Organic compound containing fluoranthene and application of organic compound in organic electronic device

Abstract

The invention belongs to the technical field of organic electroluminescence, and particularly relates to an organic compound containing fluoranthene and application of the organic compound in an organic electronic device. The organic compound provided by the invention can be used as a single host material to be matched with a proper guest material in a phosphorescent device, and can improve the luminous efficiency and service life of the device. The invention further provides a solution of the light-emitting device which is low in manufacturing cost, high in efficiency and long in service life.

Description

Technical Field

[0001] This application belongs to the technical field of organic electroluminescence, and more specifically, relates to an organic compound containing fluoranthene and its application in organic electronic devices. Background Art

[0002] In the context of the continuous development of information technology, people's demand for display technologies and lighting devices is increasing day by day. Organic light-emitting diodes (OLEDs) have been widely used in the fields of lighting and display due to their advantages such as active light emission, high contrast ratio, high color gamut, wide viewing angle, no glare, fast response speed, and easy realization of flexible display, and are considered by the industry to be one of the most promising display and lighting technologies.

[0003] The basic device structure of an OLED is composed of a thin and transparent indium tin oxide (ITO) with conductive properties, connected to the positive electrode of the power supply, and another metal cathode, wrapped into a sandwich-like structure. The entire structure layer includes: a hole injection / transport layer (HIL / HTL), a light-emitting layer (EML), and an electron injection / transport layer (EIL / ETL). When power is supplied to an appropriate voltage, the holes injected from the positive electrode and the electrons injected from the cathode will recombine in the light-emitting layer to generate light, and the primary colors red, green, and blue (RGB) are generated according to the materials used, constituting the basic colors.

[0004] In order to improve the luminous efficiency of organic light-emitting diodes, various luminescent material systems based on fluorescence and phosphorescence have been developed. Organic light-emitting diodes using fluorescent materials have the characteristic of high reliability, but their internal electroluminescence quantum efficiency is limited to 25% under electrical excitation because the ratio of singlet excited states to triplet excited states of excitons generated by current is 1:3. In contrast, organic light-emitting diodes using phosphorescent materials have achieved an almost 100% internal electroluminescence quantum efficiency, so the development of phosphorescent emitters has been widely studied.

[0005] The phosphorescent light-emitting layer usually adopts a host-guest structure, and the phosphorescent host material plays an important role in improving color purity, luminous efficiency, and stability. Therefore, in order to improve the optoelectronic performance of organic electroluminescent devices, it is urgent to develop new phosphorescent light-emitting layer host materials. Summary of the Invention

[0006] Aiming at the defects of the prior art, this application provides an organic compound containing fluoranthene, which can be used as a host material in phosphorescent OLED devices, thereby improving the optoelectronic performance of the devices.

[0007] To achieve the above object, in the first aspect, this application provides an organic compound containing fluoranthene, having the structure shown in formula (I),

[0008] (I) Wherein: L 1 and L 2 are independently selected from a single bond, a substituted or unsubstituted heteroaromatic group having 5 - 30 ring atoms, or a substituted or unsubstituted aromatic group having 6 - 30 carbon atoms; R 1 and R 2 are independently selected from hydrogen, deuterium, a substituted or unsubstituted heteroaromatic group having 5 - 30 ring atoms, a substituted or unsubstituted aromatic group having 6 - 30 carbon atoms, or -N(Ar 1 )(Ar 2 ); Ar 1 and Ar 2 are independently selected from a substituted or unsubstituted heteroaromatic group having 5 - 30 ring atoms, or a substituted or unsubstituted aromatic group having 6 - 30 carbon atoms; and at least one of said R 1 and R 2 is selected from the structural formula (A - 1) or (A - 2): ; * represents the connection site; Said substituted or unsubstituted means that the defined group is unsubstituted or substituted by a substituent R, and each occurrence of the substituent R is independently selected from deuterium, halogen, cyano, isocyano, a straight-chain alkyl group having 1 - 30 carbon atoms, a branched-chain alkyl group having 3 - 30 carbon atoms, a cyclic alkyl group having 3 - 30 carbon atoms, a heteroaromatic group having 5 - 30 ring atoms, an aromatic group having 6 - 30 carbon atoms, or a combination of one or more of them, and the number of substituents R is from single substitution to maximum substitution.

[0009] In a second aspect, the present application provides a mixture comprising the fluoranthene-containing organic compound described above, and further comprising at least one other organic functional material; Preferably, the organic functional material is selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a light-emitting guest material, or a light-emitting host material.

[0010] More preferably, the organic functional material is selected from a light-emitting host material or a light-emitting guest material.

[0011] Even more preferably, the organic functional material is selected from a phosphorescent light-emitting guest material.

[0012] In a third aspect, the present application provides an organic electroluminescent device, which includes an anode, a cathode, and one or more organic functional layers located between the anode and the cathode, and at least one of the organic functional layers contains the fluoranthene-containing organic compound or the mixture described above.

[0013] Compared with the prior art, the technical solution of the present application has the following beneficial effects: The organic compound of the present invention can be used as a single host material in phosphorescent light-emitting devices, and it has good optoelectronic properties; when the fluoranthene-containing organic compound described in the present invention is used as an electrophosphorescent light-emitting host material and is used in an OLED device in combination with a suitable phosphorescent guest material, the luminous efficiency and lifespan of the device can be improved; the present invention further provides a solution for manufacturing a light-emitting device with low manufacturing cost, high efficiency, and long lifespan. Detailed implementation manners

[0014] In order to make the objectives, technical solutions, and advantages of the present application clearer, the present application will be further described in detail below in conjunction with embodiments. It should be understood that the specific embodiments described herein are only used to explain the present application and are not used to limit the present application.

[0015] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the technical field to which the present invention belongs. The terms used in the description of the present invention herein are only for the purpose of describing specific embodiments and are not intended to limit the present invention.

[0016] The "halogen" described in the present invention includes a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0017] In the present invention, the "number of ring atoms" refers to the number of atoms among the atoms constituting the ring itself of a structural compound obtained by bonding atoms into a ring (for example, a monocyclic compound, a fused-ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms of a thienyl group is 5, and the number of ring atoms of carbazole is 13.

[0018] In the present invention, the "number of carbon atoms" refers to the number of carbon atoms among the atoms constituting the ring itself of a structural compound obtained by bonding carbon atoms into a ring (for example, a monocyclic compound, a fused-ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of carbon atoms" described below unless otherwise specified. For example, the number of carbon atoms of a phenyl group is 6, the number of carbon atoms of a naphthyl group is 10, and the number of carbon atoms of a phenanthryl group is 14.

[0019] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived by removing one or more hydrogen atoms from an aromatic ring compound, which can be a monocyclic aryl group, a fused-ring aryl group, or a polycyclic aryl group. For polycyclic ring species, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6 to 30 ring atoms" refers to an aryl group containing 6 to 30 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 20 ring atoms; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, binaphthylenyl, acenaphthylenyl, and their derivatives.

[0020] "Heteroaryl or heteroaromatic group" refers to a group in which at least one carbon atom in an aryl group is replaced by a non-carbon atom, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms" refers to a heteroaryl group having 5 to 30 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 20 ring atoms. Suitable examples include, but are not limited to: thienyl, furyl, pyrrolyl, dioxolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuryl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuryl, thienofuryl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, peridinyl, quinazolinone, dibenzothienyl, dibenzofuryl, carbazolyl, and their derivatives.

[0021] The number of carbon atoms in a "linear alkyl" is selected from 1 - 30, preferably from 1 - 20, and further preferably from 1 - 10. Non-limiting examples of linear alkyls include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-octyl, etc.

[0022] The number of carbon atoms in a "branched alkyl" is selected from 3 - 30, preferably from 3 - 20, and further preferably from 3 - 10. Non-limiting examples of branched alkyls include isopropyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, etc.

[0023] The number of carbon atoms in a "cyclic alkyl" is selected from 3 - 30, preferably from 3 - 20, and further preferably from 3 - 10. Non-limiting examples of cyclic alkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0024] In the present invention, when a single bond connecting between groups penetrates through the corresponding ring, it means that the single bond can connect to any connectable site on the ring.

[0025] The terms "comprising", "including", "having", "containing", "involving" or other variant forms thereof herein are inclusive or open-ended and do not exclude other unenumerated elements or method steps.

[0026] In this specification, "independently selected from" may either mean that among different groups, the specific options expressed between the same symbols do not affect each other, or it may mean that within the same group, the specific options expressed between the same symbols do not affect each other.

[0027] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, the orientation words such as "upper", "lower", "top", and "bottom" only represent the orientation in a certain specific state and do not mean that the relevant structures can only exist in the stated orientation; on the contrary, if the structure can be transformed in position, such as being inverted, the orientation of the structure is changed accordingly. Specifically, in the present invention, the "bottom" and "lower" sides of the electrode refer to the side of the electrode close to the substrate during the preparation process, and the opposite side away from the substrate is the "top" and "upper" sides.

[0028] The present invention provides an organic compound containing fluoranthene, having a structure shown in formula (I),

[0029] (I) Wherein: L 1 and L 2 are independently selected from a single bond, a substituted or unsubstituted heteroaromatic group having 5 - 30 ring atoms, or a substituted or unsubstituted aromatic group having 6 - 30 carbon atoms; R 1 and R 2 are independently selected from hydrogen, deuterium, a substituted or unsubstituted heteroaromatic group having 5 - 30 ring atoms, a substituted or unsubstituted aromatic group having 6 - 30 carbon atoms, or -N(Ar 1 )(Ar 2 ); Ar 1 and Ar 2 are independently selected from a substituted or unsubstituted heteroaromatic group having 5 - 30 ring atoms, or a substituted or unsubstituted aromatic group having 6 - 30 carbon atoms; and at least one of R 1 and R 2 is selected from structural formula (A - 1) or (A - 2): ; * represents a linking site.

[0030] The "substituted or unsubstituted" means that the defined group is unsubstituted or substituted by a substituent R. Each occurrence of the substituent R is independently selected from deuterium, halogen, cyano, isocyano, a straight-chain alkyl group having 1-30 carbon atoms, a branched-chain alkyl group having 3-30 carbon atoms, a cyclic alkyl group having 3-30 carbon atoms, a heteroaromatic group having 5-30 ring atoms, an aromatic group having 6-30 carbon atoms, or a combination of two or more thereof. The number of the substituent R ranges from monosubstitution to maximum substitution.

[0031] Preferably, the fluoranthene-containing organic compound has a structure shown in any one of the general formulas (II-1)-(II-4):

[0032] .

[0033] In some embodiments, in the general formula (II-1) or the general formula (II-2), L 1 is selected from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.

[0034] In some embodiments, in the general formula (II-1) or the general formula (II-2), L 2 is selected from a single bond, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0035] In some embodiments, in the general formula (II-1) or the general formula (II-2), R 2 is selected from -H or the following groups:

[0036] wherein: each occurrence of X is independently selected from C, N, or CR 3 ; R 3 each occurrence is independently selected from hydrogen, deuterium, halogen, cyano, isocyano, a straight-chain alkyl group having 1-30 carbon atoms, a branched-chain alkyl group having 3-30 carbon atoms, a cyclic alkyl group having 3-30 carbon atoms, a heteroaromatic group having 5-30 ring atoms, an aromatic group having 6-30 carbon atoms, or a combination of two or more thereof.

[0037] In some specific embodiments, in the general formula (II-1) or general formula (II-2), is selected from -H or the following groups:

[0038]

[0039]

[0040]

[0041]

[0042]

[0043] .

[0044] In some embodiments, in the general formula (II-3) or general formula (II-4), L 2 is selected from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.

[0045] In some embodiments, in the general formula (II-3) or general formula (II-4), L 1 is selected from a single bond, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0046] In some embodiments, in the general formula (II-3) or general formula (II-4), R 1 is selected from -H or the following groups:

[0047] Wherein: each occurrence of X is independently selected from C, N or CR 3 ; R 3 Each occurrence is independently selected from hydrogen, deuterium, halogen, cyano, isocyano, a straight-chain alkyl group having 1-30 carbon atoms, a branched-chain alkyl group having 3-30 carbon atoms, a cyclic alkyl group having 3-30 carbon atoms, a heteroaromatic group having 5-30 ring atoms, and an aromatic group having 6-30 carbon atoms, or a combination of two or more thereof.

[0048] In some specific embodiments, in the general formula (II-3) or general formula (II-4), is selected from -H or the following groups:

[0049]

[0050]

[0051]

[0052]

[0053]

[0054] .

[0055] Specifically, the fluoranthene-containing organic compound according to the present invention is selected from the following structures, but not limited thereto:

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082] 。

[0083] The present invention also provides a mixture, which comprises the fluoranthene-containing organic compound as described above, and at least one other organic functional material. Preferably, the organic functional material is preferably selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminescent dopant material or a host material. Further preferably, the organic functional material is selected from a luminescent host material or a luminescent dopant material. More preferably, the organic functional material is selected from a phosphorescent luminescent dopant material.

[0084] The present invention also provides an organic electroluminescent device, which comprises an anode, a cathode and one or more organic functional layers located between the anode and the cathode, and at least one of the organic functional layers comprises the fluoranthene-containing organic compound as described above or the mixture as described above.

[0085] Furthermore, the organic electroluminescent device of the present invention comprises a substrate, and an anode layer, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode layer which are sequentially stacked on the substrate.

[0086] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL), hole transport layer (HTL), or light-emitting layer. Examples of anode materials include, but are not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known and can be easily selected and used by those of ordinary skill in the art.

[0087] The cathode may comprise a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL, ETL, or directly into the light-emitting layer. Examples of cathode materials include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF 2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. In principle, all materials that can be used as the cathode of an OLED can potentially be used as the cathode material of the device of the present invention.

[0088] The hole injection layer can be a single-layer structure composed of a single substance, or a single-layer structure or multi-layer structure composed of different substances. It is preferably selected from triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, axisene compounds, etc., including but not limited to: 2-TNATA, HATCN, copper phthalocyanine (CuPC), F4-TCNQ, PEDOT / PSS, etc., but not limited thereto.

[0089] The hole transport layer can be a single-layer structure composed of a single substance, or a single-layer structure or multi-layer structure composed of different substances. It is preferably selected from triarylamine compounds, including but not limited to: TPD, NPB, TDATA, etc., but not limited thereto.

[0090] The host material of the light-emitting layer is selected from phosphorescent materials, preferably selected from Ir-based metal complexes. It includes but is not limited to the following structures:

[0091]

[0092] .

[0093] The electron transport layer may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, high molecular compounds, etc. with high electron transport properties can be used, including but not limited to: tris(8-hydroxyquinoline)aluminum (Alq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (BeBq2), 2-(4-biphenylyl)-5-phenyloxadiazole (PBD), etc., but not limited thereto.

[0094] The electron injection layer may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. One or more of the following substances can be selected: alkali metals, alkaline earth metals, halides of alkali metals, halides of alkaline earth metals, oxides of alkali metals, oxides of alkaline earth metals, alkali metal salts, alkaline earth metal salts, other substances with high electron injection properties. Including but not limited to: Li, Ca, Sr, LiF, Liq, CsF, CaF 2 、BaO、Li 2 CO 3 、CaCO 3 、Li 2 C 2 O 4 、Cs 2 C 2 O 4 、CsAlF 4 、LiO x 、Yb, Tb, etc., but not limited thereto.

[0095] The present invention also relates to the application of the organic electroluminescent device in various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.

[0096] The present invention will be described below in conjunction with the compound preparation and device characterization examples, but the present invention is not limited to the following examples. It should be understood that the appended claims define the scope of the present invention. Under the guidance of the inventive concept of the present invention, those skilled in the art should realize that certain changes made to the embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

[0097] Compound Synthesis Example The synthesis of the above compounds, wherein the monohalogenated fluoranthene and the dihalogenated fluoranthene intermediates are both purchased from the market, and the halogenated benzocarbazole and benzocarbazole boronic acid and other intermediates are also all purchased from the market.

[0098] Synthesis Example 1: Synthesis of Compound (1)

[0099] Specific synthesis steps: Using the classical Suzuki reaction, the specific process route is as follows: Mix the above reaction substrates a and b with equal molar mass evenly, use toluene as the solvent, add 2M K 2 CO 3 aqueous solution as the base, under the action of the catalyst Pd(PPh 3 ) 4 , heat and stir under reflux overnight. Monitor the reaction with TLC thin-layer chromatography. After the reaction is complete, stop heating. When the temperature of the reaction solution drops to room temperature, add dichloromethane and H 2 O for extraction. Combine the organic phases, rotary evaporate the solvent under reduced pressure to obtain the crude product, and recrystallize with a mixed solvent of dichloromethane and ethyl acetate to obtain the white product (1). The reaction yield is: 84%, MS(ASAP) = 441.5.

[0100] Synthesis Example 2: Synthesis of Compound (2)

[0101] Specific synthesis steps: Similar to the synthesis method of Example 1, using the classical Suzuki reaction, heat and stir the above reaction substrates b and c under the action of the catalyst, and treat the reaction solution according to the post-treatment method of the classical Suzuki reaction to obtain the product (2). The reaction yield is: 86%, MS(ASAP) = 441.4.

[0102] Synthesis Example 3: Synthesis of Compound (5)

[0103] Specific synthesis steps: Similar to the synthesis method of Example 1, this compound uses two-step classical Suzuki reaction. Heat and stir the above reaction substrate d and phenylboronic acid under the action of the catalyst, and treat the reaction solution according to the post-treatment method of the classical Suzuki reaction to obtain the intermediate e. The reaction yield is: 90%, MS(ASAP) = 312.8.

[0104] Using the intermediate e and the intermediate a as the reaction substrates, heat and stir under the action of the catalyst, and treat the reaction solution according to the post-treatment method of the classical Suzuki reaction to obtain the product (5). The reaction yield is: 87%, MS(ASAP) = 517.6.

[0105] Synthesis Example 4: Synthesis of Compound (12)

[0106] Specific synthesis steps: Similar to the synthesis method of Example 1, this compound uses a two-step classical Suzuki reaction. The above reaction substrates d and f are heated and stirred under the action of a catalyst, and the reaction solution is treated according to the post-treatment method of the classical Suzuki reaction to obtain intermediate g. The reaction yield is: 88%, MS(ASAP) = 477.8.

[0107] Using intermediate g and intermediate a as reaction substrates, heating and stirring under the action of a catalyst, and treating the reaction solution according to the post-treatment method of the classical Suzuki reaction to obtain product (12). The reaction yield is: 89%, MS(ASAP) = 682.6.

[0108] Synthesis Example 5: Synthesis of Compound (9)

[0109] Specific synthesis steps: Similar to the synthesis method of Example 1, using the classical Suzuki reaction, the above reaction substrate d and two equivalents of substrate a are heated and stirred under the action of a catalyst, and the reaction solution is treated according to the post-treatment method of the classical Suzuki reaction to obtain product (9). The reaction yield is: 75%, MS(ASAP) = 680.5.

[0110] Synthesis Example 6: Synthesis of Compound (15)

[0111] Specific synthesis steps: Similar to the synthesis method of Example 1, this compound uses a two-step classical Suzuki reaction. The above reaction substrates d and h are heated and stirred under the action of a catalyst, and the reaction solution is treated according to the post-treatment method of the classical Suzuki reaction to obtain intermediate i. The reaction yield is: 92%, MS(ASAP) = 586.2.

[0112] Using intermediate i and intermediate a as reaction substrates, heating and stirring under the action of a catalyst, and treating the reaction solution according to the post-treatment method of the classical Suzuki reaction to obtain product (15). The reaction yield is: 88%, MS(ASAP) = 791.0.

[0113] Synthesis Example 7: Synthesis of Compound (23)

[0114] Specific synthesis steps: Similar to the synthesis method of Example 1, this compound uses a two-step classical Suzuki reaction. Substrate k and substrate j above are heated and stirred under the action of a catalyst, and the reaction solution is treated according to the post-treatment method of the classical Suzuki reaction to obtain intermediate l. The reaction yield is: 91%, MS(ASAP) = 557.1.

[0115] Using intermediate l and intermediate a as reaction substrates, heating and stirring under the action of a catalyst, and treating the reaction solution according to the post-treatment method of the classical Suzuki reaction to obtain product (23). The reaction yield is: 83%, MS(ASAP) = 761.9.

[0116] Synthesis Example 8: Synthesis of Compound (32)

[0117] Specific synthesis steps: Similar to the synthesis method of Example 1, using the classical Suzuki reaction, reacting reaction substrate m above with two equivalents of substrate b under the action of a catalyst, heating and stirring, and treating the reaction solution according to the post-treatment method of the classical Suzuki reaction to obtain product (32). The reaction yield is: 78%, MS(ASAP) = 607.7.

[0118] Synthesis Example 9: Synthesis of Compound (40)

[0119] Specific synthesis steps: Similar to the synthesis method of Example 1, this compound uses a two-step classical Suzuki reaction. Reacting reaction substrate n above with substrate d under the action of a catalyst, heating and stirring, and treating the reaction solution according to the post-treatment method of the classical Suzuki reaction to obtain intermediate l. The reaction yield is: 90%, MS(ASAP) = 362.9.

[0120] Using intermediate l and intermediate o as reaction substrates, heating and stirring under the action of a catalyst, and treating the reaction solution according to the post-treatment method of the classical Suzuki reaction to obtain product (40). The reaction yield is: 86%, MS(ASAP) = 567.7.

[0121] Synthesis Example 10: Synthesis of Compound (58)

[0122] Specific synthesis steps: Similar to the synthesis method of Example 1, using the classical Suzuki reaction, the above reaction substrates n and a are heated and stirred under the action of a catalyst, and the reaction solution is treated according to the post-treatment method of the classical Suzuki reaction to obtain the product (58), with a reaction yield of: 88%, MS(ASAP) = 441.5.

[0123] Synthesis Example 11: Synthesis of Compound (59)

[0124] Specific synthesis steps: Similar to the synthesis method of Example 1, using the classical Suzuki reaction, the above reaction substrates n and o are heated and stirred under the action of a catalyst, and the reaction solution is treated according to the post-treatment method of the classical Suzuki reaction to obtain the product (59), with a reaction yield of: 84%, MS(ASAP) = 441.4.

[0125] Synthesis Example 12: Synthesis of Compound (67)

[0126] Specific synthesis steps: Similar to the synthesis method of Example 1, this compound uses a two-step classical Suzuki reaction. The above reaction substrates a and d are heated and stirred under the action of a catalyst, and the reaction solution is treated according to the post-treatment method of the classical Suzuki reaction to obtain the intermediate q, with a reaction yield of: 85%, MS(ASAP) = 476.0.

[0127] Using the intermediate q and the intermediate r as reaction substrates, heating and stirring under the action of a catalyst, and treating the reaction solution according to the post-treatment method of the classical Suzuki reaction to obtain the product (67), with a reaction yield of: 84%, MS(ASAP) = 607.7.

[0128] Synthesis Example 13: Synthesis of Compound (71)

[0129] Specific synthesis steps: Similar to the synthesis method of Example 1, in the preparation process of this compound, the preparation of the intermediate q uses the classical Suzuki reaction. The above reaction substrates a and d are heated and stirred under the action of a catalyst, and the reaction solution is treated according to the post-treatment method of the classical Suzuki reaction to obtain the intermediate q, with a reaction yield of: 85%, MS(ASAP) = 476.0.

[0130] Using intermediate q and intermediate s as reaction substrates, and adopting the Hartwig reaction, under the action of a catalyst, heating and stirring, and treating the reaction solution according to the post-treatment method of the classical Hartwig reaction, product (71) was obtained, with a reaction yield of: 75%, MS(ASAP) = 718.9.

[0131] Synthesis Example 14: Synthesis of Compound (74)

[0132] Specific synthesis steps: Similar to the synthesis method of Example 1, in the preparation of intermediate q in the preparation process of this compound, the classical Suzuki reaction was adopted. Reacting the above reaction substrates a and d under the action of a catalyst, heating and stirring, and treating the reaction solution according to the post-treatment method of the classical Suzuki reaction, intermediate q was obtained, with a reaction yield of: 85%, MS(ASAP) = 476.0.

[0133] Using intermediate q and intermediate t as reaction substrates, and adopting the Hartwig reaction, under the action of a catalyst, heating and stirring, and treating the reaction solution according to the post-treatment method of the classical Hartwig reaction, product (74) was obtained, with a reaction yield of: 74%, MS(ASAP) = 658.8.

[0134] Synthesis Example 15: Synthesis of Compound (77)

[0135] Specific synthesis steps: Similar to the synthesis method of Example 1, this compound adopted a two-step classical Suzuki reaction. Reacting the above reaction substrates a and d under the action of a catalyst, heating and stirring, and treating the reaction solution according to the post-treatment method of the classical Suzuki reaction, intermediate q was obtained, with a reaction yield of: 85%, MS(ASAP) = 476.0.

[0136] Using intermediate q and intermediate u as reaction substrates, under the action of a catalyst, heating and stirring, and treating the reaction solution according to the post-treatment method of the classical Suzuki reaction, product (77) was obtained, with a reaction yield of: 80%, MS(ASAP) = 748.9.

[0137] Synthesis Example 16: Synthesis of Compound (82)

[0138] Specific synthesis steps: Similar to the synthesis method of Example 1, using the classical Suzuki reaction, the above reaction substrates n and v are heated and stirred under the action of a catalyst, and the reaction solution is treated according to the post-treatment method of the classical Suzuki reaction to obtain the product (82), and the reaction yield is: 82%, MS(ASAP) = 517.6.

[0139] Synthesis Example 17: Synthesis of Compound (85)

[0140] Specific synthesis steps: Similar to the synthesis method of Example 1, this compound uses a two-step classical Suzuki reaction. The above reaction substrates w and d are heated and stirred under the action of a catalyst, and the reaction solution is treated according to the post-treatment method of the classical Suzuki reaction to obtain the intermediate x, and the reaction yield is: 81%, MS(ASAP) = 476.1.

[0141] Using intermediate x and intermediate y as reaction substrates, heating and stirring under the action of a catalyst, and treating the reaction solution according to the post-treatment method of the classical Suzuki reaction to obtain the product (85), and the reaction yield is: 83%, MS(ASAP) = 682.8.

[0142] Device Example OLED device structure: ITO / HATCN(10nm) / NPB(35nm) / TCTA(5nm) / Organic compound containing fluoranthene: 5wt%EM1 / B3PYMPM (40nm) / LiF(1nm) / Al (150nm).

[0143] The preparation steps of OLED-1 device are as follows: a. Cleaning of the conductive glass substrate: Clean it successively with chloroform, ketone, and isopropyl alcohol, and then perform ultraviolet ozone plasma treatment; b. Preparation of the hole injection layer: Transfer the cleaned conductive glass substrate to a nitrogen glove box, and under the condition of high vacuum (1×10 -6 mbar), vacuum deposit HATCN on the ITO substrate as the hole injection layer, and the deposition thickness is 10nm.

[0144] c. Preparation of the hole transport layer: Vacuum deposit NPB on the hole injection layer as the hole transport layer, and the deposition thickness is 35nm.

[0145] d. Preparation of the light-emitting auxiliary layer: Vacuum deposit TCTA on the hole transport layer as the light-emitting auxiliary layer, and the deposition thickness is 5nm.

[0146] e. Preparation of the light-emitting layer: Vacuum deposit an organic compound (1): EM1 (weight doping ratio of 95:5) on the light-emitting auxiliary layer as the light-emitting layer, with a deposition thickness of 30 nm.

[0147] f. Preparation of the electron transport layer: Vacuum deposit B3PYMPM on the light-emitting layer as the electron transport layer, with a deposition thickness of 40 nm.

[0148] g. Preparation of the cathode layer: Vacuum deposit LiF / Al (1 nm / 150 nm) on the electron transport layer as the cathode layer; h. Encapsulation: The device is encapsulated with an ultraviolet-curing resin in a nitrogen glove box.

[0149] The structural formula of EM1 is as follows:

[0150] Fabrication method of OLED2-17 device: The fabrication method of OLED2-17 device is the same as that of OLED-1, the difference lies in the choice of the host material in the light-emitting layer. Specifically, the host material organic compound (1) in the light-emitting layer is respectively replaced by organic compound (2), organic compound (5), organic compound (9), organic compound (12), organic compound (15), organic compound (23), organic compound (32), organic compound (40), organic compound (58), organic compound (59), organic compound (67), organic compound (71), organic compound (74), organic compound (77), organic compound (82) and organic compound (85). As shown in Table 1 specifically.

[0151] Fabrication method of OLED-Ref device: The fabrication method of OLED-Ref device is the same as that of OLED-1, the difference lies in the choice of the host material in the light-emitting layer. Specifically, the host material organic compound (1) in the light-emitting layer is replaced by CBP, and the structural formula of CBP is as follows: .

[0152] The current-voltage (J-V) characteristics of each OLED device are characterized by a characterization device, and important parameters such as efficiency and lifetime are recorded at the same time. Among them, the luminous efficiency is the value obtained when the current density is 10 mA / cm 2 The lifetime LT95@1000nits refers to the time when the brightness of the device decreases from the initial brightness of 1000 nits to 95% of the initial brightness under a constant current. The specific optoelectronic properties are shown in Table 1: Table 1

[0153] After testing, the luminous efficiency and device lifetime of the OLED1-17 device prepared by the present invention are far superior to those of OLEDRef. For example, the luminous efficiency and lifetime of OLED7 (corresponding to organic compound (23)) are approximately 4.6 times and 70 times that of OLEDRef (corresponding to material (Ref)), respectively. The luminous efficiency of OLED12 (corresponding to organic compound (67)) is 4.5 times that of OLEDRef, and the lifetime is more than 55 times. It can be seen that the luminous efficiency and lifetime of the OLED device prepared with the organic mixture of the present invention are greatly improved.

[0154] As described above, the above is only a specific embodiment of the present application, but the protection scope of the present application is not limited thereto. Any person skilled in the art within the technical scope disclosed in the present application can easily think of changes or substitutions, which should be covered by the protection scope of the present application. Therefore, the protection scope of the present application should be subject to the protection scope of the claims.

Claims

1. An organic compound containing fluoranthene, characterized in that: Having a structure as shown in formula (I), (I) in: L1 and L2 are independently selected from a single bond, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms; R1 and R2 are independently selected from hydrogen, deuterium, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or -N(Ar1)(Ar2); Ar1 and Ar2 are independently selected from substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms, or substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms; At least one of R1 and R2 is selected from structural formula (A-1) or (A-2): ； * indicates the attachment site; The substitution or unsubstitution means that the defined group is not substituted or is substituted by a substituent R, and each occurrence of the substituent R is independently selected from one or a combination of two or more of deuterium, halogen, cyano, isocyano, a straight-chain alkyl group having 1 to 30 carbon atoms, a branched-chain alkyl group having 3 to 30 carbon atoms, a cyclic alkyl group having 3 to 30 carbon atoms, a heteroaromatic group having 5 to 30 ring atoms, and an aromatic group having 6 to 30 carbon atoms, wherein the number of substituents R is from a single substitution to a maximum number of substitutions.

2. The fluoranthene-containing organic compound according to claim 1, characterized in that It has a structure as shown in any one of the general formulas (II-1) to (II-4): 。 3. The fluoranthene-containing organic compound according to claim 2, characterized in that: In the general formula (II-1) or (II-2), L1 is selected from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group; and / or, In the general formula (II-1) or (II-2), L2 is selected from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

4. The fluoranthene-containing organic compound according to claim 2, characterized in that In the general formula (II-1) or (II-2), R2 is selected from -H or the following groups: Wherein: X, at each occurrence, is independently selected from C, N or CR3; Each occurrence of R3 is independently selected from one or a combination of two or more of hydrogen, deuterium, halogen, cyano, isocyano, a straight-chain alkyl group having 1 to 30 carbon atoms, a branched-chain alkyl group having 3 to 30 carbon atoms, a cyclic alkyl group having 3 to 30 carbon atoms, a heteroaromatic group having 5 to 30 ring atoms, and an aromatic group having 6 to 30 carbon atoms.

5. The fluoranthene-containing organic compound according to claim 2, characterized in that: In the general formula (II-3) or (II-4), L2 is selected from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group; and / or, In the general formula (II-3) or (II-4), L1 is selected from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

6. The fluoranthene-containing organic compound according to claim 2, characterized in that: In the general formula (II-3) or (II-4), R1 is selected from -H or the following groups: Wherein: X, at each occurrence, is independently selected from C, N or CR3; Each occurrence of R3 is independently selected from one or a combination of two or more of hydrogen, deuterium, halogen, cyano, isocyano, a straight-chain alkyl group having 1 to 30 carbon atoms, a branched-chain alkyl group having 3 to 30 carbon atoms, a cyclic alkyl group having 3 to 30 carbon atoms, a heteroaromatic group having 5 to 30 ring atoms, and an aromatic group having 6 to 30 carbon atoms.

7. The fluoranthene-containing organic compound according to claim 2, characterized in that: In the general formula (II-1) or the general formula (II-2) , or in the general formula (II-3) or the general formula (II-4) , are each independently selected from -H or the following groups: 。 8. The fluoranthene-containing organic compound according to claim 1, characterized in that: The fluoranthene-containing organic compound is selected from the following structures: 。 9. A mixture, characterized in that The method comprises the fluoranthene-containing organic compound according to any one of claims 1 to 8, and at least another organic functional material.

10. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode, a cathode and one or more organic functional layers between the anode and the cathode, wherein the at least one organic functional layer comprises the fluoranthene-containing organic compound according to any one of claims 1 to 8 or the mixture according to claim 9.

Images