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, belonging to the technical field of luminescent materials. An organic compound has a structure as shown in the general formula (1). The organic compound of the present application can make the organic electronic device have a higher device luminous efficiency and a longer device life.

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 advantages in the application of optoelectronic devices (such as flat panel displays and lighting) such as wide viewing angle, fast response time, low operating voltage, and thin panel thickness, and therefore have broad development potential.

[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 luminescent material systems based on fluorescence and phosphorescence 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 with 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 with such blue fluorescent materials needs to be further improved. Therefore, the development of blue fluorescent materials with narrow-band emission spectra and good stability is conducive to obtaining blue light devices with longer life and higher efficiency on the one hand, and on the other hand, it is conducive to improving the color gamut and thus improving the display effect.

[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] Therefore, there is an urgent need for a material to improve the performance of organic electroluminescent devices. 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 an organic compound having a structure as shown in the general formula (1):

[0009]

[0010] Wherein, Ar1 has a structure as shown in the general formula (2):

[0011] Ar2 and Ar3 are independently selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms, or a combination of these groups;

[0012] G is selected from the group consisting of a straight-chain alkyl group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination of these groups;

[0013] L1 and L2 are independently selected from a single bond, 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, R2 and R3 are each independently selected from: -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, 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 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0016] m2 is 0, 1, 2, 3 or 4;

[0017] m3 is 0, 1, 2, 3 or 4.

[0018] 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.

[0019] Correspondingly, the present application also provides a composition, comprising the above organic compound or the above mixture, and at least one organic solvent.

[0020] 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.

[0021] Optionally, in some embodiments of the present application, 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 pyrene compound;

[0022] The pyrene compound has a structure as shown in general formula (5):

[0023]

[0024] in,

[0025] Ar4, Ar5, Ar6, Ar7 are independently selected from: substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups containing 6 to 60 ring atoms, or combinations of these groups;

[0026] R9, 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, 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;

[0027] s is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0028] The beneficial effects of this application are:

[0029] The organic compound provided in the present application is an anthracene derivative containing a heterocyclic fused ring, 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 the device has a higher device luminous efficiency and a longer device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] 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.

[0031] Figure 1 It is a schematic diagram of the structure of an OLED device provided in a device embodiment of the present application.

[0032] The numbers in the figure are: 100, OLED device; 110, substrate; 120, anode; 130, hole injection layer; 140, hole transport layer; 150, light-emitting layer; 160, electron transport layer; 170, cathode. DETAILED DESCRIPTION

[0033] 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 this application.

[0034] In the description of the present application, the term "including" means "including but not limited to", and the term "plurality" means "two or more". Various embodiments of the present application may be presented in the form of a range; it should be understood that the description in the form of a range is only for convenience and brevity, and should not be understood as a rigid limitation on the scope of the present application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical values ​​within the range. For example, the range description from 1 to 6 should be considered to have 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 applies regardless of the range. In addition, whenever a numerical range is indicated herein, it is meant to include any cited number (fractional or integer) within the indicated range.

[0035] 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 of the related listed items.

[0036] In the present application, composition, printing ink and ink have the same meaning and can be interchangeable.

[0037] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0038] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0039] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0040] 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.

[0041] 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.

[0042] "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.

[0043] "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.

[0044] 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.

[0045] In the present application, "halogen" or "halo" refers to F, Cl, Br or I.

[0046] 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).

[0047] In the present application, "*" indicates a linking site.

[0048] 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. The six Rs on the benzene ring 1 May be the same as or different from each other.

[0049] 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. 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.

[0050] The cyclic alkyl and cycloalkyl mentioned in the present application have the same meaning and can be interchanged.

[0051] 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.

[0052] The present invention provides an organic compound having a structure as shown in the general formula (1):

[0053]

[0054] Wherein, Ar1 is selected from the structure shown in the general formula (2):

[0055] Ar2 and Ar3 are independently selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms, or a combination of these groups;

[0056] G is selected from a linear alkyl group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination of these groups;

[0057] L1 and L2 are independently selected from a single bond, a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms;

[0058] R1, R2 and R3 are each independently selected from the group consisting of: -D ​​(deuterium), linear alkyl with 1 to 20 C atoms, linear alkoxy with 1 to 20 C atoms, linear thioalkoxy with 1 to 20 C atoms, branched alkyl with 3 to 20 C atoms, branched alkoxy with 3 to 20 C atoms, branched 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 3 carbon atoms, 2 to 4 carbon ... 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;

[0059] m1 is 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0060] m2 is 0, 1, 2, 3 or 4;

[0061] m3 is 0, 1, 2, 3 or 4.

[0062] In some embodiments, each occurrence of R1, R2, and R3 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: a substituted or unsubstituted aryl group having 6 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryloxy group having 6 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryloxy group having 6 to 30 ring atoms, or a combination of these groups.

[0063] In some embodiments, each occurrence of R1, R2 and R3 is independently selected from -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 silyl group, a cyano group, an isocyano group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, 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.

[0064] In some embodiments, each occurrence of R1, R2 and R3 is independently selected from -D, a straight-chain alkyl group having 1 to 4 C atoms, a branched-chain alkyl group having 3 to 6 C atoms, a cyclic alkyl group having 3 to 6 C atoms, a silyl group, a cyano group, an isocyano group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 10 ring atoms, or a combination of these groups.

[0065] In some specific embodiments, R1, R2 and R3, when they appear each time, are independently selected from -D, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, Naphthyl, anthracenyl, phenanthryl, triazine, pyridyl, pyrimidinyl, imidazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, dibenzothienyl, dibenzofuranyl, phenyl-substituted carbazolyl, fluorenyl, fluorenyl substituted by alkyl having 1-6 C atoms, phenyl substituted by alkyl having 1-6 C atoms, naphthyl substituted by alkyl having 1-6 C atoms, phenyl substituted by one or more D, naphthyl substituted by one or more D, naphthyl substituted by phenyl, or a combination of these groups.

[0066] In some embodiments, m1 is selected from 0;

[0067] In some embodiments, m2 is 0 or 1. Each occurrence of R2 is independently selected from -D, methyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, phenyl-substituted carbazolyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl substituted with one or more methyl groups, phenanthrenyl, pyrenyl, fluoranthenyl, pyridinyl, pyrimidinyl, phenyl substituted with alkyl groups having 1-6 C atoms, naphthyl substituted with alkyl groups having 1-6 C atoms, phenyl substituted with one or more D, naphthyl substituted with one or more D, naphthyl substituted with phenyl, or a combination of these groups.

[0068] In one embodiment, m3 is 0 or 1. Each occurrence of R3 is independently selected from -D, methyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, phenyl-substituted carbazolyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl substituted with one or more methyl groups, phenanthrenyl, pyrenyl, fluoranthenyl, pyridyl, pyrimidinyl, phenyl substituted with alkyl groups having 1 to 6 C atoms, naphthyl substituted with alkyl groups having 1 to 6 C atoms, phenyl substituted with one or more D, naphthyl substituted with one or more D, naphthyl substituted with phenyl, or a combination of these groups.

[0069] In one embodiment, the organic compound has at least one of the structures shown in general formula (3-1) or general formula (3-2):

[0070]

[0071] In some embodiments, Ar2 is selected from substituted or unsubstituted aromatic groups containing 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups containing 6 to 30 ring atoms.

[0072] In some embodiments, Ar2 is selected from substituted or unsubstituted aromatic groups containing 6 to 16 ring atoms, substituted or unsubstituted heteroaromatic groups containing 6 to 16 ring atoms.

[0073] In some embodiments, Ar2 is selected from any of the following structures:

[0074]

[0075] in:

[0076] X, at each occurrence, is independently selected from CR4 or N;

[0077] Y is selected from NR5, CR6R7, SiR6R7, O, S, S=O or SO2;

[0078] R4, R5, R6, R7, 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, or 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 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 carbon atoms, 19 to 21 carbon atoms, 19 to 22 carbon atoms, 19 to 23 carbon atoms, 19 to 24 carbon atoms, 19 to 25 carbon atoms, 19 to 2 C atoms, alkoxycarbonyl, aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, amine, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, substituted or unsubstituted aryloxy groups having 5 to 60 ring atoms, substituted or unsubstituted heteroaryloxy groups having 5 to 60 ring atoms, or combinations of these groups; R6 and R7 may or may not form a ring with each other.

[0079] It is understood that, in the present application, when X is a linking site, X is C; and when Y is a linking site, Y is N.

[0080] In some specific embodiments, the structure of the organic compound is selected from any one of the structures shown in general formula (4-1)-(4-14):

[0081]

[0082]

[0083] In some specific examples, each occurrence of R4 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.

[0084] Further, each occurrence of R4 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.

[0085] The definition of the substituent is the same as above. Preferably, the substituent is selected from: -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 or a pyridyl group.

[0086] In one embodiment, X in the general formulae (4-1) to (4-14) is selected from CR4; each occurrence of R4 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 6 C atoms, a branched-chain alkyl group having 3 to 6 C atoms, and a cyclic alkyl group having 3 to 6 C atoms.

[0087] In one embodiment, each occurrence of R5 is independently selected from: a straight chain 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, 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; further, each occurrence of R5 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 occurrence of R5 is independently selected from: methyl, ethyl, isopropyl, tert-butyl, phenyl, pyridyl, pyrimidinyl, triazine, biphenyl, terphenyl or naphthyl.

[0088] In some specific examples, R6 and R7 are independently selected from: -H, -D, straight-chain alkyl groups with 1 to 8 C atoms, branched 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, R6 and R7 are independently selected from: -H, -D, methyl, ethyl, isopropyl, phenyl, pyridyl, pyrimidyl, triazine, biphenyl, terphenyl or naphthyl.

[0089] In a specific embodiment, Ar2 is selected from any one of the following structures:

[0090]

[0091] Wherein: * indicates the connection site.

[0092] In one embodiment, G is selected from 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, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms, or a combination of these groups.

[0093] In one embodiment, G 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.

[0094] In a specific embodiment, the G is selected from any of the following structures:

[0095]

[0096] in,

[0097] X, at each occurrence, is independently selected from CR4 or N;

[0098] Y is selected from NR5, CR6R7, SiR6R7, O, S, S=O or SO2;

[0099] R4, R5, R6, R7, 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. R6 and R7 may or may not form a ring with each other.

[0100] It is understood that, in the present application, when X is a linking site, X is C; and when Y is a linking site, Y is N.

[0101] In one embodiment, in formula (3-1) and formula (4-1)-(4-7), G is independently selected from the groups shown in formula (A-1)-(A-7):

[0102]

[0103] Wherein, * indicates the connection site.

[0104] In another embodiment, in formula (3-2), formula (4-8)-(4-14), G is independently selected from the group shown in formula (B-1)-(B-4):

[0105]

[0106] Wherein, * indicates the connection site.

[0107] Preferably, in (A-1)-(A-7) and / or (B-1)-(B-4), X is independently selected from CR4 or N at each occurrence; R4 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.

[0108] The definition of the substituent is the same as above. Preferably, the substituent is selected from -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.

[0109] In one embodiment, in (A-1)-(A-7) and / or (B-1)-(B-4), each occurrence of R4 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 6 C atoms, a branched-chain alkyl group having 3 to 6 C atoms, a cyclic alkyl group having 3 to 6 C atoms, and a phenyl group. In one embodiment, L1 and L2 are independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, and a substituted or unsubstituted heteroaromatic group having 6 to 20 ring atoms. Further, L1 and L2 are independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, and a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms.

[0110] Further, in some embodiments, L1 and L2 are each independently selected from a single bond or any of the following structures:

[0111]

[0112] in:

[0113] X1, at each occurrence, is independently selected from CR8 or N;

[0114] R8, 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.

[0115] It is understood that, in the present application, when X1 is a linking site, X1 is C.

[0116] In some specific examples, each occurrence of R8 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.

[0117] In some embodiments, L1 and L2 are independently selected from a single bond or at least one of the following groups (but not limited thereto):

[0118]

[0119]

[0120] As an example, the organic compound may include but is not limited to at least one of the following structures:

[0121]

[0122]

[0123]

[0124]

[0125] In some embodiments, the organic compound of the present application can be used as an organic functional material in a functional layer of an organic electronic device, in particular an OLED device. The functional material can be, but is not limited to, 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) or an organic dye.

[0126] In some embodiments, the organic compound of the present application can be used as a light-emitting material in a light-emitting layer of an organic electronic device. In some preferred embodiments, the organic compound of the present application is used as a host material in a light-emitting layer of an organic electronic device.

[0127] The present application also relates to a mixture, comprising at least one of the organic compounds and at least another organic functional material. The another organic functional material may be, but is not limited to, hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials, guest materials and organic dyes known in the art for use in organic electronic devices.

[0128] In some embodiments, the another organic functional material is selected from a guest material. Further, the another organic functional material is selected from a blue light guest material. Further, the blue light guest is a pyrene compound as shown in the following general formula (5).

[0129] The present application also relates to a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent.

[0130] Specifically, the at least one organic solvent is selected from aromatic or heteroaromatic based solvents, ester based solvents, aromatic ketone based solvents, aromatic ether based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate ester compounds or phosphate ester compounds.

[0131] The aromatic or heteroaromatic based solvent may be selected from, but 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.

[0132] The ester-based solvent may be selected from, but not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. At least one of octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate is particularly preferred.

[0133] The aromatic ketone-based solvent may be selected from, but not limited to, 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof, such as at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone and 2-methylpropiophenone.

[0134] The aromatic ether-based solvent may be selected from, but is not limited to, at least one of 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-ethylphenethyl 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, and ethyl-2-naphthyl ether.

[0135] The aliphatic ketone-based solvent can be selected from, but 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.; or an aliphatic ether, for example, 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.

[0136] It is understood that the organic solvent may be used alone or as a mixed solvent of two or more organic solvents.

[0137] In some embodiments, the composition of the present application comprises at least one organic compound or mixture as described above, and at least one organic solvent, and may further comprise another organic solvent.

[0138] The other organic solvent can be selected from but 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 (DMSO), tetralin, decalin and indene.

[0139] In some preferred embodiments, the organic solvent suitable for the present application is a solvent having a Hansen solubility parameter within the following range:

[0140] δd (dispersion force) is in the range of 17.0-23.2 MPa1 / 2, especially in the range of 18.5-21.0 MPa1 / 2;

[0141] δp (polar force) is in the range of 0.2-12.5 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2;

[0142] δh (hydrogen bonding force) is in the range of 0.9-14.2 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2.

[0143] In some embodiments, in the composition of the present application, the boiling point of the organic solvent should be considered when selecting. In at least some embodiments, 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.

[0144] It is understood that the organic solvent can be evaporated from the composition system to form a film comprising the organic compound of the present application.

[0145] In some embodiments, the composition is a solution. In other embodiments, the composition is a suspension.

[0146] In the composition, the content of the organic compound or the mixture may be 0.01-10 wt %, preferably 0.1-8 wt %, more preferably 0.2-5 wt %, and further more preferably 0.25-3 wt %.

[0147] 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. In some embodiments, the composition is used to prepare an organic electronic device by a printing or coating preparation method. The printing or coating preparation method can be, but is not limited to, inkjet printing, gravure printing, spray printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spray coating, brush coating, pad printing, slit extrusion coating, etc. Preferred are gravure printing, spray printing and inkjet printing.

[0148] The solution or suspension may further include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives may be selected from but not limited to at least one of surfactant compounds, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives. Different printing or coating methods may have different requirements for coatings or printing inks, and the concentration, viscosity, etc. of the solution or suspension may be adjusted accordingly to adapt to different printing or coating methods.

[0149] The present application also provides an application of the organic compound, mixture or composition as described above in an organic electronic device. The technical solution is as follows:

[0150] The present application provides an organic electronic device, comprising the organic compound or mixture as described above, or prepared from the composition.

[0151] Furthermore, the organic electronic device comprises an anode, a cathode, and one or more organic functional layers located between the anode and the cathode; the organic functional layers comprise the organic compound or mixture as described above or are prepared from the above composition.

[0152] The organic functional layer is selected from a hole injection layer (HIL), a hole transport layer (HTL), an emitting layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0153] The organic electronic device may be, but is not limited to, an organic light emitting diode (OLED device), an organic photovoltaic cell (OPV), an organic light emitting cell (OLEEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor, and an organic plasmon emitting diode (Organic Plasmon Emitting Diode), etc. The organic electronic device is preferably an OLED device. Further, in one embodiment, the organic compound is used for the light emitting layer of the OLED device, and the light emitting layer comprises the organic compound or mixture as described above, or is prepared from the composition.

[0154] In some embodiments, the one or more organic functional layers of the organic electronic device at least include a light-emitting layer. The material of the light-emitting layer includes a host material and a guest material. The host material includes the organic compound described above, and the guest material includes a pyrene organic compound.

[0155] The present application further relates to an organic electronic device, the organic electronic device comprising: a cathode, an anode, and one or more organic functional layers located between the cathode and the anode, the organic functional layers at least comprising a light-emitting layer, the light-emitting layer material comprising a host material and a guest material, the host material comprising an organic compound of general formula (1), the guest material comprising a pyrene compound;

[0156] The pyrene compound (pyrene organic compound) has a structure as described in general formula (5):

[0157]

[0158] in:

[0159] Ar4, Ar5, Ar6, Ar7 are independently selected from: substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups containing 6 to 60 ring atoms, or combinations of these groups;

[0160] R9, 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, 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;

[0161] s is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0162] The organic compound is shown in the general formula (1), and further description is given in detail above, which will not be repeated here.

[0163] In some embodiments, Ar4, Ar5, Ar6, and Ar7 are independently selected from: a substituted or unsubstituted aromatic group containing 6 to 14 ring atoms, a substituted or unsubstituted heteroaromatic group containing 6 to 14 ring atoms, or a combination of these groups.

[0164] Further, in some embodiments, Ar4, Ar5, Ar6, and Ar7 each independently comprise any of the following structures:

[0165]

[0166] in:

[0167] Each time V appears, it is independently selected from CR 10 or N;

[0168] W is selected from NR 11 , CR 11 R 12 、SiR 11 R 12 , O, S, S=O or SO2;

[0169] R 10 , R 11 , R 12 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, ...

[0170] Furthermore, in some embodiments, R9, R 10 , R 11 , R 12Each occurrence is independently selected from: -H, -D, straight-chain alkyl having 1 to 10 C atoms, branched-chain alkyl or cyclic alkyl having 3 to 10 C atoms or phenyl.

[0171] In some embodiments, the pyrene organic compound is selected from the following structural formula:

[0172]

[0173] Among them, R 10 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, cyclic alkyl or phenyl.

[0174] Furthermore, in some embodiments, the pyrene organic compound is selected from the following general formula:

[0175]

[0176] Among them, R 10 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, cyclic alkyl or phenyl; W is as described above.

[0177] As an example, the pyrene compound described in the present application can be selected from but not limited to any one of the following structural formulas (BD-1) to (BD-24):

[0178]

[0179]

[0180] It is understandable that the organic electronic device may also be provided with some functional layers conventionally used in organic electronic devices to help improve device performance, such as an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, a hole transport layer, a hole injection layer, a hole blocking layer, a light extraction layer, etc.

[0181] In one embodiment, the organic electronic device comprises a cathode, an electron transport layer, a light-emitting layer, a hole transport layer, and an anode.

[0182] In one embodiment, the organic electronic device comprises a cathode, an electron transport layer, a light-emitting layer, a hole transport layer, a hole injection layer, and an anode.

[0183] In one embodiment, the organic electronic device comprises a cathode, an electron transport layer, a light emitting layer, an electron blocking layer, a hole transport layer, a hole injection layer, and an anode.

[0184] 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.

[0185] In some embodiments, the organic electronic device further comprises a substrate. The substrate may be located on the side of the anode away from the light-emitting layer, or on the side of the cathode away from the light-emitting layer. The substrate may be opaque or transparent. It is understood that when the substrate is transparent, the organic electronic device is a transparent light-emitting device. The substrate may also be rigid or elastic, for example, the material of the substrate may be plastic, metal, semiconductor wafer or glass. Preferably, the substrate has a smooth surface, and a substrate without surface defects is a particularly ideal choice. In a preferred embodiment, the substrate is a flexible substrate. The material of the flexible substrate may be a polymer film or plastic. The glass transition temperature Tg of the flexible substrate is above 150°C, preferably above 200°C, more preferably above 250°C, and most preferably above 300°C. As an example, the material of the flexible substrate may be polyethylene terephthalate (PET) (PET) or polyethylene glycol (2,6-naphthalene) (PEN).

[0186] The material of the anode is an anode material known in the art for organic electronic devices, such as a conductive metal, a conductive metal oxide or a conductive polymer. In some embodiments, the work function of the anode material and the HOMO energy level or valence band energy level of the p-type semiconductor material as a hole injection layer or a hole transport layer or an electron blocking layer are less than 0.5 eV, preferably less than 0.3 eV, and preferably less than 0.2 eV. As an example, the material of the anode can be selected from but not limited to at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO and aluminum-doped zinc oxide (AZO). 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.

[0187] The material of the cathode is a cathode material known in the art for organic electronic devices, such as a conductive metal or a conductive metal oxide. In some embodiments, the absolute value of the difference between the work function of the cathode material and the LUMO energy level or conduction band energy level of the luminophore in the light-emitting layer or the n-type semiconductor material as the electron injection layer or the electron transport layer or the hole blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes of OLEDs may be used as cathode materials for the device of the present application. As an example, the material of the cathode may be selected from but 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 and ITO. 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.

[0188] The material of the hole transport layer is a hole transport layer material known in the art, for example, it can be selected from but not limited to poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTXX), 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene (spiro-omeTXD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TXPC), N,N'-bis(1-naphthyl)-N,N'-diphenyl-1,1'-diphenyl-4, At least one of 4′-diamine (NPB), 4,4′-bis(N-carbazole)-1,1′-biphenyl (CBP), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4′-(N-(p-butylphenyl))diphenylamine)] (TFB), poly(9-vinylcarbazole) (PVK), polytriphenylamine (Poly-TPD), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT:PSS) and 4,4′,4″-tri(carbazole-9-yl)triphenylamine (TCTX).

[0189] The material of the electron transport layer is a material known in the art for electron transport layers, for example, can be selected from but not limited to at least one of ET and Liq, PBD (2-(4-biphenyl)-5-phenyloxadiazole), 8-hydroxyquinoline aluminum (Xlq3) and graphene.

[0190] Among them, the chemical structural formulas of ET and Liq are as follows:

[0191]

[0192] The material of the hole injection layer is a material known in the art for hole injection layers, for example, it can be selected from but not limited to at least one of 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HXT-CN), PEDOT (polyethylene dioxythiophene), PEDOT:PSS and its derivatives doped with s-MoO3 (PEDOT:PSS:s-MoO3).

[0193] In at least one preferred embodiment, the organic electronic device is an OLED device. More preferably, the organic electronic device is a solution-type OLED.

[0194] The light emitting wavelength of the organic electronic device is between 300nm and 1000nm, preferably between 350nm and 900nm, and more preferably between 400nm and 800nm.

[0195] The present application also relates to an electronic device comprising the organic electronic device, which may be, but is not limited to, a display device, a lighting device, a light source, a sensor, and the like.

[0196] 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.

[0197] Example 1

[0198] This embodiment provides an organic compound (Compound 1).

[0199] The synthetic route of compound 1 in this example is as follows:

[0200]

[0201] Synthesis of intermediate 1-1:

[0202] Dissolve indole (23.4 g, 200 mmol) in DMF (100 ml), dissolve bromine (32 g, 200 mmol) in DMF (50 ml), and slowly add dropwise to the indole solution. Stir at room temperature for 2 h. After the reaction is completed, add sodium thiosulfate aqueous solution to remove the remaining bromine, and remove most of the solvent by rotary evaporation, then extract and wash the liquid, and perform organic phase column chromatography (eluent PE: DCM = 5: 1) and recrystallize to obtain intermediate 1-1, yield: 94%. MS (ASAP) = 195.0.

[0203] Synthesis of intermediate 1-2:

[0204] Intermediate 1-1 (10 g, 51 mmol) and 2-nitro-5-chlorophenylboronic acid (12.4 g, 61 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd(PPh3)4 (2.9 g, 2.5 mmol) and potassium carbonate (27.6 g, 200 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 was PE:DCM=3:1) and recrystallized to obtain intermediate 1-2 with a yield of 63%. MS (ASAP) = 272.0.

[0205] Synthesis of intermediate 1-3:

[0206] Place intermediate 1-2 (8 g, 29 mmol) in a 100 ml two-necked bottle, add 30 ml of dichlorobenzene until completely dissolved, add triethyl phosphite (16.6 g, 100 mmol), and stir at 180°C for 12 h under a nitrogen atmosphere. After cooling, remove the solvent by distillation under reduced pressure, then add dichloromethane, wash the liquid with water, perform organic phase column chromatography (eluent: PE:DCM=5:1) and recrystallize to obtain intermediate 1-3 with a yield of 53%. MS (ASAP) = 240.1.

[0207] Synthesis of intermediate 1-4:

[0208] Weigh intermediate 1-3 (10 g, 41.7 mmol), iodobenzene (20.4 g, 100 mmol), Pd2(dba)3 (2.9 g, 3.2 mmol), t-Bu3P (0.78 g, 3.9 mmol), sodium tert-butoxide (15.5 g, 162 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, and react at 80°C for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE:DCM=6:1) to obtain a white solid, namely intermediate 1-4. Yield: 82%. MS (ASAP) = 392.1.

[0209] Synthesis of compound 1:

[0210] Intermediate 1-4 (3.9 g, 10 mmol), 10-(1-naphthyl)-9-anthraceneboronic acid (5.4 g, 14 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 mmol) and potassium carbonate (6.9 g, 50 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 column chromatographed (eluent was PE:DCM=5:1) and recrystallized to obtain compound 1 with a yield of 58%. MS (ASAP) = 660.3.

[0211] Example 2

[0212] This example provides an organic compound (Compound 2).

[0213] The synthetic route of compound 2 in this example is as follows:

[0214]

[0215] Synthesis of intermediate 2-1:

[0216] Weigh intermediate 1-1 (10 g, 41.7 mmol), iodobenzene (8.6 g, 42 mmol), Pd2(dba)3 (1.9 g, 2.1 mmol), t-Bu3P (0.51 g, 2.5 mmol), sodium tert-butoxide (20 g, 209 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, and react at 80°C for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE:DCM=8:1) to obtain a white solid, namely intermediate 2-1. Yield: 72%. MS (ASAP) = 271.0.

[0217] Synthesis of intermediate 2-2:

[0218] Intermediate 2-1 (10 g, 37 mmol) and 2-nitro-5-chlorophenylboronic acid (7.4 g, 37 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd(PPh3)4 (0.86 g, 0.74 mmol) and potassium carbonate (25.5 g, 185 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:DCM=3:1) and recrystallized to obtain intermediate 2-2 with a yield of 81%. MS (ASAP) = 348.1.

[0219] Synthesis of intermediate 2-3:

[0220] In a 100 ml two-necked bottle, add intermediate 2-2 (8 g, 23 mmol), add 30 ml of dichlorobenzene until completely dissolved, add triethyl phosphite (19.1 g, 115 mmol), and stir at 180 ° C for 12 h under nitrogen atmosphere. After cooling, remove the solvent by vacuum distillation, then add dichloromethane, wash with water, and the organic phase is subjected to column chromatography (eluent PE: DCM = 4: 1) and recrystallized to obtain intermediate 2-3, yield: 57%. MS (ASAP) = 316.1.

[0221] Synthesis of intermediate 2-4:

[0222] Weigh intermediate 2-3 (6.3 g, 20 mmol), 2-iodonaphthalene (5.1 g, 20 mmol), Pd2(dba)3 (0.92 g, 1 mmol), t-Bu3P (0.24 g, 1.2 mmol), sodium tert-butoxide (20 g, 209 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, and react at 80°C for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE:DCM=8:1) to obtain a white solid, namely intermediate 2-4. Yield: 78%. MS (ASAP) = 442.1.

[0223] Synthesis of compound 2:

[0224] Intermediate 2-4 (4.4 g, 10 mmol) and 10-phenyl-9-anthraceneboronic acid (4.2 g, 14 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 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 column chromatographed (eluent was PE:DCM=5:1) and recrystallized to obtain compound 2 with a yield of 64%. MS (ASAP) = 660.3.

[0225] Example 3

[0226] This example provides an organic compound (Compound 3).

[0227] The synthetic route of compound 3 in this example is as follows:

[0228]

[0229] Synthesis of intermediate 3-1:

[0230] Weigh intermediate 2-3 (6.3 g, 20 mmol), 2-bromodibenzofuran (4.9 g, 20 mmol), Pd2(dba)3 (0.92 g, 1 mmol), t-Bu3P (0.24 g, 1.2 mmol), sodium tert-butoxide (19 g, 200 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, and react at 80°C for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE:DCM=8:1) to obtain a white solid, namely intermediate 3-1. Yield: 72%. MS (ASAP) = 482.1.

[0231] Synthesis of compound 3:

[0232] Intermediate 3-1 (4.8 g, 10 mmol), 10-deuterated phenyl-9-anthraceneboronic acid (4.2 g, 14 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 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 column chromatographed (eluent was PE:DCM=5:1) and recrystallized to obtain compound 3 with a yield of 66%. MS (ASAP) = 705.3.

[0233] Example 4

[0234] This example provides an organic compound (Compound 4).

[0235] The synthetic route of compound 4 in this example is as follows:

[0236]

[0237] Synthesis of intermediate 4-1:

[0238] Weigh intermediate 2-3 (6.3 g, 20 mmol), 2-bromobiphenyl (4.6 g, 20 mmol), Pd2(dba)3 (0.92 g, 1 mmol), t-Bu3P (0.24 g, 1.2 mmol), sodium tert-butoxide (19 g, 200 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, and react at 80°C for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE:DCM=8:1) to obtain a white solid, namely intermediate 4-1. Yield: 77%. MS (ASAP) = 468.1.

[0239] Synthesis of compound 4:

[0240] Intermediate 4-1 (4.7 g, 10 mmol), 10-(2-deuterated naphthyl)-9-anthraceneboronic acid (5.0 g, 14 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 mmol) and potassium carbonate (6.9 g, 50 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 column chromatographed (eluent was PE:DCM=5:1) and recrystallized to obtain compound 4 with a yield of 71%. MS (ASAP) = 743.3.

[0241] Example 5

[0242] This example provides an organic compound (Compound 5).

[0243] The synthetic route of compound 5 in this example is as follows:

[0244]

[0245] Synthesis of intermediate 5-1:

[0246] 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 5-1 with a yield of 76%. MS (ASAP) = 408.1.

[0247] Synthesis of intermediate 5-2:

[0248] 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, 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.

[0249] Synthesis of compound 5:

[0250] Intermediate 5-2 (3.7 g, 10 mmol) and intermediate 3-1 (4.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 mmol) and potassium carbonate (6.2 g, 45 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 column chromatographed and recrystallized to obtain compound 5 with a yield of 48%. MS (ASAP) = 776.3.

[0251] Example 6

[0252] This embodiment provides an organic compound (Compound 6).

[0253] The synthetic route of compound 6 in this example is as follows:

[0254]

[0255] Synthesis of intermediate 6-1:

[0256] 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 intermediate 6-1 with a yield of 58%. MS (ASAP) = 422.0.

[0257] Synthesis of intermediate 6-2:

[0258] 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, 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.

[0259] Synthesis of compound 6:

[0260] Intermediate 6-2 (3.9 g, 10 mmol) and intermediate 4-1 (4.7 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 mmol) and potassium carbonate (4.1 g, 30 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 column chromatographed and recrystallized to obtain compound 6 with a yield of 69%. MS (ASAP) = 776.3.

[0261] Example 7

[0262] This embodiment provides an organic compound (Compound 7).

[0263] The synthetic route of compound 7 in this example is as follows:

[0264]

[0265] Synthesis of intermediate 7-1:

[0266] Intermediate 2-1 (10 g, 37 mmol) and 2-nitrobenzene boronic acid (6.2 g, 37 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd(PPh3)4 (0.86 g, 0.74 mmol) and potassium carbonate (25.5 g, 185 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:DCM=3:1) and recrystallized to obtain intermediate 7-1 with a yield of 72%. MS (ASAP) = 314.1.

[0267] Synthesis of intermediate 7-2:

[0268] In a 100ml two-necked bottle, add intermediate 7-1 (10g, 32mmol), add 30ml dichlorobenzene until completely dissolved, add triethyl phosphite (26g, 159mmol), and stir at 180°C for 12h under nitrogen atmosphere. After cooling, remove the solvent by distillation under reduced pressure, then add dichloromethane, wash the liquid with water, and the organic phase is subjected to column chromatography (eluent PE:DCM=3:1) and recrystallized to obtain intermediate 7-2, yield: 59%. MS (ASAP) = 282.1.

[0269] Synthesis of compound 7:

[0270] Weigh intermediate 7-2 (5.6 g, 20 mmol), 10-(1-naphthyl)-9-bromoanthracene (11.5 g, 30 mmol), Pd2(dba)3 (0.92 g, 1 mmol), t-Bu3P (0.24 g, 1.2 mmol), sodium tert-butoxide (20 g, 209 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, and react at 80°C for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE:DCM=8:1) to obtain a white solid, namely compound 7. Yield: 67%. MS (ASAP) = 584.2.

[0271] Example 8

[0272] This example provides an organic compound (Compound 8).

[0273] The synthetic route of compound 8 in this example is as follows:

[0274]

[0275] Synthesis of intermediate 8-1:

[0276] 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 ml / 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 8-1 with a yield of 64%. MS (ASAP) = 456.1.

[0277] Synthesis of intermediate 8-2:

[0278] Intermediate 8-1 (4.6 g, 10 mmol) and 4-chlorophenylboronic acid (1.6 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 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 8-2 with a yield of 55%. MS (ASAP) = 488.1.

[0279] Synthesis of compound 8:

[0280] Weigh intermediate 8-2 (9.8 g, 20 mmol), intermediate 7-2 (5.6 g, 20 mmol), Pd2(dba)3 (0.92 g, 1 mmol), t-Bu3P (0.24 g, 1.2 mmol), sodium tert-butoxide (20 g, 209 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, and react at 80°C for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE:DCM=8:1) to obtain a white solid, namely compound 8. Yield: 73%. MS (ASAP) = 734.3.

[0281] Example 9

[0282] This embodiment provides an organic compound (Compound 9).

[0283] The synthetic route of compound 9 in this example is as follows:

[0284]

[0285] Synthesis of intermediate 9-1:

[0286] 9-Bromo-10-(4-tert-butylphenyl)anthracene (3.9 g, 10 mmol) and 6-bromo-2-naphthaleneboronic acid (2.5 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 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 intermediate 9-1 with a yield of 71%. MS (ASAP) = 514.1.

[0287] Synthesis of compound 9:

[0288] Weigh intermediate 9-1 (10.3 g, 20 mmol), intermediate 7-2 (5.6 g, 20 mmol), Pd2(dba)3 (1.8 g, 2.0 mmol), t-Bu3P (0.51 g, 2.5 mmol), sodium tert-butoxide (9.6 g, 100 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, react at 80°C for 12 h. Spin dry, wash with water, column chromatography (eluent: PE:DCM=4:1) to obtain a white solid with a yield of 81%. MS (ASAP) = 716.3.

[0289] Example 10

[0290] This embodiment provides an organic compound (Compound 10).

[0291] The synthetic route of compound 10 in this example is as follows:

[0292]

[0293] Synthesis of intermediate 10-1:

[0294] Weigh intermediate 1-1 (10 g, 41.7 mmol), 2-iodonaphthalene (10.7 g, 42 mmol), Pd2(dba)3 (1.9 g, 2.1 mmol), t-Bu3P (0.51 g, 2.5 mmol), sodium tert-butoxide (20 g, 209 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, and react at 80°C for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE:DCM=8:1) to obtain a white solid, namely intermediate 10-1. Yield: 64%. MS (ASAP) = 321.0.

[0295] Synthesis of intermediate 10-2:

[0296] Intermediate 10-1 (10 g, 31 mmol) and 2-nitrobenzene boronic acid (5.2 g, 31 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 10 ml), and Pd(PPh3)4 (0.86 g, 0.74 mmol) and potassium carbonate (25.5 g, 185 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:DCM=3:1) and recrystallized to obtain intermediate 10-2 with a yield of 79%. MS (ASAP) = 364.1.

[0297] Synthesis of intermediate 10-3:

[0298] In a 100 ml two-necked bottle, add intermediate 10-2 (10 g, 27 mmol), add 30 ml of dichlorobenzene until completely dissolved, add triethyl phosphite (23 g, 137 mmol), and stir at 180 ° C for 12 h under nitrogen atmosphere. After cooling, remove the solvent by vacuum distillation, then add dichloromethane, wash with water, and the organic phase is subjected to column chromatography (eluent PE: DCM = 4: 1) and recrystallized to obtain intermediate 10-3, yield: 46%. MS (ASAP) = 332.1.

[0299] Synthesis of compound 10:

[0300] Weigh the intermediate 10-3 (6.6 g, 20 mmol), 10-phenyl-9-(4-bromophenyl)anthracene (8.2 g, 20 mmol), Pd2(dba)3 (0.92 g, 1 mmol), t-Bu3P (0.24 g, 1.2 mmol), sodium tert-butoxide (20 g, 209 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, and react at 80°C for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE:DCM=8:1) to obtain a white solid, namely compound 10. Yield: 72%. MS (ASAP) = 660.3.

[0301] Embodiment 11

[0302] This embodiment provides an organic compound (Compound 11).

[0303] The synthetic route of compound 11 in this example is as follows:

[0304]

[0305] Synthesis of intermediate 11-1:

[0306] 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 ml / 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 73%. MS (ASAP) = 456.1.

[0307] Synthesis of intermediate 11-2:

[0308] Intermediate 11-1 (4.6 g, 10 mmol) and 4-chlorophenylboronic acid (1.6 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 ml / 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 11-2 with a yield of 59%. MS (ASAP) = 488.1.

[0309] Synthesis of compound 11:

[0310] Weigh intermediate 11-2 (9.8 g, 20 mmol), intermediate 10-3 (6.6 g, 20 mmol), Pd2(dba)3 (0.92 g, 1 mmol), t-Bu3P (0.24 g, 1.2 mmol), sodium tert-butoxide (20 g, 209 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, and react at 80°C for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE:DCM=8:1) to obtain a white solid, namely compound 11. Yield: 77%. MS (ASAP) = 784.3.

[0311] Example 12

[0312] This embodiment provides an organic compound (Compound 12).

[0313] The synthetic route of compound 12 in this example is as follows:

[0314]

[0315] Synthesis of intermediate 12-1:

[0316] 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 ml / 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 column chromatographed and recrystallized to obtain intermediate 12-1 with a yield of 65%. MS (ASAP) = 448.1

[0317] Synthesis of compound 12:

[0318] Weigh intermediate 12-1 (9.0 g, 20 mmol), intermediate 10-3 (6.6 g, 20 mmol), Pd2(dba)3 (1.8 g, 2.0 mmol), t-Bu3P (0.51 g, 2.5 mmol), sodium tert-butoxide (9.6 g, 100 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, and react at 80°C for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE:DCM=5:1) to obtain a white solid with a yield of 83%. MS (ASAP) = 700.3.

[0319] Comparative Example 1

[0320] The organic compound in this comparative example is BH-Ref, and its chemical structure is as follows:

[0321]

[0322] The following is a detailed description of the preparation process of an organic electronic device (OLED device) comprising the above compound through a specific embodiment. The structure of the OLED device is: ITO / HIL / HTL / EML / ETL / cathode. Figure 1 , Figure 1 The structure of an OLED device is shown. The OLED device 100 includes an anode (ITO) 120, a hole injection layer (HIL) 130, a hole transport layer (HTL) 140, a light emitting layer (EML) 150, an electron transport layer (ETL) 160, and a cathode 170 stacked on a substrate 110.

[0323] Preparation of OLED devices:

[0324] The structural formulas of Liq, ET and BD-1, the compounds that may be involved in the preparation of OLEDs, are as follows:

[0325]

[0326] Device Example 1

[0327] This embodiment provides an OLED device, and the preparation steps are as follows:

[0328] a. Cleaning of ITO (indium tin oxide) conductive glass substrate: Use various solvents (such as one or more of chloroform, acetone or isopropyl alcohol) for cleaning, and then perform ultraviolet ozone treatment.

[0329] b. HIL (hole injection layer, 40 nm): 40 nm PEDOT (polyethylenedioxythiophene, Clevios TM AI4083) was spin-coated as the HIL in a clean room and treated on a hot plate at 180°C for 10 min.

[0330] c. HTL (hole transport layer, 20 nm): 20 nm of PVK (Sigma Aldrich, average Mn 25,000-50,000) was spin-coated in a nitrogen glove box from 5 mg / ml PVK added to toluene solvent, followed by treatment on a hot plate at 180°C for 60 min.

[0331] 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), and the solution solubility was 15 mg / ml. It was then treated on a hot plate at 140° C. for 10 minutes. The host used compound 1 of Example 1, and the guest material was selected from BD-1.

[0332] 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 two layers 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 cathode with a thickness of 100 nm was deposited.

[0333] f. Packaging: The device is packaged with UV-curable resin in a nitrogen glove box.

[0334] Device Examples 2 to 12

[0335] The technical solutions of the OLED devices of device embodiments 2-12 are different from those of device embodiment 1, except that the main material in embodiment 1 is replaced by compound 1 with the corresponding compound in Table 1; and other conditions are the same as those of device embodiment 1.

[0336] Device Comparison Example 1

[0337] The embodiment of the OLED device of device comparative example 1 is different from that of device example 1 in that compound 1 in example 1 is replaced by the corresponding compound in Table 1 (BH-ref).

[0338] Test Example 1

[0339] The current-voltage (JV) characteristics of each OLED device were characterized by characterization equipment, and important parameters such as luminous efficiency (CE@1knits) and lifetime (LT90@1knits) were recorded. The results are shown in Table 1.

[0340] Table 1

[0341]

[0342] It can be seen from Table 1 that compared with the blue light OELD device prepared by using the organic compound of Comparative Example 1 as the main material in the light-emitting layer (device comparative example 1), the OELD devices 1 to 12 prepared by using the organic compounds 1 to 12 of Examples 1 to 12 as the main material in the light-emitting layer in the present application have higher luminous efficiency and longer life. Specifically, the luminous efficiency of the blue light OELD device prepared by using the compounds 1 to 12 of Examples 1 to 12 as the main material in the light-emitting layer is in the range of 5-8 cd / A, which has a more excellent luminous efficiency.

[0343] In summary, the organic compound provided by the present application is an anthracene derivative containing heterocyclic fused rings, which has fluorescence emission at a blue light wavelength and can be used as a main material in the light-emitting layer of an organic electronic device. Moreover, the use of the organic compound of the present application can enable the organic electronic device to have a higher luminous efficiency and a longer device life.

[0344] 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.

[0345] 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.

[0346] 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 general formula (3-2): Ar2 is selected from Any of; Ar3 is selected from phenyl or naphthyl; G is selected from phenyl or naphthyl; L1 and L2 are each independently selected from a single bond; R1, R2 and R3 are all H; m1 is 0, 1, 2, 3, 4, 5, 6, 7 or 8; m2 is 0, 1, 2, 3 or 4; m3 is 0, 1, 2, 3 or 4.

2. An organic compound, characterized in that The organic compound comprises at least one of the following structures:

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

4. A composition, characterized in that The method comprises the organic compound according to any one of claims 1 to 2 or the mixture according to claim 3, and further comprises an organic solvent.

5. An organic electronic device, characterized in that: The invention comprises an anode, a cathode and an organic functional layer located between the anode and the cathode; the organic functional layer comprises the organic compound according to any one of claims 1 to 2 or the mixture according to claim 3, or is prepared from the composition according to claim 4.

6. The organic electronic device according to claim 5, 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 pyrene compound; The pyrene compound has a structure as shown in general formula (5): in, Ar4, Ar5, Ar6, Ar7 are independently selected from: substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups containing 6 to 60 ring atoms, or combinations of these groups; R9, 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, 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; s is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

7. The organic electronic device according to claim 5, characterized in that: The Ar4, Ar5, Ar6, and Ar7 are independently selected from at least one of the following structures: in, Each time V appears, it is independently selected from CR 10 or N; W is selected from NR 11 , CR 11 R 12 、SiR 11 R 12 , O, S, S=O or SO2; R 10 , R 11 , R 12 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, ...

8. The organic electronic device according to claim 6, characterized in that: The pyrene compounds include the following structures:

9. The organic electronic device according to claim 6, characterized in that: The pyrene compound includes at least one of the following structures:

10. The organic electronic device according to claim 6, characterized in that: The pyrene compound includes at least one of the structures shown in formula (BD-1) to (BD-24): 。

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