural formulas of PD, HT, BP, BD, BH-1, ET-1, and Liq are shown below:

[0175]

[0176] The following specific examples illustrate the fabrication process of OLED devices using the above-mentioned materials.

[0177] Taking the fabrication method of OLED device using compound P-1 as the host material of the first emitting layer 1341 as an example, the resulting OLED device is denoted as "OLED-1 device". The fabrication method of OLED-1 device includes the following steps:

[0178] Step a: Cleaning of the ITO conductive glass substrate.

[0179] An ITO conductive glass substrate (including a substrate 110 and a first electrode (anode) 120) is provided, and the substrate is ultrasonically cleaned using one or more cleaning agents such as deionized water, acetone, isopropanol or chloroform to improve the power function of the anode.

[0180] Step b: Form a hole injection layer 131 on the first electrode (anode) 120.

[0181] by Hole injection materials PD and HT are deposited on the first electrode (anode) 120 at a deposition rate of 3:97, resulting in a hole injection layer 131 with a thickness of 30 nm.

[0182] Step c: Form a hole transport layer 132 on the hole injection layer 131.

[0183] by Hole transport material HT is deposited on hole injection layer 131 at a certain evaporation rate to obtain hole transport layer 132 with a thickness of 60 nm.

[0184] Step d: forming a light-emitting auxiliary layer 133 on the hole transport layer 132.

[0185] The light-emitting auxiliary material BP was evaporated on the hole transport layer 132 at an evaporation rate of 0.1 A to obtain a light-emitting auxiliary layer 133 with a thickness of 10 nm.

[0186] Step e: forming a first light-emitting layer 1341 on the light-emitting auxiliary layer 133.

[0187] The evaporation rate of the light-emitting auxiliary layer 133 was 0.1 A. The evaporation rate of the light-emitting auxiliary layer 133 was 0.1 A.

[0188] Step f: forming a second light-emitting layer 1342 on the first light-emitting layer 1341.

[0189] The evaporation rate of the light-emitting auxiliary layer 133 was 0.1 A. The evaporation rate of the light-emitting auxiliary layer 133 was 0.1 A.

[0190] Step g: forming an electron transport layer 135 on the second light-emitting layer 1342.

[0191] In a vacuum chamber, the electron transport material ET-1 and Liq were placed in different evaporation crucibles, and ET-1 and Liq were co-deposited at a weight ratio of 5:5 under a high vacuum environment (1 x 10 -6 millibar) to form an electron transport layer 135 with a thickness of 30 nm on the second light-emitting layer 1342.

[0192] Step h: forming an electron injection layer 136 on the electron transport layer 135.

[0193] The evaporation rate of the light-emitting auxiliary layer 133 was 0.1 A. The evaporation rate of the light-emitting auxiliary layer 133 was 0.1 A.

[0194] Step i: forming a second electrode (cathode) 140 on the electron injection layer 136.

[0195] The evaporation rate of the light-emitting auxiliary layer 133 was 0.1 A. The evaporation rate of the light-emitting auxiliary layer 133 was 0.1 A.

[0196] Step j: placing the device obtained by layer-by-layer deposition in a nitrogen atmosphere glove box, and encapsulating using ultraviolet curing resin to finally obtain an OLED-1 device.​

[0197] In this embodiment, the prepared OLED-1 device structure is: ITO / PD:HT (3:97, 30 nm) / HT (60 nm) / BP (10 nm) / compound P-1:BD (2%, 10 nm) / BH-1:BD (2%, 10 nm) / ET-1:Liq (5:5, 30 nm) / Liq (1 nm) / Al (100 nm).

[0198] Preparation of OLED-2 to OLED-41 devices:

[0199] Referring to the preparation method of device OLED-1, the compounds synthesized in Examples 2 to 41 were respectively selected as the host material of the first light-emitting layer 1341 of the OLED device, and OLED-2 to OLED-41 devices were prepared correspondingly. It can be understood that in the preparation methods of the above OLED-1 to OLED-41 devices, except that the host material of the first light-emitting layer 1341 is different, other experimental conditions are the same.

[0200] Preparation of OLED-REF01 to OLED-REF04 comparative device:

[0201] Referring to the preparation method of device OLED-1, comparative compounds REF01 to REF04 were respectively selected as the host material of the first light-emitting layer 1341, and comparative devices OLED-REF01 to OLED-REF04 were prepared correspondingly. Compared with the preparation method of OLED-1 device, except that the host material of the first light-emitting layer 1341 is different, other experimental conditions are the same in the preparation method of OLED-REF01 to OLED-REF04 devices.

[0202] In this application, the current-voltage (J-V) characteristics of OLED-1 to OLED-41, OLED-REF01 to OLED-REF04 devices were characterized, and important parameters such as voltage, color coordinates and lifetime were recorded, as shown in Table 3. Among them, the lifetime (LT95) is the time used for the device brightness to drop from the initial 1knit to 95% under constant current.

[0203] Table 3

[0204]

[0205]

[0206]

[0207] Preparation of OLED-42 device:

[0208] The organic light-emitting device provided by the embodiment can be an OLED device, and the preparation method of the OLED device is described below by taking the preparation of the organic light-emitting device 100 shown in FIG. 1 as an example. Figure 1 The preparation method of the OLED device is described below by taking the preparation of the organic light-emitting device 100 shown in FIG. 1 as an example.

[0209] In the following preparation method of the OLED device, ITO conductive glass is used as an anode substrate, PEDOT:PSS (poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid), Clevios TM ) is used as a hole injection material, PVK (poly(9-vinylcarbazole), Sigma Aldrich, number average molecular weight 25,000-50,000) is used as a hole transport material, BH-2 is used as a second compound of the host material of the light-emitting layer, ET-2 and 8-hydroxyquinoline lithium (Liq) are used as electron transport materials, Liq is used as an electron injection material, and Al is used as a cathode material. In addition, the organic compounds in the foregoing synthesis embodiments are used as the first compound of the host material of the light-emitting layer 134 to prepare corresponding OLED devices, respectively. Among them, the chemical structural formulas of BH-2, ET-2 and Liq are as follows:

[0210]

[0211] The preparation method of the OLED device is described below by taking the preparation of the organic light-emitting device 100 shown in FIG. 1 as an example.

[0212] Step a: cleaning of the ITO conductive glass substrate.

[0213] An ITO conductive glass substrate (including a substrate 110 and a first electrode (anode) 120) is provided, and the substrate is ultrasonically cleaned with a cleaning agent such as one or more of deionized water, acetone, isopropanol or chloroform to improve the work function of the anode.

[0214] Step b: forming a hole injection layer 131 on the first electrode (anode) 120.

[0215] The hole injection material PEDOT:PSS is spin-coated on the first electrode (anode) 120, and then heat-treated on a hot plate at 180°C for 10 min to obtain a hole injection layer 131 with a thickness of 20 nm.

[0216] Step c: forming a hole transport layer 132 on the hole injection layer 131.

[0217] A 5 mg / mL toluene solution of hole transport material PVK was spin-coated on the hole injection layer 131, and then heat-treated on a hot plate at 180°C for 60 min to obtain a hole transport layer 132 with a thickness of 40 nm.

[0218] Step d: A light-emitting layer 134 was formed on the hole transport layer 132.

[0219] A 15 mg / mL methyl benzoate solution was prepared with the compound P-1 and BH-2 of the present application as the host material and BD as the dopant material, and the mass ratio of the compound P-1, BH-2 and BD was 48.5:48.5:3. After spin-coating, the solution was heat-treated on a hot plate at 140°C for 10 min to obtain a light-emitting layer 134 with a thickness of 35 nm.

[0220] Step e: An electron transport layer 135 was formed on the light-emitting layer 134.

[0221] In a vacuum chamber, the electron transport material ET-2 and Liq were placed in different evaporation crucibles, and ET-2 and Liq were co-deposited at a weight ratio of 5:5 under a high vacuum environment (1×10 -6 millibar) to form an electron transport layer 135 with a thickness of 30 nm on the light-emitting layer 134.

[0222] Step f: An electron injection layer 136 was formed on the electron transport layer 135.

[0223] The electron injection material Liq was evaporated on the electron transport layer 135 at an evaporation rate of 1 nm to obtain an electron injection layer 136 with a thickness of 1 nm.

[0224] Step g: A second electrode (cathode) 140 was formed on the electron injection layer 136.

[0225] The cathode material Al was evaporated on the electron injection layer 136 at an evaporation rate of 100 nm to obtain a cathode with a thickness of 100 nm.

[0226] Step h: The obtained device was placed in a nitrogen atmosphere glove box, and encapsulated using ultraviolet curing resin to finally obtain an OLED-42 device.

[0227] In this embodiment, the structure of the prepared OLED-42 device was: ITO / PEDOT:PSS (20 nm) / PVK (40 nm) / compound P-1:BH-2:BD (48.5:48.5:3, 35 nm) / ET-2:Liq (5:5, 30 nm) / Liq (1 nm) / Al (100 nm).

[0228] Preparation of OLED-43 to OLED-52 devices:

[0229] Referring to the preparation method of the device OLED-42, the compound synthesized in the examples was selected as the first compound of the light-emitting layer 134 host material, and the corresponding OLED-43 to OLED-52 devices were prepared. It can be understood that in the preparation method of the above OLED-42 to OLED-52 devices, except that the first compound of the light-emitting layer host 134 material is different, other experimental conditions are the same. Preparation of OLED-REF05 to OLED-REF08 comparative devices:

[0230] Referring to the preparation method of the device OLED-42, the compound synthesized in the examples was selected as the first compound of the light-emitting layer 134 host material, and the corresponding OLED-43 to OLED-52 devices were prepared. It can be understood that in the preparation method of the above OLED-42 to OLED-52 devices, except that the first compound of the light-emitting layer host 134 material is different, other experimental conditions are the same. Preparation of OLED-REF05 to OLED-REF08 comparative devices:

[0231] Table 4

[0232]

[0233]

[0234] From the results in Table 3, it can be seen that the voltages of the OLED-1 to OLED-41 devices of the present application are lower than those of the comparative REF01 to REF03 devices, the lifetimes of the OLED-1 to OLED-41 devices are significantly higher than those of the comparative OLED-REF01 to OLED-REF04 devices, wherein the voltage of the comparative OLED-REF04 device is reduced, but its lifetime is also significantly reduced. The OLED-1 to OLED-41 devices of the present application have both low voltage and high lifetime. Therefore, the OLED-1 to OLED-41 devices prepared by using the organic compounds provided in the examples 1 to 41 as the blue light host material in the first light-emitting layer have excellent effects in voltage and lifetime, and can not only reduce the device voltage, but also greatly improve the device lifetime without affecting the color, and have excellent comprehensive performance.

[0235] As shown in Table 4, when the organic compounds of Examples 42 to 52 and BH-2 were blended as the main material, the voltages of the OLED-42 to OLED-52 devices prepared in this application were all lower than those of the comparative OLED-REF05, OLED-REF06, and OLED-REF08 devices. The lifetimes of the OLED-42 to OLED-52 devices were significantly higher than those of the comparative OLED-REF05 to OLED-REF08 devices. While the voltage of the comparative REF07 device decreased and its lifetime increased somewhat, the increase in lifetime was significantly less than that of the devices in this application. The OLED-1 to OLED-41 devices of this application combined both lower voltage and higher lifetime. The OLED-42 to OLED-52 devices prepared in this application using the organic compounds of Examples 42 to 52 and BH-2 as the main material exhibit excellent performance in terms of voltage and lifetime, reducing device voltage and significantly improving device lifetime without affecting color temperature.

[0236] Among them, when using comparative compounds REF01 and REF05 as the host materials for the light-emitting layer, the lifetime of the corresponding devices was slightly improved, but the increase was relatively small. This is related to the excited state energy levels, electron delocalization strength, and steric hindrance brought about by the different fused-ring furans of the comparative compounds. For example, the phenanthrene-furan fused-ring mode and connection sites of comparative compound REF05 result in a more linear molecular structure and less steric hindrance than compound P-33 in the embodiments of this application (see Figures 7-8 This directly affects the π-π stacking of the host and guest materials after they are mixed and formed into a film. In contrast, the compounds in this application are more likely to construct sterically hindered orthorhombic configurations, and the host-guest relationship can be constructed by widening the intermolecular distance. The energy transfer channels are also more easily adjusted to modify the excited-state energy levels and improve energy transfer efficiency, thereby further enhancing device performance. Among these, Figure 3 This is the UV-Vis spectrum of compound P-33 in toluene. Figure 4 This is the PL spectrum of compound P-33 in toluene. Figure 5 This is the UV-Vis spectrum of compound P-204 in toluene. Figure 6 The PL spectrum of compound P-204 in toluene. Figure 7 This is the ground state configuration of compound P-33. Figure 8 This is the ground state configuration of compound REF05.

[0237] In summary, compared with the compound used in the comparative example, the organic compound provided in the embodiments of the present application utilizes the TTA effect of the fused ring molecular structure of anthracene combined with benzophenanthrene and furan and the adjustable excited state energy level to construct more exciton transmission channels, improve the utilization rate of excitons, avoid the quenching problem caused by the accumulation of long-lived excitons, and thus reduce the voltage and greatly improve the device lifetime. Therefore, when the organic compound of the present application is used as the host material of the first light-emitting layer (located between the light-emitting auxiliary layer and the second light-emitting layer) or one of the blended host materials of the light-emitting layer, the driving voltage and the lifetime of the organic light-emitting device can be effectively improved.

[0238] In the description of the present application, the terms "first", "second" are only for the purpose of description, and cannot be understood as indicating or implying relative importance or implicitly indicating the number of the indicated technical features. Therefore, the features defined with "first", "second" can explicitly or implicitly include one or more features. In the description of the present application, the meaning of "multiple" is two or more, unless otherwise specifically limited.

[0239] In the above embodiments, the description of each embodiment has its own emphasis, and the parts not described in detail in a certain embodiment can be referred to the related description of other embodiments.

[0240] The embodiments, implementation manners and related technical features of the present application can be combined or replaced with each other without conflict.

[0241] The above is only the preferred embodiment of the present application, and does not limit the present application in any form. Any simple modification, equivalent change and modification made to the above embodiments according to the technical essence of the present application without departing from the technical solution of the present application still falls within the scope of the technical solution of the present application.

Claims

1. An organic compound characterized in that, The chemical structural formula of the organic compound is shown in general formula (1): wherein, Ar 1 at least one selected from the group consisting of a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms; Ar 2 is selected from the structures represented by formula (2): Ar 3 is selected from the structures represented by formula (3): wherein * represents a connecting site or a fused site; R 1 and R 2 is at least one selected from the group consisting of hydrogen, deuterium, a straight-chain alkyl group having 1 to 16 carbon atoms, a branched-chain alkyl group having 3 to 16 carbon atoms, a cyclic alkyl group having 3 to 16 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 16 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 16 carbon atoms; L 1 and L 2 at least one selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 16 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 16 carbon atoms; n1 is selected from any one integer from 1 to 8; n2 is selected from any one integer from 1 to 11.

2. The organic compound according to claim 1, characterized by Ar 2 selected from any one of the following groups of substituted or unsubstituted: wherein Ar 2 is substituted to form a connection site with L 2 ; any H in the above groups is not substituted, or is substituted with R 2 .

3. The organic compound according to claim 1, wherein Ar 2 any one selected from the group consisting of 4. The organic compound according to claim 1, wherein Ar 1 selected from any one or a combination of any number of the following groups of substituted or unsubstituted: wherein any one H in 1 is replaced with a linking site to L 1 .

5. The organic compound according to claim 1, wherein L 1 and L 2 is selected from at least one of a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted dibenzofuran; R 1 and R 2 is selected from at least one of hydrogen, deuterium, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene.

6. The organic compound according to claim 1, wherein The organic compound is selected from any one of the compounds shown in formula P-1 to formula P-520:

7. A mixture characterized in that, The mixture comprises at least one organic functional material and at least one organic compound according to any one of claims 1 to 6, wherein the organic functional material is selected from at least one of hole injection material, hole transport material, electron injection material, electron transport material, light-emitting auxiliary material, hole blocking material, guest material, host material and quantum dot material.

8. A composition characterized in that, The composition comprises at least one organic solvent and at least one organic compound according to any one of claims 1 to 6, or the composition comprises at least one organic solvent and the mixture according to claim 7.

9. An organic light emitting device, characterized by, The organic light-emitting device comprises: a first electrode; a second electrode, which is disposed opposite to the first electrode; and an organic functional layer, which is located between the first electrode and the second electrode; wherein the material of the organic functional layer comprises at least one organic compound according to any one of claims 1 to 6, or the material of the organic functional layer comprises the mixture according to claim 7, or the organic functional layer is made of the composition according to claim 8.

10. A display panel, characterized by, The display panel comprises the organic light-emitting device according to claim 9.

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