Organic Compounds and Their Applications

Abstract

The present invention relates to an organic compound and an organic electroluminescence device using the organic compound. The organic compound has a structure represented by formula (1). The organic electroluminescence device has excellent device performance and stability. [Formula 1] TIFF2024525820000074.tif58166

Description

[Technical Field]

[0001] The present invention relates to an organic compound, in particular to a compound that can be used in an organic electroluminescence device, and also to an organic electroluminescence device using the organic compound. [Background technology]

[0002] Organic electroluminescent devices (OLEDs) are a type of device with a quasi-sandwich structure, consisting of a positive electrode layer, a negative electrode layer, and an organic functional material layer sandwiched between the electrode layers. When a voltage is applied to the electrodes of an OLED device, positive charges are injected from the positive electrode and negative charges are injected from the negative electrode. Under the influence of an electric field, the positive and negative charges migrate, merge, and recombine within the organic layer to emit light. OLED devices have attracted much attention in the fields of new display technology and new lighting technology due to their advantages such as high brightness, fast response, wide viewing angle, simple processing, and flexibility. Currently, this technology is widely applied to display panels for new lighting fixtures, smartphones, and tablets, and is expanding into large display products such as televisions. It is a new display technology that is rapidly developing and has high technical requirements.

[0003] When selecting OLED emitting materials, singlet-emitting fluorescent materials are long-lived and inexpensive, but have low efficiency, while triplet-emitting phosphorescent materials are highly efficient but expensive, and the lifespan issue of blue-emitting materials remains unresolved. Adachi of Kyushu University in Japan proposed a new organic emitting material, namely thermally activated delayed fluorescence (TADF) materials. The singlet-triplet energy gap (ΔEST) of this type of material is very small (<0.3 eV), and triplet excitons are converted to singlet excitons through reverse intersystem crossing (RISC) to emit light, allowing the internal quantum efficiency of the device to reach 100%. Prior art has used the "multiple resonance-induced thermally activated delayed fluorescence (MR-TADF)" technique to design new structural compounds. For example, Patent Documents 1, 2, and 3 describe polycyclic aromatic compounds formed by connecting multiple aromatic rings with boron and nitrogen or oxygen atoms, i.e., rigid molecular systems containing special boron (B), nitrogen (N), and oxygen (O) atoms. While this type of thermally activated delayed fluorescent molecule has a high radiative transition rate and high color purity, its large HOMO-LUMO overlap results in a large difference (ΔEst) between the singlet and triplet energies of the material, resulting in a severe decrease in device efficiency. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Patent application CN107851724 [Patent Document 2] Patent application CN108431984 [Patent Document 3] Patent application CN110407858 Summary of the Invention [Means for solving the problem]

[0005] In one aspect, the present invention provides an organic compound having a structure as shown in formula (1): [ka] In formula (1), D 1 and D 2 are each independently selected from one of NR5, NR6, O, or S; W 1 and W 2 are each independently C, CH, or CR7; Ring Ar1, ring Ar2, ring Ar3 and ring Ar4 are each independently selected from a C6-C60 aromatic ring or a C3-C60 heteroaromatic ring, wherein the heteroatom in the heteroaromatic ring group is selected from one or more of Si, Ge, N, P, O, S and Se; The rings Ar3 and R6 are not connected to each other, or are connected via a CC single bond, or are connected via O, S or Se, or are connected to each other via CR8R9 or NR 10 are connected via Ring Ar4 and ring R5 are not connected to each other, or are connected to each other via a CC single bond, or are connected to each other via O, S or Se, or are connected to each other via CR8R9 or NR 10 are connected via R6 and W 2 and may be unconnected, or may be connected via a CC single bond, or may be connected via O, S or Se, or may be connected via CR8R9 or NR 10 are connected via R5 and W 1 and may be unconnected, or may be connected via a CC single bond, or may be connected via O, S or Se, or may be connected via CR8R9 or NR 10 are connected via R1, R2, R3 and R4 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C30 linear alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C7-C30 aralkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C2-C30 aliphatic chain hydrocarbyl amine group, a substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbyl amine group, a substituted or unsubstituted C6-C30 arylamine group, a substituted or unsubstituted C3-C30 heteroarylamine group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 arylboryl group and a substituted or unsubstituted C3-C60 heteroaryl group; n1, n2, n3 and n4 are each independently selected from integers of 0 to 10, preferably n1, n2, n3 and n4 are each independently selected from integers of 1 to 5; When n1 is an integer greater than 1, a plurality of R1's may be the same or different, and a plurality of R1's may be linked to form a ring; When n2 is an integer greater than 1, a plurality of R2 may be the same or different, and a plurality of R2 may be linked to form a ring; When n3 is an integer greater than 1, multiple R3s may be the same or different, and multiple R3s may be linked to form a ring; When n4 is an integer greater than 1, multiple R4s may be the same or different, and multiple R4s may be linked to form a ring; R5 and R6 are each independently selected from a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C3 to C60 heteroaryl group; preferably, R5 and R6 are each independently selected from a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C3 to C30 heteroaryl group; more preferably, R5 and R6 are each independently selected from a substituted or unsubstituted benzene ring, naphthalene ring, or anthracene ring; most preferably, R5 and R6 are each independently a substituted or unsubstituted benzene ring. R7 is deuterium, halogen, cyano group, substituted or unsubstituted C1 to C10 chain alkyl group, substituted or unsubstituted C3 to C10 cycloalkyl group, substituted or unsubstituted C7 to C30 aralkyl group, substituted or unsubstituted C1 to C30 alkoxy group, substituted or unsubstituted C2 to C30 aliphatic chain hydrocarbylamine group, substituted or unsubstituted C4 to C30 cyclic aliphatic chain hydrocarbylamine group, substituted or unsubstituted C6 to C30 arylamine group, substituted or unsubstituted C3 to C30 heteroarylamine group, substituted or unsubstituted R7 is selected from one of a substituted C6 to C30 aryloxy group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group, preferably R7 is selected from one of a deuterium, a halogen, a cyano group, a C1 to C6 chain alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, more preferably R7 is selected from one of a deuterium, a halogen, a cyano group, and a substituted or unsubstituted benzene ring; R8, R9 and R 10 are each independently a substituted or unsubstituted C1 to C10 chain alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C7 to C30 aralkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 aliphatic chain hydrocarbylamine group, a substituted or unsubstituted C4 to C30 cyclic aliphatic chain hydrocarbylamine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C3 to C30 heteroarylamine group, a substituted or unsubstituted R8 and R9 are each independently selected from a C6 to C30 chain alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C3 to C60 heteroaryl group, a substituted or unsubstituted C1 to C10 chain alkyl group, a substituted or unsubstituted C7 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group; The above R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10each independently has a substituent, the substituent is each independently selected from one or a combination of two of a halogen, a cyano group, a C1 to C20 chain alkyl group, a C3 to C20 cycloalkyl group, a C1 to C10 alkoxy group, a C6 to C30 arylamino group, a C3 to C30 heteroarylamino group, a C6 to C30 aryloxy group, a C6 to C30 aryl group, a substituted or unsubstituted C6 to C60 arylboryl group, and a C3 to C30 heteroaryl group.

[0006] Furthermore, in the general formula (1), 1 is NR5, D 2 is NR6, and R5 and R6 are the same or different, preferably R5 and R6 are the same.

[0007] Furthermore, the general formula (1) is more preferably the following structural formula (1-1), (1-2), (1-3), (1-4), (1-5) or (1-6), [ka] In formulas (1-1), (1-2), (1-3), (1-4), (1-5) and (1-6), W 1 and W 2 , R1-R6, Ar1-Ar4 and n1-n4 are all defined the same as in formula (1).

[0008] More preferably, the rings Ar1, Ar2, Ar3, and Ar4 are each independently selected from a C6 to C60 aromatic ring or a C3 to C30 heteroaromatic ring, more preferably, the rings Ar1, Ar2, Ar3, and Ar4 are each independently selected from a C6 to C30 aromatic ring or a C3 to C20 heteroaromatic ring, more preferably, the rings Ar1, Ar2, Ar3, and Ar4 are each independently selected from a benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, a furan, or a thiophene, and most preferably, the rings Ar1, Ar2, Ar3, and Ar4 are each independently a benzene ring.

[0009] Furthermore, the above R1, R2, R3 and R4 each independently represent a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a 2-methylbutyl group, an n-pentyl group, an s-pentyl group, a cyclopentyl group, a neopentyl group, an n-hexyl group, a cyclohexyl group, a neohexyl group, an n-heptyl group, a cycloheptyl group, an n-octyl group, a cyclooctyl group, a 2-ethylhexyl group, a trifluoromethyl group, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, a cyano group, a halogen atom ... , phenyl group, naphthyl group, anthracenyl group, benzanthracenyl group, phenanthrenyl group, benzophenanthrenyl group, pyrenyl group, chrysene group, perylene group, fluoranthenyl group, tetracenyl group, pentacenyl group, benzopyrenyl group, biphenyl group, diphenyl group, terphenyl group, trimerized phenyl group, quaterphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrenyl group, dihydropyrenyl group, tetrahydropyrenyl group, cis or trans indenofluorenyl group, trimerized indenyl group, isotrimerized indenyl group Indenyl group, spirotrimerized indenyl group, spiroisotrimerized indenyl group, furyl group, benzofuryl group, isobenzofuryl group, dibenzofuryl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, pyrrolyl group, isoindolyl group, carbazolyl group, indenocarbazolyl group, pyridyl group, quinolyl group, isoquinolyl group, acridinyl group, phenanthridinyl group, benzo-5,6-quinolyl group, benzo-6,7-quinolyl group, benzo-7,8-quinolyl group, pyrazolyl group, indazolyl group, imidazolyl group, benzyl midazolyl group, naphthimidazolyl group, phenanthroiimidazolyl group, pyridinoimidazolyl group, pyrazinoimidazolyl group, quinoxanoimidazolyl group, oxazolyl group, benzoxazolyl group, naphthoxazolyl group, anthraoxazolyl group, phenanthrooxazolyl group, 1,2-thiazolyl group, 1,3-thiazolyl group, benzothiazolyl group, pyridazinyl group, benzopyridazinyl group, pyrimidinyl group, benzopyrimidinyl group, quinoxalinyl group, 1,5-diazaanthracenyl group, 2,7-diazapyrenyl group, 2,3-diazapyrenyl group, 1,a 6-diazapyrenyl group, a 1,8-diazapyrenyl group, a 4,5-diazapyrenyl group, a 4,5,9,10-tetraazapyrylene group, a pyrazinyl group, a phenazinyl group, a phenothiazinyl group, a naphthyridinyl group, an azacarbazolyl group, a benzocarbolinyl group, a phenanthrolinyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, a benzotriazolyl group, a 1,2,3-oxadiazolyl group, a 1,2,4-oxadiazolyl group, a 1,2,5-oxadiazolyl group, a 1,2,3-thiadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,2,5-thiadiazolyl group, The substituent is selected from one of the following groups: 1,3,4-thiadiazolyl group, 1,3,5-triazinyl group, 1,2,4-triazinyl group, 1,2,3-triazinyl group, tetrazolyl group, 1,2,4,5-tetrazinyl group, 1,2,3,4-tetrazinyl group, 1,2,3,5-tetrazinyl group, purinyl group, pteridinyl group, indolizinyl group, benzothiadiazolyl group, diphenylboryl group, dimesitylboryl group, dipentafluorophenylboryl group, and bis(2,4,6-triisopropylphenyl)boryl group, or a combination of the two groups listed above.

[0010] R5 and R6 each independently represent a phenyl group, a naphthyl group, an anthracenyl group, a benzanthracenyl group, a phenanthrenyl group, a benzophenanthrenyl group, a pyrenyl group, a chrysene group, a perylene group, a fluoranthenyl group, a tetracenyl group, a pentacenyl group, a benzopyrenyl group, a biphenyl group, a diphenyl group, a terphenyl group, a trimerized phenyl group, a quaterphenyl group, a fluorenyl group, a spirobifluorenyl group, a dihydrophenanthrenyl group, a dihydropyrenyl group, a tetrahydropyrenyl group, or a cis- or trans-indenofluorenyl group. group, trimerized indenyl group, isotrimerized indenyl group, spirotrimerized indenyl group, spiroisotrimerized indenyl group, furyl group, benzofuryl group, isobenzofuryl group, dibenzofuryl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, pyrrolyl group, isoindolyl group, carbazolyl group, indenocarbazolyl group, pyridyl group, quinolyl group, isoquinolyl group, acridinyl group, phenanthridinyl group, benzo-5,6-quinolyl group, benzo-6,7-quinolyl group, benzo-7,8-quinolyl group, pyrazolyl group, i anthrazolyl group, imidazolyl group, benzimidazolyl group, naphthimidazolyl group, phenanthroiimidazolyl group, pyridinoimidazolyl group, pyrazinoimidazolyl group, quinoxanoimidazolyl group, oxazolyl group, benzoxazolyl group, naphthoxazolyl group, anthraoxazolyl group, phenanthrooxazolyl group, 1,2-thiazolyl group, 1,3-thiazolyl group, benzothiazolyl group, pyridazinyl group, benzopyridazinyl group, pyrimidinyl group, benzopyrimidinyl group, quinoxalinyl group, 1,5-diazaanthracenyl group, 2,7-diazapyrene group, nyl group, 2,3-diazapyrenyl group, 1,6-diazapyrenyl group, 1,8-diazapyrenyl group, 4,5-diazapyrenyl group, 4,5,9,10-tetraazapyrylene group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbolinyl group, phenanthrolinyl group, 1,2,3-triazolyl group, 1,2,4-triazolyl group, benzotriazolyl group, 1,2,3-oxadiazolyl group, 1,2,4-oxadiazolyl group, 1,2,5-oxadiazolyl group, 1,2,3-thiadiazolyl group, 1,2,is selected from one of the following substituents: 4-thiadiazolyl group, 1,2,5-thiadiazolyl group, 1,3,4-thiadiazolyl group, 1,3,5-triazinyl group, 1,2,4-triazinyl group, 1,2,3-triazinyl group, tetrazolyl group, 1,2,4,5-tetrazinyl group, 1,2,3,4-tetrazinyl group, 1,2,3,5-tetrazinyl group, purinyl group, pteridinyl group, indolizinyl group, and benzothiadiazolyl group, or a combination of two of the above groups; R7 is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a 2-methylbutyl group, an n-pentyl group, an s-pentyl group, a cyclopentyl group, a neopentyl group, an n-hexyl group, a cyclohexyl group, a neohexyl group, an n-heptyl group, a cycloheptyl group, an n-octyl group, a cyclooctyl group, a 2-ethylhexyl group, a trifluoromethyl group, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, a cyano group, a halogen atom, a phenyl group, a naphthyl group, an anthracenyl group, a benzyl group, a benzo ... Anthracenyl group, phenanthrenyl group, benzophenanthrenyl group, pyrenyl group, chrysene group, perylene group, fluoranthenyl group, tetracenyl group, pentacenyl group, benzopyrenyl group, biphenyl group, diphenyl group, terphenyl group, trimerized phenyl group, quaterphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrenyl group, dihydropyrenyl group, tetrahydropyrenyl group, cis or trans indenofluorenyl group, trimerized indenyl group, isotrimerized indenyl group, spirotrimerized indenyl group, spiroiso Trimerized indenyl group, furyl group, benzofuryl group, isobenzofuryl group, dibenzofuryl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, pyrrolyl group, isoindolyl group, carbazolyl group, indenocarbazolyl group, pyridyl group, quinolyl group, isoquinolyl group, acridinyl group, phenanthridinyl group, benzo-5,6-quinolyl group, benzo-6,7-quinolyl group, benzo-7,8-quinolyl group, pyrazolyl group, indazolyl group, imidazolyl group, benzimidazolyl group, naphthimidazolyl group, phenanthroimine group, dazolyl group, pyridinoimidazolyl group, pyrazinoimidazolyl group, quinoxanoimidazolyl group, oxazolyl group, benzoxazolyl group, naphthoxazolyl group, anthraoxazolyl group, phenanthrooxazolyl group, 1,2-thiazolyl group, 1,3-thiazolyl group, benzothiazolyl group, pyridazinyl group, benzopyridazinyl group, pyrimidinyl group, benzopyrimidinyl group, quinoxalinyl group, 1,5-diazaanthracenyl group, 2,7-diazapyrenyl group, 2,3-diazapyrenyl group, 1,6-diazapyrenyl group, 1,8-diazapyrenyl group, 4,5-diazapyrenyl group, 4,5,9,10-tetraazapyrylene group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbolinyl group, phenanthrolinyl group, 1,2,3-triazolyl group, 1,2,4-triazolyl group, benzotriazolyl group, 1,2,3-oxadiazolyl group, 1,2,4-oxadiazolyl group, 1,2,5-oxadiazolyl group, 1,2,3-thiadiazolyl group, 1,2,4-thiadiazolyl group The substituent is selected from one of the following groups: thiadiazolyl group, 1,2,5-thiadiazolyl group, 1,3,4-thiadiazolyl group, 1,3,5-triazinyl group, 1,2,4-triazinyl group, 1,2,3-triazinyl group, tetrazolyl group, 1,2,4,5-tetrazinyl group, 1,2,3,4-tetrazinyl group, 1,2,3,5-tetrazinyl group, purinyl group, pteridinyl group, indolizinyl group, and benzothiadiazolyl group, or a combination of the above two groups.

[0011] R8, R9 and R 10each independently represents a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a 2-methylbutyl group, an n-pentyl group, an s-pentyl group, a cyclopentyl group, a neopentyl group, an n-hexyl group, a cyclohexyl group, a neohexyl group, an n-heptyl group, a cycloheptyl group, an n-octyl group, a cyclooctyl group, a 2-ethylhexyl group, a trifluoromethyl group, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, a phenyl group, a naphthyl group, an anthracenyl group, or a benzanthracenyl group , phenanthrenyl group, benzophenanthrenyl group, pyrenyl group, chrysene group, perylene group, fluoranthenyl group, tetracenyl group, pentacenyl group, benzopyrenyl group, biphenyl group, diphenyl group, terphenyl group, trimerized phenyl group, quaterphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrenyl group, dihydropyrenyl group, tetrahydropyrenyl group, cis or trans indenofluorenyl group, trimerized indenyl group, isotrimerized indenyl group, spirotrimerized indenyl group, spiroisotrimerized indenyl group , furyl group, benzofuryl group, isobenzofuryl group, dibenzofuryl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, pyrrolyl group, isoindolyl group, carbazolyl group, indenocarbazolyl group, pyridyl group, quinolyl group, isoquinolyl group, acridinyl group, phenanthridinyl group, benzo-5,6-quinolyl group, benzo-6,7-quinolyl group, benzo-7,8-quinolyl group, pyrazolyl group, indazolyl group, imidazolyl group, benzimidazolyl group, naphthimidazolyl group, phenanthrilimidazolyl group, pyridinoimidazolyl group, azolyl group, pyrazinoimidazolyl group, quinoxanoimidazolyl group, oxazolyl group, benzoxazolyl group, naphthoxazolyl group, anthraoxazolyl group, phenanthrooxazolyl group, 1,2-thiazolyl group, 1,3-thiazolyl group, benzothiazolyl group, pyridazinyl group, benzopyridazinyl group, pyrimidinyl group, benzopyrimidinyl group, quinoxalinyl group, 1,5-diazaanthracenyl group, 2,7-diazapyrenyl group, 2,3-diazapyrenyl group, 1,6-diazapyrenyl group, 1,8-diazapyrenyl group, 4,5-diazapyrenyl group, 4,5,9,10-tetraazaperylene group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbolinyl group, phenanthrolinyl group, 1,2,3-triazolyl group, 1,2,4-triazolyl group, benzotriazolyl group, 1,2,3-oxadiazolyl group, 1,2,4-oxadiazolyl group, 1,2,5-oxadiazolyl group, 1,2,3-thiadiazolyl group, 1,2,4-thiadiazolyl group, 1,2 ,5-thiadiazolyl group, 1,3,4-thiadiazolyl group, 1,3,5-triazinyl group, 1,2,4-triazinyl group, 1,2,3-triazinyl group, tetrazolyl group, 1,2,4,5-tetrazinyl group, 1,2,3,4-tetrazinyl group, 1,2,3,5-tetrazinyl group, purinyl group, pteridinyl group, indolizinyl group, benzothiadiazolyl group, or a combination of the above two groups.

[0012] In the present specification, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents, and when there are multiple substituents, they can be selected from different substituents. When the same expression is referred to in the present invention, they all have the same meaning, and the selection range of the substituent is as shown above and will not be repeated here. In this specification, the expressions Ca to Cb indicate that the number of carbon atoms in the group is a to b, and unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms in substituents. In this specification, the term "independently" means that when there are multiple subjects, they may be the same or different. In this specification, examples of halogen include fluorine, chlorine, bromine, iodine, and the like.

[0013] In this specification, unless otherwise specified, all aryl groups and heteroaryl groups include monocyclic and fused ring groups. The monocyclic aryl group refers to a group containing one or more phenyl groups in a molecule. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are connected via a single bond, such as a phenyl group, a diphenyl group, or a terphenyl group. The fused ring aryl group refers to a group containing at least two benzene rings in a molecule, but the benzene rings are not independent of each other and share the ends of the rings and are fused to each other, such as a naphthyl group or anthracenyl group. The monocyclic heteroaryl group refers to a group containing at least one heteroaryl group in a molecule. When a molecule contains one heteroaryl group and another group (e.g., an aryl group, a heteroaryl group, an alkyl group, etc.), the heteroaryl group and the other group are independent of each other and are connected via a single bond, such as in pyridine, furan, and thiophene. A fused-ring heteroaryl group refers to a group formed by the fusion of at least one phenyl group and at least one heteroaryl group, or at least two types of heteroaromatic rings, such as in quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, and dibenzothiophene.

[0014] In this specification, the C6 to C60 aryl group is preferably a C6 to C30 aryl group, and preferably the aryl group is a group selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, an indenyl group, a fluorenyl group and derivatives thereof, a fluoranthenyl group, a triphenylene group, a pyrenyl group, a perylene group, a chrysene group, and a tetracenyl group. The biphenyl group is selected from a 2-biphenyl group, a 3-biphenyl group, and a 4-biphenyl group; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, and m-terphenyl-2-yl; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracenyl group is selected from the group consisting of a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group; and the fluorocarbon group is selected from the group consisting of a fluorocarbon group, ... The fluorenyl group is selected from the group consisting of 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group and 9-fluorenyl group, the derivative of the fluorenyl group is selected from the group consisting of 9,9'-dimethylfluorene, 9,9'-spirobifluorene and benzofluorene, the pyrenyl group is selected from the group consisting of 1-pyrenyl group, 2-pyrenyl group and 4-pyrenyl group, and the tetracenyl group is selected from the group consisting of 1-tetracenyl group, 2-tetracenyl group and 9-tetracenyl group.

[0015] In this specification, the C3-C60 heteroaryl group is preferably a C4-C30 heteroaryl group, and the heteroaryl group is preferably a furyl group, a thienyl group, a pyrrolyl group, a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an indolyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, or a derivative thereof, wherein the derivative of the carbazolyl group is preferably 9-phenylcarbazole, 9-naphthylcarbazole, benzocarbazole, dibenzocarbazole, or indolocarbazole.

[0016] In this specification, the aryloxy group can be a monovalent group composed of the above-mentioned aryl group, heteroaryl group, and oxygen. In this specification, the alkoxy group may be a monovalent group composed of the above-mentioned chain alkyl group or cycloalkyl group and oxygen. Examples of the C6 to C60 arylamine group referred to in this specification include a phenylamine group, a methylphenylamine group, a naphthylamine group, an anthracenylamine group, a phenanthrenylamine group, and a biphenylamine group.

[0017] Examples of the C6 to C60 heteroarylamino group referred to in this specification include a pyridylamino group, a pyrimidinylamino group, and a dibenzofuranylamino group.

[0018] Furthermore, the compound represented by general formula (1) of the present invention may preferably be a compound with a specific structure such as C1-1 to C1-135, C2-1 to C2-78, C3-1 to C3-78, C4-1 to C4-43, C5-1 to C5-43, or C6-1 to C6-43, and these compounds are merely representative. [ka] TIFF0007719545000004.tif210166TIFF0007719545000005.tif166166TIFF0007719545000006.tif204166TIFF0007719545000007.tif197166TIFF0007719545000008.tif216166TIFF0007719545000009.tif229166TIFF0007719545000010.tif127166TIFF0007719545000011.tif216166TIFF0007719545000012.tif197166TIFF0007719545000013.tif197166TIFF0007719545000014.tif216166TIFF0007719545000015.tif216166TIFF0007719545000016.tif191166TIFF0007719545000017.tif204166TIFF0007719545000018.tif242166TIFF0007719545000019.tif197166TIFF0007719545000020.tif235166TIFF0007719545000021.tif242166

[0019] The structural features of this type of compound in the present invention are as follows: In the mother core structure of general formula (1), two boron atoms are designed at the 1st and 4th positions of the central benzene ring, and two nitrogen atoms or two combinations of nitrogen, oxygen, and sulfur atoms are designed to be introduced at the 2nd and 5th positions of the central benzene ring. Meanwhile, the HOMO and LUMO can be separated by utilizing the resonance effect between boron and nitrogen atoms, or between boron and oxygen atoms, or between boron, nitrogen, and oxygen atoms. At the same time, the hybrid fused ring unit of boron atoms and nitrogen, oxygen, and sulfur atoms has a rigid framework structure, which can reduce the relaxation degree of the excited state structure, thereby achieving a narrower half-width. On the other hand, the structural scheme of the general formula of the compound of the present invention is compared with the multi-resonance structural schemes commonly used in the prior art, such as nitrogen-boron-nitrogen, oxygen-boron-oxygen, nitrogen-boron-oxygen, boron-nitrogen-boron, etc., the structure of the compound of the present invention restricts the resonance between boron atoms and nitrogen atoms and oxygen atoms, so it does not have thermally activated delayed fluorescence properties. Therefore, when the compound of the present invention is used as an emission layer material of a sensitized organic electroluminescence device, it can effectively shorten the excitation lifetime of the device, reduce the device roll-off under high brightness, and extend the device lifetime.

[0020] Moreover, the preparation process of the compounds of the present invention is simple and easy, the raw materials are readily available, and it is suitable for mass production.

[0021] A second aspect of the present invention simultaneously protects the application of a compound represented by any one of the above general formulas (1), (1-1), (1-2), (1-3), (1-4), (1-5) and (1-6), wherein the application is as a functional material for an organic electronic device, and the organic electronic device includes an organic electroluminescence device, an optical sensor, a solar cell, a lighting device, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner or electronic paper, and is preferably an organic electroluminescence device.

[0022] In a third aspect, the present invention further provides an organic electroluminescent device comprising a substrate comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer comprises a compound represented by any one of general formulas (1), (1-1), (1-2), (1-3), (1-4), (1-5) and (1-6) above.

[0023] Specifically, one embodiment of the present invention provides an organic electroluminescence device comprising a substrate, and an anode layer, a plurality of light-emitting functional layers, and a cathode layer sequentially formed on the substrate, wherein the light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, the hole injection layer being formed on the anode layer, the hole transport layer being formed on the hole injection layer, and the cathode layer being formed on the electron transport layer, and the light-emitting layer being between the hole transport layer and the electron transport layer, and wherein the light-emitting layer comprises a compound of the general formula of the present invention shown in the above formula (1). [Effects of the Invention]

[0024] The OLED devices prepared using the compounds of the present invention have low starting voltage, high luminous efficiency and better service life, which can meet the requirements of panel manufacturers for high performance materials. DETAILED DESCRIPTION OF THE INVENTION

[0025] Specific methods for preparing the novel compounds of the present invention will be described in detail below with reference to several synthesis examples, but the preparation methods of the present invention are not limited to these synthesis examples.

[0026] The various chemicals used in this invention, such as petroleum ether, ethyl acetate, sodium sulfate, toluene, tetrahydrofuran, dichloromethane, acetic acid, potassium carbonate, and other basic scientific raw materials, are all purchased from Shanghai Titan Science and Technology Co., Ltd. and Xilong Chemical Industry Co., Ltd. The mass spectrometer used to identify the following compounds is a ZAB-HS mass spectrometer (Micromass, UK).

[0027] The synthesis method of the compound of the present invention will be briefly explained below. Synthesis Examples Representative synthesis routes: [ka] More specifically, methods for synthesizing representative compounds of the present invention are shown below. Synthesis Examples

[0028] Synthetic Example 1: Synthesis of Compound C1-1 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (8.55 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add phenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature. After 6 h, stop the reaction. Remove the solvent by spin-drying under vacuum. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C1-1 (2.80 g, 32% yield, 99% HPLC purity) as a yellow solid. MALDI-TOF-MS result: Molecular ion peak: 584.36. Elemental analysis results: Theoretical: C: 86.33%, H: 5.18%, B: 3.70%, N: 4.79%. Experimental: C: 86.31%, H: 5.19%, N: 4.82%.

[0029] Synthetic Example 2: Synthesis of Compound C1-11 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (8.55 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature to quench the reaction after 6 h. Remove the solvent by spin-drying under vacuum. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C1-11 (3.61 g, 36% yield, 99% HPLC purity) as a yellow solid. MALDI-TOF-MS result: Molecular ion peak: 668.41. Elemental analysis results: Theoretical: C: 86.24%, H: 6.33%, B: 3.23%, N: 4.19%. Experimental: C: 86.20%, H: 6.34%, N: 4.22%.

[0030] Synthetic Example 3: Synthesis of Compound C1-16 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (8.49 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature. After 6 h, stop the reaction. Spin-dry the solvent under vacuum and pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C1-16 (4.49 g, 45% yield, 99% HPLC purity) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 664.41. Elemental analysis results: Theoretical: C: 86.77%, H: 5.76%, B: 3.25%, N: 4.22%. Experimental: C: 86.74%, H: 5.75%, N: 4.21%.

[0031] Synthetic Example 4: Synthesis of Compound C1-17 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (8.49 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature. After 6 h, stop the reaction. Spin-dry the solvent under vacuum and pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C1-17 (0.89 g, 9% yield, 99% HPLC purity) as an orange-red solid. MALDI-TOF-MS result: Molecular ion peak: 664.52. Elemental analysis results: Theoretical: C: 86.77%, H: 5.76%, B: 3.25%, N: 4.22%. Experimental: C: 86.78%, H: 5.79%, N: 4.19%.

[0032] Synthetic Example 5: Synthesis of Compounds C1-21 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (8.55 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trifluoromethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature to quench the reaction after 6 h. Remove the solvent by spin-drying under vacuum. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C1-21 (3.11 g, 21% yield, 99% HPLC purity) as a yellow solid. MALDI-TOF-MS result: Molecular ion peak: 988.43. Elemental analysis results: Theoretical: C: 58.34%, H: 2.04%, B: 2.19%, N: 2.83%, F: 34.60%. Experimental: C: 58.78%, H: 2.06%, N: 2.81%.

[0033] Synthetic Example 6: Synthesis of Compound C1-28 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (8.55 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2-thiophenemagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature. After 6 h, stop the reaction. Remove the solvent under vacuum and evaporate. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C1-28 (2.77 g, 31% yield, 99% HPLC purity) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 596.22 Elemental analysis results: Theoretical: C: 76.53%, H: 4.39%, B: 3.63%, N: 4.70%, S: 10.75%; Experimental: C: 76.50%, H: 4.39%, S: 10.72%.

[0034] Synthetic Example 7: Synthesis of Compound C1-38 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (8.97 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature to quench the reaction after 6 h. Remove the solvent under vacuum and evaporate. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C1-38 (2.92 g, 28% yield, 99% HPLC purity) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 696.52 Elemental analysis results: Theoretical: C: 82.78%, H: 5.50%, B: 3.10%, N: 4.02%, O: 4.59%, Experimental: C: 82.79%, H: 5.49%, N: 4.05%.

[0035] Synthetic Example 8: Synthesis of Compound C1-42 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (11.86 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature. After 6 h, stop the reaction. Spin-dry the solvent under vacuum and pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C1-42 (4.67 g, 35% yield, 99% HPLC purity) as an orange-yellow solid. MALDI-TOF-MS result: Molecular ion peak: 888.78 Elemental analysis results: Theoretical: C: 86.48%, H: 7.94%, B: 2.43%, N: 3.15%, Experimental: C: 86.51%, H: 7.88%, N: 3.17%.

[0036] Synthetic Example 9: Synthesis of compound C1-78 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (11.50 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,6-dimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature. After 6 h, stop the reaction. Remove the solvent by spin-drying under vacuum. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C1-78 (1.88 g, 15% yield, 99% purity by HPLC) as a reddish-brown solid. MALDI-TOF-MS results: Molecular ion peak: 836.51. Elemental analysis results: Theoretical: C: 89.01%, H: 5.06%, B: 2.58%, N: 3.35%. Experimental: C: 88.96%, H: 5.02%, N: 3.37%.

[0037] Synthetic Example 10: Synthesis of compound C1-117 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (10.18 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature. After 6 h, stop the reaction. Remove the solvent under vacuum and spun dry. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C1-117 (2.33 g, 20% yield, 99% HPLC purity) as an orange-red solid. MALDI-TOF-MS results: Molecular ion peak: 776.51. Elemental analysis results: Theoretical: C: 86.60%, H: 7.01%, B: 2.78%, N: 3.61%. Experimental: C: 86.65%, H: 6.96%, N: 3.59%.

[0038] Synthetic Example 11: Synthesis of compound C1-121 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (13.45 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature to quench the reaction after 6 h. Spin-dry the solvent under vacuum and pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C1-121 (1.79 g, 12% yield, 99% HPLC purity) as a dark red solid. MALDI-TOF-MS result: Molecular ion peak: 994.71 Elemental analysis results: Theoretical: C: 86.93%, H: 5.27%, B: 2.17%, N: 5.63%, Experimental: C: 86.85%, H: 5.21%, N: 5.59%.

[0039] Synthetic Example 12: Synthesis of compound C1-129 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (8.19 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature to quench the reaction after 6 h. Remove the solvent by spin-drying under vacuum. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C1-129 as an orange-red solid (1.93 g, 20% yield, 99% purity by HPLC). MALDI-TOF-MS results: Molecular ion peak: 644.45; Elemental analysis results: Theoretical values: C: 82.01%, H: 5.32%, B: 3.36%, N: 4.35%, O: 4.97%; Experimental values: C: 82.05%, H: 5.31%, N: 4.31%.

[0040] Synthetic Example 13: Synthesis of Compound C2-7 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (7.40 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature to quench the reaction after 6 h. Remove the solvent under vacuum and evaporate. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C1-117 (2.93 g, 33% yield, 99% HPLC purity) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 591.41 Elemental analysis results: Theoretical: C: 85.30%, H: 5.97%, B: 3.66%, N: 2.37%, O: 2.71%, Experimental: C: 85.35%, H: 5.96%, N: 2.39%.

[0041] Synthetic Example 14: Synthesis of compound C2-21 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (8.06 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature to quench the reaction after 6 h. Remove the solvent by spin-drying under vacuum. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C2-21 (2.67 g, 28% yield, 99% HPLC purity) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 635.31 Elemental analysis results: Theoretical values: C: 85.06%, H: 6.82%, B: 3.40%, N: 2.20%, O: 2.52%, Experimental values: C: 85.08%, H: 6.86%, N: 2.19%.

[0042] Synthetic Example 15: Synthesis of compound C2-48 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (8.93 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,6-dimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature. After 6 h, stop the reaction. Remove the solvent under vacuum and spun dry. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C2-48 (1.50 g, 15% yield, 99% HPLC purity) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 665.63. Elemental analysis results: Theoretical: C: 86.64%, H: 5.60%, B: 3.25%, N: 2.10%, O: 2.40%. Experimental: C: 85.58%, H: 5.56%, N: 2.13%.

[0043] Synthetic Example 16: Synthesis of compounds C3-7 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (7.64 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature. After 6 h, the reaction was stopped. The solvent was removed by spin-drying under vacuum. The residue was then passed through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C3-7 (1.69 g, 16% yield, 99% HPLC purity) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 703.31. Elemental analysis results: Theoretical values: C: 61.49%, H: 2.86%, B: 3.07%, F: 27.02%, N: 1.99%, S: 4.56%. Experimental values: C: 61.45%, H: 2.88%, N: 2.02%, S: 4.58%.

[0044] Synthetic Example 17: Synthesis of Compounds C3-37 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (7.64 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add a solution of pentafluorophenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature. After 6 h, stop the reaction. Remove the solvent by spin-drying under vacuum. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C3-37 (2.10 g, 23% yield, 99% purity by HPLC) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 607.41. Elemental analysis results: Theoretical: C: 83.05%, H: 5.81%, B: 3.56%, N: 2.31%, S: 5.28%. Experimental: C: 83.09%, H: 5.78%, N: 2.32%, S: 5.31%.

[0045] Synthetic Example 18: Synthesis of compound C4-2 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (6.30 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature to quench the reaction after 6 h. Remove the solvent by spin-drying under vacuum. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C4-2 (2.33 g, 30% yield, 99% HPLC purity) as a yellow solid. MALDI-TOF-MS result: Molecular ion peak: 518.31 Elemental analysis results: Theoretical: C: 83.43%, H: 6.22%, B: 4.17%, O: 6.17%, Experimental: C: 83.45%, H: 6.28%.

[0046] Synthetic Example 19: Synthesis of compound C4-20 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (8.34 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature. After 6 h, stop the reaction. Spin-dry the solvent under vacuum and pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C4-20 (2.36 g, 24% yield, 99% HPLC purity) as a yellow solid. MALDI-TOF-MS result: Molecular ion peak: 654.38 Elemental analysis results: Theoretical: C: 69.76%, H: 4.62%, B: 3.30%, F: 17.42%, O: 4.89%, Experimental: C: 69.78%, H: 4.58%.

[0047] Synthetic Example 20: Synthesis of compound C5-2 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (6.54 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature to quench the reaction after 6 h. Remove the solvent by spin-drying under vacuum. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C5-2 (1.76 g, 22% yield, 99% HPLC purity) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 534.31. Elemental analysis results: Theoretical values: C: 80.92%, H: 6.04%, B: 4.05%, O: 2.99%, S: 6.00%. Experimental values: C: 80.95%, H: 5.98%, S: 6.02%.

[0048] Synthetic Example 21: Synthesis of compound C5-4 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (6.96 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature to quench the reaction after 6 h. Remove the solvent by spin-drying under vacuum. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C5-4 (2.36 g, 28% yield, 99% HPLC purity) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 562.48 Elemental analysis results: Theoretical values: C: 81.16%, H: 6.45%, B: 3.84%, O: 2.84%, S: 5.70%, Experimental values: C: 81.15%, H: 6.42%, S: 5.72%.

[0049] Synthetic Example 22: Synthesis of compound C6-2 [ka] Under a nitrogen gas atmosphere, a pentane solution of n-butyllithium (12 mL, 2.50 M, 30 mmol) was slowly added to a t-butylbenzene (150 mL) solution of the bromide precursor (6.78 g, 15 mmol) at 0°C, then the mixture was heated to 25°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to -30°C, and boron tribromide (7.52 g, 30 mmol) was slowly added. The mixture was heated to 60°C and stirred for 2 hours. N,N-diisopropylethylamine (7.76 g, 60 mmol) was added at room temperature, and the mixture was reacted for 12 hours at 130°C. Add 2,4,6-trimethylphenylmagnesium bromide in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) at room temperature to quench the reaction after 6 h. Remove the solvent by spin-drying under vacuum. Pass the mixture through a silica gel column (eluent: dichloromethane:petroleum ether = 1:10) to obtain the target compound C6-2 (1.95 g, 23% yield, 99% purity by HPLC) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 565.58 Elemental analysis results: Theoretical values: C: 78.60%, H: 6.24%, B: 3.82%, S: 11.34%, Experimental values: C: 78.55%, H: 6.30%, S: 11.38%.

[0050] The optical properties of representative fused ring compounds of the present invention prepared in the above synthesis examples of the present invention are shown in Table 1. [Table 1] TIFF0007719545000046.tif13166

[0051] Note: In Table 1, ΔEst is the difference between the singlet and triplet energy levels, and is calculated by dividing the compound by 10 -5The test sample is prepared by dissolving it in toluene at a concentration of 1000 mol / L, and the difference in onset value between the fluorescence spectrum and the phosphorescence spectrum is measured. The instrument is Edinburgh FLS1000 (UK), and the half-width is the peak width at half the peak height of the fluorescence spectrum at room temperature, that is, the distance between the two points where this line intersects with both sides of the peak when a line is drawn parallel to the bottom of the peak through the midpoint of the peak height. Here, the fluorescence spectrum is measured by dissolving the compound in toluene at 10 -5 The test sample is prepared by dissolving it in toluene at a concentration of mol / L, and the measurement is carried out using a fluorescence spectrometer (Edinburgh FLS1000 (UK)).

[0052] From Table 1, it can be seen that the fused ring compounds of the examples provided by the present invention have a large ΔEst (>0.3 eV) and do not have the thermally activated delayed fluorescence effect. At the same time, the luminescent compounds provided by the present invention show a narrow half-width (<35 nm).

[0053] Hereinafter, the compounds of the present invention will be specifically applied to organic electroluminescence devices to test their actual performance, thereby demonstrating and verifying the technical effects and advantages of the present invention.

[0054] An organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer located between the two electrodes. The organic material can be divided into multiple regions, for example, the organic material layer can include a hole transport region, an emissive layer, and an electron transport region.

[0055] The anode material may be an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof. The cathode material may be a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0056] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL) containing only one type of compound or a single-layer hole transport layer containing multiple types of compounds. The hole transport region can also be a multilayer structure containing at least one layer selected from the group consisting of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0057] The material of the hole transport region can be selected from, but is not limited to, conductive polymers or conductive dopant-containing polymers such as phthalocyanine derivatives such as CuPc, polyphenylene vinylene, polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonic acid) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonic acid) (PANI / PSS), aromatic amine derivatives, and the like.

[0058] The light-emitting layer can contain a light-emitting dye (dopant) that can emit different wavelength spectrums, or can simultaneously contain a sensitizer and a host material (host). The light-emitting layer can be a monochromatic light-emitting layer that emits a single color, such as red, green, or blue. Monochromatic light-emitting layers of various different colors can be arranged on a plane according to a pixel pattern or stacked to form a colored light-emitting layer. When different colored light-emitting layers are stacked, they can be isolated from each other or connected to each other. The light-emitting layer can also be a single colored light-emitting layer that can simultaneously emit different colors, such as red, green, and blue.

[0059] The electron transport region can be a single-layer electron transport layer (ETL) including a single electron transport layer containing only one compound and a single electron transport layer containing multiple compounds, or a multilayer electron transport region including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0060] Specifically, the method for preparing an organic electroluminescent device of the present invention includes the following steps: 1. A glass plate coated with anode material is ultrasonically treated with a commercially available cleaning agent, rinsed with deionized water, ultrasonically removed from an acetone:ethanol mixture, baked in a clean environment until completely free of moisture, cleaned with ultraviolet light and ozone, and irradiated with low-energy cation beams. 2. Place the glass plate with the anode in a vacuum chamber and measure 1 x 10 -5 ~8×10 -4 The chamber is evacuated to a vacuum of 100 Pa, and a hole injection material is vacuum-deposited on the anode layer to form a hole injection layer, the deposition rate being 0.1 to 0.5 nm / s. 3. A hole transport layer is formed on the hole injection layer by vacuum-depositing a hole transport material, and the deposition rate is 0.1 to 0.5 nm / s. 4. The organic light-emitting layer of the device is vacuum-deposited on the hole-transporting layer. The organic light-emitting layer materials include a host material, a sensitizer, and a dye. The deposition rates of the host material, the sensitizer material, and the dye are adjusted using a multi-source co-evaporation method so that the dye reaches a predetermined doping ratio. 5. An electron transporting material of the device is vacuum-deposited on the organic light-emitting layer to form an electron transporting layer, and the deposition rate is 0.1 to 0.5 nm / s. 6. On the electron transport layer, LiF is vacuum-deposited at 0.1 to 0.5 nm / s as an electron injection layer, and an Al layer is vacuum-deposited at 0.5 to 1 nm / s as a cathode of the device.

[0061] An embodiment of the present invention further provides a display device, the display device including the organic electroluminescent element provided above. The display device may specifically be a display element such as an OLED display, as well as any product or component having a display function, such as a television, a digital camera, a mobile phone, or a tablet computer, including the display element. The display device has the same advantages as the organic electroluminescent element described above over the prior art, and the advantages will not be repeated here.

[0062] The organic electroluminescent device of the present invention will be further described below through specific examples.

[0063] Device Example 1 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C1-1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light-emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C1-1 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light-emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0064] The organic electroluminescence device D1 prepared in this example was measured for its performance, and the results are as follows: 2 When the characteristics of the device were measured, it was found that the device emitted sky blue light with a wavelength of 495 nm, a half-width of 30 nm, CIE color coordinates (x, y) = (0.11, 0.52), and an external quantum efficiency EQE of 28.3% (driving voltage was 2.6 V).

[0065] Device Example 2 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C1-11(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C1-11 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0066] Organic electroluminescent device D prepared in this example 2 The device performance was measured as follows: When a DC voltage was applied and the characteristics were measured at 10 cd / m2, sky blue light was emitted with a wavelength of 497 nm, a half-width of 2920 nm, CIE color coordinates (x, y) = (0.12, 0.55), and an external quantum efficiency EQE of 29.1% (driving voltage was 2.5 V).

[0067] Device Example 3 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C1-16(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C1-16 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metal aluminum (150 nm).

[0068] The device performance results of the organic electroluminescence device D3 prepared in this example were measured as follows: When a DC voltage was applied and the characteristics were measured at 10 cd / m2, green light was emitted with a wavelength of 521 nm, a half-width of 27 nm, CIE color coordinates (x, y) = (0.23, 0.70), and an external quantum efficiency EQE of 32.6% (driving voltage was 2.4 V).

[0069] Device Example 4 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C1-17(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C1-17 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0070] The device performance results of the organic electroluminescence device D4 prepared in this example are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, yellow light emission with a wavelength of 552 nm, a half-width of 25 nm, CIE color coordinates (x, y) = (0.40, 0.60), and an external quantum efficiency EQE of 31.2% can be obtained (driving voltage is 2.3 V).

[0071] Device Example 5 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C1-21(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C1-21 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0072] The device performance results of the organic electroluminescence device D5 prepared in this example are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, yellow light emission with a wavelength of 565 nm, a half-width of 27 nm, CIE color coordinates (x, y) = (0.47, 0.53), and an external quantum efficiency EQE of 25.2% can be obtained (driving voltage is 2.3 V).

[0073] Device Example 6 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C1-28(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C1-28 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metal aluminum (150 nm).

[0074] The device performance results of the organic electroluminescence device D6 prepared in this example are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, green light is emitted with a wavelength of 535 nm, a half-width of 33 nm, CIE color coordinates (x, y) = (0.30, 0.68), and an external quantum efficiency EQE of 28.7% (driving voltage is 2.3 V).

[0075] Device Example 7 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C1-38(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C1-38 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0076] The device performance results of the organic electroluminescence device D7 prepared in this example are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, green light is emitted with a wavelength of 540 nm, a half-width of 33 nm, CIE color coordinates (x, y) = (0.33, 0.65), and an external quantum efficiency EQE of 29.3% (driving voltage is 2.4 V).

[0077] Device Example 8 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C1-42(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C1-42 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metal aluminum (150 nm).

[0078] The device performance results of the organic electroluminescence device D8 prepared in this example are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, green light is emitted with a wavelength of 536 nm, a half-width of 30 nm, CIE color coordinates (x, y) = (0.33, 0.63), and an external quantum efficiency EQE of 32.0% (driving voltage is 2.4 V).

[0079] Device Example 9 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C1-78(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material with a band gap of the organic light emitting layer. The sensitizer is a sensitizer, and the doping concentration is 20 wt %. The C1-78 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0080] The device performance results of the organic electroluminescence device D9 prepared in this example are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, orange-yellow light emission with a wavelength of 572 nm, a half-width of 32 nm, CIE color coordinates (x, y) = (0.50, 0.49), and an external quantum efficiency EQE of 26.8% can be obtained (driving voltage is 2.2 V).

[0081] Device Example 10 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C1-117(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C1-117 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metal aluminum (150 nm).

[0082] Organic electroluminescent device D prepared in this example 1 The device performance results for Example 0 are as follows: When a DC voltage is applied and the characteristics are measured for emission at 10 cd / m2, yellow light emission is obtained with a wavelength of 560 nm, a half-width of 26 nm, CIE color coordinates (x, y) = (0.44, 0.55), and an external quantum efficiency EQE of 27.9% (driving voltage is 2.3 V).

[0083] Device Example 11 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C1-121(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C1-121 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metal aluminum (150 nm).

[0084] Organic electroluminescent device D prepared in this example 1 The device performance results for 1 are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, red light is emitted with a wavelength of 612 nm, a half-width of 32 nm, CIE color coordinates (x, y) = (0.66, 0.33), and an external quantum efficiency EQE of 26.6% (driving voltage is 2.1 V).

[0085] Device Example 12 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C1-129(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C1-129 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metal aluminum (150 nm).

[0086] Organic electroluminescent device D prepared in this example 1 The device performance results for 2 are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, yellow light emission is obtained with a wavelength of 556 nm, a half-width of 34 nm, CIE color coordinates (x, y) = (0.42, 0.57), and an external quantum efficiency EQE of 28.1% (driving voltage is 2.3 V).

[0087] Device Example 13 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C2-7(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C2-7 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metal aluminum (150 nm).

[0088] Organic electroluminescent device D prepared in this example 1 The device performance results for 3 are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, green light is emitted with a wavelength of 505 nm, a half-width of 28 nm, CIE color coordinates (x, y) = (0.15, 0.63), and an external quantum efficiency EQE of 29.7% (driving voltage is 2.4 V).

[0089] Device Example 14 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C2-21(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C2-21 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0090] Organic electroluminescent device D prepared in this example 1 The device performance results for 4 are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, green light is emitted with a wavelength of 512 nm, a half-width of 28 nm, CIE color coordinates (x, y) = (0.21, 0.68), and an external quantum efficiency EQE of 30.2% (driving voltage is 2.1 V).

[0091] Device Example 15 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C2-48(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C2-48 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metal aluminum (150 nm).

[0092] Organic electroluminescent device D prepared in this example 1 The device performance results for 5 are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, yellow light emission is obtained with a wavelength of 550 nm, a half-width of 33 nm, CIE color coordinates (x, y) = (0.39, 0.59), and an external quantum efficiency EQE of 27.7% (driving voltage is 2.3 V).

[0093] Device Example 16 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C3-7(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, and in this embodiment it is 5 nm. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, and in this embodiment it is 30 nm. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C3-7 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, and in this embodiment it is 30 nm. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, and in this embodiment it is 30 nm. The electron injection layer and cathode materials are LiF (0.5 nm) and metal aluminum (150 nm).

[0094] Organic electroluminescent device D prepared in this example 1 The device performance of 6 was measured as follows: When a DC voltage was applied and the characteristics were measured at 10 cd / m2, green light was emitted with a wavelength of 510 nm, a half-width of 32 nm, CIE color coordinates (x, y) = (0.18, 0.67), and an external quantum efficiency EQE of 29.1% (driving voltage was 2.4 V).

[0095] Device Example 17 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C3-37(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C3-37 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metal aluminum (150 nm).

[0096] Organic electroluminescent device D prepared in this example 1 The device performance results for 7 are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, green light is emitted with a wavelength of 529 nm, a half-width of 31 nm, CIE color coordinates (x, y) = (0.26, 0.68), and an external quantum efficiency EQE of 28.3% (driving voltage is 2.4 V).

[0097] Device Example 18 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C4-2(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C4-2 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0098] Organic electroluminescent device D prepared in this example 1 The device performance results for 8 are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, blue light emission is obtained with a wavelength of 483 nm, a half-width of 29 nm, CIE color coordinates (x, y) = (0.12, 0.28), and an external quantum efficiency EQE of 29.8% (driving voltage is 2.6 V).

[0099] Device Example 19 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C4-20(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material with the band gap of the organic light emitting layer, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C4-20 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metal aluminum (150 nm).

[0100] Organic electroluminescent device D prepared in this example 1 The device performance results for 9 are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, blue light emission is obtained with a wavelength of 475 nm, a half-width of 29 nm, CIE color coordinates (x, y) = (0.13, 0.22), and an external quantum efficiency EQE of 28.2% (driving voltage is 2.7 V).

[0101] Device Example 20 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C5-2(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C5-2 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0102] Organic electroluminescent device D prepared in this example 2 The device performance results for Example 0 are as follows: When a DC voltage is applied and the characteristics are measured for emission at 10 cd / m2, sky blue light emission is obtained with a wavelength of 496 nm, a half-width of 30 nm, CIE color coordinates (x, y) = (0.13, 0.56), and an external quantum efficiency EQE of 28.7% (driving voltage is 2.6 V).

[0103] Device Example 21 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C5-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C5-4 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0104] Organic electroluminescent device D prepared in this example 2 The device performance results for 1 are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, green light is emitted with a wavelength of 501 nm, a half-width of 30 nm, CIE color coordinates (x, y) = (0.14, 0.60), and an external quantum efficiency EQE of 29.1% (driving voltage is 2.4 V).

[0105] Device Example 22 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C6-2(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C6-2 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0106] Organic electroluminescent device D prepared in this example 2 The device performance results for 2 are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, green light is emitted with a wavelength of 508 nm, a half-width of 32 nm, CIE color coordinates (x, y) = (0.16, 0.67), and an external quantum efficiency EQE of 28.2% (driving voltage is 2.4 V).

[0107] Comparative Example 1 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, and in this embodiment it is 5 nm. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, and in this embodiment it is 30 nm. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C1 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, and in this embodiment it is 30 nm. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, and in this embodiment it is 30 nm. The materials of the electron injection layer and the cathode are selected as LiF (0.5 nm) and metal aluminum (150 nm).

[0108] The organic electroluminescent device CD prepared in this example 1 The device performance was measured as follows: When a DC voltage was applied and the characteristics were measured at 10 cd / m2, blue light was emitted with a wavelength of 464 nm, a half-width of 28 nm, CIE color coordinates (x, y) = (0.15, 0.09), and an external quantum efficiency EQE of 26.2% (driving voltage was 2.9 V).

[0109] Comparative Example 2 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C2(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C2 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metal aluminum (150 nm).

[0110] The organic electroluminescent device CD prepared in this example 2 The device performance was measured as follows: When a DC voltage was applied and the characteristics were measured for emission at 10 cd / m2, yellow light emission was obtained with a wavelength of 451 nm, a half-width of 31 nm, CIE color coordinates (x, y) = (0.13, 0.16), and an external quantum efficiency EQE of 27.2% (driving voltage was 3.0 V).

[0111] Comparative Example 3 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C3(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, and in this embodiment it is 5 nm. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, and in this embodiment it is 30 nm. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C3 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, and in this embodiment it is 30 nm. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, and in this embodiment it is 30 nm. The electron injection layer and cathode materials are selected to be LiF (0.5 nm) and metal aluminum (150 nm).

[0112] The organic electroluminescence device CD3 prepared in this example was measured for its performance, and the results are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, blue light emission is obtained with a wavelength of 431 nm, a half-width of 28 nm, CIE color coordinates (x, y) = (0.13, 0.06), and an external quantum efficiency EQE of 18.2% (driving voltage is 3.4 V).

[0113] Comparative Example 4 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, and in this embodiment it is 5 nm. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, and in this embodiment it is 30 nm. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C4 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, and in this embodiment it is 30 nm. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, and in this embodiment it is 30 nm. The electron injection layer and cathode materials are selected to be LiF (0.5 nm) and metal aluminum (150 nm).

[0114] The organic electroluminescence device CD4 prepared in this example was measured for its performance, and the results are as follows: When a DC voltage is applied and the characteristics are measured at 10 cd / m2, blue light emission is obtained with a wavelength of 428 nm, a half-width of 29 nm, CIE color coordinates (x, y) = (0.12, 0.06), and an external quantum efficiency EQE of 16.5% (driving voltage is 3.4 V).

[0115] Comparative Example 5 The structure of the organic electroluminescent device prepared in this example is as follows: ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:3wt%C5(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm) Here, the anode material is ITO, the hole injection layer material is HI, and the total thickness is generally 5 to 30 nm, 5 nm in this embodiment. The hole transport layer material is HT, and the total thickness is generally 5 to 500 nm, 30 nm in this embodiment. The host is a host material of the organic light emitting layer band gap, the sensitizer is a sensitizer, and the doping concentration is 20 wt %. C2 is a dye, and the doping concentration is 3 wt %. The thickness of the organic light emitting layer is generally 1 to 200 nm, 30 nm in this embodiment. The electron transport layer material is ET, and the thickness is generally 5 to 300 nm, 30 nm in this embodiment. The electron injection layer and cathode materials are LiF (0.5 nm) and metal aluminum (150 nm).

[0116] The organic electroluminescent device CD prepared in this example 2 The device performance was measured as follows: When a DC voltage was applied and the characteristics were measured at 10 cd / m2, blue light was emitted with a wavelength of 452 nm, a half-width of 32 nm, CIE color coordinates (x, y) = (0.13, 0.08), and an external quantum efficiency EQE of 21.1% (driving voltage was 3.2 V).

[0117] The structural formulas of the various organic materials used in the above examples are as follows: [Table 2] TIFF0007719545000048.tif185166

[0118] The above C1-C5 compounds as comparative compounds are compounds in the prior art, and their synthesis methods can be found in patent applications CN107851724, CN108431984, CN110407858, CN110776509, etc., and will not be repeated here.

[0119] The performance of the organic electroluminescence devices prepared in the above examples and comparative examples is shown in Table 3 below. [Table 3] TIFF0007719545000050.tif89166

[0120] As for Examples 1 to 22 and Comparative Examples 1 and 2, when the other materials in the organic electroluminescent device structure are the same, the compounds described in the present invention have very narrow electroluminescence spectra. At the same time, compared to the multi-resonant TADF dyes with nitrogen-boron-nitrogen structures in the comparative examples, the devices prepared with the compounds provided by the present invention have lower lighting voltages and significantly improved roll-off. This is mainly because the structure of the compounds of the present invention restricts the resonance between the boron atom and the nitrogen and oxygen atoms, and they do not exhibit thermally activated delayed fluorescence properties. When the compounds of the present invention are used as light-emitting layer materials in sensitized organic electroluminescent devices, the excitons do not remain in the triplet state, thereby reducing roll-off at high luminance levels and extending the device's lifetime. As far as Examples 1-22 and Comparative Examples 3, 4 and 5 are concerned, when other materials are the same in the organic electroluminescent device structure, the compounds mentioned in the present invention have very narrow electroluminescence spectrum.At the same time, when boron nitrogen or boron oxygen are adjacent in Comparative Examples, the device prepared by the compounds provided by the present invention has low lighting voltage, and efficiency and roll-off are greatly improved.

[0121] According to the above experimental data, the new organic material of the present invention is an organic light-emitting functional material with good performance as a light-emitting guest in organic electroluminescence devices, and is expected to be put into practical use.

[0122] Although the present invention has been described above with reference to the embodiments, the present invention is not limited to the above embodiments, and those skilled in the art can make various modifications and improvements based on the concept of the present invention, and the scope of the present invention is summarized in the appended claims.

[0123] Obviously, the above examples are merely examples for clear explanation and are not intended to limit the embodiments. Those skilled in the art can make other different modifications or amendments based on the above description. It is not necessary and cannot be possible to cover all the embodiments here. Any obvious modifications or variations derived therefrom still fall within the scope of protection of the present invention.

Claims

1. An organic compound having a structure represented by formula (1): [Chemical Formula 1] Formula (1): where: D １ is NR ５ , O or S; D 2 is selected from NR 6 ; W １ and W ２ are each independently C, CH, or CR ７ and Ring Ar １ , Ring Ar ２ , Ring Ar ３ and ring Ar ４ are each independently selected from a benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, furan, and thiophene; Ring Ar ３ and R ６ and are connected via a C—C single bond, or via O, S, or Se, or CR ８ R ９ or NR １０ are connected via Ring Ar ４ and Ring R ５ and are connected via a C—C single bond, or via O, S, or Se, or CR ８ R ９ or NR １０ are connected via R ６ and W ２ and are not connected, or are connected via a C-C single bond, or are connected via O, S or Se, or are connected via CR ８ R ９ or NR １０ are connected via R ５ and W １ and are not connected, or are connected via a C-C single bond, or are connected via O, S or Se, or are connected via CR ８ R ９ or NR １０ are connected via R １ , R ２ , R ３ and R ４ are each independently selected from one of hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1 to C30 linear alkyl group, substituted or unsubstituted C3 to C20 cycloalkyl group, substituted or unsubstituted C7 to C30 aralkyl group, substituted or unsubstituted C1 to C30 alkoxy group, substituted or unsubstituted C2 to C30 aliphatic chain hydrocarbyl amine group, substituted or unsubstituted C4 to C30 cyclic aliphatic chain hydrocarbyl amine group, substituted or unsubstituted C6 to C30 aryl amine group, substituted or unsubstituted C3 to C30 heteroaryl amine group, substituted or unsubstituted C6 to C30 aryloxy group, substituted or unsubstituted C6 to C60 arylboryl group, substituted or unsubstituted C6 to C60 aryl group, and substituted or unsubstituted C3 to C60 heteroaryl group; n1, n2, n3, and n4 are each independently selected from integers of 1 to 5; When n1 is an integer greater than 1, a plurality of R １ are the same or different, and multiple R １ can be linked to form a ring, When n2 is an integer greater than 1, a plurality of R ２ are the same or different, and multiple R ２ can be linked to form a ring, When n3 is an integer greater than 1, a plurality of R ３ are the same or different, and multiple R ３ can be linked to form a ring, When n4 is an integer greater than 1, a plurality of R ４ are the same or different, and multiple R ４ can be linked to form a ring, R ５ and R ６ are each independently selected from a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C3 to C60 heteroaryl group; R ７ is selected from one of deuterium, halogen, cyano group, substituted or unsubstituted C1 to C10 linear alkyl group, substituted or unsubstituted C3 to C10 cycloalkyl group, substituted or unsubstituted C7 to C30 aralkyl group, substituted or unsubstituted C1 to C30 alkoxy group, substituted or unsubstituted C2 to C30 aliphatic chain hydrocarbyl amine group, substituted or unsubstituted C4 to C30 cyclic aliphatic chain hydrocarbyl amine group, substituted or unsubstituted C6 to C30 aryl amine group, substituted or unsubstituted C3 to C30 heteroaryl amine group, substituted or unsubstituted C6 to C30 aryloxy group, substituted or unsubstituted C6 to C60 aryl group, and substituted or unsubstituted C3 to C60 heteroaryl group; R ８ , R ９ and R １０ are each independently selected from one of a substituted or unsubstituted C1 to C10 linear alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C7 to C30 aralkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 aliphatic chain hydrocarbyl amine group, a substituted or unsubstituted C4 to C30 cyclic aliphatic chain hydrocarbyl amine group, a substituted or unsubstituted C6 to C30 aryl amine group, a substituted or unsubstituted C3 to C30 heteroaryl amine group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group; The above R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ and R １０ each independently has a substituent, the substituent is each independently selected from one or a combination of two of a halogen, a cyano group, a C1 to C20 linear alkyl group, a C3 to C20 cycloalkyl group, a C1 to C10 alkoxy group, a C6 to C30 arylamino group, a C3 to C30 heteroarylamino group, a C6 to C30 aryloxy group, a C6 to C30 aryl group, a substituted or unsubstituted C6 to C60 arylboryl group, and a C3 to C30 heteroaryl group. An organic compound characterized by:

2. n1, n2, n3, and n4 are each independently selected from integers of 1 to 5; The R ５ and R ６ are each independently selected from a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group; The R ７ is selected from the group consisting of deuterium, halogen, cyano, C1-C6 linear alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; The R ８ , R ９ and R １０ are each independently selected from one of a substituted or unsubstituted C1 to C10 linear alkyl group, a substituted or unsubstituted C7 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group. The organic compound according to claim 1.

3. R 5 and R 6 are each independently selected from the group consisting of a substituted or unsubstituted benzene ring, a naphthalene ring, and an anthracene ring. The organic compound according to claim 2.

4. R 5 and R 6 are each independently a substituted or unsubstituted benzene ring. The organic compound according to claim 3.

5. R 7 is selected from the group consisting of deuterium, halogen, cyano group, and substituted or unsubstituted benzene ring. The organic compound according to claim 2.

6. In formula (1), the D １ is NR ５ and D ２ is NR ６ and R ５ and R ６ are the same or different The organic compound according to claim 1.

7. R 5 and R 6 are the same. The organic compound according to claim 6.

8. It has a structure represented by any one of the following structural formulas (1-1), (1-2), or (1-3): 【Chemistry 2-1】 【change】 【change】 Here, W １ , W ２ , R １ -R ６ , Ar １ -Ar ４ and n1-n4 are all defined the same as in formula (1). The organic compound according to claim 1.

9. It has a structure represented by any one of the following structural formulas (1-4), (1-5), or (1-6): 【Chemistry 3-1】 【change】 【change】 Here, R １ -R ４ , Ar １ -Ar ４ and n1-n4 are all defined the same as in formula (1). The organic compound according to claim 1.

10. The ring Ar １ , Ring Ar ２ , Ring Ar ３ and ring Ar ４ are each independently selected from a C6 to C60 aromatic ring or a C3 to C30 heteroaromatic ring 10. The organic compound according to claim 1.

11. Ring Ar 1 , ring Ar 2 , ring Ar 3 and ring Ar 4 are each independently selected from a C6 to C30 aromatic ring or a C3 to C20 heteroaromatic ring. The organic compound according to claim 10.

12. Ring Ar １ , Ring Ar ２ , Ring Ar ３ and ring Ar ４ are each independently selected from a benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, furan, and thiophene. The organic compound according to claim 11.

13. The ring Ar １ , Ring Ar ２ , Ring Ar ３ and ring Ar ４ are each independently a benzene ring The organic compound according to claim 12.

14. The R １ , R ２ , R ３ and R ４ each independently represents a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a 2-methylbutyl group, an n-pentyl group, an s-pentyl group, a cyclopentyl group, a neopentyl group, an n-hexyl group, a cyclohexyl group, a neohexyl group, an n-heptyl group, a cycloheptyl group, an n-octyl group, a cyclooctyl group, a 2-ethylhexyl group, a trifluoromethyl group, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, a cyano group, a halogen atom, a phenyl group, a naphthyl group, an anthracenyl group, benzanthracenyl group, phenanthrenyl group, benzophenanthrenyl group, pyrenyl group, chrysene group, perylene group, fluoranthenyl group, tetracenyl group, pentacenyl group, benzopyrenyl group, biphenyl group, diphenyl group, terphenyl group, trimerized phenyl group, quaterphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrenyl group, dihydropyrenyl group, tetrahydropyrenyl group, cis or trans indenofluorenyl group, trimerized indenyl group, isotrimerized indenyl group, spirotrimerized indenyl group, spiro Isotrimerized indenyl group, furyl group, benzofuryl group, isobenzofuryl group, dibenzofuryl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, pyrrolyl group, isoindolyl group, carbazolyl group, indenocarbazolyl group, pyridyl group, quinolyl group, isoquinolyl group, acridinyl group, phenanthridinyl group, benzo-5,6-quinolyl group, benzo-6,7-quinolyl group, benzo-7,8-quinolyl group, pyrazolyl group, indazolyl group, imidazolyl group, benzimidazolyl group, naphthimidazolyl group, phenanthroy group midazolyl group, pyridinoimidazolyl group, pyrazinoimidazolyl group, quinoxanoimidazolyl group, oxazolyl group, benzoxazolyl group, naphthoxazolyl group, anthraoxazolyl group, phenanthrooxazolyl group, 1,2-thiazolyl group, 1,3-thiazolyl group, benzothiazolyl group, pyridazinyl group, benzopyridazinyl group, pyrimidinyl group, benzopyrimidinyl group, quinoxalinyl group, 1,5-diazaanthracenyl group, 2,7-diazapyrenyl group, 2,3-diazapyrenyl group, 1,6-diazapyrenyl group, 1,8-diazapyrenyl group, 4,5-diazapyrenyl group, 4,5,9,10-tetraazapyrylene group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbolinyl group, phenanthrolinyl group, 1,2,3-triazolyl group, 1,2,4-triazolyl group, benzotriazolyl group, 1,2,3-oxadiazolyl group, 1,2,4-oxadiazolyl group, 1,2,5-oxadiazolyl group, 1,2,3-thiadiazolyl group, 1,2,4-thiadiazolyl group, 1,2,5-thiadiazolyl group, 1,3,4-thiadiazolyl group a 1,3,5-triazinyl group, a 1,2,4-triazinyl group, a 1,2,3-triazinyl group, a tetrazolyl group, a 1,2,4,5-tetrazinyl group, a 1,2,3,4-tetrazinyl group, a 1,2,3,5-tetrazinyl group, a purinyl group, a pteridinyl group, an indolizinyl group, a benzothiadiazolyl group, a diphenylboryl group, a dimesitylboryl group, a dipentafluorophenylboryl group, or a bis(2,4,6-triisopropylphenyl)boryl group, or a combination of the two groups mentioned above; The R ５ and R ６ each independently represents a phenyl group, a naphthyl group, an anthracenyl group, a benzanthracenyl group, a phenanthrenyl group, a benzophenanthrenyl group, a pyrenyl group, a chrysene group, a perylene group, a fluoranthenyl group, a tetracenyl group, a pentacenyl group, a benzopyrenyl group, a biphenyl group, a diphenyl group, a terphenyl group, a trimerized phenyl group, a quaterphenyl group, a fluorenyl group, a spirobifluorenyl group, a dihydrophenanthrenyl group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis- or trans-indenofluorenyl group, or a trimerized indenyl group group, isotrimerized indenyl group, spirotrimerized indenyl group, spiroisotrimerized indenyl group, furyl group, benzofuryl group, isobenzofuryl group, dibenzofuryl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, pyrrolyl group, isoindolyl group, carbazolyl group, indenocarbazolyl group, pyridyl group, quinolyl group, isoquinolyl group, acridinyl group, phenanthridinyl group, benzo-5,6-quinolyl group, benzo-6,7-quinolyl group, benzo-7,8-quinolyl group, pyrazolyl group, indazolyl group, imidazolyl group a benzimidazolyl group, a naphthimidazolyl group, a phenanthroiimidazolyl group, a pyridinoimidazolyl group, a pyrazinoimidazolyl group, a quinoxanoimidazolyl group, an oxazolyl group, a benzoxazolyl group, a naphthoxazolyl group, an anthraoxazolyl group, a phenanthrooxazolyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a benzopyridazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a quinoxalinyl group, a 1,5-diazaanthracenyl group, a 2,7-diazapyrenyl group, a 2,3-diazapyren ...5-diazaanthracenyl group, a 2,7-diazapyrenyl group, a 2,3-diazapyrenyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a benzopyrimidinyl group, a quinoxalinyl group, a 1,5-diazaanthracenyl group, a 2,7-diazapyrenyl group, a 2,3-diazapyrenyl group, a 1,2-th a 1,6-diazapyrenyl group, a 1,8-diazapyrenyl group, a 4,5-diazapyrenyl group, a 4,5,9,10-tetraazaperylene group, a pyrazinyl group, a phenazinyl group, a phenothiazinyl group, a naphthyridinyl group, an azacarbazolyl group, a benzocarbolinyl group, a phenanthrolinyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, a benzotriazolyl group, a 1,2,3-oxadiazolyl group, a 1,2,4-oxadiazolyl group, a 1,2,5-oxadiazolyl group, a 1,2,3-thiadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,2,is selected from one of the following substituents: 5-thiadiazolyl group, 1,3,4-thiadiazolyl group, 1,3,5-triazinyl group, 1,2,4-triazinyl group, 1,2,3-triazinyl group, tetrazolyl group, 1,2,4,5-tetrazinyl group, 1,2,3,4-tetrazinyl group, 1,2,3,5-tetrazinyl group, purinyl group, pteridinyl group, indolizinyl group, and benzothiadiazolyl group, or a combination of the two groups mentioned above; The R ７ is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, an t-butyl group, a 2-methylbutyl group, an n-pentyl group, an s-pentyl group, a cyclopentyl group, a neopentyl group, an n-hexyl group, a cyclohexyl group, a neohexyl group, an n-heptyl group, a cycloheptyl group, an n-octyl group, a cyclooctyl group, a 2-ethylhexyl group, a trifluoromethyl group, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, a cyano group, a halogen, a phenyl group, a naphthyl group, an anthracenyl group, or a benzanthracenyl group. group, phenanthrenyl group, benzophenanthrenyl group, pyrenyl group, chrysene group, perylene group, fluoranthenyl group, tetracenyl group, pentacenyl group, benzopyrenyl group, biphenyl group, diphenyl group, terphenyl group, trimerized phenyl group, quaterphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrenyl group, dihydropyrenyl group, tetrahydropyrenyl group, cis or trans indenofluorenyl group, trimerized indenyl group, isotrimerized indenyl group, spirotrimerized indenyl group, spiroisotrimerized indenyl group, furyl group, benzofuryl group, isobenzofuryl group, dibenzofuryl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, pyrrolyl group, isoindolyl group, carbazolyl group, indenocarbazolyl group, pyridyl group, quinolyl group, isoquinolyl group, acridinyl group, phenanthridinyl group, benzo-5,6-quinolyl group, benzo-6,7-quinolyl group, benzo-7,8-quinolyl group, pyrazolyl group, indazolyl group, imidazolyl group, benzimidazolyl group, naphthimidazolyl group, phenanthroiimidazolyl group, pyridinoyl group, midazolyl group, pyrazinoimidazolyl group, quinoxanoimidazolyl group, oxazolyl group, benzoxazolyl group, naphthoxazolyl group, anthraoxazolyl group, phenanthrooxazolyl group, 1,2-thiazolyl group, 1,3-thiazolyl group, benzothiazolyl group, pyridazinyl group, benzopyridazinyl group, pyrimidinyl group, benzopyrimidinyl group, quinoxalinyl group, 1,5-diazaanthracenyl group, 2,7-diazapyrenyl group, 2,3-diazapyrenyl group, 1,6-diazapyrenyl group, 1,8-diazapyrenyl group, 4,5-diazapyrenyl group, 4,5,9,10-tetraazaperylene group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbolinyl group, phenanthrolinyl group, 1,2,3-triazolyl group, 1,2,4-triazolyl group, benzotriazolyl group, 1,2,3-oxadiazolyl group, 1,2,4-oxadiazolyl group, 1,2,5-oxadiazolyl group, 1,2,3-thiadiazolyl group, 1,2,4-thiadiazolyl group, 1, One of the following substituents is selected from a 2,5-thiadiazolyl group, a 1,3,4-thiadiazolyl group, a 1,3,5-triazinyl group, a 1,2,4-triazinyl group, a 1,2,3-triazinyl group, a tetrazolyl group, a 1,2,4,5-tetrazinyl group, a 1,2,3,4-tetrazinyl group, a 1,2,3,5-tetrazinyl group, a purinyl group, a pteridinyl group, an indolizinyl group, and a benzothiadiazolyl group, or is selected from a combination of the two groups mentioned above: The R ８ , R ９ and R １０ each independently represents a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a 2-methylbutyl group, an n-pentyl group, an s-pentyl group, a cyclopentyl group, a neopentyl group, an n-hexyl group, a cyclohexyl group, a neohexyl group, an n-heptyl group, a cycloheptyl group, an n-octyl group, a cyclooctyl group, a 2-ethylhexyl group, a trifluoromethyl group, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, a phenyl group, a naphthyl group, an anthracenyl group, or a benzanthracenyl group , phenanthrenyl group, benzophenanthrenyl group, pyrenyl group, chrysene group, perylene group, fluoranthenyl group, tetracenyl group, pentacenyl group, benzopyrenyl group, biphenyl group, diphenyl group, terphenyl group, trimerized phenyl group, quaterphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrenyl group, dihydropyrenyl group, tetrahydropyrenyl group, cis or trans indenofluorenyl group, trimerized indenyl group, isotrimerized indenyl group, spirotrimerized indenyl group, spiroisotrimerized indenyl group , furyl group, benzofuryl group, isobenzofuryl group, dibenzofuryl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, pyrrolyl group, isoindolyl group, carbazolyl group, indenocarbazolyl group, pyridyl group, quinolyl group, isoquinolyl group, acridinyl group, phenanthridinyl group, benzo-5,6-quinolyl group, benzo-6,7-quinolyl group, benzo-7,8-quinolyl group, pyrazolyl group, indazolyl group, imidazolyl group, benzimidazolyl group, naphthimidazolyl group, phenanthrilimidazolyl group, pyridinoimidazolyl group, a quinoxanoimidazolyl group, an oxazolyl group, a benzoxazolyl group, a naphthoxazolyl group, an anthraoxazolyl group, a phenanthrooxazolyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a benzopyridazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a quinoxalinyl group, a 1,5-diazaanthracenyl group, a 2,7-diazapyrenyl group, a 2,3-diazapyrenyl group, a 1,6-diazapyrenyl group, a 1,8-diazapyrenyl group, a 4,5-diazapyrenyl group, a 4,5,9,10-tetraazaperylene group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbolinyl group, phenanthrolinyl group, 1,2,3-triazolyl group, 1,2,4-triazolyl group, benzotriazolyl group, 1,2,3-oxadiazolyl group, 1,2,4-oxadiazolyl group, 1,2,5-oxadiazolyl group, 1,2,3-thiadiazolyl group, 1,2,4-thiadiazolyl group, 1,2 a 1,5-thiadiazolyl group, a 1,3,4-thiadiazolyl group, a 1,3,5-triazinyl group, a 1,2,4-triazinyl group, a 1,2,3-triazinyl group, a tetrazolyl group, a 1,2,4,5-tetrazinyl group, a 1,2,3,4-tetrazinyl group, a 1,2,3,5-tetrazinyl group, a purinyl group, a pteridinyl group, an indolizinyl group, or a benzothiadiazolyl group, or a combination of the two groups mentioned above, 10. The organic compound according to claim 1.

15. Selected from compounds having the following specific structures: 【Chemistry 4-1】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 The organic compound according to claim 1.

16. Use of an organic compound according to any one of claims 1 to 15, The use includes use as a functional material in an organic electronic device, and the organic electronic device includes an organic electroluminescence device, an optical sensor, a solar cell, a lighting device, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner, or electronic paper; Furthermore, the compound is used as a light-emitting layer material in an organic electroluminescence device, specifically as a light-emitting material in a light-emitting layer.

10. The use characterized by:

17. An organic electroluminescence element, 16. A device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layer comprises a compound according to any one of claims 1 to 15, The light-emitting functional layer further includes a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region being formed on the anode layer, the cathode layer being formed on the electron transport region, and a light-emitting layer being between the hole transport region and the electron transport region, wherein the light-emitting layer contains the organic compound according to any one of claims 1 to 15. An organic electroluminescence element characterized by:

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