Organic compounds, mixtures, compositions and organic electronic devices

Abstract

The present application discloses an organic compound, a mixture, a composition and an organic electronic device. An organic compound has a structure as shown in the general formula (1). The organic compound of the present application can effectively improve the luminous efficiency and life of the device.

Description

Technical Field

[0001] The present application relates to the technical field of luminescent materials, and in particular to an organic compound, a mixture, a composition and an organic electronic device. Background Art

[0002] Organic semiconductor materials have diversity in synthesis, relatively low manufacturing costs and excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have broad development potential in optoelectronic devices (such as flat-panel displays and lighting) due to their wide viewing angle, fast response time, low operating voltage and thin panel thickness.

[0003] Organic electroluminescence refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic electroluminescent elements that use organic electroluminescence usually have a structure with a positive electrode and a negative electrode and an organic layer between them. In order to improve the efficiency and life of the organic electroluminescent element, the organic layer has a multilayer structure, and each layer contains different organic substances. Specifically, it can include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In this organic electroluminescent element, when a voltage is applied between the two electrodes, holes are injected from the positive electrode into the organic layer, and electrons are injected from the negative electrode into the organic layer. When the injected holes meet the electrons, excitons are formed, and light is emitted when the excitons transition back to the ground state. This organic electroluminescent element has the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0004] In order to improve the luminous efficiency of organic electroluminescent elements, various fluorescent and phosphorescent luminescent material systems have been developed. Whether it is fluorescent materials or phosphorescent materials, the development of excellent blue light materials is a huge challenge. In general, the organic light-emitting diodes using blue fluorescent materials currently used have higher reliability. However, the emission spectrum of most blue fluorescent materials is too wide and the color purity is poor, which is not conducive to high-end display. In addition, the synthesis of such fluorescent materials is also complex, which is not conducive to large-scale mass production. At the same time, the stability of OLEDs using such blue fluorescent materials needs to be further improved.

[0005] The current blue light organic electroluminescent element adopts a host-guest doping structure for the light-emitting layer, and the blue light host material is mostly anthracene-based condensed ring derivatives, but the light-emitting layer material has poor stability, resulting in a short device life. At the same time, these materials are difficult to achieve deep blue light emission and are difficult to meet the needs of full-color display.

[0006] The development of blue fluorescent materials with narrow-band emission spectra and good stability is beneficial to obtaining blue light devices with longer life and higher efficiency on the one hand, and to improving the color gamut and thus improving the display effect on the other hand. Summary of the invention

[0007] The embodiment of the present application provides an organic compound, which can improve the technical problems of low luminous efficiency and short life of the above-mentioned existing blue light fluorescent organic electronic devices.

[0008] In order to achieve the above-mentioned purpose, the present invention provides a structure as shown in the general formula (1):

[0009]

[0010] In the formula,

[0011] Ar1 is selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms, or a combination of these groups;

[0012] Ar2 is independently selected from a benzene ring or a naphthalene ring;

[0013] L1 and L2 are independently selected from a single bond, or a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms;

[0014] R1 and R2 are each independently selected from the group consisting of: -D ​​(deuterium), straight-chain alkyl with 1 to 20 C atoms, straight-chain alkoxy with 1 to 20 C atoms, straight-chain thioalkoxy with 1 to 20 C atoms, branched-chain alkyl with 3 to 20 C atoms, branched-chain alkoxy with 3 to 20 C atoms, branched-chain thioalkoxy with 3 to 20 C atoms, cyclic alkyl with 3 to 20 C atoms, cyclic alkoxy with 3 to 20 C atoms, cyclic thioalkoxy with 3 to 20 C atoms, silyl, keto with 1 to 20 C atoms, 2 to 20 C atoms, 3 to 4 carbon atoms, 5 to 6 carbon atoms, 6 to 8 carbon atoms, 7 to 8 carbon atoms, 8 to 9 carbon atoms, 9 to 10 carbon atoms, 10 to 11 carbon atoms, 12 to 13 carbon atoms, 13 to 14 carbon atoms, 14 to 15 carbon atoms, 15 to 16 carbon atoms, 16 to 17 carbon atoms, 17 to 18 carbon atoms, 18 to 19 carbon atoms, 19 to 20 ... C atoms, alkoxycarbonyl, aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, substituted or unsubstituted amine, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted aromatic radicals having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic radicals having 5 to 60 ring atoms, substituted or unsubstituted aryloxy radicals having 5 to 60 ring atoms, substituted or unsubstituted heteroaryloxy radicals having 5 to 60 ring atoms, or combinations of these;

[0015] m1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0016] m2 is selected from 0, 1, 2 or 3.

[0017] Correspondingly, the present application also provides a mixture, comprising the above-mentioned organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials, guest materials or organic dyes.

[0018] Correspondingly, the present application also provides a composition, comprising the above organic compound or the above mixture, and at least one organic solvent.

[0019] Correspondingly, the present application also provides an organic electronic device, comprising at least one functional layer, wherein the functional layer comprises the above organic compound or the above mixture, or the functional layer is prepared from the above composition.

[0020] The beneficial effects of this application are:

[0021] The organic compound of the present application is an anthracene derivative containing an oxygen atom heterocycle, which can be used as a host material in the light-emitting layer of an organic electronic device. The organic compound of the present application has a fluorescence emission at a blue light wavelength, so the organic compound can be used in a blue light organic light-emitting electronic device, and has a higher device luminous efficiency and a longer device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings required for use in the description of the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without creative work.

[0023] Figure 1 It is a schematic diagram of the structure of the OLED device provided in device embodiment 1 of the present application.

[0024] The numbers in the figure are: 10, substrate; 20, anode; 30, hole injection layer; 40, hole transport layer; 50, light-emitting layer; 60, electron transport layer; 70, cathode. DETAILED DESCRIPTION

[0025] The following will be combined with the drawings in the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present application. In the description of the present application, the term "including" means "including but not limited to", and the term "multiple" means "two or more". Various embodiments of the present application may exist in the form of a range; it should be understood that the description in the form of a range is only for convenience and simplicity, and should not be understood as a hard limit to the scope of the present application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single values ​​within the range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the range, such as 1, 2, 3, 4, 5 and 6, which are applicable regardless of the range. In addition, whenever a numerical range is indicated in this article, it is meant to include any quoted numbers (fractions or integers) within the indicated range.

[0026] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those generally understood by those skilled in the art to which the present application belongs. The terms used herein in the specification of the present application are only for the purpose of describing specific embodiments and are not intended to limit the present application. The term "and / or" used herein includes any and all combinations of one or more related listed items.

[0027] In the present application, composition, printing ink and ink have the same meaning and can be interchangeable.

[0028] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0029] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0030] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0031] 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 atoms, cyano groups, isocyano groups, nitro groups, halogen groups, alkyl groups containing 1-20 C atoms, heterocyclic groups containing 3-20 ring atoms, aromatic groups containing 6-20 ring atoms, heteroaromatic groups containing 5-20 ring atoms, -NR'R", silane groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, haloformyl groups, formyl groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups and trifluoromethyl groups, 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 atoms, , cyano, isocyano, nitro or halogen, alkyl containing 1-10 C 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 C 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 and trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art.

[0032] In the present application, the "number of 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) formed 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 "number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0033] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which may 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 may be 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 derivatives thereof. 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), specifically acenaphthene, fluorene, 9,9-diarylfluorene, triarylamine or diaryl ether systems should also be included in the definition of aromatic groups.

[0034] "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, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazolyl, pyrimid ... oxazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothiophenyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0035] In the present application, "alkyl" can represent straight chain, branched and / or cyclic alkyl. The carbon number of alkyl can be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Non-limiting examples of alkyl 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, adamantyl, etc.

[0036] In the present application, "halogen" or "halo" refers to F, Cl, Br or I.

[0037] In the present application, the term "alkoxy" refers to a group having an -O-alkyl group, i.e., an alkyl group as defined above is connected to a parent core structure 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).

[0038] In the present application, "*" indicates a linking site.

[0039] 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 1 May be the same as or different from each other.

[0040] 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.

[0041] The cyclic alkyl or cycloalkyl described in the present application have the same meaning and can be interchanged.

[0042] The embodiments of the present application provide an organic compound, a mixture, a composition and an organic electronic device. The following are detailed descriptions of each. It should be noted that the description order of the following embodiments is not intended to limit the preferred order of the embodiments.

[0043] The present invention provides an organic compound having a structure as shown in the general formula (1):

[0044]

[0045] in,

[0046] Ar1 is selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms, or a combination of these groups;

[0047] Ar2 is independently selected from a benzene ring or a naphthalene ring.

[0048] L1 and L2 are independently selected from a single bond, or a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms;

[0049] R1 and R2 are each independently selected from the group consisting of: -D ​​(deuterium), straight-chain alkyl with 1 to 20 C atoms, straight-chain alkoxy with 1 to 20 C atoms, straight-chain thioalkoxy with 1 to 20 C atoms, branched-chain alkyl with 3 to 20 C atoms, branched-chain alkoxy with 3 to 20 C atoms, branched-chain thioalkoxy with 3 to 20 C atoms, cyclic alkyl with 3 to 20 C atoms, cyclic alkoxy with 3 to 20 C atoms, cyclic thioalkoxy with 3 to 20 C atoms, silyl, keto with 1 to 20 C atoms, 2 to 20 C atoms, 3 to 4 carbon atoms, 5 to 6 carbon atoms, 6 to 8 carbon atoms, 7 to 8 carbon atoms, 8 to 9 carbon atoms, 9 to 10 carbon atoms, 10 to 11 carbon atoms, 12 to 13 carbon atoms, 13 to 14 carbon atoms, 14 to 15 carbon atoms, 15 to 16 carbon atoms, 16 to 17 carbon atoms, 17 to 18 carbon atoms, 18 to 19 carbon atoms, 19 to 20 ... C atoms, alkoxycarbonyl, aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, substituted or unsubstituted amine, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted aromatic radicals having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic radicals having 5 to 60 ring atoms, substituted or unsubstituted aryloxy radicals having 5 to 60 ring atoms, substituted or unsubstituted heteroaryloxy radicals having 5 to 60 ring atoms, or combinations of these;

[0050] m1 is 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0051] m2 is 0, 1, 2 or 3.

[0052] In some embodiments, each occurrence of R1 and R2 is independently selected from: -D, a linear alkyl group having 1 to 10 C atoms, a linear alkoxy group having 1 to 10 C atoms, a linear thioalkoxy group having 1 to 10 C atoms, a branched alkyl group having 3 to 10 C atoms, a branched alkoxy group having 3 to 10 C atoms, a branched thioalkoxy group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a cyclic alkoxy group having 3 to 10 C atoms, a cyclic thioalkoxy group having 3 to 10 C atoms, a silyl group, a ketone group having 1 to 10 C atoms The invention also includes but is not limited to aryloxy, aryloxycarbonyl, alkyloxycarbonyl ...

[0053] In one embodiment, the organic compound is selected from at least one of the structures shown in formula (2-1)-(2-4):

[0054]

[0055] In some embodiments, Ar1 is selected from a substituted or unsubstituted aromatic group containing 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 30 ring atoms.

[0056] In some embodiments, Ar1 is selected from a substituted or unsubstituted aromatic group containing 6 to 16 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 16 ring atoms.

[0057] In some embodiments, Ar1 is selected from any of the following structures:

[0058]

[0059] in:

[0060] X, at each occurrence, is independently selected from CR3 or N;

[0061] Y is selected from NR4, CR5R6, SiR5R6, O, S, S=O or SO2;

[0062] R3, R4, R5, R6, at each occurrence, are independently selected from: -H, -D, straight-chain alkyl having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms, straight-chain thioalkoxy having 1 to 20 C atoms, branched-chain alkyl having 3 to 20 C atoms, branched-chain alkoxy having 3 to 20 C atoms, branched-chain thioalkoxy having 3 to 20 C atoms, cyclic alkyl having 3 to 20 C atoms, cyclic alkoxy having 3 to 20 C atoms, cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, Alkoxycarbonyl with 2 to 20 C atoms, aryloxycarbonyl with 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted aromatic groups with 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 60 ring atoms, substituted or unsubstituted aryloxy groups with 5 to 60 ring atoms, substituted or unsubstituted heteroaryloxy groups with 5 to 60 ring atoms, or combinations of these groups. R5 and R6 may or may not form a ring with each other.

[0063] Further, it can be understood that in the present application, when X is a linking site, X is C; when Y is a linking site, Y is N.

[0064] In some specific examples, each occurrence of R3 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a silyl group, a cyano group, an isocyano group, a nitro group, -CF3, -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups.

[0065] Further, each occurrence of R3 is independently selected from: -H, -D, a straight chain alkyl group having 1 to 8 C atoms, a branched chain alkyl group having 3 to 8 C atoms, a cyclic alkyl group having 3 to 8 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups.

[0066] The definition of the substituent is the same as above. Preferably, the substituent is selected from at least one of -D, a straight-chain alkyl group having 1 to 4 C atoms, a branched-chain alkyl group having 3 to 4 C atoms, a phenyl group, and a pyridyl group.

[0067] In one embodiment, each occurrence of R4 is independently selected from: a straight chain alkyl group having 1 to 10 C atoms, a branched chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups;

[0068] Further, each time R4 appears, it is independently selected from: a substituted or unsubstituted aromatic group having 6 to 13 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 13 ring atoms, or a combination of these groups; further, each time R4 appears, it is independently selected from: methyl, ethyl, isopropyl, tert-butyl, phenyl, pyridyl, pyrimidyl, triazine, biphenyl, terphenyl or naphthyl.

[0069] In some specific examples, R5 and R6 are independently selected from: -H, -D, straight-chain alkyl groups with 1 to 8 C atoms, branched-chain alkyl groups with 3 to 8 C atoms, cyclic alkyl groups with 3 to 8 C atoms, substituted or unsubstituted aromatic groups with 6 to 10 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 10 ring atoms, or combinations of these groups. Further, R5 and R6 are independently selected from: -H, -D, methyl, ethyl, isopropyl, phenyl, pyridyl, pyrimidyl, triazine, biphenyl, terphenyl or naphthyl.

[0070] In a specific embodiment, Ar1 is selected from any of the following structures:

[0071]

[0072] Wherein, * indicates the connection site.

[0073] Further, in some embodiments, L1 and L2 are each independently selected from a single bond and at least one of the structures shown below:

[0074]

[0075] in:

[0076] Each occurrence of X1 is independently selected from CR7 or N;

[0077] R7, at each occurrence, is independently selected from: -H, -D, straight-chain alkyl having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms, straight-chain thioalkoxy having 1 to 20 C atoms, branched-chain alkyl having 3 to 20 C atoms, branched-chain alkoxy having 3 to 20 C atoms, branched-chain thioalkoxy having 3 to 20 C atoms, cyclic alkyl having 3 to 20 C atoms, cyclic alkoxy having 3 to 20 C atoms, cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, 2 to 2 , alkyloxycarbonyl having 5 to 60 ring atoms, substituted or unsubstituted aryloxy having 5 to 60 ring atoms, substituted or unsubstituted heteroaryloxy having 5 to 60 ring atoms, or a combination of these groups.

[0078] It is understood that, in the present application, when X1 is a linking site, X1 is C.

[0079] In some specific examples, each occurrence of R7 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 4 C atoms, a branched-chain alkyl group having 3 to 4 C atoms, an aromatic group having 6 to 14 ring atoms, a heteroaromatic group having 6 to 14 ring atoms, an aromatic group having 6 to 14 ring atoms substituted by a straight-chain alkyl group having 1 to 4 C atoms or a branched-chain alkyl group having 3 to 4 C atoms, and a heteroaromatic group having 6 to 14 ring atoms substituted by a straight-chain alkyl group having 1 to 4 C atoms or a branched-chain alkyl group having 3 to 6 C atoms.

[0080] In some embodiments, L1 and L2 are independently selected from a single bond or any of the following groups:

[0081]

[0082] In some embodiments, the structure of the organic compound described in the present application includes the following structure, but is not limited thereto:

[0083]

[0084]

[0085]

[0086]

[0087] The organic compound of the present application can be used as a functional material in the functional layer of an electronic device, especially in an OLED device. The functional material can be selected from at least one of a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), an emitter, a host material (Host) and an organic dye.

[0088] In one embodiment, the organic compound described in the present application can be used as a light-emitting material in a light-emitting layer, and preferably, can be used as a main material of the light-emitting layer in the light-emitting layer.

[0089] An embodiment of the present application also provides a mixture, comprising at least one of the organic compounds described above, and an organic functional material, wherein the organic functional material includes but is not limited to at least one of a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), a light-emitting material (Emitter), a host material (Host) and an organic dye.

[0090] In one embodiment, the organic functional material includes a guest material; further, the another organic functional material includes a blue light guest material.

[0091] The present application also provides a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent. The at least one organic solvent is selected from aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, or boric acid esters or phosphate esters, or a mixture of two or more solvents.

[0092] The aromatic or heteroaromatic solvents of the present application 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, dimethylnaphthalene, 3-isopropyl At least one of biphenyl, 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, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, and ethyl 2-furoate.

[0093] The aromatic ketone solvents of the present application include but are not limited to: 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, and 2-methylpropiophenone.

[0094] The aromatic ether solvents of 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-ethylphenylethyl 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.

[0095] The aliphatic ketone solvents of 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, phorone, isophorone, di-n-amyl ketone, etc.; the aliphatic ether solvents of the present application include but are not limited to at least one of 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, and tetraethylene glycol dimethyl ether.

[0096] The ester solvents of the present application include but are not limited to: at least one of alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, and alkyl oleate. At least one of octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate is particularly preferred.

[0097] In the embodiments of the present application, the organic solvent may be used alone or as a mixture of two or more organic solvents.

[0098] In certain preferred embodiments, a composition of the present application comprises at least one organic compound or mixture as described above and at least one organic solvent as described above, and may further comprise another organic solvent. Another organic solvent includes, but is not limited to, methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene and / or mixtures thereof.

[0099] In some preferred embodiments, solvents particularly suitable for the present application are solvents having a Hansen solubility parameter within the following ranges:

[0100] δd (dispersion force) is in the range of 17.0 to 23.2 MPa1 / 2, especially in the range of 18.5 to 21.0 MPa1 / 2;

[0101] δp (polar force) is in the range of 0.2 to 12.5 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2;

[0102] δh (hydrogen bonding force) is in the range of 0.9 to 14.2 MPa1 / 2, and particularly in the range of 2.0 to 6.0 MPa1 / 2.

[0103] In the composition of the present application, the boiling point parameter of the organic solvent should be considered when selecting. In the present application, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; more preferably ≥250°C; and most preferably ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet print head. The organic solvent can evaporate from the solvent system to form a film containing a functional material.

[0104] In a preferred embodiment, the composition of the present application is a solution.

[0105] In another preferred embodiment, the composition of the present application is a suspension.

[0106] The composition in the embodiments of the present application may include 0.01 wt % to 10 wt % of the compound or mixture of the present application, preferably 0.1 wt % to 8 wt %, more preferably 0.2 to 5 wt %, and most preferably 0.25 wt % to 3 wt %.

[0107] The present application also relates to the use of the composition as a coating or printing ink in the preparation of an organic electronic device, and a preparation method by printing or coating is particularly preferred.

[0108] Among them, suitable printing or coating techniques include (but are not limited to) inkjet printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spraying, brushing or pad printing, slot extrusion coating, etc. The preferred ones are gravure printing, spray printing and inkjet printing. The solution or suspension may further include one or more components such as surfactant compounds, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc. Relevant printing technology and its related requirements for relevant solutions, such as solvents and concentrations, viscosity, etc.

[0109] The present application also provides a use of the organic compound, mixture or composition as described above in an organic electronic device.

[0110] The embodiment of the present application also provides an organic electronic device, comprising a first electrode, a second electrode, and at least one organic functional layer located between the first electrode and the second electrode, wherein the organic functional layer comprises the organic compound, mixture or is prepared from the above-mentioned composition. The functional layer is selected from at least one of a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0111] In the present application, the organic electronic device can be selected from but not limited to, organic light emitting diodes (OLEDs), organic photovoltaic cells, organic light emitting cells, organic field effect transistors, organic light emitting field effect transistors, organic lasers, organic spintronic devices, organic sensors and organic plasmon emission diodes, etc., and OLEDs are particularly preferred.

[0112] The present application further relates to an organic electronic device, the organic electronic device comprising: a cathode, an anode, and at least one organic functional layer located between the cathode and the anode, the organic functional layer comprising a light-emitting layer, the light-emitting layer material comprising a host material and a guest material, the host material comprising the compound of formula (1), the guest material comprising the compound of formula (2):

[0113]

[0114] in:

[0115] Ar3-Ar6 are independently selected from substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 6 to 60 ring atoms, or combinations of these groups;

[0116] R8, at each occurrence, is independently selected from: -H, -D, straight-chain alkyl with 1 to 20 C atoms, straight-chain alkoxy with 1 to 20 C atoms, straight-chain thioalkoxy with 1 to 20 C atoms, branched-chain alkyl with 3 to 20 C atoms, branched-chain alkoxy with 3 to 20 C atoms, branched-chain thioalkoxy with 3 to 20 C atoms, cyclic alkyl with 3 to 20 C atoms, cyclic alkoxy with 3 to 20 C atoms, cyclic thioalkoxy with 3 to 20 C atoms, silyl, keto with 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, amine, CF3, Cl, Br, F, I, substituted or unsubstituted aromatic radical having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic radical having 5 to 60 ring atoms, substituted or unsubstituted aryloxy radical having 5 to 60 ring atoms, substituted or unsubstituted heteroaryloxy radical having 5 to 60 ring atoms, or combinations of these radicals;

[0117] s is selected from any integer from 0 to 8; specifically, s is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0118] The further description of the organic compound represented by formula (1) is as described above.

[0119] In one embodiment, Ar3-Ar6 are independently selected from substituted or unsubstituted aromatic groups containing 6 to 14 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 6 to 14 ring atoms, or combinations thereof.

[0120] In one embodiment, the Ar3-Ar6 comprises at least one of the following structures:

[0121]

[0122] in:

[0123] Each occurrence of V is independently selected from CR9 or N;

[0124] W is selected from NR 10 , CR 10 R 11 、SiR 10 R 11 , O, S, S=O or SO2;

[0125] R9-R 11 Each occurrence is independently selected from: -H, -D, straight-chain alkyl having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms, straight-chain thioalkoxy having 1 to 20 C atoms, branched-chain alkyl having 3 to 20 C atoms, branched-chain alkoxy having 3 to 20 C atoms, branched-chain thioalkoxy having 3 to 20 C atoms, cyclic alkyl having 3 to 20 C atoms, cyclic alkoxy having 3 to 20 C atoms, cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, cycloalkyl having 2 to 20 C atoms, cycloalkyl having 3 ... The invention also includes but is not limited to alkyloxycarbonyl, ...

[0126] Furthermore, R9-R 11 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these groups.

[0127] Furthermore, R8-R 11 Each occurrence is independently selected from -H, -D, straight-chain alkyl having 1 to 10 C atoms, branched-chain alkyl having 3 to 10 C atoms or cyclic alkyl or phenyl.

[0128] In one embodiment, the guest material comprises a structure as shown in formula (III):

[0129]

[0130] Preferably, R9, at each occurrence, is independently selected from -H, -D, straight chain alkyl having 1 to 10 C atoms, or branched or cyclic alkyl having 3 to 10 C atoms, or phenyl.

[0131] Furthermore, the guest material includes at least one of the structures shown in the following general formula:

[0132]

[0133] Preferably, R9, at each occurrence, is independently selected from -H, -D, straight chain alkyl having 1 to 10 C atoms, or branched or cyclic alkyl having 3 to 10 C atoms, or phenyl.

[0134] The guest material described in the present application includes at least one of the structures shown in formula (BD-1) to (BD-24), but is not limited thereto:

[0135]

[0136]

[0137] In one embodiment, the organic electronic device comprises an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode.

[0138] In one embodiment, the organic electronic device comprises an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode.

[0139] In one embodiment, the organic electronic device comprises an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, and a cathode.

[0140] Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire contents of these three patent documents are hereby incorporated herein by reference.

[0141] The above-mentioned light-emitting device (organic electronic device), especially OLED, comprises an anode and a cathode arranged on a substrate, and at least one light-emitting layer arranged between the anode and the cathode.

[0142] The substrate can be opaque or transparent. A transparent substrate can be used to make a transparent light-emitting device. For example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or elastic. The substrate can be plastic, metal, semiconductor wafer or glass. It is best that the substrate has a smooth surface. Substrates without surface defects are particularly ideal. In a preferred embodiment, the substrate is flexible and can be selected from polymer films or plastics, and its glass transition temperature Tg is above 150°C, preferably above 200°C, more preferably above 250°C, and preferably above 300°C. Examples of suitable flexible substrates include poly (ethylene terephthalate) (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0143] The anode may include a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL) or the hole transport layer (HTL) or the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light-emitting body in the light-emitting layer or the p-type semiconductor material as the HIL or HTL or the electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known and can be easily selected for use by a person of ordinary skill in the art. The anode material 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 is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present application.

[0144] The cathode may include a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the light-emitting body in the light-emitting layer or the n-type semiconductor material as the electron injection layer (EIL) or the electron transport layer (ETL) or the hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes of OLEDs may be used as cathode materials for the device of the present application. Examples of cathode materials include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0145] In a preferred embodiment, the organic electronic device described in the present application is selected from solution-type OLED.

[0146] In a preferred embodiment, in the light-emitting device according to the present application, the light-emitting layer thereof is prepared by the composition according to the present application.

[0147] According to the light-emitting device of the present application, the light-emitting wavelength is between 300 and 1000 nm, preferably between 350 and 900 nm, and more preferably between 400 and 800 nm.

[0148] The present application also relates to the application of the organic electronic device according to the present application in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, etc. For example, the present application is applied to OLED panel display.

[0149] The present application also relates to electronic devices including the organic electronic device according to the present application, including, but not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0150] The present application has been subjected to multiple tests, and part of the test results are now cited as references to further describe the invention in detail, which is described in detail below in conjunction with specific embodiments.

[0151] Example 1

[0152] This embodiment provides an organic compound (Compound 1).

[0153] The synthetic route of compound 1 is:

[0154]

[0155] Synthesis of intermediate 1-1:

[0156] 1,9-dibromodibenzofuran (10 g, 30.7 mmol) and o-hydroxyphenylboronic acid (4.2 g, 30.7 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 10 ml), and Pd(PPh3)4 (1.8 g, 1.5 mmol) and potassium carbonate (21 g, 154 mmol) were added. Stir at 100 ° C for 12 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was chromatographed by column (eluent: PE) to obtain a white solid with a yield of 54%. MS (ASAP) = 338.0.

[0157] Synthesis of intermediate 1-2:

[0158] Dissolve the intermediate 1-1 (5 g, 14.8 mmol) in DMF (100 ml) solution and add potassium carbonate (10.2 g, 74 mmol). Stir at 150 ° C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract with DCM and wash with water, and obtain a white solid by organic phase column chromatography (eluent: DCM: PE = 1: 5), with a yield of 67%. MS (ASAP) = 258.1.

[0159] Synthesis of intermediate 1-3:

[0160] Place intermediate 1-2 (10 g, 41 mmol) in a 250 ml two-necked bottle, add 100 ml of DMF until the solid is completely dissolved, weigh NBS (7.4 g, 41 mmol) and place it in a constant pressure dropping funnel, dissolve it in 50 ml of DMF, slowly add dropwise, and react at room temperature for 12 hours. Spin dry, wash with water, and column chromatography (eluent: PE) to obtain a white solid with a yield of 88%. MS (ASAP) = 336.0.

[0161] Synthesis of compound 1:

[0162] Intermediate 1-3 (10 g, 29.8 mmol) and 10-(1-naphthyl)-9-anthraceneboronic acid (15.5 g, 44.6 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd(PPh3)4 (0.69 g, 0.6 mmol) and potassium carbonate (21.4 g, 155 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed (eluent was PE) and recrystallized to obtain compound 1 with a yield of 77%. MS (ASAP) = 560.2.

[0163] Example 2

[0164] This example provides an organic compound (Compound 2).

[0165] The synthetic route of compound 2 is:

[0166]

[0167] Synthesis of compound 2:

[0168] Intermediate 1-3 (10 g, 29.8 mmol) and 10-(phenyl)-9-anthraceneboronic acid (13.3 g, 44.6 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.4 g, 1.2 mmol) and potassium carbonate (16.6 g, 120 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: PE) and recrystallization to obtain compound 2 with a yield of 92%. MS (ASAP) = 510.2.

[0169] Example 3

[0170] This example provides an organic compound (Compound 3).

[0171] The synthetic route of compound 3 is:

[0172]

[0173] Synthesis of intermediate 3-1:

[0174] 1,9-dibromodibenzofuran (10 g, 30.7 mmol) and 2-hydroxy-4-aminophenylboronic acid (4.7 g, 30.7 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.8 g, 1.5 mmol) and potassium carbonate (21 g, 154 mmol) were added. Stir at 100 ° C for 12 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was chromatographed by column (eluent: PE) to obtain a white solid with a yield of 51%. MS (ASAP) = 353.0.

[0175] Synthesis of intermediate 3-2:

[0176] Dissolve the intermediate 3-1 (10 g, 28.3 mmol) in DMF (100 ml) solution and add potassium carbonate (19.5 g, 141 mmol). Stir at 150 ° C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract with DCM and wash with water, and obtain a white solid by organic phase column chromatography (eluent: DCM: PE = 1: 5), with a yield of 62%. MS (ASAP) = 273.1.

[0177] Synthesis of intermediate 3-3:

[0178] Weigh the intermediate 3-2 (10 g, 36.6 mmol) in a 250 mL three-necked flask, add 100 ml of tetrahydrofuran, 20 ml of dilute hydrochloric acid, place in an ice bath, weigh NaNO2 (3.0 g, 44 mmol) and dissolve in 20 ml of water, slowly drop into the tetrahydrofuran solution of the intermediate 3-2, stir for 1 hour in an ice bath, weigh KI (7.3 g, 44 mmol) and dissolve in 50 ml of water, slowly drop into the above reaction solution. React at room temperature for 12 hours. After the reaction is completed, add sodium thiosulfate aqueous solution, extract with dichloromethane, spin dry, wash with water, column chromatography (eluent is PE: DCM = 2: 1) to obtain a white solid with a yield of 87%. MS (ASAP) = 384.0.

[0179] Synthesis of compound 3:

[0180] Intermediate 3-3 (10 g, 26 mmol), 10-(deuterated phenyl)-9-anthraceneboronic acid (11.8 g, 39 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd(PPh3)4 (0.60 g, 0.52 mmol) and potassium carbonate (17.9 g, 130 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed (eluent was PE) and recrystallized to obtain compound 3 with a yield of 91%. MS (ASAP) = 517.2.

[0181] Example 4

[0182] This example provides an organic compound (Compound 4).

[0183] The synthetic route of compound 4 is:

[0184]

[0185] Synthesis of intermediate 4-1:

[0186] 1,9-dibromodibenzofuran (8.0 g, 24.5 mmol) and 2-hydroxy-5-aminophenylboronic acid (3.8 g, 24.5 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.8 g, 1.5 mmol) and potassium carbonate (21 g, 154 mmol) were added. Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: DCM:PE=1:2) to obtain a white solid with a yield of 51%. MS (ASAP) = 353.0.

[0187] Synthesis of intermediate 4-2:

[0188] Dissolve the intermediate 4-1 (8.0 g, 22.7 mmol) in DMF (100 ml) solution and add potassium carbonate (15.6 g, 113 mmol). Stir at 150 ° C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract with DCM and wash with water, and obtain a white solid by organic phase column chromatography (eluent: DCM: PE = 1: 2), with a yield of 62%. MS (ASAP) = 273.1.

[0189] Synthesis of intermediate 4-3:

[0190] Weigh the intermediate 4-2 (5.0 g, 18.3 mmol) in a 250 mL three-necked flask, add 100 ml of tetrahydrofuran, 20 ml of dilute hydrochloric acid, place in an ice bath, weigh NaNO2 (1.5 g, 21.8 mmol) and dissolve it in 20 ml of water, slowly drop it into the tetrahydrofuran solution of the intermediate 4-2, stir for 1 hour in an ice bath, weigh KI (3.6 g, 21.8 mmol) and dissolve it in 50 ml of water, slowly drop it into the above reaction solution. React at room temperature for 12 hours. After the reaction is completed, add sodium thiosulfate aqueous solution, extract with dichloromethane, spin dry, wash with water, column chromatography (eluent is PE: DCM = 2: 1) to obtain a white solid with a yield of 82%. MS (ASAP) = 384.0.

[0191] Synthesis of compound 4:

[0192] Intermediate 4-3 (8.0 g, 20.8 mmol), 10-(1-deuterated naphthyl)-9-anthraceneboronic acid (11.1 g, 31.2 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd(PPh3)4 (0.58 g, 0.5 mmol) and potassium carbonate (14.3 g, 104 mmol) were added. Stir at 100 ° C for 12 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was column chromatographed (eluent was PE) and recrystallized to obtain compound 4, with a yield of 81%. MS (ASAP) = 569.2.

[0193] Example 5

[0194] This example provides an organic compound (Compound 5).

[0195] The synthetic route of compound 5 is:

[0196]

[0197] Synthesis of intermediate 5-1:

[0198] 9,10-Dibromoanthracene (3.4 g, 10 mmol) and 3,5-diphenyl-phenylboronic acid (2.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 5-1 with a yield of 69%. MS (ASAP) = 484.1.

[0199] Synthesis of intermediate 5-2:

[0200] Prepare a dry 250mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh the intermediate 5-1 (5.0g, 10.3mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (4.1ml, 10.3mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (1.5g, 10.3mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 83%. MS (ASAP) = 450.2.

[0201] Synthesis of compound 5:

[0202] Weigh intermediate 5-2 (4.5 g, 10 mmol), intermediate 3-3 (3.8 g, 10 mmol) and dissolve in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.2 g, 1.0 mmol) and potassium carbonate (6.9 g, 50 mmol). Stir at 100 ° C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, organic phase column chromatography (eluent PE) and recrystallization to obtain compound 5, yield: 87%. MS (ASAP) = 662.2.

[0203] Example 6

[0204] This embodiment provides an organic compound (Compound 6).

[0205] The synthetic route of compound 6 is:

[0206]

[0207] Synthesis of intermediate 6-1:

[0208] The intermediate 9-bromo-10-(2-naphthyl)anthracene (3.8 g, 10 mmol) and 2-bromo-pyridine-5-boronic acid (2.0 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain the intermediate 6-1 with a yield of 83%. MS (ASAP) = 459.1.

[0209] Synthesis of intermediate 6-2:

[0210] Prepare a dry 250mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh the intermediate 6-1 (5.0g, 10.9mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (4.4ml, 10.9mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (1.6g, 10.9mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 84%. MS (ASAP) = 425.2.

[0211] Synthesis of compound 6:

[0212] Weigh intermediate 6-2 (4.3 g, 10 mmol), intermediate 4-3 (3.8 g, 10 mmol) and dissolve in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd(PPh3)4 (1.2 g, 1.0 mmol) and potassium carbonate (6.9 g, 50 mmol). Stir at 100 ° C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, organic phase column chromatography (eluent PE) and recrystallization to obtain compound 6, yield: 82%. MS (ASAP) = 637.2.

[0213] Example 7

[0214] This example provides an organic compound (Compound 7).

[0215] The synthetic route of compound 7 is:

[0216]

[0217] Synthesis of intermediate 7-1:

[0218] 9,10-Dibromoanthracene (6.8 g, 20 mmol), 9,9-dimethylfluorene-2-boric acid (4.8 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (2.3 g, 2 mmol) and potassium carbonate (14 g, 100 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 7-1 with a yield of 69%. MS (ASAP) = 448.1.

[0219] Synthesis of intermediate 7-2:

[0220] Prepare a dry 250mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh the intermediate 7-1 (5.0g, 11.1mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (4.5ml, 11.1mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (1.6g, 11.1mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 94%. MS (ASAP) = 414.2.

[0221] Synthesis of compound 7:

[0222] Intermediate 7-2 (8.3 g, 20 mmol) and intermediate 1-3 (6.7 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.2 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: PE) and recrystallization to obtain compound 7 with a yield of 66%. MS (ASAP) = 626.2.

[0223] Example 8

[0224] This example provides an organic compound (Compound 8).

[0225] The synthetic route of compound 8 is:

[0226]

[0227] Synthesis of intermediate 8-1:

[0228] The intermediate 9-bromo-10-(2,4,6-trimethylphenyl)anthracene (10 g, 26.7 mmol) and 6-bromo-2-naphthaleneboronic acid (6.7 g, 26.7 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (2.3 g, 2 mmol) and potassium carbonate (20.7 g, 150 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain the intermediate 8-1 with a yield of 77%. MS (ASAP) = 500.1.

[0229] Synthesis of intermediate 8-2:

[0230] Prepare a dry 250mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh the intermediate 8-1 (10g, 20mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (8.0ml, 20mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (2.9g, 20mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 85%. MS (ASAP) = 466.2.

[0231] Synthesis of compound 8:

[0232] Intermediate 8-2 (4.6 g, 10 mmol) and intermediate 1-3 (3.4 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.2 g, 1.0 mmol) and potassium carbonate (6.2 g, 45 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain compound 8 with a yield of 62%. MS (ASAP) = 678.3.

[0233] Example 9

[0234] This embodiment provides an organic compound (Compound 9).

[0235] The synthetic route of compound 9 is:

[0236]

[0237] Synthesis of intermediate 9-1:

[0238] 9,10-Dibromoanthracene (6.8 g, 20 mmol) and 2-biphenylboronic acid (4.0 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.2 g, 1 mmol) and potassium carbonate (6.9 g, 50 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 9-1 with a yield of 76%. MS (ASAP) = 408.1.

[0239] Synthesis of intermediate 9-2:

[0240] Prepare a dry 250mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh the intermediate 9-1 (5.0g, 12mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (4.9ml, 12mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (1.8g, 12mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 82%. MS (ASAP) = 374.2.

[0241] Synthesis of compound 9:

[0242] Intermediate 9-2 (3.7 g, 10 mmol) and intermediate 3-3 (3.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.2 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: PE) and recrystallization to obtain compound 9 with a yield of 67%. MS (ASAP) = 586.2.

[0243] Example 10

[0244] This embodiment provides an organic compound (Compound 10).

[0245] The synthetic route of compound 10 is:

[0246]

[0247] Synthesis of intermediate 10-1:

[0248] The intermediate 9,10-dibromoanthracene (6.7 g, 20 mmol) and dibenzo[b,d]furan-2-boronic acid (4.3 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.2 g, 1 mmol) and potassium carbonate (14 g, 100 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain the intermediate 10-1 with a yield of 58%. MS (ASAP) = 422.0.

[0249] Synthesis of intermediate 10-2:

[0250] Prepare a dry 250mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh the intermediate 10-1 (5.0g, 11.8mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (4.7ml, 11.8mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (1.7g, 11.8mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 88%. MS (ASAP) = 388.1.

[0251] Synthesis of compound 10:

[0252] Intermediate 10-2 (3.9 g, 10 mmol) and intermediate 3-3 (3.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain compound 10 with a yield of 79%. MS (ASAP) = 600.2.

[0253] Embodiment 11

[0254] This embodiment provides an organic compound (Compound 11).

[0255] The synthetic route of compound 11 is:

[0256]

[0257] Synthesis of intermediate 11-1:

[0258] 9,10-Dibromoanthracene (3.4 g, 10 mmol) and fluoranthene 3-boric acid (2.5 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 11-1 with a yield of 62%. MS (ASAP) = 456.1.

[0259] Synthesis of intermediate 11-2:

[0260] Prepare a dry 250mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh the intermediate 11-1 (10g, 22mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (8.8ml, 22mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (3.2g, 22mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 89%. MS (ASAP) = 422.2.

[0261] Synthesis of intermediate 11-3:

[0262] Intermediate 8-2 (4.2 g, 10 mmol) and intermediate 3-3 (3.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain intermediate 11-3 with a yield of 78%. MS (ASAP) = 634.2.

[0263] Synthesis of intermediate 11-4:

[0264] Place intermediate 11-3 (10 g, 15.8 mmol) in a 250 ml two-necked bottle, add 100 ml of DMF until the solid is completely dissolved, weigh NBS (2.8 g, 15.8 mmol) and place in a constant pressure dropping funnel, dissolve in 50 ml of DMF, slowly add dropwise, and react at room temperature for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE) to obtain a white solid with a yield of 82%. MS (ASAP) = 712.1.

[0265] Synthesis of compound 11:

[0266] Intermediate 11-4 (10 g, 14 mmol) and phenylboronic acid (2.6 g, 21 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd(PPh3)4 (0.35 g, 0.3 mmol) and potassium carbonate (9.7 g, 70 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed (eluent was PE) and recrystallized to obtain compound 11 with a yield of 79%. MS (ASAP) = 710.2.

[0267] Example 12

[0268] This embodiment provides an organic compound (Compound 12).

[0269] The synthetic route of compound 12 is:

[0270]

[0271] Synthesis of intermediate 12-1:

[0272] 1,9-dibromodibenzofuran (10 g, 30.7 mmol) and 3-hydroxy-2-naphthaleneboronic acid (5.8 g, 30.7 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 10 ml), and Pd(PPh3)4 (1.8 g, 1.5 mmol) and potassium carbonate (21 g, 154 mmol) were added. Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: DCM: PE = 1: 2) to obtain a white solid with a yield of 52%. MS (ASAP) = 388.0.

[0273] Synthesis of intermediate 12-2:

[0274] Dissolve the intermediate 12-1 (10 g, 25.8 mmol) in DMF (100 ml) solution and add potassium carbonate (17.8 g, 129 mmol). Stir at 150 ° C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract with DCM and wash with water, and obtain a white solid by organic phase column chromatography (eluent: DCM: PE = 1: 5) with a yield of 72%. MS (ASAP) = 308.1.

[0275] Synthesis of intermediate 12-3:

[0276] Place intermediate 12-2 (10 g, 32.5 mmol) in a 250 ml two-necked bottle, add 100 ml of DMF until the solid is completely dissolved, weigh NBS (5.8 g, 32.5 mmol) and place it in a constant pressure dropping funnel, dissolve it in 50 ml of DMF, slowly add dropwise, and react at room temperature for 12 hours. Spin dry, wash with water, and column chromatography (eluent: PE) to obtain a white solid with a yield of 37%. MS (ASAP) = 386.0.

[0277] Synthesis of compound 12:

[0278] Intermediate 12-3 (3.9 g, 10 mmol) and 10-(9-phenanthrenyl)-9-anthraceneboronic acid (4.0 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd(PPh3)4 (0.58 g, 0.5 mmol) and potassium carbonate (6.9 g, 50 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: PE) and recrystallization to obtain compound 12 with a yield of 77%. MS (ASAP) = 660.2.

[0279] Example 13

[0280] This embodiment provides an organic compound (Compound 13).

[0281] The synthetic route of compound 13 is:

[0282]

[0283] Synthesis of intermediate 13-1:

[0284] 1,9-dibromodibenzofuran (10 g, 30.7 mmol) and 1-hydroxy-2-naphthaleneboronic acid (5.8 g, 30.7 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 10 ml), and Pd(PPh3)4 (1.8 g, 1.5 mmol) and potassium carbonate (21 g, 154 mmol) were added. Stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: DCM: PE = 1: 2) to obtain a white solid with a yield of 55%. MS (ASAP) = 388.0.

[0285] Synthesis of intermediate 13-2:

[0286] Dissolve the intermediate 13-1 (12 g, 30.9 mmol) in DMF (100 ml) solution and add potassium carbonate (21.3 g, 155 mmol). Stir at 150 ° C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract with DCM and wash with water, and obtain a white solid by organic phase column chromatography (eluent: DCM: PE = 1: 5) with a yield of 68%. MS (ASAP) = 308.1.

[0287] Synthesis of intermediate 13-3:

[0288] Place intermediate 13-2 (8.0 g, 26 mmol) in a 250 ml two-necked bottle, add 100 ml of DMF until the solid is completely dissolved, weigh NBS (4.6 g, 26 mmol) and place it in a constant pressure dropping funnel, dissolve it in 50 ml of DMF, slowly add dropwise, and react at room temperature for 12 hours. Spin dry, wash with water, and column chromatography (eluent: PE) to obtain a white solid with a yield of 28%. MS (ASAP) = 386.0.

[0289] Synthesis of compound 13:

[0290] Intermediate 13-3 (5 g, 13 mmol) and 10-(3-pyridyl)-9-anthraceneboronic acid (3.9 g, 13 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd(PPh3)4 (0.69 g, 0.6 mmol) and potassium carbonate (9.0 g, 65 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: PE) and recrystallization to obtain compound 13 with a yield of 71%. MS (ASAP) = 561.2.

[0291] Embodiment 14

[0292] This embodiment provides an organic compound (Compound 14).

[0293] The synthetic route of compound 14 is:

[0294]

[0295] Synthesis of intermediate 14-1:

[0296] 9,10-Dibromoanthracene (3.4 g, 10 mmol) and 1-pyreneboronic acid (2.5 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 14-1 with a yield of 71%. MS (ASAP) = 456.1.

[0297] Synthesis of intermediate 14-2:

[0298] Intermediate 14-1 (3.4 g, 10 mmol) and 4-aminophenylboronic acid (1.4 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain intermediate 14-2 with a yield of 71%. MS (ASAP) = 469.2.

[0299] Synthesis of intermediate 14-3:

[0300] Weigh the intermediate 14-2 (8.0 g, 17 mmol) in a 250 mL three-necked flask, add 100 ml of tetrahydrofuran, 20 ml of dilute hydrochloric acid, place in an ice bath, weigh NaNO2 (1.4 g, 20 mmol) and dissolve it in 20 ml of water, slowly drop it into the tetrahydrofuran solution of the intermediate 14-2, stir for 1 hour in an ice bath, weigh KI (3.4 g, 20 mmol) and dissolve it in 50 ml of water, slowly drop it into the above reaction solution. React at room temperature for 12 hours. After the reaction is completed, add sodium thiosulfate aqueous solution, extract with dichloromethane, spin dry, wash with water, column chromatography (eluent is PE: DCM = 2: 1) to obtain a white solid with a yield of 81%. MS (ASAP) = 580.1.

[0301] Synthesis of intermediate 14-4:

[0302] Prepare a dry 250mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh the intermediate 14-3 (10g, 17mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (6.9ml, 17mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (2.5g, 17mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 89%. MS (ASAP) = 498.2.

[0303] Synthesis of compound 14:

[0304] Intermediate 14-4 (5.0 g, 10 mmol) and intermediate 3-3 (3.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.2 g, 1.0 mmol) and potassium carbonate (6.2 g, 45 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain compound 14 with a yield of 61%. MS (ASAP) = 710.2.

[0305] Embodiment 15

[0306] This embodiment provides an organic compound (Compound 15).

[0307] The synthetic route of compound 15 is:

[0308]

[0309] Synthesis of intermediate 15-1:

[0310] The intermediate 10-(phenyl)-9-anthraceneboronic acid (10 g, 30 mmol) and 2-amino-5-pyridineboronic acid (4.2 g, 30 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.7 g, 1.5 mmol) and potassium carbonate (20.7 g, 150 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain the intermediate 15-1 with a yield of 82%. MS (ASAP) = 346.2.

[0311] Synthesis of intermediate 15-2:

[0312] Weigh the intermediate 15-1 (12g, 34.7mmol) in a 250mL three-necked flask, add 100ml of tetrahydrofuran, 20ml of dilute hydrochloric acid, place in an ice bath, weigh NaNO2 (2.9g, 41.6mmol) and dissolve it in 20ml of water, slowly drop it into the tetrahydrofuran solution of the intermediate 14-2, stir for 1 hour in an ice bath, weigh KI (6.9g, 41.6mmol) and dissolve it in 50ml of water, slowly drop it into the above reaction solution. React at room temperature for 12h. After the reaction is completed, add sodium thiosulfate aqueous solution, extract with dichloromethane, spin dry, wash with water, column chromatography (eluent is PE:DCM=2:1) ​​to obtain a white solid with a yield of 55%. MS (ASAP) = 457.0.

[0313] Synthesis of intermediate 15-3:

[0314] Prepare a dry 250mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh the intermediate 15-2 (8.0g, 17.5mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (7.0ml, 17.5mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (2.6g, 17mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 78%. MS (ASAP) = 375.1.

[0315] Synthesis of compound 15:

[0316] Intermediate 15-3 (3.8 g, 10 mmol) and intermediate 1-3 (3.4 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.2 g, 1.0 mmol) and potassium carbonate (6.2 g, 45 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain compound 15 with a yield of 85%. MS (ASAP) = 587.2.

[0317] Preparation of OLED devices:

[0318] In the examples of the present application, the organic compound synthesized as above is used to prepare an OLED device.

[0319] The compound structures involved in preparing OLED devices in the embodiments of the present application include:

[0320]

[0321] The following is a detailed description of the preparation process of an OLED device using the above compound through a specific embodiment. The structure of the OLED device is: ITO / HIL / HTL / EML / ETL / cathode. The schematic diagram of the OLED device is shown in FIG. Figure 1 As shown, the OLED device 100 includes an anode 20 disposed on a substrate 10, a hole injection layer (HIL) 30 disposed on the ITO anode 20, a hole transport layer (HTL) 40 disposed on the hole injection layer (HIL) 30, a light-emitting layer 50 disposed on the hole transport layer (HTL) 40, an electron transport layer (ETL) 60 disposed on the light-emitting layer 50, and a cathode 70 disposed on the electron transport layer (ETL) 60.

[0322] Device Example 1

[0323] This embodiment provides an OLED device, and the preparation steps are as follows:

[0324] a. Cleaning of ITO (indium tin oxide) conductive glass substrates: using various solvents (such as one or more of chloroform, acetone or isopropyl alcohol) for cleaning, followed by ultraviolet ozone treatment;

[0325] b. HIL (hole injection layer, 40 nm): 60 nm PEDOT (polyethylenedioxythiophene, Clevios TM AI4083) was spin-coated as HIL in a clean room and treated on a hot plate at 180 °C for 10 min;

[0326] c. HTL (hole transport layer, 20 nm): 20 nm of PVK (Sigma Aldrich, average Mn 25,000-50,000) was prepared by spin coating in a nitrogen glove box. The solution used was PVK added to toluene solvent at a concentration of 5 mg / ml, followed by treatment on a hot plate at 180 °C for 60 min.

[0327] d. EML (organic light-emitting layer, 40 nm): EML was formed by spin coating in a nitrogen glove box. The solution used was a methyl benzoate solution of different host and guest (the weight ratio of host and guest was 95:5), the solution solubility was 15 mg / ml, and then treated on a hot plate at 140° C. for 10 minutes. The guest structure was BD, the host material was compound 1 of Example 1, and the guest material was selected from BD-1.

[0328] e. Electron transport layer and cathode: The heat-treated substrate was transferred to a vacuum chamber, and then ET and Liq were placed in different evaporation units under high vacuum (1×10 -6 The electrodes were co-deposited at a ratio of 50 wt % in 400 mbar (0.1 wt %) to form an electron transport layer with a thickness of 20 nm on the light-emitting layer, and then an Al (aluminum) cathode with a thickness of 100 nm was deposited.

[0329] f. Packaging: The device is packaged with UV-curable resin in a nitrogen glove box.

[0330] Device Examples 2 to 15

[0331] The implementation schemes of the OLED devices of device examples 2 to 15 are different from those of device example 1 in that the host materials are different, and compound 1 in example 1 is replaced by the compounds in Table 1.

[0332] The current-voltage (JV) characteristics of each OLED device were characterized using a characterization apparatus, while important parameters such as efficiency, lifetime, and external quantum efficiency were recorded. The results are shown in Table 1.

[0333] Table 1

[0334]

[0335] After testing, the color coordinates of the blue light devices prepared using Compound 1-Compound 15 as the main materials in the light-emitting layer are better than those of the comparative compounds. In addition, the luminous efficiency of the blue light devices prepared using Compound 1-Compound 15 as the main materials in the light-emitting layer of the EML layer is in the range of 5-8cd / A, which has a more excellent luminous efficiency.

[0336] 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.

[0337] In summary, the organic compound provided in the present application is a blue light fluorescent organic compound, which can improve the problems of low luminous efficiency and short life of existing blue light fluorescent organic electronic devices by introducing hole transport groups.

[0338] In the above embodiments, the description of each embodiment has its own emphasis. For parts that are not described in detail in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.

[0339] The above is a detailed introduction to an organic compound, mixture, composition and organic electronic device provided in the embodiments of the present application. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the method of the present application and its core idea. At the same time, for technicians in this field, according to the ideas of the present application, there will be changes in the specific implementation methods and application scopes. In summary, the content of this specification should not be understood as a limitation on the present application.

Claims

1. An organic compound, characterized in that It has a structure as shown in the general formula (1): In the formula, Ar1 is selected from one of the following structures: * indicates the attachment site; Ar2 is selected from phenyl or naphthyl; L1 is selected from a single bond or one of the structures shown below: * indicates the attachment site; L2 is selected from a single bond; R1, R2 are selected from -D; m1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; m2 is selected from 0, 1, 2 or 3.

2. A mixture, characterized in that It includes the organic compound as described in claim 1, and also includes an organic functional material; the organic functional material is selected from at least one of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminescent material, a host material and an organic dye.

3. A composition, characterized in that The method comprises the organic compound as claimed in claim 1 or the mixture as claimed in claim 2, and further comprises an organic solvent.

4. An organic electronic device, characterized in that: The invention comprises a first electrode, a second electrode and an organic functional layer located between the first electrode and the second electrode; the organic functional layer comprises the organic compound according to claim 1 or the mixture according to claim 2, or is prepared from the composition according to claim 3.

5. The organic electronic device according to claim 4, characterized in that: The organic functional layer includes a light-emitting layer, the light-emitting layer includes a host material and a guest material, the host material includes the organic compound, and the guest material includes a structure as shown in general formula (2): in, Ar3-Ar6 are independently selected from at least one of the structures shown below: Each occurrence of V is independently selected from CR9 or N; W is selected from NR 10 , CR 10 R 11 、SiR 10 R 11 , O, S, S=O or SO2; R9-R 11 Each occurrence is independently selected from: -H, -D, straight-chain alkyl having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms, straight-chain thioalkoxy having 1 to 20 C atoms, branched-chain alkyl having 3 to 20 C atoms, branched-chain alkoxy having 3 to 20 C atoms, branched-chain thioalkoxy having 3 to 20 C atoms, cyclic alkyl having 3 to 20 C atoms, cyclic alkoxy having 3 to 20 C atoms, -CF3, -Cl, -Br, -F, -I, aromatic groups having 6 to 30 ring atoms, heteroaromatic groups having 5 to 30 ring atoms; R8, at each occurrence, is independently selected from: -H, -D, a linear alkyl group having 1 to 10 C atoms, a branched alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, or a phenyl group; s is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

6. The organic electronic device according to claim 5, characterized in that The guest material comprises a structure as shown in formula (III):

7. The organic electronic device according to claim 6, characterized in that: The guest material includes at least one of the following structures:

8. The organic electronic device according to claim 5, characterized in that: The guest material includes at least one of the structures represented by formula (BD-1) to (BD-24):

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