Organic compounds and organic electroluminescent devices and electronic devices

Abstract

The application relates to the field of organic materials, and provides an organic compound, an organic electroluminescent device and an electronic device. The organic compound has a structure as shown in formula 1, the organic compound is applied to a light-emitting layer of an organic electroluminescent device as an organic light-emitting material, and the performance of the device can be improved.

Description

Technical Field

[0001] This application relates to the field of organic materials, and in particular to an organic compound and an organic electroluminescent device and electronic device. Background Technology

[0002] With the advent of the information age, display technology has become widespread and applied in daily life and production. Organic light-emitting diodes (OLEDs) represent a new generation of display light-emitting technology. Compared to inorganic LED technology, organic light-emitting materials have lower production costs, lighter weight, greater flexibility, and controllable photophysical properties. This allows for the production of flexible curved folding screens with higher purity and larger dimensions, thus offering broader application scenarios and possibilities. Furthermore, the simple synthesis and ease of control of small organic light-emitting molecules make them the preferred material for the OLED light-emitting layer.

[0003] Currently, organic light-emitting materials are mainly classified into traditional fluorescent materials, heavy metal organic complex phosphorescent materials, and thermally activated delayed phosphors (TADF). The theoretical exciton utilization rate of traditional fluorescent materials can only reach a maximum of 25%, while the theoretical exciton utilization rate of heavy metal organic complex phosphorescent materials can reach 100%. However, the heavy metals used are all precious metals, which are expensive and scarce, thus limiting the application of organic light-emitting materials. Therefore, developing novel organic light-emitting materials is extremely urgent and necessary for the further development of OLED technology.

[0004] As a third-generation organic light-emitting material, thermally activated delayed fluorescence (TEFL) materials boast a theoretical exciton utilization rate of 100%, are easy to synthesize and prepare, and have low cost, making them a hot topic in organic light-emitting material research. However, when TFL materials are used as the emitting layer in OLED devices, they still suffer from significant device efficiency roll-off and short lifetime. Therefore, to make OLED devices more commercially viable, it is necessary to design a class of TFL materials with higher stability to improve the performance of OLED devices. Summary of the Invention

[0005] The purpose of this application is to provide an organic compound, its application, an organic electroluminescent device, and an electronic device. The organic compound, when used as an organic light-emitting material in an organic electroluminescent device, can improve the device's performance.

[0006] In a first aspect, this application provides an organic compound having a structure as shown in Formula 1:

[0007]

[0008] Where X represents O, S, or C(R)a R b ),

[0009] R a and R b They may be the same or different, and each is independently a hydrogen or an alkyl group having 1-10 carbon atoms;

[0010] R1 and R2 may be the same or different, and each is an alkyl group having 1-10 carbon atoms;

[0011] L, L1 and L2 may be the same or different, and each is an independent single bond, a substituted or unsubstituted aryl group with 6-25 carbon atoms, or a substituted or unsubstituted heteroaryl group with 3-25 carbon atoms;

[0012] A is a substituted or unsubstituted alkyl group with 1-30 carbon atoms, a substituted or unsubstituted aryl group with 6-40 carbon atoms, or a substituted or unsubstituted saturated or unsaturated heterocyclic group with 3-40 carbon atoms.

[0013] A1 and A2 may be the same or different, and each is independently hydrogen, a substituted or unsubstituted aryl group with 6-40 carbon atoms, or a substituted or unsubstituted saturated or unsaturated heterocyclic group with 3-40 carbon atoms.

[0014] In L, L1, L2, A, A1, and A2, the substituents are the same or different, and each is independently a deuterium, halogen group, cyano, hydroxyl, nitro, carbonyl, malononitrile, alkenyl with 2-10 carbon atoms, alkyl with 1-10 carbon atoms, aryl with 6-18 carbon atoms, heteroaryl with 3-18 carbon atoms, alkoxy with 1-10 carbon atoms, aryloxy with 6-18 carbon atoms, arylformyl with 6-18 carbon atoms, arylsulfonyl with 6-18 carbon atoms, or arylsulfinyl with 6-18 carbon atoms.

[0015] Secondly, this application provides an organic electroluminescent device, the organic electroluminescent device including an anode and a cathode disposed opposite to each other; and an organic light-emitting layer disposed between the anode and the cathode, wherein the organic light-emitting layer contains the organic compound.

[0016] Thirdly, this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0017] The organic compound provided in this application is a diindole[3,2-c:2′,3′-h]xanthracene ring derivative. This compound, using the diindole[3,2-c:2′,3′-h]xanthracene ring as a donor, possesses a large stereorigid structure. This allows the organic compound (thermally activated delayed fluorescence molecule) formed by its combination with different acceptors to exhibit a large torsion angle between the acceptor and donor. This effectively reduces the singlet-triplet splitting energy of the organic light-emitting material, ensuring rapid energy transfer in the luminescent layer and mitigating the annihilation of triplet excitons. Therefore, the organic compound of this application, when used as an organic light-emitting material in OLED devices, can effectively improve the luminous efficiency and extend the lifespan of OLED devices, thereby adapting to and meeting the needs of the OLED industry.

[0018] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0019] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0020] Explanation of reference numerals in the attached figures

[0021] 100: Organic electroluminescent device; 1: Anode; 2: Hole injection layer; 3: Hole transport layer

[0022] 4: Organic light-emitting layer; 5: Electron transport layer; 6: Electron injection layer; 7: Cathode Detailed Implementation

[0023] To facilitate understanding of this application, a more complete description will be provided below with reference to the accompanying drawings. Preferred embodiments of this application are shown in the drawings. However, this application can be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a more thorough and complete understanding of the disclosure of this application.

[0024] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0025] The inventors of this application discovered that the diindole[3,2-c:2′,3′-h]xanthracene ring contains multiple sites with nitrogen atoms. These nitrogen atoms play an electron-donating conjugating role, increasing the electron cloud density of the diindole[3,2-c:2′,3′-h]xanthracene ring unit. This structure is a structural unit with good electron-donating performance. Furthermore, the diindole[3,2-c:2′,3′-h]xanthracene ring unit has numerous modification sites, facilitating halogenation substitution and metal coupling reactions, thus enabling the construction of novel luminescent organic molecules. Simultaneously, the nitrogen atoms on the indole ring are easily modified, allowing for the regulation of organic molecule solubility through the introduction of alkyl chains. Moreover, the diindole[3,2-c:2′,3′-h]xanthracene ring unit with its heptagonal ring structure exhibits significant steric rigidity. When combined with different acceptors to form thermally activated delayed fluorescence molecules, it displays a large torsion angle between the acceptor and donor, ensuring rapid energy transfer in the luminescent layer and suppressing the annihilation of triplet excitons. Based on these findings, this application is filed.

[0026] A first aspect of this application provides an organic compound having the structure shown in Formula 1:

[0027]

[0028] Where X represents O, S, or C(R) a R b ),

[0029] R a and R b They may be the same or different, and each is independently a hydrogen or an alkyl group having 1-10 carbon atoms;

[0030] R1 and R2 may be the same or different, and each is an alkyl group having 1-10 carbon atoms;

[0031] L, L1 and L2 may be the same or different, and each is an independent single bond, a substituted or unsubstituted aryl group with 6-25 carbon atoms, or a substituted or unsubstituted heteroaryl group with 3-25 carbon atoms;

[0032] A is a substituted or unsubstituted alkyl group with 1-30 carbon atoms, a substituted or unsubstituted aryl group with 6-40 carbon atoms, or a substituted or unsubstituted saturated or unsaturated heterocyclic group with 3-40 carbon atoms.

[0033] A1 and A2 may be the same or different, and each is independently hydrogen, a substituted or unsubstituted aryl group with 6-40 carbon atoms, or a substituted or unsubstituted saturated or unsaturated heterocyclic group with 3-40 carbon atoms.

[0034] In L, L1, L2, A, A1, and A2, the substituents are the same or different, and each is independently a deuterium, halogen group, cyano, hydroxyl, nitro, carbonyl, malononitrile, alkenyl with 2-10 carbon atoms, alkyl with 1-10 carbon atoms, aryl with 6-18 carbon atoms, heteroaryl with 3-18 carbon atoms, alkoxy with 1-10 carbon atoms, aryloxy with 6-18 carbon atoms, arylformyl with 6-18 carbon atoms, arylsulfonyl with 6-18 carbon atoms, or arylsulfinyl with 6-18 carbon atoms.

[0035] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents. For example, "substituted or unsubstituted phenyl" refers to a phenyl with substituents or an unsubstituted phenyl. The number of substituents can be one or more, including deuterium, halogen groups, cyano, hydroxyl, nitro, carbonyl, malononitrile, alkenyl, alkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, arylformyl, arylsulfonyl, arylsulfinyl, etc. It should be understood that when the functional group has substituents, the number of carbon atoms refers to the total number of carbon atoms of the functional group and its substituents. For example, when A is a methyl-substituted phenyl, then the total number of carbon atoms in A is 7, that is, A is a methyl-substituted phenyl with 7 carbon atoms.

[0036] In this application, aryl refers to an aromatic hydrocarbon group derived from an aromatic ring compound by losing one hydrogen atom. Aryl can be a monocyclic aryl (such as phenyl), a fused-ring aryl (such as naphthyl), two or more monocyclic aryl groups (such as biphenyl) conjugated by carbon-carbon bonds, monocyclic and fused-ring aryl groups conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. Specific examples of aryl include, but are not limited to, phenyl, naphthyl, anthracene, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, etc. Alkyl, dibenzocycloalkyl (such as fluorenyl, dihydroanthracene), etc.

[0037] In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0038] In this application, a heterocyclic group refers to a monocyclic or polycyclic group having a heteroatom (-X-) in its cyclic structure and / or having a heteroatom group (=X) attached to its cyclic structure. The heteroatom X can be at least one of B, O, N, P, Si, Se, and S. Specifically, in a heterocyclic group, the heteroatom in the cyclic structure is, for example, at least one of B, O, N, and S, and the heteroatom group attached to the cyclic structure is, for example, a carbonyl group (=O). The heterocyclic group is, for example, a saturated or unsaturated 3- to 15-membered heterocyclic group. Saturated heterocyclic groups include heterocyclic alkyl groups, and unsaturated heterocyclic groups include heteroaryl and heterocyclic alkenyl groups. The number of unsaturated double bonds in the heterocyclic alkenyl group can be one or more, and examples of heterocyclic alkenyl groups include, but are not limited to, pyranyl groups.

[0039] In this application, a heteroaryl group refers to a group formed by replacing at least one carbon atom with a heteroatom on the basis of an aryl group. The heteroatom can be at least one of B, O, N, P, Si, Se, and S, and the number of heteroatoms in a heteroaryl group can be 1, 2, 3, 4, 5, or more. A heteroaryl group can be a monocyclic heteroaryl or a fused-ring heteroaryl. It should be understood that a fused aryl (hetero) group with one or more (2 or more) carbonyl groups attached to it is also considered a heteroaryl group. Specific examples of heteroaryl groups include, but are not limited to, thiophene, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazole, benzoxazolyl, benzimidazolyl, and benzothiazolyl. Azolyl, benzocarbazoyl, benzothiophene, dibenzothiophene, thiophene-thiophene, benzofuranyl, phenanthrolinel, isoxazolyl, thiadiazoyl, phenothiazinyl, phenothiazinyl, dibenzo-p-dioxinyl, quinazolinoneyl, benzothiadiazoyl, benzotriazolyl, thiaanthryl, phenothiazinyl, phenothiazinyl, thiaanthrenetetroxide, phenothiazindioxide, anthraquinoneyl, phenothiazindioxide, thioxanthiumdioxide, etc.

[0040] In this application, the term "hybrid aryl" refers to a divalent group formed by the further loss of a hydrogen atom by a heteroaryl group.

[0041] In this application, "alkenyl" refers to a monovalent residue comprising a hydrocarbon having at least one unsaturated site, i.e., a carbon-carbon sp2 double bond, by losing a hydrogen atom. Phrases containing this term, such as "alkenyl with 2-10 carbon atoms," refer to straight-chain alkenyl groups with 2-10 carbon atoms or branched alkenyl groups with 3-10 carbon atoms. The number of carbon atoms in an alkenyl group is, for example, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkenyl groups include, but are not limited to, vinyl (-CH=CH2) and allyl (-CH2CH=CH2).

[0042] In this application, the alkyl group can be an alkyl group having 1-10 carbon atoms, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, 1-butyl (n-Bu, n-butyl, -CH2CH2CH2CH3), 2-methyl-1-propyl (i-Bu, i-butyl, -CH2CH(CH3)2), 2-butyl (s-Bu, s-butyl, -CH(CH3)CH2CH3), 2-methyl-2-propyl (t-Bu, t-butyl, -C(CH3)3), and 1-pentyl. (n-pentyl, -CH2CH2CH2CH2CH3), 2-pentyl (-CH(CH3)CH2CH2CH3), 3-pentyl (-CH(CH2CH3)2), 2-methyl-2-butyl (-C(CH3)2CH2CH3), 3-methyl-2-butyl (-CH(CH3)CH(CH3)2), 3-methyl-1-butyl (-CH2CH2CH(CH3)2), 2-methyl-1-butyl ( -CH2CH(CH3)CH2CH3), 1-hexyl(-CH2CH2CH2CH2CH2CH3), 2-hexyl(-CH(CH3)CH2CH2CH2CH3), 3-hexyl(-CH(CH2CH3)(CH2CH2CH3)), 2-methyl-2-pentyl(-C(CH3)2CH2CH2CH3), 3-methyl-2-pentyl(-CH(CH3)CH(CH3)CH2CH3), 4-methyl-2-pentyl(-CH(CH3)CH2CH(CH3)2), 3-methyl-3-pentyl(-C(CH3)(CH2CH3)2), 2-methyl-3-pentyl(-CH(CH2CH3)CH(CH3)2), 2,3-dimethyl-2-butyl(-C(CH3)2CH(CH3)2), 3,3-dimethyl-2-butyl(-CH(CH3)C(CH3)3 and octyl.

[0043] In this application, "alkoxy" refers to a group with the structure -OR, i.e., an alkyl group R as defined above, which is attached to an adjacent group via an oxygen atom. Phrases containing this term, such as "alkoxy group having 1-10 carbon atoms," mean that the alkyl moiety contains 1-10 carbon atoms. Examples of alkoxy groups include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-OC(CH3)3 or -OtBu).

[0044] In this application, halogen groups include chlorine, fluorine, bromine, and iodine.

[0045] In this application, the aryl sulfonyl group with 6-18 carbon atoms has, for example, 6, 12, or 18 carbon atoms. Examples of aryl sulfonyl groups include, but are not limited to, phenyl sulfonyl groups.

[0046] In this application, the aryl sulfinyl group having 6-18 carbon atoms has, for example, 6, 12, or 18 carbon atoms. Examples of aryl sulfinyl groups include, but are not limited to, phenyl sulfinyl groups.

[0047] In this application, the arylformyl group with 6-18 carbon atoms has, for example, 6, 12, or 18 carbon atoms. Examples of arylformyl groups include, but are not limited to, phenylformyl groups.

[0048] In this application, the number of carbon atoms in the aryl group used as a substituent can be 6-18, for example 6, 10, 12, 13, 14, or 18. Examples of aryl groups used as substituents include, but are not limited to, phenyl, naphthyl, biphenyl, fluorenyl, and phenanthrene.

[0049] In this application, the number of carbon atoms in the heteroaryl group used as a substituent can be 3-18, for example 3, 4, 6, 10, 12, 13, 14, or 18. Examples of heteroaryl groups used as substituents include, but are not limited to, pyridinyl, pyrimidinyl, quinolinyl, and piperazineyl.

[0050] In this application, The term "linking bond" refers to a non-positioned linking bond that extends from the ring system. This indicates that one end of the linker can connect to any position in the ring system it traverses, and the other end connects to the rest of the molecule. For example, as shown in equation (Q), the naphthyl group represented by equation (Q) is connected to other positions in the molecule via two non-positional linkers that traverse different benzene rings, representing any possible connection configuration shown in equations (Q-1) to (Q-6):

[0051]

[0052] For another example, as shown in equation (Z), the naphthyl group represented by equation (Z) is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This can represent any of the connection methods shown in equations (Z-1) and (Z-2):

[0053]

[0054] In this application, a non-orienting substituent refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent can be attached to any possible position in the ring system. For example, as shown in the following formula (E), the substituent R in formula (E) is connected to the naphthalene ring by a non-orienting linking bond, which means that it includes any of the possible connection methods shown in formulas (E-1) to (E-14):

[0055]

[0056] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40.

[0057] In this application, the number of carbon atoms in the substituted or unsubstituted heterocyclic group can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40.

[0058] In some embodiments, the organic compound has a structure of one of the following formulas 1-1 to 1-4:

[0059]

[0060] In some implementations, R a and R b They may be the same or different, and each is independently hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl.

[0061] In some embodiments, R1 and R2 may be the same or different, and each is independently methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl or n-hexyl.

[0062] Optionally, L, L1, and L2 may be the same or different, and each may be a single bond, or a substituted or unsubstituted aryl group with 6-18 carbon atoms.

[0063] Optionally, L, L1, and L2 may be the same or different, and each may independently be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene.

[0064] Optionally, the substituents in L, L1 and L2 are each independently deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0065] In one specific embodiment, L, L1, and L2 may be the same or different, and each independently consists of a single bond and one of the following groups:

[0066]

[0067] In some embodiments, A is an alkyl group having 1-10 carbon atoms, a substituted or unsubstituted aryl group having 6-25 carbon atoms, or a substituted or unsubstituted unsaturated heterocyclic group having 5-25 carbon atoms.

[0068] In some embodiments, A1 and A2 may be the same or different, and each is independently hydrogen, a substituted or unsubstituted aryl group having 6-25 carbon atoms, or a substituted or unsubstituted unsaturated heterocyclic group having 3-25 carbon atoms.

[0069] Optionally, in A, A1, and A2, the heteroatom in each heterocyclic group is independently one or more of O, S, N, and B.

[0070] Optionally, A1 and A2 may be the same or different, and each may be hydrogen, a substituted or unsubstituted aryl group having 6-18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 6-18 carbon atoms.

[0071] Optionally, the substituents in A, A1, and A2 are each independently deuterium, fluorine, cyano, hydroxyl, nitro, carbonyl, malononitrile, alkenyl with 2-5 carbon atoms, alkyl with 1-4 carbon atoms, aryl with 6-12 carbon atoms, heteroaryl with 5-12 carbon atoms, alkoxy with 1-4 carbon atoms, aryloxy with 6-12 carbon atoms, arylformyl with 6-12 carbon atoms, arylsulfonyl with 6-12 carbon atoms, or arylsulfinyl with 6-12 carbon atoms.

[0072] In some embodiments, A is an alkyl group having 1-10 carbon atoms, or a group W that is substituted or unsubstituted by one or more substituents M1, wherein group W is selected from one of the following groups:

[0073]

[0074] Each substituent M1 is independently deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, phenoxy, phenyl, naphthyl, benzoyl, benzenesulfonyl, or benzenesulfinyl.

[0075] Optionally, A is methyl, ethyl, n-propyl, isopropyl, tert-butyl, or one of the following groups:

[0076]

[0077]

[0078] In some embodiments, A1 and A2 may be the same or different, and each independently represents: hydrogen, an alkyl group having 1-4 carbon atoms, or a group Z substituted or unsubstituted by one or more substituents M2, wherein group Z is selected from one of the following groups:

[0079]

[0080] Each substituent M2 is independently deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, phenoxy, phenyl, naphthyl, benzoyl, benzenesulfonyl, or benzenesulfinyl.

[0081] Further optionally, A1 and A2 may be the same or different, and each independently represents one of the following groups: hydrogen, methyl, ethyl, n-propyl, isopropyl, tert-butyl, and the group consisting of:

[0082]

[0083] In some embodiments, in Formula 1, L1 and L2 are both single bonds, and A1 and A2 are both H, that is, the structure of the organic compound is as shown in Formula A:

[0084]

[0085] In one specific implementation, L1 and L2 are both single bonds, and A1 and A2 are both H bonds. It is one of the following groups:

[0086]

[0087]

[0088] In another specific implementation, for and They may be the same or different, and each independently belongs to one of the following groups:

[0089]

[0090]

[0091] In some implementations... same.

[0092] In some embodiments, the organic compound has a structure of one of the following formulas 2-1 to 2-50:

[0093]

[0094]

[0095]

[0096]

[0097] Where X is O, S, or C(R) a R b ), R a and R b All are H or all are methyl.

[0098] In this application, the chemical structure contains "-C6H". 13 "" indicates n-hexyl, and "-C4H9" indicates n-butyl.

[0099] Optionally, the organic compound is one of the following compounds:

[0100]

[0101]

[0102]

[0103] This application does not specifically limit the synthetic methods of the provided organic compounds. Those skilled in the art can determine suitable synthetic methods based on the organic compounds described in the Synthesis Examples section of this application, combined with the preparation methods provided. In other words, the Synthesis Examples section of this application exemplarily provides methods for preparing organic compounds, and the raw materials used can be obtained commercially or by methods well known in the art. Those skilled in the art can obtain all the organic compounds provided in this application based on these exemplary preparation methods. All specific preparation methods for these organic compounds are not detailed here, and should not be construed as limiting this application.

[0104] The organic compound described in this application, as an organic light-emitting material, exhibits higher stability, a more matched energy level band gap, and faster energy transfer. This organic light-emitting material (thermally activated delayed fluorescence material) serves as the light-emitting layer in OLED devices, mitigating the annihilation effect between exciton triplet states in the light-emitting layer, thereby improving device efficiency and extending lifetime. The organic light-emitting material can be used to form the functional layer of OLED devices through spin coating, inkjet printing, vacuum evaporation, or other methods.

[0105] A second aspect of this application provides an organic electroluminescent device, including an anode and a cathode disposed opposite to each other; and an organic light-emitting layer disposed between the anode and the cathode, wherein the organic light-emitting layer contains the organic compound.

[0106] In some embodiments, the organic light-emitting layer comprises a host material and a guest material, wherein the guest material includes the organic compounds described in this application.

[0107] In this application, the host material of the organic light-emitting layer can be a metal chelating compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, and this application does not impose any special limitations on this. In some embodiments, the host material includes at least one of TATC (CAS No.: 139092-78-7), CBP (CAS No.: 58328-31-7), TPD (CAS No.: 65181-78-4), and mCP (CAS No.: 550378-78-4).

[0108] This application does not particularly limit the material of the anode, and it can be any anode material capable of transmitting holes. Anode materials include, for example, one or a combination of metals, metal oxides, and conductive polymers. In some embodiments, the anode material is selected from at least one of indium tin oxide (ITO), indium zinc oxide (IZO), and indium gallium zinc oxide (IGZO).

[0109] This application does not specifically limit the material of the cathode; it can be any cathode material capable of transporting electrons. The cathode material may include metals, such as one or more of magnesium (Mg), calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum (Al), silver (Ag), tin, and lead, or an alloy of at least two of these. In some embodiments, the cathode material is selected from at least one of Al, Ag, Mg, and Mg-Ag alloys.

[0110] In some embodiments, the organic electroluminescent device further includes a hole functional layer disposed between the anode and the organic light-emitting layer, and an electron functional layer disposed between the cathode and the organic light-emitting layer. The hole functional layer includes a hole injection layer and / or a hole transport layer, and the electron functional layer includes an electron injection layer and / or an electron transport layer.

[0111] In one implementation, such as Figure 1 As shown, the organic electroluminescent device 100 includes an anode 1, a hole injection layer 2, a hole transport layer 3, an organic light-emitting layer 4, an electron transport layer 5, an electron injection layer 6, and a cathode 7, which are stacked sequentially.

[0112] In this application, the material of the hole injection layer 2 can be a benzidine derivative, a starburst-like aryl amine compound, a phthalocyanine derivative, or other materials; this application does not impose any special limitations on this. In one specific embodiment, the material of the hole injection layer 2 is HAT-CN.

[0113] In this application, the hole transport material of the hole transport layer 3 can be selected from various electron-rich organic materials that are conducive to hole transport, such as aromatic amine derivatives, carbazole derivatives, etc. In one specific embodiment, the hole transport material is NPB.

[0114] In this application, the material of the electron transport layer 5 can typically include metal complexes and / or nitrogen-containing heterocyclic derivatives, specific examples including but not limited to TPBi, BCP, Bphen, NBphen, DBimiBphen, BimiBphen, etc. In one specific embodiment, the material of the electron transport layer is TPBi.

[0115] In this application, the electron injection layer 6 enhances the ability of the cathode 7 to inject electrons into the electron transport layer 5. The electron injection layer may include inorganic materials such as alkali metal sulfides and alkali metal halides, or it may include complexes of alkali metals and organic compounds. In one specific embodiment, the material of the electron injection layer is LiQ.

[0116] A third aspect of this application provides an electronic device including the aforementioned organic electroluminescent device.

[0117] In this application, the electronic device may be a display device, a lighting device, an optical communication device, or other types of electronic devices. Specific examples include, but are not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, and optical modules.

[0118] The present application will be described below with specific synthesis examples and embodiments.

[0119] Unless otherwise stated, the synthetic routes for organic compounds can be as follows:

[0120]

[0121] Z can be H or Br.

[0122] Synthesis example 1

[0123] Synthesis of compound M1:

[0124]

[0125] (1) 10H-phenoxazine (1.83 g, 10 mmol), 4'-bromo-[1,1'-biphenyl]-2,4,6-trimethylonitrile (3.68 g, 12 mmol), Pd2(dba)3 (320 mg, 0.35 mmol), sodium tert-butoxide (3.84 g, 40 mmol) and tritert-butylphosphine (0.5 g, 2.5 mmol) were added to 200 mL of toluene, stirred and heated to 85 °C, and reacted for 24 h. The mixture was extracted with dichloromethane, dried, and column filtered to obtain intermediate M1-1 (3.36 g, 82% yield).

[0126] (2) Intermediate M1-1 (2.05 g, 5 mmol) was added to 100 mL of THF and stirred in an ice bath for 10 min. Then, NBS (1.78 g, 10 mmol) was dissolved in 30 mL of THF and slowly added dropwise to the reaction apparatus. After the addition was complete, the reaction was allowed to proceed for 10 min. The ice bath was removed and the temperature was raised to 25 °C. The reaction was allowed to proceed for 40 min. The reaction was quenched by adding 20 mL of sodium sulfite (1.04 g, 10 mmol) aqueous solution. The mixture was extracted with dichloromethane, dried, and passed through a column to obtain intermediate M1-2 (2.68 g, 95% yield).

[0127] (3) Intermediate M1-2 (2.98 g, 5 mmol), pinacol diboronate (5.08 g, 20 mmol), potassium acetate (1.96 g, 20 mmol) and Pd(dppf)Cl2 (181 mg, 0.25 mmol) were added to 150 mL of redistilled dioxane, stirred and heated to reflux and reacted for 24 h. The mixture was extracted with dichloromethane, dried and column filtered to obtain intermediate M1-3 (2.75 g, yield 83%).

[0128] (4) Intermediate M1-3 (3.31 g, 5 mmol), o-bromonitrobenzene (3.03 g, 15 mmol), potassium phosphate (12.7 g, 60 mmol) and Pd(PPh3)4 (0.29 g, 0.25 mmol) were added to a mixed solution of 200 mL toluene, 40 mL ethanol and 252.6 mL water. The mixture was stirred and heated to 85 °C and reacted for 24 h. The mixture was then extracted with dichloromethane, dried and column filtered to obtain intermediate M1-4 (2.6 g, yield 79%).

[0129] (5) M1-4 (0.65 g, 1 mmol) and PPh3 (2 g, 8 mmol) were dissolved in 20 mL of o-dichlorobenzene (ODB), stirred and heated to reflux, and the reaction was continued for 24 h. The reaction was then stopped, and o-dichlorobenzene was removed by vacuum distillation. The crude product was separated by column chromatography to obtain a yellowish-brown solid. This solid was directly added to the next reaction step, and a solution of 1-iodomethane (846 mg, 6 mmol) and potassium hydroxide (336 mg, 6 mmol) in dimethyl sulfoxide (40 mL) was added. The mixture was stirred and heated to 85 °C, and the reaction was continued for 24 h. The product was extracted with dichloromethane, dried, and column-sected to obtain compound M1 (308 mg, 50% yield). Mass spectrometry: m / z = 617.20 [M+H] + .

[0130] NMR data for compound M1: 1 HNMR (400MHz, CDCl3) δ8.35(s,2H),7.98-7.96(m,2H),7.85-7.84(m,2H),7.47-7.42(m,4H),7.25-7.20(m,6H),6.99-6.97(m,2H),4.37(s,6H).

[0131] Synthesis example 2

[0132] Synthesis of compound M2:

[0133]

[0134] (1) M2-4 was synthesized according to the method of M1-1, except that 4'-bromo-[1,1'-biphenyl]-2,4,6-trimethylonitrile was replaced with 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine to obtain intermediate M2-1 (4.32 g, yield 88%).

[0135] (2) M2-2 was synthesized according to the method of M1-2, except that intermediate M1-1 was replaced with intermediate M2-1 to obtain intermediate M2-2 (3.0g, yield 93%).

[0136] (3) M2-3 was synthesized according to the method of M1-3, except that intermediate M1-2 was replaced with M2-2 to obtain intermediate M2-3 (3.15g, yield 85%).

[0137] (4) M2-4 was synthesized according to the method of M1-4, except that intermediate M1-3 was replaced with M2-3 to obtain intermediate M2-4 (2.75g, yield 75%).

[0138] (5) M2 was synthesized according to the method of M1, except that intermediate M1-4 was replaced with M2-4. The mixture was purified by column chromatography to obtain compound M2 (415 mg, yield 60%). Mass spectrometry: m / z = 697.26 [M+H] + .

[0139] NMR data for compound M2: 1 HNMR (400MHz, CDCl3) δ8.67 (dd, 4H, J = 8.3Hz, 1.4Hz), 7.98-7.96 (m, 2H), 7.85-7.84 (m, 2H), 7.58 (t, 2H J=7.2Hz),7.54(t,4H,J=7.2Hz),7.47-7.42(m,4H),7.25-7.20(m,6H),6.99-6.97(m,2H),4.37(s,6H).

[0140] Synthesis example 3

[0141] Synthesis of compound M3

[0142]

[0143] (1) M3-1 was synthesized according to the method of M1-1, except that 4'-bromo-[1,1'-biphenyl]-2,4,6-tricarboxynitrile was replaced with 4-bromobenzoylbenzene to obtain intermediate M3-1 (3.27 g, yield 90%).

[0144] (2) M3-2 was synthesized according to the method of M1-2, except that intermediate M1-1 was replaced with M3-1 to obtain intermediate M3-2 (2.48g, yield 96%).

[0145] (3) M3-3 was synthesized according to the method of M1-3, except that intermediate M1-2 was replaced with M3-2 to obtain intermediate M3-3 (2.52g, yield 82%).

[0146] (4) M3-4 was synthesized according to the method of M1-4, except that intermediate M1-3 was replaced with M3-3 to obtain intermediate M3-4 (2.57g, yield 85%).

[0147] (5) M3 was synthesized according to the method of M1, except that intermediate M1-4 was replaced with M3-4. The solution was purified by column chromatography to obtain compound M3 (256 mg, 45% yield). Mass spectrometry: m / z = 570.21 [M+H] + .

[0148] NMR data for compound M3: 1HNMR(400MHz, CDCl3)δ7.98-7.96(m,2H),7.85-7.84(m,2H),7.81-7.74(m,4H),7.69 -7.65(m,1H),7.47-7.42(m,4H),7.25-7.20(m,6H),6.99-6.97(m,2H),4.37(s,6H).

[0149] Synthesis example 4-15

[0150] The compound was prepared according to the method of Synthesis Example 1, except that 4'-bromo-[1,1'-biphenyl]-2,4,6-tricarboxynitrile was replaced with raw material 1. In addition, in the synthesis of M9, iodomethane in step (5) was replaced with 1-iodohexane. The prepared compound and its total yield and mass spectrometry results are shown in Table 1.

[0151] Table 1

[0152]

[0153]

[0154]

[0155] Synthesis Example 16-22

[0156] The compounds listed in Table 2 were prepared according to the method of Synthesis Example 1, except that 10H-phenoxazine in step (1) was replaced by reactant 2, and 4'-bromo-[1,1'-biphenyl]-2,4,6-trimethylnitrile in step (1) was replaced by reactant 3. The prepared compounds, their total yields and mass spectrometry results are shown in Table 2.

[0157] Table 2

[0158]

[0159]

[0160]

[0161] Synthesis example 23

[0162] Synthesis of compound M23

[0163]

[0164] (1) Dissolve M11 (63.8 mg, 0.13 mmol) in 30 mL of redistilled THF, wrap the two-necked bottle with tin foil to protect it from light, and place it in an ice bath and stir for 10 min. Dissolve N-bromosuccinimide (NBS, 71.2 mg, 0.4 mmol) in 10 mL of redistilled THF and slowly inject it into the reaction flask with a syringe. Continue to react in an ice bath for 1 h, then raise the temperature to 25 °C and continue to react for 3 h. Add 10 mL of sodium thiosulfate aqueous solution (concentration 30 wt%) to the reaction flask to quench the reaction, then extract, dry and collect the filtrate to obtain the crude product. Separate the crude product by column chromatography to obtain intermediate M23-6 (64.7 mg, yield 77%).

[0165] NMR data for M23-6: 1 H NMR (500MHz, CDCl3) δ7.98-7.96(m,2H),7.85-7.84(m,2H),7.47-7.42(m,4H),7.25-7.20(m,4H),6.99-6.97(m,2H),4.37(s,6H).

[0166]

[0167] (2) M23-6 (1.16 g, 1.8 mmol), 2',4',6'-tricyano-[1,1'-diphenyl]-4-yl)boronic acid (1.48 g, 5.41 mmol), potassium phosphate (1.40 g, 6.6 mmol), and Pd(PPh3)4 (0.21 g, 0.18 mmol) were dissolved in 50 mL toluene, 10 mL ethanol, and 5 mL water. The mixture was stirred and heated to 85 °C for 24 h. The mixture was extracted with dichloromethane, dried, and column chromatography was performed to obtain compound M23 (1.36 g, 80% yield). Mass spectrometry: m / z = 945.28 [M+H] + .

[0168] NMR data for compound M23: 1 HNMR (500MHz, CDCl3) δ9.11(s,4H),7.98-7.96(m,2H),7.85-7.84(m,2H),7.47-7.42(m,12H),7.25-7.20(m,4H),6.99-6.97(m,2H),4.37(s,6H).

[0169] Synthesis example 24

[0170]

[0171] (1) M23-6 (1.17 g, 1.8 mmol), pinacol diboronate (1.82 g, 7.2 mmol), potassium acetate (705 mg, 7.2 mmol) and Pd(dppf)Cl2 (132 mg, 0.18 mmol) were added to 50 mL of redistilled dioxane, stirred and heated to 110 °C, and reacted for 24 h. The mixture was extracted with dichloromethane, dried, and column filtered to obtain boric acid intermediate M24-1 (1.15 g, yield 86%).

[0172] (2) M24-1 (1.54 g, 1.8 mmol), 4-bromobenzo[c][1,2,5]thiadiazole-5,6-dianitronidazole (1.43 g, 5.41 mmol), potassium phosphate (1.40 g, 6.6 mmol), and Pd(PPh3)4 (0.21 g, 0.18 mmol) were dissolved in 50 mL toluene, 10 mL ethanol, and 5 mL water. The mixture was stirred and heated to 85 °C for 24 h. The mixture was extracted with dichloromethane, dried, and column chromatography was performed to obtain compound M24 (927 mg, 60% yield). Mass spectrometry: m / z = 859.15 [M+H] + .

[0173] NMR data for compound M24: 1 HNMR (500MHz, CDCl3) δ8.54(s,2H),7.98-7.96(m,2H),7.85-7.84(m,2H),7.47-7.42(m,4H),7.25-7.20(m,4H),6.99-6.97(m,2H),4.37(s,6H).

[0174] Example 1: Fabrication of Organic Electroluminescent Devices

[0175] The OLED device in this embodiment is composed of: ITO / HAT-CN (30nm) / NPB (50nm) / TCTA:M1 (60nm) / TPBi (50nm) / / LiQ (1nm) / Al (120nm). The specific fabrication method is as follows:

[0176] First, the ITO substrate (45nm thick) was cleaned in the following order: ultrasonication with 5wt% KOH solution for 15min, ultrasonication with pure water for 15min, ultrasonication with isopropanol for 15min, and drying in an oven for 1h; then the substrate was transferred to a UV-OZONE device for surface treatment for 15min, and immediately transferred to a glove box after treatment.

[0177] HAT-CN was vacuum-deposited on a clean ITO substrate to form a hole injection layer (HIL) with a thickness of 30 nm. NPB was then vacuum-deposited on the hole injection layer to form a hole transport layer (HTL) with a thickness of 50 nm.

[0178] Compound M1 was used as a guest material (dopant) and coated onto the hole transport layer along with the host material TCTA by inkjet printing (the mass ratio of dopant to host material was 2:98, the solvent was xylene, and the concentration of the light-emitting layer material was 20 mg / mL). The mixture was then dried at 140 °C to form an organic light-emitting layer (EML) with a thickness of 60 nm.

[0179] Then, TPBi is vacuum-deposited on the organic light-emitting layer to form an electron transport layer (ETL) with a thickness of 50 nm. LiQ is then vacuum-deposited on the electron transport layer to form an electron injection layer (EIL) with a thickness of 1 nm.

[0180] Next, Al is deposited on the electron injection layer to form a cathode with a thickness of 120 nm.

[0181] Finally, the OLED device was prepared by UV curing and encapsulation followed by heating and baking for 20 minutes.

[0182] Example 2-24

[0183] Organic electroluminescent devices were prepared according to the method of Example 1, except that, in forming the organic light-emitting layer, the compounds listed in Table 3 below (“Guest Materials” column) were used instead of compound M1 in Example 1.

[0184] Comparative Example 1

[0185] Organic electroluminescent devices were prepared according to the method of Example 1, except that Pm2 was used instead of compound M1 in Example 1 in forming the organic light-emitting layer.

[0186] The structures of the main materials used in the above embodiments and comparative examples are shown below:

[0187]

[0188] The performance of the organic electroluminescent devices prepared in the examples and comparative examples was analyzed. The efficiency of the devices was tested under dark conditions at 25°C, achieving a value of 1000 Cd / m². 2 The lifetime of the device was tested under certain brightness conditions when the brightness decayed to 80%, and the results are shown in Table 3.

[0189] Table 3

[0190]

[0191]

[0192] As can be seen from the above, using the organic compounds of this application as guest materials for the light-emitting layer can effectively improve the external quantum efficiency of OLED devices and extend the lifespan of the devices.

[0193] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above 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.

[0194] The embodiments described above are merely illustrative of several implementation methods of this application, and while the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the invention patent. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of this application, and these all fall within the protection scope of this application. Therefore, the protection scope of this patent application should be determined by the appended claims.

Claims

1. An organic compound, characterized in that, The organic compound is one of the following formulas 1-1 to 1-4: ； Where X represents O, S, or C(R) a R b ), R a and R b They may be the same or different, and each is independently a hydrogen or an alkyl group having 1-10 carbon atoms; R1 and R2 are the same, and are alkyl groups with 1-10 carbon atoms; Both L1 and L2 are single bonds, and both A1 and A2 are H bonds. It is one of the following groups: for , and Same, and is one of the following groups:

2. The organic compound according to claim 1, characterized in that, R a and R b The same or different, and each independently being hydrogen, methyl, ethyl, n-propyl, isopropyl, or tert-butyl; and / or R1 and R2 may be the same or different, and each can be methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl or n-hexyl.

3. The organic compound according to claim 1, characterized in that, The organic compound is one of the following compounds: 。 4. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes: The anode and cathode are arranged opposite each other; and An organic light-emitting layer disposed between the anode and the cathode, wherein the organic light-emitting layer comprises an organic compound according to any one of claims 1-3.

5. The organic electroluminescent device according to claim 4, characterized in that, The organic light-emitting layer comprises a host material and a guest material, wherein the guest material includes the organic compound.

6. The organic electroluminescent device according to claim 5, characterized in that, The main material includes at least one of TATC, CBP, TPD and mCP.

7. An electronic device, characterized in that, Includes the organic electroluminescent device according to any one of claims 4 to 6.

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