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

Abstract

The invention relates to an organic compound, a mixture, a composition and an organic light-emitting device, the organic compound has a structure represented by a formula (1): # imgabs0 #, the organic compound of the application is an organic conjugated molecule based on bis-arylamine, two arylamine groups are connected through two rigid fluorenyl groups to form a partial plane linear core skeleton, and the partial plane linear core skeleton is connected through two rigid fluorenyl groups. Compared with the prior art, the organic compound provided by the invention has strong hole transport capability and high stability, and in addition, the organic compound provided by the invention has an appropriate highest occupied molecular orbital energy level, and can effectively reduce the energy level barrier between a hole transport layer and a light-emitting layer and optimize the carrier transport process, so that the organic compound provided by the invention can improve the efficiency of the organic light-emitting device and improve the light-emitting efficiency of the organic light-emitting device. High light-emitting efficiency is achieved, and the service life of the organic light-emitting device is prolonged.

Description

Technical Field

[0001] The present application relates to the field of display, and in particular to an organic compound, a mixture, a composition and an organic light-emitting device. Background Art

[0002] Organic light-emitting diodes (OLEDs) generally include a positive electrode, a negative electrode, and an organic functional layer located between the positive electrode and the negative electrode. Organic electroluminescent devices use organic substances in the organic functional layer to convert electrical energy into light energy, thereby realizing organic electroluminescence. In order to improve the luminous efficiency and service life of organic electroluminescent devices, the organic functional layer often includes a multilayer structure, and the organic substances in each layer are different. Specifically, the organic functional layer generally includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. When the organic electroluminescent device is working, by applying a voltage between the positive electrode and the negative electrode, the positive electrode injects holes into the organic functional layer, and the negative electrode injects electrons into the organic functional layer. The injected holes meet with the electrons to form excitons, and the excitons emit light when they return to the ground state through radiation transition, thereby realizing the luminescence of the organic electroluminescent device. With the characteristics of self-luminescence, high brightness, high efficiency, low voltage drive, wide viewing angle, high contrast, and high response, organic electroluminescent devices have broad application prospects and broad development potential.

[0003] In order to improve the luminous efficiency of organic electroluminescent elements and extend the service life of the elements, the development and matching of luminescent auxiliary layer materials are crucial. By adopting luminescent auxiliary materials with suitable transmission capabilities, organic electroluminescent devices can achieve a balance in carrier transmission, block reverse electron migration, and allow electrons and holes to recombine in the central area of ​​the luminescent layer, thereby reducing the quenching of excitons, effectively improving luminous efficiency and device life. How to design new luminescent auxiliary materials with better performance to adjust the balance of hole and electron transmission in the element, thereby improving the efficiency and life of the device, has always been a problem that technicians in this field need to solve. Summary of the invention

[0004] The embodiments of the present application provide an organic compound, a mixture, a composition and an organic light-emitting device. The organic compound provided in the present application has good performance in transmitting and adjusting charge balance, and can be used as a light-emitting auxiliary material in an organic light-emitting device to improve the luminous efficiency and life of the device.

[0005] An embodiment of the present application provides an organic compound having a structure represented by formula (1):

[0006]

[0007] in,

[0008] Ar 1 ,Ar 2 ,Ar 3 and Ar 4 independently selected from substituted or unsubstituted aromatic groups having 6 to 20 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms;

[0009] R 1 , R 2 , R 3 and R 4 Independently selected from -CD3, substituted or unsubstituted straight-chain alkyl having 1 to 8 C atoms, substituted or unsubstituted branched-chain alkyl having 3 to 12 C atoms, or substituted or unsubstituted phenyl;

[0010] L 1 and L 2 Independently selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 20 ring atoms.

[0011] In some embodiments, the organic compound has a structure represented by formula (A), formula (B) or formula (C):

[0012] In some embodiments, Ar 1 ,Ar 2 ,Ar 3 and Ar 4 Independently selected from any one of the following structures:

[0013] in,

[0014] X is independently selected from O, S, N-Ph or CR 5 R 6 ;

[0015] R 5 and R 6 independently selected from H, D, a substituted or unsubstituted straight-chain alkyl group having 1 to 20 C atoms, a substituted or unsubstituted branched-chain alkyl group having 3 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 20 ring atoms;

[0016] Ar 1 ,Ar 2 ,Ar 3 and Ar 4 In the structures represented, hydrogen on the benzene ring is not substituted or is substituted by D, a straight-chain alkyl group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, or an aromatic group having 6 to 20 ring atoms.

[0017] In some embodiments, L1 and L 2 are independently selected from a single bond, or a substituted or unsubstituted phenylene group.

[0018] In some embodiments, the organic compound is selected from any one of Formula (A-1) to Formula (C-56):

[0019]

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026] An embodiment of the present application also provides a mixture, which includes at least one organic compound as described above and at least one organic functional material, and the organic functional material is selected from hole injection materials, hole transport materials, electron injection materials, electron transport materials, luminescence auxiliary materials, hole blocking materials, organic light-emitting guest materials, organic host materials and inorganic quantum dot materials.

[0027] An embodiment of the present application further provides a composition, which includes at least one organic compound as described above and at least one organic solvent, or the composition includes the mixture as described above and at least one organic solvent.

[0028] In some embodiments, the organic compound accounts for 0.01 wt % to 20 wt % of the composition, or the mixture accounts for 0.01 wt % to 20 wt % of the composition.

[0029] An embodiment of the present application further provides an organic light-emitting device, comprising:

[0030] a first electrode;

[0031] a second electrode, disposed opposite to the first electrode; and

[0032] an organic functional layer, located between the first electrode and the second electrode;

[0033] The material of the organic functional layer includes at least one organic compound as described above, or the material of the organic functional layer includes the mixture as described above.

[0034] In some embodiments, the organic functional layer comprises at least:

[0035] a light-emitting layer, located between the first electrode and the second electrode; and

[0036] a light-emitting auxiliary layer, located on a side of the light-emitting layer close to the first electrode, or located on a side of the light-emitting layer close to the second electrode;

[0037] Wherein, the material of the light-emitting auxiliary layer includes at least one organic compound as described above.

[0038] The present application provides an organic compound, a mixture, a composition and an organic light-emitting device. The organic compound of the present application is an organic conjugated molecule based on diarylamine, wherein two arylamine groups are connected by two rigid fluorene groups to form a planar linear core skeleton, which has strong hole transport capability and high stability. The connecting group L between the arylamine group and the fluorene group is 1 and L 2 When it is an aromatic group, it can further extend the conjugation, lengthen the linear structure, and further enhance the hole transport capability and stability; in addition, the organic compound of the present application has a suitable highest occupied molecular orbital energy level, which can effectively reduce the energy barrier between the hole transport layer and the light-emitting layer, and optimize the carrier transport process. Therefore, the organic compound of the present application can improve the efficiency of the organic light-emitting device, achieve high luminous efficiency, and extend the life of the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0039] Figure 1 A schematic structural diagram of an organic light-emitting device provided in an embodiment of the present application.

[0040] Figure 2 and Figure 3 It is a molecular structure diagram of organic compound A-1 in Example 1 of the present application.

[0041] Figure 4 It is the HOMO distribution diagram of the organic compound A-1 molecule in Example 1 of the present application.

[0042] Figure 5 It is the LUMO distribution diagram of the organic compound A-1 molecule in Example 1 of the present application.

[0043] Figure 6 It is a molecular structure diagram of the organic compound REF03 in Comparative Example 3 of the present application.

[0044] Description of reference numerals:

[0045] 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; 135, electron transport layer; 136, electron injection layer; 140, second electrode. DETAILED DESCRIPTION

[0046] It should be understood that the specific embodiments described herein are only used to illustrate and explain the present application, and are not used to limit the present application. In the present application, unless otherwise stated, the directional words used, such as "upper" and "lower", generally refer to the upper and lower parts of the device in actual use or working state, specifically the drawing direction in the accompanying drawings. In the present application, "optionally", "optional", and "optional" refer to being optional, that is, any one of the two parallel schemes of "yes" or "no". If multiple "optional" items appear in a technical scheme, unless otherwise specified and there is no contradiction or mutual restriction, each "optional" item is independent of each other. In the present application, the technical features described in an open manner include closed technical schemes composed of the listed features, and also include open technical schemes of the listed features.

[0047] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0048] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0049] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0050] In the present application, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0051] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to: deuterium atom, cyano, isocyano, nitro or halogen, alkyl containing 1-20 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silane, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom, , cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from but not limited to: deuterium atom, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups can also be further substituted by substituents acceptable in the art.

[0052] In the present application, "ring atoms" refers to the number of atoms in the atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) obtained by atoms bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "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 thienyl group is 5.

[0053] In the present application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For a polycyclic ring, at least one is an aromatic ring system. For example, "substituted or unsubstituted aromatic group having 6 to 40 ring atoms" refers to an aromatic group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aromatic group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, and the aromatic group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, naphthyl, fluorenyl, dinaphthylenyl, acenaphthene and its derivatives. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), such as acenaphthene, fluorene, or 9,9'-diarylfluorene, triarylamine, diaryl ether system should also be included in the definition of aromatic group.

[0054] In the present application, "heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted, and suitable examples include but are not limited to: thienyl, furanyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidine yl, triazine, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothienyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0055] In the present application, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Phrases containing this term, such as "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence may be independently C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl 2-Hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, 2-tridecyl, 2-tetradecyl, 2-pentadecyl, 2-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-octylhexadecyl, 2-octadecyl, 2-octadecyl, 2-nonadecyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, 2-heneicosyl, 2-heneicosyl, 2-heconicosyl, 2-docosyl, 2-tricosyl, 2-tetracosyl, 2-pentacosyl, 2-hexacosyl, 2-heptacosyl, 2-octacosyl, 2-nonacosyl, 2-triacontyl, etc.

[0056] In the present application, "amino" refers to an amine derivative having the structural characteristics of the formula -N(X)2, wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, etc. Non-limiting types of amines include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclyl), -NH(heterocyclyl), -N(aryl), -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0057] In the present application, unless otherwise defined, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, haloformyl refers to -C(=O)Z (wherein Z represents halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0058] In the present application, the term "alkoxy" refers to a group having a structure of "-O-alkyl", i.e., an alkyl group as defined above is connected to other groups via an oxygen atom. Phrases containing the term, suitable examples include, but are not limited to, methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt) and tert-butoxy (-OC(CH3)3 or -OtBu).

[0059] In the present application, "*" connected to a single bond indicates a connection or fusion site.

[0060] In the present application, when a linking site is not specified in a group, it means that an optional linking site in the group can be used as a linking site.

[0061] In the present application, when the fusion site is not specified in the group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in the ortho position in the group are fusion sites.

[0062] In the present application, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other, for example The six Rs on the benzene ring may be the same as or different from each other.

[0063] In the present application, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example In which R is connected to any substitutable position of the benzene ring; express Can be used with The benzene ring can be fused at any position.

[0064] The cyclic alkyl group or cycloalkyl group described in the present application have the same meaning and can be interchanged.

[0065] The present application provides an organic compound having a structure represented by formula (1):

[0066]

[0067] in,

[0068] Ar 1 ,Ar 2 ,Ar 3 and Ar 4 independently selected from substituted or unsubstituted aromatic groups having 6 to 20 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms;

[0069] R 1 , R 2 , R 3 and R4 Independently selected from -CD3, substituted or unsubstituted straight-chain alkyl having 1 to 8 C atoms, substituted or unsubstituted branched-chain alkyl having 3 to 12 C atoms, or substituted or unsubstituted phenyl;

[0070] L 1 and L 2 Independently selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 20 ring atoms.

[0071] In some embodiments, the organic compound has a structure represented by formula (A), formula (B) or formula (C):

[0072] In some embodiments, Ar 1 ,Ar 2 ,Ar 3 and Ar 4 Independently selected from any one of the following structures:

[0073] in,

[0074] X is independently selected from O, S, N-Ph or CR 5 R 6 ;

[0075] R 5 and R 6 independently selected from H, D, a substituted or unsubstituted straight-chain alkyl group having 1 to 20 C atoms, a substituted or unsubstituted branched-chain alkyl group having 3 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 20 ring atoms;

[0076] Ar 1 ,Ar 2 ,Ar 3 and Ar 4 In the structures represented, hydrogen on the benzene ring is not substituted or is substituted by D, a straight-chain alkyl group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, or an aromatic group having 6 to 20 ring atoms.

[0077] In some embodiments, L 1 and L 2 are independently selected from a single bond, or a substituted or unsubstituted phenylene group.

[0078] In some embodiments, the organic compound is selected from any one of Formula (A-1) to Formula (C-56):

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] The organic compound provided in the present application is an organic conjugated molecule based on diarylamine, and the two aromatic amine groups are connected by two rigid fluorene groups to form a planar linear core skeleton, and therefore, it has strong hole transport ability and high stability. Specifically, as shown in the figure below, the connection method of the fluorene ring No. 3 site in the organic compound structure of the present application makes the organic compound have a flat molecular skeleton, and the flat molecular skeleton also brings uniform HOMO and LUMO distribution, which is conducive to improving the carrier transport ability and improving the hole transport ability. In addition, the linker L between the aromatic amine group and the fluorene group 1 and L 2 When it is an aromatic group, it can further extend the conjugation and lengthen the linear structure, further improving the stability and hole transport ability of the organic compound.

[0086]

[0087] In addition, the organic compound of the present application has a suitable highest occupied molecular orbital energy level, which can effectively reduce the energy barrier between the hole transport layer and the light-emitting layer and optimize the carrier transport process.

[0088] In the present application, the organic compound is an aromatic amine organic compound, which can be used as an organic functional material in an organic functional layer of an organic light-emitting device. The organic functional layer includes but is not limited to: a hole injection layer (HIL), a hole transport layer (HTL), an electron injection layer (EIL), an electron transport layer (ETL), a light-emitting auxiliary layer (Prime), a hole blocking layer (HBL) or a light-emitting layer (EML). The organic compound of the present application can be applied to any of the above-mentioned organic functional layers.

[0089] Preferably, the organic compound can be used as an organic functional material in the light-emitting auxiliary layer of an organic light-emitting device. The light-emitting auxiliary layer has a suitable transmission capacity, can transmit holes, and block the reverse migration of electrons, so that the organic light-emitting device reaches a balance of carrier transmission, so that electrons and holes recombine in the central area of ​​the light-emitting layer, thereby reducing the quenching of excitons, and effectively improving the luminous efficiency and life of the organic light-emitting device. Compared with the hole transport layer, the light-emitting auxiliary layer, in addition to having the hole transport capacity, also plays a role in blocking excitons, reducing interface hole accumulation, and further regulating the transmission capacity. The organic compound of the present application can effectively block the excitons and electrons of the light-emitting layer, confine the excitons in the light-emitting layer, avoid reverse carrier transmission, and thereby improve the efficiency of the organic light-emitting device and increase the life of the organic light-emitting device.

[0090] The present application also provides a mixture, which includes at least one organic compound as described above 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, luminescence auxiliary materials, hole blocking materials, organic light-emitting guest materials, organic host materials, organic dyes and inorganic quantum dot materials.

[0091] The present application also provides a composition, which comprises at least one organic compound as described above and at least one organic solvent, or the composition comprises the mixture as described above and at least one organic solvent.

[0092] Wherein, the organic solvent comprises at least one of aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, boric acid esters or phosphate compounds. Preferably, the organic solvent is selected from aromatic or heteroaromatic based solvents.

[0093] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic solvents. Aromatic or heteroaromatic solvents include but are not limited to: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, 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, dimethyl Naphthalene, 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-furoate, ethyl 2-furoate, etc.

[0094] In some embodiments, the organic solvent is selected from aromatic ketone-based solvents. Aromatic ketone-based solvents include but are not limited to: 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0095] In some embodiments, the organic solvent is selected from aromatic ether-based solvents. Aromatic ether-based solvents 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-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether.

[0096] In some embodiments, the organic solvent is selected from a solvent based on aliphatic ketone or aliphatic ether. Aliphatic ketone-based solvents include but are not limited to: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; aliphatic ether-based solvents include but are not limited to: amyl 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.

[0097] In some embodiments, the organic solvent is selected from ester-based solvents. Ester-based solvents 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, isononyl isononanoate, etc. are preferred.

[0098] In some embodiments, the composition further comprises at least one cosolvent. The cosolvent includes but is not limited to: at least one of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, and indene.

[0099] In the present application, the above organic solvents may be used alone or in combination of two or more organic solvents.

[0100] In some embodiments, the organic solvent of the present application may be a solvent having a Hansen solubility parameter within the following range:

[0101] δd (dispersion force) is between 17.0 and 23.2 MPa 1 / 2 range, especially in the range of 18.5~21.0MPa 1 / 2 scope;

[0102] δp (polar force) 0.2~12.5MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 scope;

[0103] δh (hydrogen bond force) is between 0.9 and 14.2 MPa 1 / 2 range, especially in the range of 2.0~6.0MPa1 / 2 range.

[0104] In the composition of the present application, the boiling point parameter of the organic solvent should be considered when selecting. The boiling point of the organic solvent of the present application is ≥150°C, preferably ≥180°C, more preferably ≥200°C, more preferably ≥250°C, and most preferably ≥275°C or ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of inkjet print heads. In the present application, the organic solvent can be evaporated from the solvent system to form a film containing organic functional materials.

[0105] In some embodiments, the composition can be a solution.

[0106] In some embodiments, the composition may be a suspension.

[0107] In some embodiments, the content of the organic compound or the mixture in the composition is 0.01wt% to 20wt%. Preferably, the content of the organic compound or the mixture in the composition is 0.1wt% to 15wt%. More preferably, the content of the organic compound or the mixture in the composition is 0.2wt% to 10wt%.

[0108] In some embodiments, the composition can be used as a coating or printing ink for preparing an organic light-emitting device, for example, the organic light-emitting device can be prepared by printing or coating.

[0109] 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, twist roller printing, lithography, flexographic printing, rotary printing, spraying, brushing or pad printing, slot extrusion coating, etc. Preferred are gravure printing, nozzle printing and inkjet printing.

[0110] In some embodiments, the composition may further include one or more other components, such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., to adjust the viscosity, film-forming properties, adhesion properties, etc. of the composition.

[0111] The organic compound, the mixture and the composition provided in the present application can be used in an organic light-emitting device.

[0112] The organic light-emitting device may be, but is not limited to, an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting cell (OLEEC), an organic field effect transistor (OFET), an organic light-emitting field-effect transistor (OLEFET), an organic laser, an organic spin electronic device, an organic sensor, and an organic plasmon emitting diode (OLED), etc., but is not limited thereto. OLED, OLEEC, and OLEFET are preferred.

[0113] The present application also provides an organic light emitting device 100, see Figure 1 , the organic light emitting device 100 comprises:

[0114] A first electrode 120;

[0115] A second electrode 140, disposed opposite to the first electrode 120;

[0116] An organic functional layer 130 is located between the first electrode 120 and the second electrode 140;

[0117] 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.

[0118] For details, please refer to Figure 1 , is a schematic diagram of the structure of an organic light-emitting device provided in the present application. The organic light-emitting device 100 includes a substrate 110, a first electrode 120 located on the substrate, an organic functional layer 130 located on a side of the first electrode 120 away from the substrate 110, and a second electrode 140 located on a side of the organic functional layer 130 away from the first electrode 120. The organic light-emitting device 100 may be an OLED device, but is not limited thereto.

[0119] Wherein, the substrate 110 may be a transparent substrate or an opaque substrate. When the substrate 110 is a transparent substrate, a transparent organic light-emitting device may be manufactured, for example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate 110 may be a rigid substrate or a flexible substrate. The material of the substrate 110 may include but is not limited to plastic, metal, semiconductor wafer or glass. Preferably, the substrate 110 includes at least one smooth surface to form the first electrode 120 on the surface; more preferably, the surface has no surface defects. Preferably, the substrate 110 is a flexible substrate, and its material is a polymer film or plastic, including but not limited to polyethylene terephthalate (PET material) and polyethylene glycol (2,6-naphthalene) (PEN material), and its glass transition temperature T g The glass transition temperature is preferably 150°C or higher. g More than 200°C, the preferred glass transition temperature T g More preferably, the glass transition temperature T g Over 300℃.

[0120] The first electrode 120 may be an anode, which is an electrode for injecting holes, and the anode may inject holes into the organic functional layer, such as injecting holes into the hole injection layer, the hole transport layer or the light emitting layer. The anode may include at least one of a conductive metal, a conductive metal oxide or a conductive polymer. The absolute value of the difference between the work function of the anode and the HOMO (Highest Occupied Molecular Orbital) energy level or valence band energy level of the light emitting material in the light emitting layer or the p-type semiconductor material in the hole injection layer, the hole transport layer or the electron blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and 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), etc., or other suitable and known anode materials, which can be easily selected and used by ordinary technicians in the field. The material of the anode 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 (e-beam), etc. In some embodiments, the anode can be a patterned structure, such as: patterned ITO conductive substrates are commercially available and can be used to prepare the organic light-emitting device of the present application.

[0121] The second electrode 140 may be a cathode, which is an electrode for injecting electrons, and the cathode may inject electrons into the organic functional layer, such as injecting electrons into the electron injection layer, the electron transport layer or the light-emitting layer. The cathode may include at least one of a conductive metal or a conductive metal oxide. The absolute value of the difference between the work function of the cathode and the LUMO (Lowest Unoccupied Molecular Orbital) energy level or conduction band energy level of the luminescent material in the light-emitting layer or the n-type semiconductor material as the electron injection layer, the electron transport layer or the hole blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. All materials that can be used as cathodes of organic light-emitting devices may be used as cathode materials of the device of the present application, and the materials of the cathode include but are 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, etc. The cathode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.

[0122] The organic functional layer 130 includes one or more film layers, and the organic functional layer 130 may include at least one of a hole injection layer (HIL) 131, a hole transport layer (HTL) 132, a light-emitting auxiliary layer (Prime) 133, a light-emitting layer 134, an electron transport layer (ETL) 135, and an electron injection layer (EIL) 136. The organic functional layer 130 includes at least the light-emitting layer 134.

[0123] In some embodiments, the organic functional layer 130 includes at least a light-emitting layer 134 and a light-emitting auxiliary layer 133, and the material of the light-emitting auxiliary layer includes at least one organic compound as described above. The organic compound provided in the present application has good performance in transporting holes and adjusting charge balance. When used as the material of the light-emitting auxiliary layer, it can better enable the organic light-emitting device to achieve a balance in carrier transport, thereby effectively improving the luminous efficiency and life of the organic light-emitting device.

[0124] In some embodiments, the light emitting wavelength of the organic light emitting device 100 is in the range of 300 nm to 1000 nm, preferably 350 nm to 900 nm, and more preferably 400 nm to 800 nm.

[0125] The organic light-emitting device 100 of the present application can be applied to various electronic devices, including but not limited to: display devices, lighting devices, light sources, sensors, etc.

[0126] The organic compound and the organic light-emitting device of the present application are further described below in conjunction with specific embodiments.

[0127] 1. Synthesis of organic compounds

[0128] Example 1

[0129] The synthetic route of organic compound A-1 is as follows:

[0130]

[0131] Synthesis of intermediate I-2:

[0132] Weigh I-1 (0.5 mol) and diboronic acid pinacol ester (0.6 mol) into a clean three-necked flask, add Pd(dppf)Cl2 (10 mmol) and potassium acetate (2.0 mol) dissolved in 1,4-dioxane, replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 6 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain intermediate I-1 with a yield of 86.7%. The electrospray ionization mass spectrometry (ESI-MS) result of intermediate I-2 is: m / z [H + ]=355.

[0133] Synthesis of intermediate I-3:

[0134] Weigh I-1 (0.4 mol) and I-2 (0.4 mol) into a clean three-necked flask, add Pd(PPh3)4 (4.0 mmol), potassium carbonate (0.8 mol), toluene (800 mL), ethanol (200 mL), deionized water (200 mL), replace nitrogen three times, heat to 80 ° C and reflux for 12 h; cool naturally and wash the separated liquid with water, dry the organic phase and spin dry it, and obtain the intermediate I-3 by column chromatography with a yield of 81.1%, m / z [H + ]=455.

[0135] Synthesis of compound A-1:

[0136] Weigh I-3 (0.1 mol) and I-4 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.8 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; cool naturally and wash with water, dry the organic phase and spin dry, and obtain compound A-1 by column chromatography with a yield of 72.2%, m / z [H + ]=721.

[0137] Example 2

[0138] The synthetic route of organic compound A-5 is as follows:

[0139]

[0140] The synthesis of intermediate I-3 is referred to Synthesis Example 1 and will not be described in detail.

[0141] Synthesis of intermediate I-5:

[0142] Weigh I-3 (0.22 mol) and I-4 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 8 h; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain intermediate I-5, the yield is 78.0%, m / z [H + ]=588.

[0143] Synthesis of compound A-5:

[0144] Weigh I-5 (0.1 mol) and I-6 (0.1 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; wash with water after natural cooling, dry the organic phase and spin dry, and obtain compound A-5 by column chromatography with a yield of 79.1%, m / z [H + ]=873.

[0145] Example 3

[0146] The synthetic route of organic compound A-16 is as follows:

[0147]

[0148] The synthesis of intermediate I-5 refers to Synthesis Example 2 and will not be described in detail.

[0149] Synthesis of compound A-16:

[0150] Weigh I-5 (0.1 mol) and I-7 (0.1 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain compound A-16, the yield is 70.1%, m / z [H + ]=847.

[0151] Example 4

[0152] The synthetic route of organic compound A-21 is as follows:

[0153]

[0154] The synthesis of intermediate I-5 refers to Synthesis Example 2 and will not be described in detail.

[0155] Synthesis of compound A-21:

[0156] Weigh I-5 (0.1 mol) and I-8 (0.1 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain compound A-21, the yield is 53.3%, m / z [H + ]=913.

[0157] Example 5

[0158] The synthetic route of organic compound A-24 is as follows:

[0159]

[0160] The synthesis of intermediate I-3 is referred to Synthesis Example 1 and will not be described in detail.

[0161] Synthesis of compound A-24:

[0162] Weigh I-3 (0.1 mol) and I-9 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.8 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain compound A-24, the yield is 73.9%, m / z [H + ]=953.

[0163] Example 6

[0164] The synthetic route of organic compound A-38 is as follows:

[0165]

[0166] The synthesis of intermediate I-5 refers to Synthesis Example 2 and will not be described in detail.

[0167] Synthesis of compound A-38:

[0168] Weigh I-5 (0.1 mol) and I-10 (0.1 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain compound A-38, the yield is 72.0%, m / z [H + ]=927.

[0169] Example 7

[0170] The synthetic route of organic compound A-46 is as follows:

[0171]

[0172] The synthesis of intermediate I-5 refers to Synthesis Example 2 and will not be described in detail.

[0173] Synthesis of compound A-46:

[0174] Weigh I-5 (0.1 mol) and I-11 (0.1 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain compound A-46, the yield is 77.9%, m / z [H + ]=886.

[0175] Example 8

[0176] The synthetic route of organic compound A-49 is as follows:

[0177]

[0178] The synthesis of intermediate I-3 is referred to Synthesis Example 1 and will not be described in detail.

[0179] Synthesis of compound A-49:

[0180] Weigh I-3 (0.1 mol) and I-12 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.8 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain compound A-49, the yield is 73.2%, m / z [H+ ]=741.

[0181] Example 9

[0182] The synthetic route of organic compound A-55 is as follows:

[0183]

[0184] The synthesis of intermediate I-3 is referred to Synthesis Example 1 and will not be described in detail.

[0185] Synthesis of compound A-55:

[0186] Weigh I-3 (0.1 mol) and I-13 (0.2 mol) into a clean three-necked flask, add Pd132 (2.0 mmol), X-Phos (4.0 mmol), potassium carbonate (0.4 mol) and dissolve in anhydrous toluene, ethanol and deionized water, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain compound A-55, the yield is 40.9%, m / z [H + ]=873.

[0187] Example 10

[0188] The synthetic route of organic compound B-7 is as follows:

[0189]

[0190] Synthesis of intermediate I-15:

[0191] Weigh I-14 (0.5 mol) and diboronic acid pinacol ester (0.6 mol) into a clean three-necked flask, add Pd(dppf)Cl2 (10 mmol) and potassium acetate (2.0 mol) dissolved in 1,4-dioxane, replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 6 hours; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain intermediate I-15, the yield is 82.7%, m / z [H + ]=355.

[0192] Synthesis of intermediate I-16:

[0193] Weigh I-14 (0.4 mol) and I-15 (0.4 mol) into a clean three-necked flask, add Pd(PPh3)4 (4.0 mmol), potassium carbonate (0.8 mol), toluene (800 mL), ethanol (200 mL), deionized water (200 mL), replace nitrogen three times, heat to 80 ° C and reflux for 12 h; cool naturally and wash the separated liquid with water, dry the organic phase and spin dry it, and obtain the intermediate I-16 by column chromatography with a yield of 89.8%, m / z [H + ]=455.

[0194] Synthesis of compound B-7:

[0195] Weigh I-16 (0.1 mol) and I-17 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.8 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain compound B-7, the yield is 71.1%, m / z [H + ]=873.

[0196] Embodiment 11

[0197] The synthetic route of organic compound B-10 is as follows:

[0198]

[0199] The synthesis of intermediate I-16 can be referred to Synthesis Example 11 and will not be described in detail.

[0200] Synthesis of intermediate I-18:

[0201] Weigh I-16 (0.22 mol) and I-4 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 8 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain intermediate I-18, the yield is 70.8%, m / z [H + ]=588.

[0202] Synthesis of compound B-10:

[0203] Weigh I-18 (0.1 mol) and I-19 (0.1 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain compound B-10, the yield is 72.5%, m / z [H + ]=873.

[0204] Example 12

[0205] The synthetic route of organic compound B-20 is as follows:

[0206]

[0207] The synthesis of intermediate I-16 can be referred to Synthesis Example 11 and will not be described in detail.

[0208] Synthesis of intermediate I-20:

[0209] Weigh I-16 (0.22 mol) and I-9 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 8 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain intermediate I-20, the yield is 75.1%, m / z [H + ]=704.

[0210] Synthesis of compound B-20:

[0211] Weigh I-20 (0.1 mol) and I-21 (0.1 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain compound B-20, the yield is 66.7%, m / z [H + ]=913.

[0212] Example 13

[0213] The synthetic route of organic compound B-27 is as follows:

[0214]

[0215] The synthesis of intermediate I-18 can be referred to Synthesis Example 11 and will not be described in detail.

[0216] Synthesis of compound B-27:

[0217] Weigh I-18 (0.1 mol) and I-22 (0.1 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain compound B-27, the yield is 73.9%, m / z [H + ]=887.

[0218] Embodiment 14

[0219] The synthetic route of organic compound B-39 is as follows:

[0220]

[0221] The synthesis of intermediate I-18 can be referred to Synthesis Example 11 and will not be described in detail.

[0222] Synthesis of compound B-39:

[0223] Weigh I-18 (0.1 mol) and I-23 (0.1 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain compound B-39, the yield is 68.0%, m / z [H + ]=927.

[0224] Embodiment 15

[0225] The synthetic route of organic compound B-48 is as follows:

[0226]

[0227] The synthesis of intermediate I-18 can be referred to Synthesis Example 11 and will not be described in detail.

[0228] Synthesis of compound B-48:

[0229] Weigh I-18 (0.1 mol) and I-24 (0.1 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain compound B-48, the yield is 71.6%, m / z [H + ]=903.

[0230] Example 16

[0231] The synthetic route of organic compound B-54 is as follows:

[0232]

[0233] The synthesis of intermediate I-15 can be referred to Synthesis Example 10 and will not be described in detail.

[0234] Synthesis of intermediate I-26:

[0235] Weigh I-25 (0.4 mol) and I-15 (0.4 mol) into a clean three-necked flask, add Pd(PPh3)4 (4.0 mmol), potassium carbonate (0.8 mol), toluene (800 mL), ethanol (200 mL), deionized water (200 mL), replace nitrogen three times, heat to 80 ° C and reflux for 12 h; wash the separated liquid with water after natural cooling, dry the organic phase and spin dry it, and obtain the intermediate I-16 by column chromatography with a yield of 80.2%, m / z [H + ]=580.

[0236] Synthesis of compound B-54:

[0237] Weigh I-26 (0.1 mol) and I-4 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.8 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain compound B-54, the yield is 75.9%, m / z [H + ]=845.

[0238] Embodiment 17

[0239] The synthetic route of organic compound C-1 is as follows:

[0240]

[0241] Synthesis of intermediate I-28:

[0242] Weigh I-27 (0.5 mol) and diboronic acid pinacol ester (0.6 mol) into a clean three-necked flask, add Pd(dppf)Cl2 (10 mmol) and potassium acetate (2.0 mol) dissolved in 1,4-dioxane, replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 6 hours; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain intermediate I-28, the yield is 77.9%, m / z [H + ]=355.

[0243] Synthesis of intermediate I-29:

[0244] Weigh I-27 (0.4 mol) and I-28 (0.4 mol) into a clean three-necked flask, add Pd(PPh3)4 (4.0 mmol), potassium carbonate (0.8 mol), toluene (800 mL), ethanol (200 mL), deionized water (200 mL), replace nitrogen three times, heat to 80 ° C and reflux for 12 h; wash with water after natural cooling, dry the organic phase and spin dry, and obtain intermediate I-29 by column chromatography with a yield of 88.1%, m / z [H + ]=455.

[0245] Synthesis of compound C-1:

[0246] Weigh I-29 (0.1 mol) and I-4 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.8 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; cool naturally and wash with water, dry the organic phase and spin dry, and obtain compound C-1 by column chromatography with a yield of 77.9%, m / z [H + ]=721.

[0247] Embodiment 18

[0248] The synthetic route of organic compound C-7 is as follows:

[0249]

[0250] The synthesis of intermediate I-29 can be referred to Synthesis Example 17 and will not be described in detail.

[0251] Synthesis of compound C-7:

[0252] Weigh I-29 (0.1 mol) and I-17 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.8 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain compound C-7, the yield is 66.0%, m / z [H + ]=873.

[0253] Embodiment 19

[0254] The synthetic route of organic compound C-14 is as follows:

[0255]

[0256] The synthesis of intermediate I-29 can be referred to Synthesis Example 17 and will not be described in detail.

[0257] Synthesis of compound C-14:

[0258] Weigh I-29 (0.1 mol) and I-30 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.8 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain compound C-14, the yield is 63.8%, m / z [H + ]=821.

[0259] Embodiment 20

[0260] The synthetic route of organic compound C-21 is as follows:

[0261]

[0262] The synthesis of intermediate I-29 can be referred to Synthesis Example 17 and will not be described in detail.

[0263] Synthesis of intermediate I-31:

[0264] Weigh I-29 (0.22 mol) and I-4 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 8 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain intermediate I-31, the yield is 71.9%, m / z [H + ]=588.

[0265] Synthesis of compound C-21:

[0266] Weigh I-31 (0.1 mol) and I-8 (0.1 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 18 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain compound C-21, the yield is 41.8%, m / z [H + ]=913.

[0267] Embodiment 21

[0268] The synthetic route of organic compound C-25 is as follows:

[0269]

[0270] The synthesis of intermediate I-31 refers to Synthesis Example 20 and will not be described in detail.

[0271] Synthesis of compound C-25:

[0272] Weigh I-31 (0.1 mol) and I-32 (0.1 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.4 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain compound C-25, the yield is 58.6%, m / z [H + ]=811.

[0273] Embodiment 22

[0274] The synthetic route of organic compound C-33 is as follows:

[0275]

[0276] The synthesis of intermediate I-29 can be referred to Synthesis Example 17 and will not be described in detail.

[0277] Synthesis of compound C-33:

[0278] Weigh I-29 (0.1 mol) and I-32 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.8 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain compound C-33, the yield is 59.0%, m / z [H + ]=901.

[0279] Embodiment 23

[0280] The synthetic route of organic compound C-50 is as follows:

[0281]

[0282] Synthesis of intermediate I-34:

[0283] Weigh I-33 (0.5 mol) and diboronic acid pinacol ester (0.6 mol) into a clean three-necked flask, add Pd(dppf)Cl2 (10 mmol) and potassium acetate (2.0 mol) dissolved in 1,4-dioxane, replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 6 h; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain intermediate I-34, the yield is 79.1%, m / z [H + ]=361.

[0284] Synthesis of intermediate I-35:

[0285] Weigh I-34 (0.4 mol) and I-33 (0.4 mol) into a clean three-necked flask, add Pd(PPh3)4 (4.0 mmol), potassium carbonate (0.8 mol), toluene (800 mL), ethanol (200 mL), deionized water (200 mL), replace nitrogen three times, heat to 80 ° C, reflux reaction for 12 h; cool naturally and wash with water, dry the organic phase and spin dry, column chromatography to obtain intermediate I-35, the yield is 82.2%, m / z [H + ]=467.

[0286] Synthesis of compound C-50:

[0287] Weigh I-35 (0.1 mol) and I-4 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.8 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; wash with water after natural cooling, dry the organic phase and spin dry, and obtain compound C-50 by column chromatography with a yield of 75.1%, m / z [H + ]=733.

[0288] Embodiment 24

[0289] The synthetic route of organic compound C-51 is as follows:

[0290]

[0291] Synthesis of intermediate I-37:

[0292] Weigh I-36 (0.5 mol) and diboronic acid pinacol ester (0.6 mol) into a clean three-necked flask, add Pd(dppf)Cl2 (10 mmol) and potassium acetate (2.0 mol) dissolved in 1,4-dioxane, replace nitrogen three times, heat to 100 ° C under nitrogen atmosphere and reflux for 6 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain intermediate I-37, the yield is 81.9%, m / z [H + ]=383.

[0293] Synthesis of intermediate I-38:

[0294] Weigh I-37 (0.4 mol) and I-36 (0.4 mol) into a clean three-necked flask, add Pd(PPh3)4 (4.0 mmol), potassium carbonate (0.8 mol), toluene (800 mL), ethanol (200 mL), deionized water (200 mL), replace nitrogen three times, heat to 80 ° C and reflux for 12 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain intermediate I-38, the yield is 86.3%, m / z [H + ]=511.

[0295] Synthesis of compound C-51:

[0296] Weigh I-38 (0.1 mol) and I-4 (0.2 mol) into a clean three-necked flask, add Pd2(dba)3 (2.0 mmol), X-Phos (4.0 mmol), sodium tert-butoxide (0.8 mol) and dissolve in anhydrous toluene, replace nitrogen three times, heat to 110 ° C and reflux for 12 h; wash with water after natural cooling, dry the organic phase and spin dry, column chromatography to obtain compound C-51, the yield is 67.3%, m / z [H + ]=777.

[0297] Comparative Example 1

[0298] Compound REF01:

[0299]

[0300] Comparative Example 2

[0301] Compound REF02:

[0302]

[0303] Comparative Example 3

[0304] Compound REF03:

[0305]

[0306] It should be noted that the raw materials used in the above examples, unless otherwise specified, are commercially available products.

[0307] 2. Energy level calculation of organic compounds

[0308] In the present application examples, the energy level of the organic compound plays a key role. The highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level and the first excited singlet (S1) energy level of the compounds obtained in Examples 1 to 24 of the present application and the comparative compounds REF01, REF02 and REF03 can be obtained by theoretical calculation, and the results are shown in Table 1. Specifically, the theoretical calculation part is mainly calculated by Gaussian 09W (Gaussian Inc.) software package, and the specific simulation method can be found in WO2011141110 or described in the following examples. It should be noted that the values ​​of HOMO, LUMO and S1 depend on the measurement method, calculation method or evaluation method used, and even when the measurement method is the same, the evaluation method is not necessarily the same. For example, when the HOMO value is measured by cyclic voltammetry, the HOMO value obtained based on the starting point or peak value of the CV curve is not the same. Therefore, a reasonable and meaningful comparison should be carried out with the same measurement method and the same evaluation method. In the description of the embodiments of the present application, the ground state (S0) configuration is calculated according to the density functional theory (DFT) under the B3LYP / 6-31G(d) or B3LYP / 6-31G(d,p) basis set, and the HOMO, LUMO, and S1 values ​​of the material are calculated according to the optimized S0 configuration using the time-dependent density functional theory (TD-DFT) under the B3PW91 / 6-31G(d) or B3PW91 / 6-31G(d,p) basis set, and the unit is Hartree.

[0309] Table 1

[0310]

[0311]

[0312] From the results in Table 1, it can be seen that the HOMO energy level of the organic compounds provided in Examples 1 to 24 of the present application ranges from -5.19 eV to -5.46 eV, and it is easier to lose electrons to reach an excited state, which can ensure effective hole transport and charge collection. At the same time, the S1 energy level of the organic compounds provided in Examples 1 to 24 of the present application is higher than that of compound REF01 and compound REF02, which is more conducive to blocking excited excitons in the light-emitting layer.

[0313] For further information, see Figure 2-Figure 5 ,in Figure 2 and Figure 3 is the molecular structure diagram of the organic compound A-1 in Example 1 obtained based on GaussView 6.0 (Gaussian Inc.) software, Figure 4 and Figure 5HOMO distribution diagram and LUMO distribution diagram of the organic compound A-1 molecule in Example 1. Figure 2-Figure 3 It shows that the connection mode of the fluorene ring No. 3 site makes the organic compound A-1 have a flat molecular skeleton, and the dihedral angle between the two fluorene planes is about 141°. The flat molecular skeleton brings a uniform HOMO and LUMO distribution, which is beneficial to improve the carrier transport capacity.

[0314] See also Figure 6 , Figure 6 The molecular structure diagram of the organic compound REF03 in Comparative Example 3 obtained based on GaussView 6.0 (Gaussian Inc.) software, the fluorene ring connection mode of the compound REF03 makes it have an orthogonal skeleton, and the dihedral angle between the two fluorene planes is about 92°. The organic compound of the present application and the organic compound REF03 in Comparative Example 3 have different skeleton spatial conformations and dihedral angles. The difference in spatial structure and stacking mode will affect the thermal stability, hole transport ability and device performance of the organic compound and the organic light-emitting device.

[0315] 3. Preparation and characterization of organic light-emitting devices

[0316] In this embodiment, the organic light-emitting device includes a substrate 110, a first electrode 120, 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, an electron injection layer 136, and a second electrode 140, which are stacked in sequence, wherein the first electrode 120 is an anode and the second electrode 140 is a cathode.

[0317] In the following method for preparing an OLED device, ITO conductive glass is used as an anode substrate, PD is used as a hole injection material, HT is used as a hole transport material, Host is used as a main material of the light-emitting layer, Dopant is used as a doping material of the light-emitting layer, HB is used as a hole blocking material, ET and 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 of the above-mentioned Examples 1 to 24 and Comparative Examples 1 to 3 are used as light-emitting auxiliary materials to prepare corresponding OLED devices respectively. Among them, the chemical structures of PD, HT, Host, Dopant, ET and Liq are as follows:

[0318]

[0319] Taking the preparation method of preparing an OLLED device using compound A-1 as a light-emitting auxiliary material as an example, the prepared OLED device is recorded as "OLED-1 device". The preparation method of the OLED-1 device includes the following steps:

[0320] Step a: Cleaning of ITO conductive glass substrate (including substrate 110 and first electrode (anode) 120). Provide an ITO conductive glass substrate and perform ultrasonic cleaning on the substrate using one or more cleaning agents such as deionized water, acetone, isopropanol or chloroform to improve the work function of the anode.

[0321] Step b: forming a hole injection layer 131 on the anode. The hole injection materials PD and HT were evaporated on the anode at a evaporation rate of 3:97, and the hole injection layer 131 with a thickness of 30 nm was obtained.

[0322] Step c: forming a hole transport layer 132 on the hole injection layer 131. The hole transport material HT is evaporated on the hole injection layer 131 at an evaporation rate of , to obtain a hole transport layer 132 with a thickness of 60 nm.

[0323] Step d: forming a light-emitting auxiliary layer 133 on the hole transport layer 132. The compound A-1 provided in the above-mentioned embodiment 1 was evaporated on the hole transport layer 132 at an evaporation rate of , to obtain a light-emitting auxiliary layer 133 with a thickness of 10 nm.

[0324] Step e: forming a light-emitting layer 134 on the light-emitting auxiliary layer 133. Host and Dopant are evaporated on the light-emitting auxiliary layer 133 at a evaporation rate of 98:2, and the light-emitting layer 134 with a thickness of 25 nm is obtained.

[0325] Step f: forming an electron transport layer 135 on the light emitting layer 134. In a vacuum chamber, the electron transport material ET and Liq are placed in different evaporation crucibles and placed in a high vacuum environment (1×10 -6 ET and Liq were co-deposited at a weight ratio of 5:5 under 300 mbar to form an electron transport layer 135 with a thickness of 30 nm on the light emitting layer 134.

[0326] Step g: forming an electron injection layer 136 on the electron transport layer 135. The electron injection material Liq is evaporated on the electron transport layer 135 at an evaporation rate of to obtain an electron injection layer 136 with a thickness of 1 nm.

[0327] Step h: forming a second electrode (cathode) 140 on the electron injection layer 136. The cathode material Al is evaporated on the electron injection layer 136 at an evaporation rate of to obtain a cathode with a thickness of 100 nm.

[0328] Step i: placing the device obtained by layer-by-layer deposition in a nitrogen atmosphere glove box, and encapsulating it with a UV-curable resin to finally obtain an OLED device.

[0329] In this embodiment, the structure of the prepared OLED-1 device is: ITO / PD:HT(3:97, 30nm) / HT(60nm) / Compound A-1(10nm) / Host:Dopant(2%, 25nm) / ET:Liq(5:5, 30nm) / Liq(1nm) / Al(100nm).

[0330] Referring to the preparation method of device OLED-1, compounds A-5 to C-51 synthesized in Examples 2 to 24 were selected as the luminescent auxiliary materials of the OLED device, and OLED-2 to OLED-24 devices were prepared accordingly. It can be understood that in the preparation methods of the above OLED-1 to OLED-24 devices, except for the different luminescent auxiliary materials, other experimental conditions are the same.

[0331] Further, referring to the preparation method of device OLED-1, the compounds REF01 to REF03 of Comparative Examples 1 to 3 were used as luminescent auxiliary materials to prepare Comparative Example OLED-REF01, OLED-REF02 and OLED-REF03 devices. Compared with the preparation method of OLED-1 device, the preparation methods of OLED-REF01 to OLED-REF03 devices are the same except for the different luminescent auxiliary materials.

[0332] In this application, the current-voltage (JV) characteristics of OLED-1 to OLED-24, OLED-REF01, OLED-REF02 and OLED-REF03 devices were characterized, and important parameters such as luminous efficiency and lifetime were recorded, as shown in Table 2. The luminous efficiency is the current density of 10 mA / cm 2 The relative value obtained when the device is powered on, the lifespan (LT95) is the time it takes for the device brightness to drop from the initial 1knit to 95% under constant current.

[0333] Table 2

[0334]

[0335]

[0336] It can be seen from the data in Table 2 that when the organic compounds provided in Examples 1 to 24 of the present application are used as light-emitting auxiliary materials, the lifespans of the prepared OLED-1 to OLED-24 devices are all higher than those of the comparative examples OLED-REF01 to OLED-REF03, and the lifespans of the OLED-1 to OLED-24 devices of the present application are significantly higher than those of the comparative examples OLED-REF01 and OLED-REF02. The luminous efficiency of the OLED-1 to OLED-24 devices of the present application is higher than that of the comparative examples OLED-REF01 to OLED-REF03, or the difference is not much. The voltages of the OLED-1 to OLED-24 devices of the present application are all lower than those of the comparative examples OLED-REF01 to OLED-REF03. It is proved that the organic compounds of the present application can significantly improve the lifespan of the organic light-emitting device, or can simultaneously improve the lifespan and luminous efficiency of the organic light-emitting device. The reason is that the organic compounds provided in the present application have both a diarylamine and a rigid conjugated difluorene ring skeleton, and form a planar linear core skeleton, which has a strong hole transport capability and high stability, and is conducive to improving the efficiency and lifespan of the organic light-emitting device.

[0337] In addition, by comparing the OLED-1 device of the present application with the OLED-REF03 device of the comparative example, it can be seen that the luminous efficiency and life of the OLED-1 device are significantly higher than those of the OLED-REF03 device. The compound A-1 used in the OLED-1 device and the compound REF03 used in the OLED-REF03 device have similar structures, and only the molecular spatial structures are different. The connection method of the fluorene ring No. 3 site in the compound A-1 gives it a flat molecular skeleton, and the dihedral angle between the two fluorene planes is about 141°. The connection method of the fluorene ring of the compound REF03 gives it an orthogonal skeleton, and the dihedral angle between the two fluorene planes is about 92°. From the data of the OLED-1 device of the present application and the OLED-REF03 device of the comparative example, it can be seen that the different spatial conformations and dihedral angles of the compounds have a significant impact on the performance of the organic light-emitting device. The connection method of the fluorene ring No. 3 site in the organic compound of the present application forms a flat molecular skeleton, which makes the compound have better thermal stability and is more conducive to improving the carrier transport capability, thereby more effectively improving the luminous efficiency and life of the organic light-emitting device.

[0338] In summary, the organic compound of the present application is an organic conjugated molecule based on diarylamine, and the two aromatic amine groups are connected by two rigid fluorene groups to form a planar linear core skeleton with strong hole transport ability and high stability. Among them, the connection method of the two fluorene rings at site 3 makes the molecule have a flat molecular skeleton, and the near-planar structure further improves the chemical stability and thermal stability of the organic compound, and further improves the hole transport ability, and has a sufficiently high excited state energy level. When the organic compound of the present application is used as a material for the light-emitting auxiliary layer, it can effectively block the excitons and electrons of the light-emitting layer, confine the excitons in the light-emitting layer, avoid reverse carrier transmission, and thus improve the efficiency of the organic light-emitting device, achieve high luminous efficiency of the organic light-emitting device, and increase the life of the organic light-emitting device.

[0339] The technical features of the above-described embodiments may be arbitrarily combined. To make the description concise, not all possible combinations of the technical features in the above-described embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0340] The above-described embodiments only express several implementation methods of the present application, and the descriptions thereof are relatively specific and detailed, but they cannot be construed as limiting the scope of the patent application. It should be pointed out that, for a person of ordinary skill in the art, several variations and improvements can be made without departing from the concept of the present application, and these all belong to the protection scope of the present application. Therefore, the protection scope of the patent application shall be subject to the attached claims.

Claims

1. An organic compound, characterized in that The organic compound has a structure represented by formula (1): in, Ar 1 ,Ar 2 ,Ar 3 and Ar 4 independently selected from substituted or unsubstituted aromatic groups having 6 to 20 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms; R 1 , R 2 , R 3 and R 4 Independently selected from -CD3, substituted or unsubstituted straight-chain alkyl having 1 to 8 C atoms, substituted or unsubstituted branched-chain alkyl having 3 to 12 C atoms, or substituted or unsubstituted phenyl; L 1 and L 2 Independently selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 20 ring atoms.

2. The organic compound according to claim 1, characterized in that The organic compound has a structure represented by formula (A), formula (B) or formula (C):

3. The organic compound according to claim 1 or 2, characterized in that Ar 1 ,Ar 2 ,Ar 3 and Ar 4 Independently selected from any one of the following structures: in, X is independently selected from O, S, N-Ph or CR 5 R 6 ; R 5 and R 6 independently selected from H, D, a substituted or unsubstituted straight-chain alkyl group having 1 to 20 C atoms, a substituted or unsubstituted branched-chain alkyl group having 3 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 20 ring atoms; Ar 1 ,Ar 2 ,Ar 3 and Ar 4 In the structures represented, hydrogen on the benzene ring is not substituted or is substituted by D, a straight-chain alkyl group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, or an aromatic group having 6 to 20 ring atoms.

4. The organic compound according to claim 1 or 2, characterized in that L 1 and L 2 are independently selected from a single bond, or a substituted or unsubstituted phenylene group.

5. The organic compound according to claim 1 or 2, characterized in that The organic compound is selected from any one of formula (A-1) to formula (C-56):

6. A mixture, characterized in that The mixture comprises 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 hole injection materials, hole transport materials, electron injection materials, electron transport materials, luminescence auxiliary materials, hole blocking materials, organic light-emitting guest materials, organic host materials and inorganic quantum dot materials.

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

8. The composition according to claim 7, characterized in that The mass percentage of the organic compound in the composition is 0.01 wt % to 20 wt %, or the mass percentage of the mixture in the composition is 0.01 wt % to 20 wt %.

9. An organic light-emitting device, characterized in that: include: a first electrode; a second electrode, arranged opposite to the first electrode; as well as an organic functional layer, located between the first electrode and the second electrode; The material of the organic functional layer includes at least one organic compound as claimed in any one of claims 1 to 5, or the material of the organic functional layer includes the mixture as claimed in claim 6.

10. The organic light emitting device according to claim 9, characterized in that: The organic functional layer at least comprises: a light-emitting layer, located between the first electrode and the second electrode; and a light-emitting auxiliary layer, located on a side of the light-emitting layer close to the first electrode, or located on a side of the light-emitting layer close to the second electrode; Wherein, the material of the light-emitting auxiliary layer includes at least one organic compound as described in any one of claims 1 to 5.

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