Organic compounds and their uses

Abstract

This application relates to an organic compound, an electron transport material, an organic electroluminescent device, and a display panel. The organic compound is shown in general formula (1). This organic compound combines triazine structural units and dibenzo5-membered ring structural units in an ortho-positional connection via benzene rings, and has a high glass transition temperature. Using it as an electron transport material to prepare light-emitting devices can improve device efficiency, extend device lifetime, and reduce driving voltage.

Description

Technical Field

[0001] This application relates to the field of organic optoelectronic materials technology, and in particular to an organic compound and its uses. Background Technology

[0002] Organic light-emitting diodes (OLEDs), as a new generation of display technology, have advantages such as ultra-thinness, self-illumination, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, and low energy consumption. They have been widely used in industries such as flat panel displays, flexible displays, solid-state lighting, and automotive displays.

[0003] Currently, luminescent material systems based on fluorescence and phosphorescence have been developed. Organic light-emitting diodes (OLEDs) using fluorescent materials exhibit high reliability, but their internal electroluminescence quantum efficiency under electrical excitation is limited to 25% due to the 1:3 branching ratio of singlet to triplet excited states of the exciton. Conversely, OLEDs using phosphorescent materials have achieved nearly 100% internal electroluminescence quantum efficiency. However, the stability of phosphorescent OLEDs still needs improvement. Besides the luminescent material itself, the electron transport material is also crucial for OLED stability.

[0004] The electron transport material used in traditional OLED devices is aluminum 8-hydroxyquinoline (Alq3), but Alq3 has relatively low electron mobility. Currently, commonly used electron transport materials on the market, such as bathophenanthroline (BPhen), bathocuproine (BCP), and TmPyPB, can generally meet the electron mobility requirements of organic electroluminescent panels, but their glass transition temperatures are low. The Joule heat generated during device operation can lead to molecular degradation and changes in molecular structure, resulting in insufficient material stability. Summary of the Invention

[0005] In view of the shortcomings of the prior art, the purpose of this application is to provide an organic compound, an electron transport material, an organic electroluminescent device, and a display panel, which aims to solve the problem of poor thermal stability of existing electron transport materials.

[0006] The first aspect of this application provides an organic compound, as shown in general formula (1):

[0007]

[0008] Wherein, R is selected from substituted or unsubstituted aromatic groups containing 6-20 C atoms or substituted or unsubstituted heteroaromatic groups containing 5-30 ring atoms;

[0009] X is selected from CR 1 R2 SiR 3 R 4 NR 5 C (=O), S, S (=O)2 or O;

[0010] Each occurrence of X1 and X2 is independently selected from either non-existent or CR. 6 Multiple X1s may exist simultaneously or may not be selected at the same time; multiple X2s may exist simultaneously or may not exist at the same time; and X1 and X2 may not exist at the same time.

[0011] When neither X1 nor X2 exists, X3 also does not exist, and X4, X5, and X6 are all selected from CR. 7 When X1 exists, X2 does not exist, and X3 is selected from CR. 8 X4 and X5 are selected from C, and X6 is selected from R. 9 When X2 exists, X1 does not exist, and X3 is selected from CR. 10 X6 and X5 are selected from C, and X4 is selected from R. 11 ;

[0012] V is selected independently from CR each time it appears. 12 ;

[0013] Ra and Rb are each independently selected from substituted or substituted aromatic groups containing 6-20 C atoms;

[0014] R 1 ~R 12 Each is independently selected from H, D, or substituted or unsubstituted alkyl groups containing 1-6 C atoms, or substituted or unsubstituted aromatic groups containing 6-12 C atoms.

[0015] In a second aspect, this application provides an electron transport material comprising the aforementioned organic compound.

[0016] In a third aspect, this application provides an organic electroluminescent device, wherein the electron transport layer of the organic electroluminescent device comprises at least one of the organic compounds or electron transport materials as described above.

[0017] In a fourth aspect, this application provides a display panel including the aforementioned organic electroluminescent device.

[0018] Compared with the prior art, this application has the following beneficial effects:

[0019] The organic compound provided in this application combines triazine structural units and dibenzo5-membered ring structural units through ortho-linked benzene rings. This facilitates a reduction in molecular packing density, enhances molecular rigidity, and consequently increases the glass transition temperature and thermal stability of the material. Using this compound to fabricate light-emitting devices improves device efficiency, extends device lifetime, and reduces driving voltage. The organic compound according to this application can also serve as an electron transport material, exhibiting high carrier transport rates and balanced carrier transport performance. This facilitates a balance between hole and electron transport in the device while simultaneously achieving a wider carrier recombination region, thus improving luminous efficiency. This provides a solution for light-emitting devices with low manufacturing cost, high efficiency, long lifetime, and low driving voltage. Attached Figure Description

[0020] Figure 1 This is a schematic diagram of the OLED device structure in one embodiment of this application. Detailed Implementation

[0021] The organic compounds and their uses described in this application are further described in detail below with reference to specific embodiments. 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.

[0022] 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 invention pertains. The terminology used herein in the specification of this invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0023] the term

[0024] Unless otherwise stated or in case of contradiction, the terms or phrases used herein shall have the following meanings:

[0025] In this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0026] In this application, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined group is substituted, it should be understood that it may be substituted by a group acceptable in the art, including but not limited to: C 1-30Alkyl groups, cycloalkyl groups containing 3-20 ring atoms, heterocyclic groups containing 3-20 ring atoms, aryl groups containing 5-20 ring atoms, heteroaryl groups containing 5-20 ring atoms, silyl groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, haloformyl groups, formyl groups, -NRR′ groups, cyano groups, isocyano groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, trifluoromethyl groups, nitro groups, or halogen groups, and the above groups may be further substituted with substituents acceptable in the art; it is understood that R and R′ in -NRR′ are each independently substituted with groups acceptable in the art, including but not limited to H, C 1-6 Alkyl group, cycloalkyl group containing 3-8 ring atoms, heterocyclic group containing 3-8 ring atoms, aryl group containing 5-20 ring atoms, or heteroaryl group containing 5-10 ring atoms; the C 1-6 Alkyl, cycloalkyl containing 3-8 ring atoms, heterocyclic group containing 3-8 ring atoms, aryl group containing 5-20 ring atoms, or heteroaryl group containing 5-10 ring atoms may optionally be further substituted with one or more of the following groups: C 1-6 Alkyl groups, cycloalkyl groups containing 3-8 ring atoms, heterocyclic groups containing 3-8 ring atoms, halogens, hydroxyl groups, nitro groups, or amino groups.

[0027] In this application, "ring atom number" refers to the number of atoms in the ring itself of a structural compound (e.g., a monocyclic compound, a fused-ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) obtained by atomic bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, a benzene ring has 6 ring atoms, a naphthalene ring has 10 ring atoms, and a thiophene group has 5 ring atoms.

[0028] The term "alkyl" refers to a saturated hydrocarbon containing a primary (normal) carbon atom, or a secondary carbon atom, or a tertiary carbon atom, or a quaternary carbon atom, or a combination thereof. Phrases containing this term, such as "alkyl containing 1-6 carbon atoms," can independently be C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, or C6 alkyl each time they appear. Suitable examples include, but are not limited to: methyl (Me, -CH3), ethyl (Et, -CH2CH3), 1-propyl (n-Pr, n-propyl, -CH2CH2CH3), 2-propyl (i-Pr, i-propyl, -CH(CH3)2), 1-butyl (n-Bu, n-butyl, -CH2CH2CH2CH3), 2-methyl-1-propyl (i-Bu, i-butyl, -CH2CH(CH3)2), and 2-butyl (s-Bu, s-butyl, -CH(CH3)). CH2CH3), 2-methyl-2-propyl (t-Bu, t-butyl, -C(CH3)3), 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 (-CH2CH 2CH(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)CH2) CH3), 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) and 3,3-dimethyl-2-butyl (-CH(CH3)C(CH3)3). In this application, "alkyl" can be a straight-chain alkyl, branched alkyl, or cycloalkyl.

[0029] In this application, "aromatic group" and "aryl" are used interchangeably, referring to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. This group can be a monocyclic aromatic group, a fused-ring aromatic group, or a polycyclic aromatic group; for polycyclic rings, at least one must be an aromatic ring system. Suitable examples of "aromatic groups containing 6-20 carbon atoms" include, but are not limited to, benzene, biphenyl, naphthalene, anthracene, phenanthrene, dinaphthalene, triphenylene and their derivatives. Understandably, multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N, or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamines, and diaryl ether systems should also be included in the definition of aryl.

[0030] In this application, "heteroaromatic group" and "heteroaryl" are equivalent, referring to an aromatic group in which at least one carbon atom is replaced by a non-carbon atom. The non-carbon atom can be an N atom, O atom, S atom, Si atom, P atom, etc., and may further be N atom, O atom, and S atom. For example, suitable examples of "heteroaromatic group containing 5-30 ring atoms" include, but are not limited to: furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazolium, indole, carbazole, pyrroloimidazol, pyrrolopyrrole, thiophenolopyrrole, thiophenolothiophene, furanolopyrrole, furanolofuran, thiophenolofuran, benzoisoxazole, benzoisothiazol, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, o-diazonine, quinoxaline, phenanthridine, primidine, quinazoline, and quinazolineone.

[0031] "Halogen" refers to F, Cl, Br or I.

[0032] In this application, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site.

[0033] In this application, when no fusion site is specified in the group, it means that any fusionable site in the group is selected as the fusion site, preferably two or more sites in the adjacent position of the group are fusion sites.

[0034] In this application, the single bonds connecting the substituents extend through the corresponding ring, indicating that the substituent can be connected to any position on the ring, for example... R is attached to any substituted site on the benzene ring.

[0035] A first aspect of this application provides an organic compound, as shown in general formula (1):

[0036]

[0037] Wherein, R is selected from substituted or unsubstituted aromatic groups containing 6-20 C atoms or substituted or unsubstituted heteroaromatic groups containing 5-30 ring atoms;

[0038] X is selected from CR 1 R 2 SiR 3 R 4 NR 5 C (=O), S, S (=O)2 or O;

[0039] Each occurrence of X1 and X2 is independently selected from either non-existent or CR. 6 Multiple X1s may exist simultaneously or may not be selected at the same time; multiple X2s may exist simultaneously or may not exist at the same time; and X1 and X2 may not exist at the same time.

[0040] When neither X1 nor X2 exists, X3 also does not exist, and X4, X5, and X6 are all selected from CR. 7 When X1 exists, X2 does not exist, and X3 is selected from CR. 8 X4 and X5 are selected from C, and X6 is selected from R. 9 When X2 exists, X1 does not exist, and X3 is selected from CR. 10 X6 and X5 are selected from C, and X4 is selected from R. 11 ;

[0041] V is selected independently from CR each time it appears. 12 ;

[0042] Ra and Rb are each independently selected from substituted or substituted aromatic groups containing 6-20 C atoms;

[0043] R 1 ~R 12 Each is independently selected from H, D, or substituted or unsubstituted alkyl groups containing 1-6 C atoms, or substituted or unsubstituted aromatic groups containing 6-12 C atoms.

[0044] In some implementations, general formula (1) is selected from general formula (2-1) or (2-2):

[0045]

[0046] In some implementations, general formula (1) is selected from general formula (3-1) or (3-2):

[0047]

[0048] In some embodiments, R is selected from the following groups, or groups obtained by fusion of the following groups:

[0049]

[0050] Among them, X 1 Selected from CR1 or N;

[0051] Y 1 Selected from CR2R3, SiR4R5, NR6, C (=O), S, S (=O)2 or O;

[0052] Y 2 Selected from C or Si;

[0053] L1 and L2 are each independently selected from either non-existent or single-bond, and L1 and L2 are not simultaneously selected from non-existent;

[0054] R1 to R6 are each independently selected from H, D, or substituted or unsubstituted alkyl groups containing 1-6 C atoms, or substituted or unsubstituted phenyl groups.

[0055] In some embodiments, R is selected from any of the following groups:

[0056]

[0057] Among them, X 1 Y 1 Y 2 The definition is as above and will not be repeated here.

[0058] In some embodiments, R is selected from any of the following groups:

[0059]

[0060] In some embodiments, Ra and Rb are each independently selected from substituted or substituted benzenes, biphenyls, naphthalenes, and combinations thereof. Specific examples may include structures as shown below:

[0061]

[0062] Specific examples of organic compounds in this application may include, but are not limited to, any of the following structural formulas:

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072] The organic compound represented by formula (1) in this application can be prepared according to the preparation method provided in this application, but is not limited to the preparation method provided in this application. The compound represented by formula (1) in this application can be prepared according to the following synthetic route:

[0073]

[0074] The specific preparation method includes the following steps:

[0075] Compound HX-1 was subjected to a first coupling reaction with compound AX to prepare compound HX-2;

[0076] Compound HX-2 was subjected to a second coupling reaction with compound BX to prepare compound HX-3; and

[0077] The organic compound was prepared by a third coupling reaction between compound HX-3 and compound CX.

[0078] The general structural formulas of compounds HX-1, HX-2, HX-3, AX, BX, and CX are shown in the above synthetic route. Ra and Rb are defined as Ra and Rb in formula (1) above, and will not be repeated here. X1, X2, and X3 are selected from halogens, specifically F, Cl, Br, or I. A is phenyl, and in the structure of AX, either X2 or X3 must be located in the ortho position of -B(OH)2. Rm is defined as R in formula (1) above, and will not be repeated here. The specific structure of Rn is shown in the following formula:

[0079] The definitions of V, X, X1, X2, X3, X4, X5 and X6 in this formula are as described in the definitions of V, X, X1, X2, X3, X4, X5 and X6 in the above formula (1), and will not be repeated here.

[0080] The amounts of reactants used in the above preparation method are conventional amounts in the art, and the reaction conditions are also conventional reaction conditions in the art, without any special limitations.

[0081] A second aspect of this application also provides an electron transport material comprising an organic compound as shown in any embodiment of the first aspect of this application.

[0082] A third aspect of this application further provides an organic electroluminescent device, wherein the electron transport layer of the organic electroluminescent device contains an organic compound as shown in any embodiment of the first aspect of this application or an electron transport material as shown in the second aspect of this application.

[0083] The fourth aspect of this application relates to the application of the organic electroluminescent device according to the third aspect of this application in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, etc.

[0084] The fifth aspect of this application also relates to electronic devices that include the organic electroluminescent device according to the third aspect of this application, including, but not limited to, display devices, lighting devices, light sources, sensors, etc.

[0085] In some specific embodiments, a display panel is provided, including the organic electroluminescent device described above.

[0086] In addition, the organic electroluminescent device of this application will be described below with appropriate reference to the accompanying drawings.

[0087] Organic electroluminescent devices include a cathode, an anode, and one or more organic functional layers located between the cathode and the anode. The organic functional layers are selected from one or more layers including an electron injection layer, an electron transport layer, a hole blocking layer, a hole injection layer, a hole transport layer, an electron blocking layer, and an emissive layer, wherein at least one emissive layer is included. Typically, the organic functional layers include a hole injection layer, a hole transport layer, an emissive layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0088] This application does not impose any particular limitations on other aspects of organic electroluminescent devices. The device structure of organic light-emitting diodes, including the cathode, anode, and organic functional layer, will be further described below, but is not limited thereto.

[0089] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. Holes can be readily injected into the hole injection layer (HIL), hole transport layer (HTL), or light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light emitter in the light-emitting layer or the p-type semiconductor material serving as the HIL, HTL, or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to: metals such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, and their alloys; metal oxides such as indium oxide, zinc oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; and conductive polymers such as polyaniline, polypyrrole, poly(3-methylthiophene), etc. In addition to the above-mentioned hole injection materials and combinations thereof, materials known to be suitable for anode use are also included. Other suitable anode materials are known and can be readily selected and used by those skilled in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to fabricate the devices according to this application.

[0090] The cathode may comprise a conductive metal or metal oxide. Electrons can be readily injected into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the luminescent material in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL), electron transport layer (ETL), or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials suitable for use as cathodes in OLEDs can be used as cathode materials for the devices of this application. Examples of cathode materials include, but are not limited to: metals such as aluminum, magnesium, silver, indium, tin, titanium, etc., and their alloys; multilayer metal materials such as LiF / Al, LiO2 / Al, BaF2 / Al, etc.; in addition to the above materials and combinations thereof that facilitate electron injection, materials known to be suitable as cathodes are also included. Other suitable cathode materials are known and can be readily selected and used by those skilled in the art. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0091] Without limitation, the hole injection layer may be at least one of the following materials and their derivatives, or materials obtained by doping or passivation: PEODT:PSS (poly(3,4-ethylenedioxythiophene):poly(styrenesulfonic acid)), HAT-CN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene), etc.

[0092] Without limitation, the hole transport layer may be at least one of the following materials and their derivatives, or materials obtained by doping or passivation: TFB (poly[(9,9-di-n-octylfluorenyl-2,7-diyl)-alt-(4,4'-(N-(4-n-butyl)phenyl)-diphenylamine)]), PVK (polyvinylcarbazole), PFB [N,N'-(4-n-butylphenyl)-N,N'-diphenyl-p-phenylenediamine]-[9,9-di-n-octylfluorenyl-2,7-diyl] copolymer, TPD (N,N'- Bis(3-methylphenyl)-N,N′-diphenyl-1,1′-biphenyl-4,4′-diamine), TCTA (4,4',4”-tris(carbazole-9-yl)triphenylamine), TAPC (4,4′-cyclohexylbis[N,N-di(4-methylphenyl)aniline]), Poly-TBP, Poly-TPD, NPB (N,N'-diphenyl-N,N'-(1-naphthyl)-1,1′-biphenyl-4,4′-diamine), CBP (4,4'-di(9-carbazole)biphenyl), etc.

[0093] Without limitation, the hole block can be at least one of the following materials and their derivatives, as well as materials obtained by doping or passivation: TPBI (1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene).

[0094] Without limitation, the electron injection layer may be at least one of the following materials and their derivatives, as well as materials obtained by doping or passivation: Yb, LiF, lithium oxide, etc.

[0095] The luminescent layer material typically includes a luminescent object material and a host material.

[0096] In the organic electroluminescent device according to this application, the electron transport layer may include at least one of the organic compound according to this application and its derivatives, as well as materials obtained by doping or passivation thereof. The organic compound according to this application may be used alone as an electron transport layer material or mixed with other suitable electron transport layer materials. Other suitable electron transport layer materials are known and can be readily selected and used by those skilled in the art.

[0097] The organic electroluminescent device described in this application may be selected from, but is not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells, organic light-emitting cells, organic field-effect transistors, organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes, with OLEDs being particularly preferred.

[0098] Example

[0099] The following describes embodiments of this application. The embodiments described below are exemplary and are only used to explain this application, and should not be construed as limiting this application. Where the technology or conditions are not specified in the embodiments, they are performed according to the technology or conditions described in the literature in this field or according to the product instructions. Reagents or instruments used, unless otherwise specified, are all conventional products that can be obtained commercially.

[0100] The following examples illustrate the synthesis methods of organic compounds described in this application, but this application is not limited to the following embodiments.

[0101] The preparation routes of the target compounds in the following examples are shown below:

[0102]

[0103] Ra and Rb are each independently selected from substituted or substituted aromatic groups containing 6-20 C atoms; X1, X2, and X3 are selected from halogens, specifically F, Cl, Br, and I; A is an aromatic ring such as benzene or biphenyl; for the limitations of Rn and Rm, please refer to the description in the claims.

[0104] Example 1 Compound H2

[0105]

[0106] (1) Synthesis of intermediate H2-2

[0107] H2-1 (6 mmol), A2 (8 mmol), Pd(dppf)Cl2 (0.05 mmol), and K2CO3 (9 mmol) were added to a 10 mL solution of dioxane:water (4:1), mixed, and placed in a 50 mL flask. The mixture was refluxed for 24 hours. After cooling to room temperature, saturated MgSO4 aqueous solution and ethyl acetate were slowly added to the solution for extraction three times. The organic layer was then purified by rotary evaporation to remove the solvent, and the product H2-2 was obtained by column chromatography.

[0108] (2) Synthesis of intermediate H2-3

[0109] B2 (6 mmol), H2-2 (8 mmol), Pd(dppf)Cl2 (0.05 mmol), and K2CO3 (9 mmol) were added to 12 mL of a dioxane:water (4:1) solution and mixed. The mixture was then placed in a 50 mL flask and refluxed for 24 hours. After cooling to room temperature, the solution was slowly extracted three times with saturated MgSO4 aqueous solution and ethyl acetate. The organic layer was then purified by rotary evaporation to remove the solvent, followed by column chromatography to obtain product H2-3.

[0110] (3) Synthesis of intermediate H2

[0111] C2 (6 mmol), H2-3 (6 mmol), Pd(dppf)Cl2 (0.05 mmol), and K2CO3 (9 mmol) were added to a 15 mL solution of dioxane:water (4:1), mixed, and placed in a 50 mL flask. The mixture was refluxed for 24 hours. After cooling to room temperature, saturated MgSO4 aqueous solution and ethyl acetate were slowly added to the solution for extraction three times. The organic layer was then purified by rotary evaporation to remove the solvent, and the product H2 was obtained by column chromatography.

[0112] MALDI-TOF: m / z: calculated value: C 64 H 41 ON3: 867.32, measured value: 867.58.

[0113] Elemental analysis results of the compound: Calculated value: C 64 H 41 ON3 (%): C, 88.56; H, 4.76; O, 1.84; N, 4.84; Test value: C, 88.54; H, 4.77; O, 1.85; N, 4.84.

[0114] Example 2 Compound H7

[0115]

[0116] The synthesis method of H7 is similar to that of H2, except that H2-1 and A2 in reaction step (1) are replaced with equal amounts of H7-1 and A7, respectively; H2-2 and B2 in reaction step (2) are replaced with equal amounts of H7-2 and B7, respectively; and H2-3 and C2 in reaction step (3) are replaced with equal amounts of H7-3 and C7, respectively.

[0117] MALDI-TOF: m / z: calculated value: C 56 H 43 N3Si: 785.32, measured value: 785.63.

[0118] Elemental analysis results of the compound: Calculated value: C 56H 43 N3Si (%): C, 85.57; H, 5.51; N, 5.35; Si, 3.57; Test value: C, 85.59; H, 5.49; N, 5.34; Si, 3.58.

[0119] Example 3 Compound H10:

[0120]

[0121] The synthesis method of H10 is similar to that of H2, except that H2-1 and A2 in reaction step (1) are replaced with equal amounts of H10-1 and A10, respectively; H2-2 and B2 in reaction step (2) are replaced with equal amounts of H10-2 and B10, respectively; and H2-3 and C2 in reaction step (3) are replaced with equal amounts of H10-3 and C10, respectively.

[0122] MALDI-TOF: m / z: calculated value: C 55 H 33 ON3S: 783.23, measured value: 783.61.

[0123] Elemental analysis results of the compound: Calculated value: C 55 H 33 ON3S (%): C, 84.27; H, 4.24; O, 2.04; N, 5.36; S, 4.09; Test value: C, 84.23; H, 4.26; O, 2.05; N, 5.36; S, 4.10.

[0124] Example 4 Compound H12

[0125]

[0126] The synthesis method of H12 is similar to that of H2, except that H2-1 and A2 in reaction step (1) are replaced with equal amounts of H12-1 and A12, respectively; H2-2 and B2 in reaction step (2) are replaced with equal amounts of H12-2 and B12, respectively; and H2-3 and C2 in reaction step (3) are replaced with equal amounts of H12-3 and C12, respectively.

[0127] MALDI-TOF: m / z: calculated value: C 67 H 41 ON3Si: 931.30, measured value: 931.75.

[0128] Elemental analysis results of the compound: Calculated value: C 67 H 41ON3Si (%): C, 86.33; H, 4.43; O, 1.72; N, 4.51; Si, 3.01 Test values: C, 86.37; H, 4.41; O, 1.71; N, 4.51; Si, 3.01.

[0129] Example 5 Compound H14

[0130]

[0131] The synthesis method of H14 is similar to that of H2, except that H2-1 and A2 in reaction step (1) are replaced with equal amounts of H14-1 and A14, respectively; H2-2 and B2 in reaction step (2) are replaced with equal amounts of H14-2 and B14, respectively; and H2-3 and C2 in reaction step (3) are replaced with equal amounts of H14-3 and C14, respectively.

[0132] MALDI-TOF: m / z: calculated value: C 59 H 39 ON3: 805.31, measured value: 805.65.

[0133] Elemental analysis results of the compound: Calculated value: C 59 H 39 ON3 (%): C, 87.92; H, 4.88; O, 1.99; N, 5.21 Test values: C, 87.96; H, 4.87; O, 1.98; N, 5.20.

[0134] Example 6 Compound H46

[0135]

[0136] The synthesis method of H46 is similar to that of H2, except that H2-1 and A2 in reaction step (1) are replaced with equal amounts of H46-1 and A46, respectively; H2-2 and B2 in reaction step (2) are replaced with equal amounts of H46-2 and B46, respectively; and H2-3 and C2 in reaction step (3) are replaced with equal amounts of H46-3 and C46, ​​respectively.

[0137] MALDI-TOF: m / z: calculated value: C 65 H 43 ON3Si: 909.32, measured value: 909.66.

[0138] Elemental analysis results of the compound: Calculated value: C 65 H 43ON3Si (%): C, 85.78; H, 4.76; O, 1.76; N, 4.62; Si, 3.09 Test values: C, 85.73; H, 4.78; O, 1.77; N, 4.62; Si, 3.09.

[0139] Example 7 Compound H72

[0140]

[0141] The synthesis method of H72 is similar to that of H2, except that H2-1 and A2 in reaction step (1) are replaced with equal amounts of H72-1 and A72, respectively; H2-2 and B2 in reaction step (2) are replaced with equal amounts of H72-2 and B72, respectively; and H2-3 and C2 in reaction step (3) are replaced with equal amounts of H72-3 and C72, respectively.

[0142] MALDI-TOF: m / z: calculated value: C 60 H 47 N3S: 841.35, measured value: 841.74.

[0143] Elemental analysis results of the compound: Calculated value: C 60 H 47 N3S (%): C, 85.58; H, 5.63; N, 4.99; S, 3.81 Test value: C, 85.54; H, 5.65; N, 4.99; S, 3.82.

[0144] Example 8 Compound H103

[0145]

[0146] The synthesis method of H103 is similar to that of H2, except that H2-1 and A2 in reaction step (1) are replaced with equal amounts of H103-1 and A103, respectively; H2-2 and B2 in reaction step (2) are replaced with equal amounts of H103-2 and B103, respectively; and H2-3 and C2 in reaction step (3) are replaced with equal amounts of H103-3 and C103, respectively.

[0147] MALDI-TOF: m / z: calculated value: C 74 H 49 ON3: 995.39, measured value: 995.52.

[0148] Elemental analysis results of the compound: Calculated value: C 74 H 49ON3 (%): C, 89.22; H, 4.96; O, 1.61; N, 4.22 Test values: C, 89.25; H, 4.95; O, 1.60; N, 4.21.

[0149] Example 9 Compound H110

[0150]

[0151] The synthesis method of H110 is similar to that of H2, except that H2-1 and A2 in reaction step (1) are replaced with equal amounts of H110-1 and A110, respectively; H2-2 and B2 in reaction step (2) are replaced with equal amounts of H110-2 and B110, respectively; and H2-3 and C2 in reaction step (3) are replaced with equal amounts of H110-3 and C110, respectively.

[0152] MALDI-TOF: m / z: calculated value: C 67 H 39 ON3: 901.31, measured value: 901.68.

[0153] Elemental analysis results of the compound: Calculated value: C 67 H 39 ON3 (%): C, 89.21; H, 4.36; O, 1.77; N, 4.66 Test values: C, 89.19; H, 4.37; O, 1.76; N, 4.67.

[0154] Example 10 Compound H120

[0155]

[0156] The synthesis method of H120 is similar to that of H2, except that H2-1 and A2 in reaction step (1) are replaced with equal amounts of H120-1 and A120, respectively; H2-2 and B2 in reaction step (2) are replaced with equal amounts of H120-2 and B120, respectively; and H2-3 and C2 in reaction step (3) are replaced with equal amounts of H120-3 and C120, respectively.

[0157] MALDI-TOF: m / z: calculated value: C 54 H 32 ON4: 752.26, measured value: 752.61.

[0158] Elemental analysis results of the compound: Calculated value: C 54 H 32ON4 (%): C, 86.15; H, 4.28; O, 2.13; N, 7.44 Test values: C, 86.12; H, 4.29; O, 2.14; N, 7.45.

[0159] Example 11 Compound H140

[0160]

[0161] The synthesis method of H140 is similar to that of H2, except that H2-1 and A2 in reaction step (1) are replaced with equal amounts of H140-1 and A140, respectively; H2-2 and B2 in reaction step (2) are replaced with equal amounts of H140-2 and B140, respectively; and H2-3 and C2 in reaction step (3) are replaced with equal amounts of H140-3 and C140, respectively.

[0162] MALDI-TOF: m / z: calculated value: C 70 H 40 ON3: 938.32, measured value: 938.49.

[0163] Elemental analysis results of the compound: Calculated value: C 70 H 40 ON3 (%): C, 89.53; H, 4.29; O, 1.70; N, 4.47 Test values: C, 89.50; H, 4.30; O, 1.72; N, 4.48.

[0164] II. Device Application Examples

[0165] Application Example 1:

[0166] This application example provides an OLED device with the following structure: Figure 1 As shown, the structure includes, in sequence, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10. Figure 1 The arrows in the diagram represent the direction of light emission from the device.

[0167] The specific fabrication steps of the above-mentioned OLED devices are as follows:

[0168] 1) The glass substrate 1 with indium tin oxide (ITO) anode 2 (thickness of 100nm) is ultrasonically treated in isopropanol and deionized water for 30 minutes respectively, and then exposed to ozone for about 10 minutes for cleaning. The cleaned glass substrate is then mounted on a vacuum deposition equipment.

[0169] 2) On the ITO anode 2, compound a with a thickness of 10 nm is vacuum-deposited as hole injection layer 3;

[0170] 3) Compound b with a thickness of 40 nm is vacuum-deposited on hole injection layer 3 to serve as hole transport layer 4;

[0171] 4) On the hole transport layer 4, compound c with a thickness of 10 nm is vacuum evaporated to serve as an electron blocking layer 5;

[0172] 5) On the electron blocking layer 5, compounds d and e are vacuum co-deposited with a doping ratio of 6% (mass ratio) and a thickness of 20 nm to serve as the light-emitting layer 6.

[0173] 6) On the light-emitting layer 6, compound f with a thickness of 10 nm is vacuum-deposited as a hole blocking layer 7;

[0174] 7) On the hole blocking layer 7, the compound H2 provided in this scheme is prepared by vacuum evaporation with a thickness of 30 nm, as an electron transport layer 8;

[0175] 7) On the electron transport layer 8, a compound LiF with a thickness of 2 nm is vacuum evaporated to serve as the electron injection layer 9;

[0176] 8) An aluminum electrode with a thickness of 100 nm is vacuum-deposited on the electron injection layer 9 to serve as the cathode 10.

[0177] The compounds used in the fabrication of the aforementioned OLED devices are as follows:

[0178]

[0179]

[0180] Application Examples 2-11

[0181] Replace the organic compound H2 in step (7) of Application Example 1 with equal amounts of compounds H7, H10, H12, H14, H46, H72, H103, H110, H120, and H140, respectively, and the other preparation steps are the same as in Application Example 1.

[0182] Device Comparison Example 1-2

[0183] An OLED device, which differs from device embodiment 1 only in that the electron transport material H2 in step (7) is replaced with an equal amount of comparative compound 1 or comparative compound 2, while the raw materials and preparation steps are the same.

[0184] Performance evaluation of OLED devices:

[0185] The current of the OLED device at different voltages was measured using a Keithley 2365A digital nanovoltmeter, and the current density of the OLED device at different voltages was obtained by dividing the current by the emitting area. The brightness and radiant energy flux density of the OLED device at different voltages were measured using a Konicaminolta CS-2000 spectroradiometer. Based on the current density and brightness of the OLED device at different voltages, the turn-on voltage and current efficiency (CE, Cd / A) at the same current density (10 mA / cm2) were obtained, where VON is the turn-on voltage at a brightness of 1 Cd / m2. The lifetime LT95 was obtained by measuring the time it takes for the brightness of the OLED device to reach 95% of the initial brightness (under the test condition of 50 mA / cm2). The voltage / efficiency / lifetime of compound 1 was used as a 100% comparison with the performance of other device structures, and the data are shown in Table 1.

[0186] Table 1 OLED Device Performance Test Results

[0187] Application Example 1 H2 98.1％ 105.7％ 106.3％ Application Example 2 H7 97.5％ 105.4％ 107.4％ Application Example 3 H10 97.9％ 106.9％ 106.9％ Application Example 4 H12 98.1％ 106.5％ 104.6％ Application Example 5 H14 97.3％ 105.1％ 105.2％ Application Example 6 H46 98.6％ 106.3％ 107.3％ Application Example 7 H72 97.4％ 104.6％ 109.2％ Application Example 8 H103 98.7％ 103.7％ 104.5％ Application Example 9 H110 97.2％ 104.1％ 119.2％ Application Example 10 H120 97.6％ 106.3％ 115.8％ Application Example 11 H140 96.8％ 107.5％ 114.7％ Comparative Example 1 Comparative compound 1 100％ 100％ 100％ Comparative Example 2 Comparative compound 2 101.9％ 102.4％ 98.3％

[0188] As shown in Table 1, compared with comparative compounds 1 and 2, the organic light-emitting devices prepared based on the electron transport material of this application exhibit superior characteristics in terms of driving voltage, luminous efficiency, and lifetime. Comparative compounds 1 and 2 have similar structures to the organic compound of this application, but differ in the degree of functional group conjugation and the connection mode. This demonstrates that even with similar structures, differences in the type and position of the connecting groups can alter electron injection, transport characteristics, luminous efficiency, energy levels (HOMO, LUMO), and the electron balance between holes and electrons, indicating that the organic compound of this application is more suitable as an electron transport material compared to the comparative compounds. Furthermore, the enhanced steric structure of the organic compound of this application can reduce molecular forces and intermolecular stacking, thereby enhancing device stability.

[0189] 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.

[0190] 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, as shown in general formula (1): ， The general formula (1) is selected from general formula (2-1) or (2-2): 、 ； in, R is selected from any of the following groups: ； X is selected from CR 1 R 2 SiR 3 R 4 NR 5 C (=O), S, S (=O)2 or O; Each occurrence of X1 and X2 is independently selected from either non-existent or CR. 6 Multiple X1s may exist simultaneously or may not be selected at the same time; multiple X2s may exist simultaneously or may not exist at the same time; and X1 and X2 may not exist at the same time. When neither X1 nor X2 exists, X3 also does not exist, and X4, X5, and X6 are all selected from CR. 7 When X1 exists, X2 does not exist, and X3 is selected from CR. 8 X4 and X5 are selected from C, and X6 is selected from R. 9 When X2 exists, X1 does not exist, and X3 is selected from CR. 10 X6 and X5 are selected from C, and X4 is selected from R. 11 ; V is selected independently from CR each time it appears. 12 ; Ra and Rb are each independently selected from aromatic groups containing 6-20 C atoms; R 1 ~R 12 Each is independently selected from H, D, or an alkyl group containing 1-6 C atoms, or an aromatic group containing 6-12 C atoms.

2. The organic compound according to claim 1, characterized in that, General formula (1) is selected from general formula (3-1) or (3-2): 、 。 3. The organic compound according to claim 1, characterized in that, Ra and Rb are each independently selected from benzene, biphenyl, and naphthalene.

4. The organic compound according to claim 1, characterized in that, Ra and Rb are each independently selected from benzene or one of the following groups: .

5. An organic compound, characterized in that, The organic compound is any one of the following structural formulas: 、 。 6. An electron transport material, characterized in that, Includes the organic compounds described in any one of claims 1 to 5.

7. An organic electroluminescent device, characterized in that, The electron transport layer of the organic electroluminescent device comprises at least one organic compound as described in any one of claims 1 to 5 or an electron transport material as described in claim 6.

8. A display panel, characterized in that, Including the organic electroluminescent device as described in claim 7.

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