A tetraphenyl ethylene derivative and an organic electroluminescence device comprising the same

Abstract

This invention discloses a tetraphenylethylene derivative and an organic electroluminescent device containing the same. The tetraphenylethylene derivative has the structure shown in formula (1). Using the tetraphenylethylene derivative provided by this invention as the luminescent material of the organic electroluminescent device, the prepared organic electroluminescent device has a low turn-on voltage, high blue light purity, and high luminous efficiency.

Description

Technical Field

[0001] This invention belongs to the technical field of luminescent materials and luminescent devices, specifically relating to a tetraphenylethylene derivative and an organic electroluminescent device containing the derivative. Background Technology

[0002] An organic electroluminescent device includes an anode, a cathode, and a light-emitting layer between the anode and the cathode. Furthermore, there are organic electroluminescent devices with stacked layer structures, including organic layers such as hole injection layers, hole transport layers, electron injection layers, and electron transport layers.

[0003] When a voltage is applied to an organic electroluminescent device, holes are injected from the anode and electrons are injected from the cathode. In the light-emitting layer, the injected holes and electrons combine to form excitons. As the excitons return from the excited state to the ground state, energy is released in the form of light.

[0004] By using different luminescent materials in the luminescent layer, multiple colors of light can be emitted. Therefore, organic light-emitting diodes (OLEDs) are widely used in displays. Research on materials for the three primary colors—red, green, and blue—is particularly active, and through improvements to organic luminescent materials, the performance of organic light-emitting diodes is gradually increasing.

[0005] For example, Patent Document 1 (JP 161218 / 2019) discloses a technology in which anthracene-based compounds and pyrene-based compounds are used as luminescent materials for organic electroluminescent elements, which can achieve good carrier balance, thereby improving device efficiency and device lifetime.

[0006] In addition, in order to improve brightness efficiency and lifespan, a compound for light-emitting devices is disclosed in Patent Document 2 (EP 3150579B1), which has a fluoranthene skeleton and an aromatic heterocycle containing an electron acceptor N atom.

[0007] Patent document 3 (US2019 / 0013478A1) discloses a bipolar p-conjugated boron compound. This compound, as a fluorescent compound in organic electroluminescent devices, can conform to various energy levels and can be used to prepare organic electroluminescent devices with high luminous efficiency and stable storage at high temperatures.

[0008] Although the light-emitting performance of devices is constantly improving, high-performance devices place increasingly higher demands on materials. The field of organic electroluminescence still needs to develop new materials that can further improve device performance. Summary of the Invention

[0009] The purpose of this invention is to provide a tetraphenylethylene derivative, and a blue light-emitting organic electroluminescent device using the derivative, which features high luminous efficiency, low turn-on voltage, and high color purity.

[0010] The objective of this invention is achieved through the following technical solution:

[0011] A tetraphenylethylene derivative, with the following general structural formula:

[0012]

[0013] In formula (1), R1 to R4 are each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms forming a ring, substituted or unsubstituted silyl group with 3 to 30 carbon atoms, and substituted or unsubstituted alkoxy group with 1 to 30 carbon atoms.

[0014] Ar1 is selected from the following groups:

[0015]

[0016] Ar2 and Ar3 are each independently selected from substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 30 ring atoms; m and n are each independently 0 or 1;

[0017] In equation (2),

[0018] In equation (2-1),

[0019] R 11 ~R 12 Each is independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms forming a ring, and substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms;

[0020] Ar 11 and Ar 12 Each is independently selected from substituted or unsubstituted aryl groups having 6 to 18 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 18 cyclic atoms;

[0021] In equation (2-2),

[0022] R 21 ~R 22Each is independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms forming a ring, and substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms;

[0023] Ar 21 and Ar 22 Each is independently selected from substituted or unsubstituted aryl groups having 6 to 18 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 18 cyclic atoms;

[0024] In equation (2-3),

[0025] R 31 ~R 32 Each is independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms forming a ring, and substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms;

[0026] Ar 31 and Ar 32 Each is independently selected from substituted or unsubstituted aryl groups having 6 to 18 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 18 cyclic atoms;

[0027] In equation (2-4),

[0028] R 41 Selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms forming a ring, and substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms;

[0029] Ar 41 and Ar 42 Each is independently selected from substituted or unsubstituted aryl groups having 6 to 18 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 18 cyclic atoms;

[0030] In equation (2-5),

[0031] R 51 ~R 52Selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms forming a ring, and substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms;

[0032] Ar 51 and Ar 52 Each is independently selected from substituted or unsubstituted aryl groups having 6 to 18 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 18 cyclic atoms.

[0033] X1 is selected from O atom, S atom, NR or C(R)2, and R is selected from hydrogen atom or the following groups: substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 cyclic carbon atoms, substituted or unsubstituted aryl having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl having 5 to 30 cyclic atoms.

[0034] In formula (1), the preferred option is...

[0035] The halogen atom is selected from fluorine, chlorine, and bromine;

[0036] The substituted or unsubstituted alkyl group having 1 to 20 carbon atoms is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, 1,1,3,3-tetramethylpentyl, n-hexyl, 1-methylhexyl, 1,1,3,3,5,5-hexamethylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, and octadecyl;

[0037] The substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms is selected from vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, 1-methylpropenyl, 1,1-dimethylpropenyl, 2-methylpropenyl and 1,2-dimethylpropenyl.

[0038] The substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms is selected from ethynyl, propynyl, and 3-pentynyl;

[0039] The substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms forming the ring is selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, cyclooctyl, adamantyl, and norbornyl;

[0040] The substituted or unsubstituted silane with 3 to 30 carbon atoms is selected from trimethylsilane, triethylsilane, tributylsilane, dimethylethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, dimethylisopropylsilane, dimethylpropylsilane, dimethylbutylsilane, dimethyltert-butylsilane, diethylisopropylsilane, and triisopropylsilane.

[0041] The substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms is selected from methoxy, ethoxy, propoxy, isopropoxy, butoxy, isohexoxy, 2-butoxy, tert-butoxy, pentoxy, and hexoxy.

[0042] The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms is selected from phenyl, biphenyl, terphenyl, benzophenanthryl, naphthyl, anthraceneyl, phenatenyl, phenanthryl, fluorenyl, pyrene, trefyl, spirofluorenyl, perylene, and azulel;

[0043] The heteroaryl group having 5 to 30 ring atoms, whether substituted or unsubstituted, is selected from pyrroloyl, pyridyl, pyrimidinyl, pyrazinyl, indoleazinyl, triazinyl, indoleyl, isoindoleyl, imidazolyl, furanyl, thiopheneyl, benzofuranyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, benzimidazolyl, dibenzofuranyl, carbazoleyl, and phenanthrolinel.

[0044] In formula (2), the preferred option is...

[0045] The halogen atom is selected from fluorine, chlorine, and bromine;

[0046] The substituted or unsubstituted alkyl group having 1 to 20 carbon atoms is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, 1,1,3,3-tetramethylpentyl, n-hexyl, 1-methylhexyl, 1,1,3,3,5,5-hexamethylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, and octadecyl;

[0047] The substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms is selected from vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, 1-methylpropenyl, 1,1-dimethylpropenyl, 2-methylpropenyl and 1,2-dimethylpropenyl.

[0048] The substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms is selected from ethynyl, propynyl, and 3-pentynyl;

[0049] The substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms forming the ring is selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, cyclooctyl, adamantyl, and norbornyl;

[0050] The substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms is selected from methoxy, ethoxy, propoxy, isopropoxy, butoxy, isohexoxy, 2-butoxy, tert-butoxy, pentoxy, and hexoxy.

[0051] The substituted or unsubstituted aryl group having 6 to 18 cyclic carbon atoms is selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, fluorenyl and 9,9-dimethylfluorenyl, etc.

[0052] The substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms is selected from furan, thiophene, pyridine, quinoline, isoquinoline, pyrimidine, quinazoline, pyrrole, indole, pyrazine, quinoxaline, triazine, benzofuranyl, benzothiopheneyl, carbazoyl, and phenanthrolineyl.

[0053] In equation (2-5), the preferred option is...

[0054] The substituted or unsubstituted alkyl group having 1 to 30 carbon atoms is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, 1,1,3,3-tetramethylpentyl, n-hexyl, 1-methylhexyl, 1,1,3,3,5,5-hexamethylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, and octadecyl;

[0055] The substituted or unsubstituted cycloalkyl group having 3 to 30 cyclic carbon atoms is selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, cyclooctyl, adamantyl, and norbornyl;

[0056] The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms is selected from phenyl, biphenyl, terphenyl, benzophenanthryl, naphthyl, anthraceneyl, phenatenyl, phenanthryl, fluorenyl, pyrene, trefyl, spirofluorenyl, perylene, and azulel;

[0057] The substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms is selected from pyrrole, pyridinyl, pyrimidinyl, pyrazinyl, indoleazinyl, triazinyl, indoleyl, isoindoleyl, imidazolyl, furanyl, thiopheneyl, benzofuranyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, benzimidazolyl, dibenzofuranyl, carbazoleyl, and phenanthrolinel.

[0058] In equation (1),

[0059] Preferably, R1 and R3 are halogen atoms, cyano groups, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups with 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms forming a ring, substituted or unsubstituted silyl groups with 3 to 30 carbon atoms, or substituted or unsubstituted alkoxy groups with 1 to 30 carbon atoms; R2 and R4 are hydrogen atoms.

[0060] As another preferred embodiment, R1 to R4 are hydrogen atoms.

[0061] Preferably, Ar2 and Ar3 are selected from phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl.

[0062] Preferably, one of m and n is 0 and the other is 1;

[0063] More preferably, n is 1, m is 0, and Ar2 is selected from phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl.

[0064] In formula (2), the preferred option is...

[0065] In equation (2-1), R 11 ~R 12 For hydrogen atoms, Ar 11 and Ar 12 It can be phenyl, naphthyl, or biphenyl;

[0066] In equation (2-2), R 21 ~R 22 For hydrogen atoms, Ar 21 and Ar 22 It can be phenyl, naphthyl, or biphenyl;

[0067] In equation (2-3), R 31 ~R 32 For hydrogen atoms, Ar 31 and Ar 32 It can be phenyl, naphthyl, or biphenyl;

[0068] In equation (2-4), R 41 For hydrogen atoms, Ar 41 and Ar 42 It can be phenyl, naphthyl, or biphenyl;

[0069] In equation (2-5), R 51 ~R 52 For hydrogen atoms, Ar 51 and Ar 52 It can be phenyl, naphthyl, or biphenyl, and X1 is selected from O or S atoms.

[0070] An organic electroluminescent device comprising the aforementioned tetraphenylethylene derivative.

[0071] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein at least one organic layer is a light-emitting layer, and the light-emitting layer is a tetraphenylethylene derivative or a mixture containing a tetraphenylethylene derivative.

[0072] Preferably, the organic electroluminescent device is any one of the following: a monochromatic light-emitting device with fluorescence or phosphorescence, a white light-emitting device with a mixture of fluorescence and phosphorescence, a simple light-emitting device with a single light-emitting unit, and a series-connected light-emitting device with two or more light-emitting units.

[0073] Preferably, the organic electroluminescent device is applied to flat panel display devices, irregularly shaped display devices, curved display devices, flexible display devices, and lighting devices. Examples include display devices in computers and televisions, visual display devices in printers, kitchen appliances, and advertising panels, display devices in mobile phones, tablets, laptops, and digital cameras, vehicle and destination displays on buses and trains, wearable devices such as smartwatches, glasses, or clothing, and light sources, display panels, or navigation lights for instruments.

[0074] The compound of formula (1) of the present invention can be used as a luminescent material for organic electroluminescent devices, and can be used alone or as a component of a mixture in the luminescent layer of the device. According to the present invention, a blue-emitting organic electroluminescent device with high luminous efficiency and high color purity can be provided, as well as materials used in the organic thin layer of the organic luminescent device.

[0075] The present invention has the following beneficial effects:

[0076] (1) The tetraphenylethylene derivative of the present invention, when used as the light-emitting layer of an organic electroluminescent device, has high luminous efficiency, low turn-on voltage, and high color purity.

[0077] (2) The preparation method of the tetraphenylethylene derivative of the present invention is simple, the raw materials are readily available, and it is suitable for mass production. Attached Figure Description

[0078] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device provided by the present invention. Detailed Implementation

[0079] The tetraphenylethylene derivative of the present invention is represented by the following formula (1):

[0080]

[0081] In formula (1), R1 to R4 are each independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms forming a ring, substituted or unsubstituted silyl group with 3 to 30 carbon atoms, and substituted or unsubstituted alkoxy group with 1 to 30 carbon atoms.

[0082] Preferably, in the above formula (1), R1 and R3 are halogen atoms, cyano groups, or substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups with 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms forming a ring, substituted or unsubstituted silyl groups with 3 to 30 carbon atoms, or substituted or unsubstituted alkoxy groups with 1 to 30 carbon atoms; R2 and R4 are hydrogen atoms.

[0083] The substituted or unsubstituted alkyl groups of R1 and R3 having 1 to 20 carbon atoms are preferably alkyl groups having 1 to 6 carbon atoms. The substituted or unsubstituted alkenyl groups of R1 and R3 having 2 to 20 carbon atoms are preferably alkenyl groups having 2 to 6 carbon atoms. The substituted or unsubstituted alkynyl groups of R1 and R3 having 2 to 20 carbon atoms are preferably alkynyl groups having 2 to 6 carbon atoms. The substituted or unsubstituted cycloalkyl groups of R1 and R3 having 3 to 10 carbon atoms forming the ring are preferably cycloalkyl groups having 3 to 6 carbon atoms forming the ring. The substituted or unsubstituted silyl groups of R1 and R3 having 3 to 30 carbon atoms are preferably silyl groups having 3 to 12 carbon atoms. The substituted or unsubstituted alkoxy groups of R1 and R3 having 1 to 30 carbon atoms are preferably alkoxy groups having 1 to 6 carbon atoms.

[0084] As another preferred form, in the above formula (1), R1 to R4 are hydrogen atoms.

[0085] Ar1 is selected from the group represented by the following formula (2):

[0086]

[0087] Ar2 and Ar3 are each independently selected from substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 30 ring atoms; m and n are each independently 0 or 1.

[0088] In equation (2),

[0089] In equation (2-1),

[0090] R 11 ~R 12Each is independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms forming a ring, and substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms;

[0091] Ar 11 and Ar 12 Each is independently selected from substituted or unsubstituted aryl groups having 6 to 18 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 18 cyclic atoms;

[0092] In equation (2-2),

[0093] R 21 ~R 22 Each is independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms forming a ring, and substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms;

[0094] Ar 21 and Ar 22 Each is independently selected from substituted or unsubstituted aryl groups having 6 to 18 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 18 cyclic atoms;

[0095] In equation (2-3),

[0096] R 31 ~R 32 Each is independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms forming a ring, and substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms;

[0097] Ar 31 and Ar 32 Each is independently selected from substituted or unsubstituted aryl groups having 6 to 18 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 18 cyclic atoms;

[0098] In equation (2-4),

[0099] R 41Selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms forming a ring, and substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms;

[0100] Ar 41 and Ar 42 Each is independently selected from substituted or unsubstituted aryl groups having 6 to 18 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 18 cyclic atoms;

[0101] In equation (2-5),

[0102] R 51 ~R 52 Selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms forming a ring, and substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms;

[0103] Ar 51 and Ar 52 Each is independently selected from substituted or unsubstituted aryl groups having 6 to 18 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 18 cyclic atoms.

[0104] X1 is selected from O atom, S atom, NR or C(R)2, and R is selected from hydrogen atom or the following groups: substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 cyclic carbon atoms, substituted or unsubstituted aryl having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl having 5 to 30 cyclic atoms.

[0105] In this specification, "cyclic carbon atom" refers to a carbon atom that forms a saturated, unsaturated, or aromatic ring. "Atoms forming a ring" refers to carbon atoms and heteroatoms that form heterocycles (including saturated, unsaturated, or aromatic rings).

[0106] Furthermore, examples of substituents in "substituted or unsubstituted..." include alkyl, substituted or unsubstituted silyl, alkoxy, aryl, aryloxy, aralkyl, cycloalkyl, heterocyclic, halogen atom, halogenated alkyl, hydroxyl, nitro, cyano, carboxyl, etc., as described below.

[0107] Here, "unsubstituted" means that a group is replaced by a hydrogen atom, and the hydrogen atoms in this invention include light hydrogen, deuterium and tritium.

[0108] Regarding R1~R4 and R in the above equations (1) and (2), 11 ~R 12 R 21 ~R 22 R 31 ~R 32 R 41 R 51 ~R 52 R, Ar2, Ar3, Ar 11 ~Ar 12 Ar 21 ~Ar 22 Ar 31 ~Ar 32 Ar 41 and Ar 51 ~Ar 52 The groups represented, as well as the substituents in "substituted or unsubstituted...", are described in detail below.

[0109] Examples of halogen atoms include fluorine, chlorine, and bromine, with fluorine being the preferred atom.

[0110] Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl. The number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. Among these, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, and n-hexyl are preferred.

[0111] Examples of alkenyl groups include vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, and 1,2-dimethylallyl. Vinyl is preferred.

[0112] Examples of alkynyl groups include ethynyl, propynyl, and 3-pentynyl. Among these, ethynyl is preferred.

[0113] Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, adamantyl, and norbornyl. The number of carbon atoms forming the ring is preferably 3 to 10, more preferably 5 to 8, even more preferably 3 to 8, and particularly preferably 3 to 6.

[0114] Examples of silyl groups include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, and triisopropylsilyl.

[0115] Alkoxy groups are represented by -OY. Examples of Y include the alkyl groups mentioned above. Examples of alkoxy groups include methoxy and ethoxy groups.

[0116] Examples of aryl groups include phenyl, 1-naphthyl, 2-naphthyl, 3-naphthyl, 1-phenanthyl, 2-phenanthyl, 3-phenanthyl, 4-phenanthyl, 9-phenanthyl, and tetraphenyl. Benzyl, benzo[c]phenanthrene, benzo[g] It includes benzo[a]phenanthryl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, triphenyl, fluoranthyl, etc.

[0117] The number of atoms in the aryl ring is preferably 6 to 20, more preferably 6 to 12, for example, phenyl, naphthyl, phenanthryl, fluorenyl, anthracene, etc. alkyl, fluoranthyl. Particularly preferred are phenyl, naphthyl.

[0118] Examples of heteroaryl groups include pyrroleyl, pyrazinyl, pyridyl, indolyl, isoindolyl, imidazolyl, furanyl, benzofuranyl, isobenzofuranyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiopheneyl, 2-dibenzothiopheneyl, 3-dibenzothiopheneyl, 4-dibenzothiopheneyl, quinolinyl, isoquinolinyl, quinoxolinyl, 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, 9-carbazoleyl, phenanthinyl, acridineyl, phenantholinyl, phenazinyl, phenothiazinyl, phenothiazinyl, oxazolyl, oxadiazolyl, thiopheneyl, and benzothiophene.

[0119] The number of atoms in the forming ring of the above-mentioned heteroaryl group is preferably 5 to 20, more preferably 5 to 14. Preferably, it comprises 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, 9-carbazoleyl, pyridyl, or pyrimidinyl.

[0120] Specific examples of tetraphenylethylene derivatives are as follows, but not limited to:

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127] The aforementioned tetraphenylethylene derivatives can be used as luminescent materials and dopant materials for organic electroluminescent devices. When containing tetraphenylethylene derivatives as dopants, there are no particular limitations on the content; it can be 1 wt% or more, preferably 1.0–80.0 wt%, and more preferably 5.0–20.0 wt%.

[0128] The organic electroluminescent device of the present invention includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein at least one organic layer is a light-emitting layer, and at least one organic layer contains the aforementioned tetraphenylethylene derivative or is a component of a mixture.

[0129] The organic electroluminescent device materials mentioned in this invention can be used as the host material or dopant material of the luminescent layer in a fluorescent luminescent unit. They can also be used as functional layer materials in fluorescent and phosphorescent luminescent units, for example, as materials used in an anode-side organic thin film layer formed between the anode and the luminescent layer, or as materials used in a cathode-side organic thin film layer formed between the cathode and the luminescent layer; that is, materials used in hole transport layers, hole injection layers, electron transport layers, electron injection layers, hole blocking layers, and electron blocking layers.

[0130] The organic electroluminescent device of the present invention can be any one of the following: a monochromatic light-emitting device with fluorescence or phosphorescence, a white light-emitting device with a mixture of fluorescence and phosphorescence, a simple light-emitting device with a single light-emitting unit, or a series-connected light-emitting device with two or more light-emitting units.

[0131] As a representative structure of a simple organic electroluminescent device, the device structure is given below:

[0132] (1) Anode / Light-emitting unit / Cathode

[0133] The aforementioned light-emitting unit can be a stacked structure comprising multiple fluorescent and phosphorescent light-emitting layers. In this case, to prevent excitons generated in the phosphorescent light-emitting layer from diffusing into the fluorescent light-emitting layer, a spacer layer can be provided between the light-emitting layers.

[0134] The following is a representative stacked structure of the light-emitting unit.

[0135] (a) Hole transport layer / emission layer ( / electron transport layer)

[0136] (b) Hole transport layer / First phosphorescent layer / Second phosphorescent layer ( / Electron transport layer)

[0137] (c) Hole transport layer / phosphorescent layer / spacer layer / fluorescent layer ( / electron transport layer)

[0138] (d) Hole transport layer / First phosphorescent layer / Second phosphorescent layer / Spacer layer / Fluorescent layer ( / Electron transport layer)

[0139] (e) Hole transport layer / first phosphorescent layer / spacer layer / second phosphorescent layer / spacer layer / fluorescent layer ( / electron transport layer)

[0140] (f) Hole transport layer / phosphorescent layer / spacer layer / first fluorescent layer / second fluorescent layer ( / electron transport layer)

[0141] (g) Hole transport layer / electron blocking layer / electron emitting layer ( / electron transport layer)

[0142] (h) Hole transport layer / emission layer / hole blocking layer ( / electron transport layer)

[0143] (i) Hole transport layer / fluorescent layer / triple state blocking layer ( / electron transport layer)

[0144] The phosphorescent or fluorescent emitting layers described above can emit light of different colors. Specifically, in the stacked structure (d), the following example can be given: hole transport layer / first phosphorescent emitting layer (red light) / second phosphorescent emitting layer (green light) / spacer layer / fluorescent emitting layer (blue light) / electron transport layer.

[0145] An electron blocking layer can be appropriately disposed between each emitting layer and a hole transport layer or spacer layer. Similarly, a hole blocking layer can be appropriately disposed between each emitting layer and an electron transport layer. By providing electron or hole blocking layers, electrons and holes can be confined within the emitting layer, thereby increasing the likelihood of carrier recombination in the emitting layer and extending its lifetime.

[0146] As a representative structure of tandem organic electroluminescent devices, the device structure is given below:

[0147] (2) Anode / First Light-Emitting Unit / Intermediate Layer / Second Light-Emitting Unit / Cathode

[0148] The layered structure of the first light-emitting unit and the second light-emitting unit can be selected from the representative stacked structure of the emitting unit mentioned above.

[0149] Typically, the intermediate layer is also called the intermediate electrode, intermediate conductive layer, carrier forming layer, or electron layer. It can provide electrons to the first light-emitting layer and holes to the second light-emitting layer through material configuration.

[0150] A schematic diagram of an example of the organic electroluminescent device of the present invention is shown below. Figure 1As shown, the organic electroluminescent device includes a substrate 1, an anode 2, a cathode 8, and an organic thin film layer 10 (light-emitting unit 10) disposed between the anode 2 and the cathode 8. The light-emitting unit 10 includes a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, and an electron injection layer 7. An electron blocking layer can be disposed on the anode 2 side of the light-emitting layer 5, and a hole blocking layer can be disposed on the cathode 8 side of the light-emitting layer 5. Through these blocking layers, electrons and holes are confined within the light-emitting layer 5 to improve the recombination degree of excitons in the light-emitting layer 5.

[0151] In this invention, the host material bonded to the fluorescent dopant is called the fluorescent host material, and the host material bonded to the phosphorescent dopant is called the phosphorescent host material. Therefore, the fluorescent host material and the phosphorescent host material cannot be distinguished solely by differences in their molecular structures. In this invention, the term "phosphorescent host" refers to the material used to constitute a phosphorescent emitting layer containing phosphorescent dopant, and does not refer to a material that cannot be used as a fluorescent emitting layer material. The same applies to "fluorescent host".

[0152] substrate

[0153] The organic electroluminescent device of the present invention is formed on a transparent substrate. Preferably, a glass substrate with a visible light transmittance of 80% in the 400-700 nm wavelength band is used as the carrier for the organic electroluminescent device. The glass substrate can be made of soda-lime glass, barium-strontium glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, or quartz.

[0154] anode

[0155] As the anode material in the organic electroluminescent device of the present invention, it is suitable to inject holes into the hole transport layer or the light-emitting layer, and have a work function of 4.5 eV or higher. Materials such as indium tin oxide (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, and copper are suitable, but not limited to these. The anode is formed by fabricating the anode material into a thin film using a specific method, such as vapor deposition or sputtering. When light is emitted from the light-emitting layer through the anode, the transmittance of the anode to visible light is preferably 10% or higher. The film resistance of the anode is preferably several hundred Ω / ° or lower. The film thickness of the anode depends on the type of material, and is generally 10 nm to 1 μm, preferably 100 to 200 nm.

[0156] cathode

[0157] The cathode injects electrons into the electron injection layer, electron transport layer, or light-emitting layer, and is preferably formed of a material with a small work function. Examples of materials used for the cathode include, but are not limited to, indium, aluminum, magnesium, magnesium-indium alloys, magnesium-aluminum alloys, aluminum-lithium alloys, aluminum-scandium-lithium alloys, and magnesium-silver alloys. Similar to the anode, the cathode is formed by fabricating a thin film of material using methods such as vapor deposition and sputtering.

[0158] Emissive layer

[0159] The luminescent layer is an organic layer that emits light. When a doped system is used, it comprises a host material and a dopant material. The main function of the host material is to promote the recombination of electrons and holes and confine excitons within the luminescent layer. The function of the dopant material is to enable the excitons generated by recombination to emit light effectively.

[0160] To control the carrier balance in the luminescent layer, the luminescent layer can be made into a dual-host (host / co-host) layer, for example, by using a combination of electron transport host and hole transport host.

[0161] The luminescent layer can be fabricated as a double-doped layer, using a combination of two or more dopants with high quantum yields, each emitting light in its own color. For example, yellow light can be obtained by using a luminescent layer formed by co-depositing a host material, a red dopant, and a green dopant.

[0162] In a stacked structure containing two or more light-emitting layers, electrons and holes accumulate at the interface between the light-emitting layers. Therefore, the recombination region is located at the interface between the light-emitting layers to improve quantum efficiency.

[0163] The ease with which holes are injected into the luminescent layer may differ from the ease with which electrons are injected. Similarly, hole transport capability and electron transport capability, represented by the mobilities of holes and electrons in the luminescent layer respectively, may differ from each other.

[0164] The light-emitting layer is formed by known methods, such as vapor deposition, spin coating, and LB method, but is not limited to these. The light-emitting layer is preferably a molecularly deposited film. A molecularly deposited film is a thin film formed by depositing vaporized material or by solidifying the material in a solution or liquid state. Molecularly deposited films and thin films formed by the LB method (molecular stacking films) can be distinguished by differences in assembly structure, higher-order structure, and functional differences caused by structural differences.

[0165] The thickness of the light-emitting layer is preferably 5–50 nm, more preferably 7–50 nm, and most preferably 10–50 nm. If it is less than 5 nm, it may be difficult to form the light-emitting layer and the color may be difficult to control. If it exceeds 50 nm, the driving voltage may need to be increased.

[0166] (1) Fluorescent emissive layer

[0167] A fluorescent luminescent layer typically includes at least one luminescent material and at least one host material.

[0168] The host material used for the fluorescent luminescent layer is typically selected from general host materials, preferably having a wider band gap than the luminescent material, enabling efficient luminescence through an energy transfer mechanism from the host material to the luminescent material. Specific examples of preferred fluorescent host materials are substituted or unsubstituted heterocyclic compounds or substituted or unsubstituted aromatic compounds, such as oligophenylene derivatives, naphthalene derivatives, fluorene derivatives, fluoranthene derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, benzo[a]phenanthrene derivatives, benzo[a]anthene derivatives, chrysene derivatives, tetraphenylbenzene derivatives, benzo[a]chrysene derivatives, etc.

[0169] The luminescent materials used in the fluorescent luminescent layer are typically selected from general luminescent materials or fluorescent dyes, preferably materials with high absorption coefficients and high quantum efficiencies to achieve high luminous efficacy. Specific examples of preferred fluorescent luminescent materials are the aforementioned tetraphenylethylene derivatives, aromatic hydrocarbon derivatives, such as oligophenylene derivatives, naphthalene derivatives, fluorene derivatives, fluoranthene derivatives, fused fluorene derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, benzo[a]phenanthrene derivatives, chrysoprase derivatives, tetraphenylene derivatives, benzo[a]chrysoprase derivatives, etc.

[0170] (2) Phosphorescent layer

[0171] A phosphorescent emissive layer typically comprises at least one luminescent material and at least one host material. The phosphorescent host material is a compound that effectively confines the triplet energy of the phosphorescent dopant within the emissive layer, enabling the phosphorescent dopant to emit light efficiently.

[0172] The host material used for the phosphorescent emitting layer is typically selected from known phosphorescent host materials. Specific examples of preferred phosphorescent host materials include nitrogen-containing heteroaromatic hydrocarbons, such as indole derivatives, carbazole derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, quinazoline derivatives, dibenzothiophene nitride derivatives, dibenzofuran nitride derivatives, imidazole derivatives, benzimidazole derivatives, imidazole pyridine derivatives, benzimidazole phenanthridine derivatives, and benzimidazole-benzimidazole derivatives; oxygen- or sulfur-containing heteroaromatic hydrocarbons, such as thiophene derivatives, furan derivatives, benzothiophene derivatives, benzofuran derivatives, dibenzothiophene derivatives, and dibenzofuran derivatives; aryl or heteroaryl-substituted amine derivatives; metal complexes; aromatic hydrocarbon derivatives, such as benzene derivatives, naphthalene derivatives, phenanthrene derivatives, triphenyl derivatives, fluorene derivatives, etc.

[0173] The doping material used in the phosphorescent emitting layer (phosphorescent material) is a compound capable of emitting light from a triplet excited state. The phosphorescent doping material is not limited, as long as it can emit light from a triplet excited state. The phosphorescent doping material is preferably an organometallic complex containing at least one metal selected from Ir, Pt, Os, Au, Cu, Re, and Ru, and a ligand. Preferably, the ligand has an ortho-metallization bond. To obtain devices with high phosphorescent quantum yield and external quantum efficiency, the phosphorescent doping material is preferably a compound having metal atoms selected from Ir, Os, and Pt. Further preferred are metal complexes, such as iridium complexes, osmium complexes, and platinum complexes, with ortho-metallization complexes being more preferred. Among these, iridium complexes and platinum complexes are more preferred, with ortho-metallization iridium complexes being particularly preferred.

[0174] Electron transport layer

[0175] An electron transport layer is an organic layer disposed between the light-emitting layer and the cathode, which transports electrons from the cathode to the light-emitting layer. If two or more electron transport layers are provided, in some cases, the organic layer closer to the cathode can be called an electron injection layer. The electron injection layer can effectively inject electrons from the cathode into the organic layer unit.

[0176] Aromatic heterocyclic compounds having one or more heteroatoms in their molecules are preferred as electron transport materials used in electron transport layers, and nitrogen-containing heterocyclic derivatives are particularly preferred. Furthermore, nitrogen-containing heterocyclic derivatives are preferably aromatic ring compounds containing a 6- or 5-membered nitrogen heterocycle, or fused aromatic ring compounds containing a 6- or 5-membered nitrogen heterocycle.

[0177] The thickness of the electron transport layer is preferred, but not particularly limited to 1–100 nm.

[0178] Preferred examples of optional electron injection layer materials, besides nitrogen-containing heterocyclic derivatives, include inorganic compounds such as insulating materials and semiconductors. Electron injection layers containing insulating materials or semiconductors can effectively prevent current leakage, thereby improving electron injection performance.

[0179] The insulating material is preferably at least one metal compound selected from alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides. The aforementioned alkali metal chalcogenides are preferred because they further enhance the electron injection performance of the electron injection layer. Examples of preferred alkali metal chalcogenides include Li₂O, K₂O, Na₂S, Na₂Se, and Na₂O, while examples of preferred alkaline earth metal chalcogenides include CaO, BaO, SrO, BeO, BaS, and CaSe. Examples of preferred alkali metal halides include LiF, NaF, KF, LiCl, KCl, and NaCl. Examples of alkaline earth metal halides include fluorides such as CaF₂, BaF₂, SrF₂, MgF₂, and BeF₂, as well as halides other than fluorides.

[0180] Examples of semiconductors include oxides, nitrides, or oxynitrides containing at least one element from the group consisting of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb, and Zn. The semiconductor can be used alone or in combination of two or more elements. The inorganic compound contained in the electron injection layer preferably forms a microcrystalline or amorphous insulating film. If the electron injection layer is formed from such an insulating film, pixel defects (e.g., black spots) can be reduced because a more uniform film is formed. Examples of such inorganic compounds include alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides.

[0181] When using insulating materials or semiconductors, the thickness of this layer is preferably about 0.1 to 15 nm.

[0182] Hole transport layer

[0183] A hole injection / transport layer is an organic layer formed between the light-emitting layer and the anode, which functions to transport holes from the anode to the light-emitting layer. When the hole transport layer is formed of two or more layers, in some cases, the layer closer to the anode can be defined as the hole injection layer. The hole injection layer functions to effectively inject holes from the anode into the organic layer cells.

[0184] The hole transport layer can be fabricated as a two-layer structure consisting of a first hole transport layer (anode side) and a second hole transport layer (cathode side).

[0185] The thickness of the hole transport layer is preferably 10–200 nm, with no particular limitation.

[0186] n / p doping

[0187] The carrier injection characteristics of the hole transport layer and the electron transport layer can be controlled by doping with electron donor material (n) or electron acceptor material (p).

[0188] Typical examples of n-doping are electron transport materials doped with metals, such as Li and Cs, while typical examples of p-doping are hole transport materials doped with acceptor materials, such as F4TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethylethane).

[0189] Spacer layer

[0190] In organic electroluminescent devices containing a multilayered structure of fluorescent and phosphorescent emitting layers, a spacer layer is provided between the fluorescent and phosphorescent emitting layers to prevent excitons generated in the phosphorescent emitting layer from diffusing into the fluorescent emitting layer or to control carrier balance. This spacer layer can also be provided between two or more phosphorescent emitting layers.

[0191] Since the spacer layer is disposed between the light-emitting layers, a material with both electron transport and hole transport capabilities is preferred. To prevent the diffusion of triplet energy between adjacent phosphorescent light-emitting layers, the triplet energy of the material used for the spacer layer is preferably 2.6 eV or higher. The materials described regarding the hole transport layer can be used as spacer layer materials.

[0192] Barrier layer

[0193] Blocking layers, such as electron blocking layers, hole blocking layers, and triplet blocking layers, are placed near the emissive layer. Electron blocking layers prevent electrons from diffusing from the emissive layer to the hole transport layer. Hole blocking layers prevent holes from diffusing from the emissive layer to the electron transport layer.

[0194] The triplet blocking layer prevents triplet excitons generated in the luminescent layer from diffusing to adjacent layers and confines them within the luminescent layer, thereby preventing energy deactivation on molecules other than the luminescent dopant material containing the triplet excitons, such as molecules in the electron transport layer.

[0195] The material of the triplet barrier layer is preferably one with an electron mobility of 10 at an electric field strength of 0.04–0.5 MV / cm. -6 cm 2 Materials with a value of / Vs or higher. Several methods exist for measuring the electron mobility of organic materials, such as time-of-flight methods. Here, electron mobility refers to the electron mobility determined by impedance spectroscopy.

[0196] The material of the electron injection layer is preferably such that its electron mobility is 10 at an electric field strength of 0.04–0.5 MV / cm. -6 cm 2 Materials with a voltage of / Vs or higher. Within the above range, electron injection from the cathode to the electron transport layer can be facilitated, as well as electron injection into adjacent blocking and light-emitting layers, thereby enabling the drive device at lower voltages.

[0197] The present invention also relates to an electronic device comprising the organic electroluminescent device described herein.

[0198] Organic electroluminescent devices using the compound of formula (1) of the present invention can be used in panel modules for various displays.

[0199] Organic electroluminescent devices using the compounds of formula (1) of the present invention can be used as display elements for televisions, mobile phones and personal computers; or as electronic devices such as lighting devices or similar devices.

[0200] OLEDs (organic electroluminescent devices) using the compounds of formula (1) of the present invention can be used in all devices that use electroluminescence. Suitable devices are preferably fixed and mobile visual display units and lighting units. Fixed visual display units include, for example, visual display units in computers, televisions, printers, kitchen appliances and advertising panels, lighting and information panels. Mobile visual display units include, for example, visual display units in mobile phones, tablets, laptops, digital cameras, MP3 players, destination displays in vehicles, buses and trains. Other devices that can use the OLEDs of the present invention include, for example, keyboards, clothing, furniture, wallpaper, etc.

[0201] Example

[0202] The technical solution of the present invention will be described in more detail below with reference to the embodiments, but the scope of the present invention is not limited to the following examples.

[0203] Synthesis Examples

[0204] Example 1: Synthesis of Compound 1

[0205] (1) Synthesis of intermediate 1

[0206]

[0207] Intermediate a (9.16 g, 16 mmol), intermediate b (5.36 g, 16 mmol), tetrakis(triphenylphosphine)palladium (924 mg, 0.8 mmol), and potassium carbonate (6.64 g, 48 mmol) were placed in a reaction flask, the atmosphere was purged with nitrogen, and 300 mL of toluene / ethanol / water (8 / 1 / 1) was added. The mixture was reacted at 110 °C for 14 h. After cooling to room temperature, dichloromethane was added, followed by water extraction. The organic layer was collected, evaporated to dryness, and purified by column chromatography to give intermediate 1 in 50% yield.

[0208] (2) Synthesis of intermediate 2

[0209]

[0210] Intermediate 1 (4.70 g, 8.0 mmol), intermediate c (2.44 g, 9.6 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (176 mg, 0.24 mmol), and potassium acetate (2.36 g, 24 mmol) were placed in a reaction flask, the atmosphere was purged with nitrogen, 100 mL of dioxane was added, and the reaction was carried out at 104 °C for 10 h. After cooling to room temperature, dichloromethane was added, and the mixture was extracted with water. The organic layer was collected, evaporated to dryness, and purified by column chromatography to give intermediate 2 in 54% yield.

[0211] (3) Synthesis of intermediate 3

[0212]

[0213] Take intermediate d (3.79 g, 8.0 mmol), intermediate e (2.36 g, 8.0 mmol), Pd(OAc)2 (45 mg, 0.2 mmol), P(o-tolyl)3 (122 mg, 0.4 mmol), and NaO. t Bu (1.15 g, 12 mmol) was added to a reaction flask along with 15 mL of toluene. The mixture was heated to 110 °C and reacted for 12 h under argon protection. The reaction solution was cooled, and the reaction was quenched by adding 60 mL of distilled water. The mixture was then extracted with 60 mL of dichloromethane. The organic phase was washed with saturated sodium chloride solution (30 mL x 3), dried over anhydrous sodium sulfate, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by chromatography to obtain intermediate 3 in 53% yield.

[0214] (4) Synthesis of Compound 1

[0215]

[0216] Intermediate 3 (2.75 g, 4.0 mmol), intermediate 2 (2.54 g, 4.0 mmol), tetratetraphenylphosphine palladium (231 mg, 0.2 mmol), and potassium carbonate (1.66 g, 12 mmol) were placed in a reaction flask, the atmosphere was purged with nitrogen, and 50 mL of toluene / ethanol / water (8 / 1 / 1) was added. The mixture was reacted at 110 °C for 16 h. After cooling to room temperature, dichloromethane was added, followed by water extraction. The organic layer was collected, evaporated to dryness, and purified by column chromatography to give compound 1 in 50% yield.

[0217] Example 2: Synthesis of Compound 2

[0218] (1) Synthesis of intermediate 4

[0219]

[0220] Take intermediate f (3.84 g, 8.0 mmol), intermediate g (1.75 g, 8.0 mmol), Pd(OAc)2 (90 mg, 0.4 mmol), dppf (222 mg, 0.4 mmol), and NaO. t Bu (1.15 g, 12 mmol) was placed in a reaction flask, nitrogen was purged, 50 mL of toluene was added, and the reaction was carried out at 100 °C for 16 h. After cooling to room temperature, the product was diluted with toluene, filtered through a silica gel filter, and the solvent was removed from the filtrate under vacuum to obtain the crude product. The crude product was passed through a column to obtain intermediate 4, with a yield of 55%.

[0221] (2) Synthesis of Compound 2

[0222]

[0223] Intermediate 4 (2.47 g, 4.0 mmol), intermediate 2 (2.54 g, 4.0 mmol), tetratetraphenylphosphine palladium (231 mg, 0.2 mmol), and potassium carbonate (1.66 g, 12 mmol) were placed in a reaction flask, the atmosphere was purged with nitrogen, and 50 mL of toluene / ethanol / water (8 / 1 / 1) was added. The mixture was reacted at 110 °C for 16 h. After cooling to room temperature, dichloromethane was added, followed by water extraction. The organic layer was collected, evaporated to dryness, and purified by column chromatography to give compound 2 in 45% yield.

[0224] Example 3: Synthesis of Compound 3

[0225] (1) Synthesis of intermediate 5

[0226]

[0227] Take intermediate h (3.84 g, 8.0 mmol), intermediate j (1.75 g, 8.0 mmol), Pd(OAc)2 (90 mg, 0.4 mmol), dppf (222 mg, 0.4 mmol), and NaO. t Bu (1.15 g, 12 mmol) was placed in a reaction flask, nitrogen was purged, 50 mL of toluene was added, and the reaction was carried out at 100 °C for 16 h. After cooling to room temperature, the product was diluted with toluene, filtered through a silica gel filter, and the solvent was removed from the filtrate under vacuum to obtain the crude product. The crude product was passed through a column to obtain intermediate 5, with a yield of 56%.

[0228] (2) Synthesis of compound 3

[0229]

[0230] Intermediate 5 (2.47 g, 4.0 mmol), intermediate 2 (2.54 g, 4.0 mmol), tetratetraphenylphosphine palladium (231 mg, 0.2 mmol), and potassium carbonate (1.66 g, 12 mmol) were placed in a reaction flask, the atmosphere was purged with nitrogen, and 50 mL of toluene / ethanol / water (8 / 1 / 1) was added. The mixture was reacted at 110 °C for 16 h. After cooling to room temperature, dichloromethane was added, followed by water extraction. The organic layer was collected, evaporated to dryness, and purified by column chromatography to give compound 3 in 44% yield.

[0231] Example 4: Synthesis of Compound 4

[0232] (1) Synthesis of intermediate 6

[0233]

[0234] Take intermediate k (4.19 g, 8.0 mmol), intermediate m (1.96 g, 8.0 mmol), Pd(OAc)2 (45 mg, 0.2 mmol), P(o-tolyl)3 (122 mg, 0.4 mmol), and NaO. t Bu (1.15 g, 12 mmol) was added to a reaction flask along with 15 mL of toluene. The mixture was heated to 110 °C and reacted for 12 h under argon protection. The reaction solution was cooled, and the reaction was quenched by adding 60 mL of distilled water. The mixture was then extracted with 60 mL of dichloromethane. The organic phase was washed with saturated sodium chloride solution (30 mL x 3), dried over anhydrous sodium sulfate, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by chromatography to obtain intermediate 6, with a yield of 56%.

[0235] (2) Synthesis of compound 4

[0236]

[0237] Intermediate 6 (2.75 g, 4.0 mmol), intermediate 2 (2.54 g, 4.0 mmol), tetratetraphenylphosphine palladium (231 mg, 0.2 mmol), and potassium carbonate (1.66 g, 12 mmol) were placed in a reaction flask, the atmosphere was purged with nitrogen, and 50 mL of toluene / ethanol / water (8 / 1 / 1) was added. The mixture was reacted at 110 °C for 16 h. After cooling to room temperature, dichloromethane was added, followed by water extraction. The organic layer was collected, evaporated to dryness, and purified by column chromatography to give compound 4 in 50% yield.

[0238] Example 5: Synthesis of Compound 5

[0239] (1) Synthesis of intermediate 7

[0240]

[0241] Take intermediate n (4.16 g, 8.0 mmol), intermediate p (1.35 g, 8.0 mmol), Pd(OAc)2 (90 mg, 0.4 mmol), dppf (222 mg, 0.4 mmol), and NaO. t Bu (1.15 g, 12 mmol) was placed in a reaction flask, nitrogen was purged, 50 mL of toluene was added, and the reaction was carried out at 100 °C for 16 h. After cooling to room temperature, the product was diluted with toluene, filtered through a silica gel filter, and the solvent was removed from the filtrate under vacuum to obtain the crude product. The crude product was passed through a column to obtain intermediate 7, with a yield of 51%.

[0242] (2) Synthesis of compound 5

[0243]

[0244] Intermediate 7 (2.43 g, 4.0 mmol), intermediate 2 (2.54 g, 4.0 mmol), tetratetraphenylphosphine palladium (231 mg, 0.2 mmol), and potassium carbonate (1.66 g, 12 mmol) were placed in a reaction flask, the atmosphere was purged with nitrogen, and 50 mL of toluene / ethanol / water (8 / 1 / 1) was added. The mixture was reacted at 110 °C for 16 h. After cooling to room temperature, dichloromethane was added, followed by water extraction. The organic layer was collected, evaporated to dryness, and purified by column chromatography to give compound 5 in 49% yield.

[0245] Example 6: Synthesis of Compound 6

[0246] (1) Synthesis of intermediate 8

[0247]

[0248] Intermediate q (16.26 g, 64 mmol), intermediate r (31.36 g, 64 mmol), tetratetraphenylphosphine palladium (3.70 g, 3.2 mmol), and potassium carbonate (26.54 g, 192 mmol) were placed in a reaction flask, the atmosphere was purged with nitrogen, and 500 mL of toluene / ethanol / water (8 / 1 / 1) was added. The mixture was reacted at 110 °C for 14 h and then cooled to room temperature. Dichloromethane was added, followed by water extraction. The organic layer was collected, evaporated to dryness, and purified by column chromatography to give intermediate 8 in 50% yield.

[0249] (2) Synthesis of intermediate 9

[0250]

[0251] Intermediate 8 (17.2 g, 32 mmol), intermediate c (9.75 g, 38.4 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (PdCl2(dppf)) (702 mg, 0.96 mmol), and potassium acetate (9.42 g, 96 mmol) were placed in a reaction flask. Nitrogen gas was purged, and 300 mL of dioxane was added. The reaction was carried out at 104 °C for 10 h, and then cooled to room temperature. Dichloromethane was added, followed by water extraction. The organic layer was collected, evaporated to dryness, and purified by column chromatography to give intermediate 9 in 54% yield.

[0252] (3) Synthesis of intermediate 10

[0253]

[0254] Intermediate 9 (9.35 g, 16 mmol), intermediate b (5.38 g, 16 mmol), tetratetraphenylphosphine palladium (924 mg, 0.8 mmol), and potassium carbonate (6.63 g, 48 mmol) were placed in a reaction flask, the atmosphere was purged with nitrogen, and 300 mL of toluene / ethanol / water (8 / 1 / 1) was added. The mixture was reacted at 110 °C for 14 h and then cooled to room temperature. Dichloromethane was added, followed by water extraction. The organic layer was collected, evaporated to dryness, and purified by column chromatography to give intermediate 10 in 49% yield.

[0255] (4) Synthesis of intermediate 11

[0256]

[0257] Intermediate 10 (5.71 g, 8 mmol), intermediate c (2.44 g, 9.6 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (PdCl2(dppf)) (176 mg, 0.24 mmol), and potassium acetate (2.36 g, 24 mmol) were placed in a reaction flask. Nitrogen gas was purged, and 200 mL of dioxane was added. The reaction was carried out at 104 °C for 10 h, and then cooled to room temperature. Dichloromethane was added, followed by water extraction. The organic layer was collected, evaporated to dryness, and purified by column chromatography to give intermediate 11 in 51% yield.

[0258] (5) Synthesis of compound 6

[0259]

[0260] Intermediate 3 (2.75 g, 4.0 mmol), intermediate 11 (3.04 g, 4.0 mmol), tetratetraphenylphosphine palladium (231 mg, 0.2 mmol), and potassium carbonate (1.66 g, 12 mmol) were placed in a reaction flask, the atmosphere was purged with nitrogen, and 100 mL of toluene / ethanol / water (8 / 1 / 1) was added. The mixture was reacted at 110 °C for 16 h. After cooling to room temperature, dichloromethane was added, followed by water extraction. The organic layer was collected, evaporated to dryness, and purified by column chromatography to give compound 6 in 49% yield.

[0261] Example 7: Synthesis of Compound 7

[0262] (1) Synthesis of compound 7

[0263]

[0264] Intermediate 5 (2.47 g, 4.0 mmol), intermediate 11 (3.04 g, 4.0 mmol), tetraphenylphosphine palladium (231 mg, 0.2 mmol), and potassium carbonate (1.66 g, 12 mmol) were placed in a reaction flask, the atmosphere was purged with nitrogen, and 100 mL of toluene / ethanol / water (8 / 1 / 1) was added. The mixture was reacted at 110 °C for 16 h. After cooling to room temperature, dichloromethane was added, followed by water extraction. The organic layer was collected, evaporated to dryness, and purified by column chromatography to give compound 7 in 46% yield.

[0265] Example 8: Synthesis of Compound 8

[0266] (1) Synthesis of compound 8

[0267]

[0268] Intermediate 6 (2.75 g, 4.0 mmol), intermediate 11 (3.04 g, 4.0 mmol), tetraphenylphosphine palladium (231 mg, 0.2 mmol), and potassium carbonate (1.66 g, 12 mmol) were placed in a reaction flask, the atmosphere was purged with nitrogen, and 100 mL of toluene / ethanol / water (8 / 1 / 1) was added. The mixture was reacted at 110 °C for 16 h. After cooling to room temperature, dichloromethane was added, followed by water extraction. The organic layer was collected, evaporated to dryness, and purified by column chromatography to give compound 8 in 47% yield.

[0269] Application Examples

[0270] Comparative Example 1

[0271] A 120 nm thick transparent electrode made of indium tin oxide was provided on a glass substrate measuring 25 × 75 × 1.1 mm. This transparent electrode served as the anode, and after ultraviolet ozone cleaning, the glass substrate was placed in a vacuum evaporation apparatus.

[0272] First, a 5 nm thick HATCN film is deposited as a hole injection layer. Next, a 25 nm thick TAPC film is deposited on top as a hole transport layer. Then, a 15 nm thick exciton blocking layer TCTA is deposited on the TAPC. Above the TCTA, a 20 nm thick light-emitting layer P1 is deposited. Then, a 40 nm thick TPBi film is deposited on this light-emitting layer as an electron transport layer. Finally, a 1 nm thick LiF film and a 100 nm thick aluminum film are deposited to act as cathodes. This yields an organic light-emitting device.

[0273] Device structure: ITO / HATCN (5nm) / TPAC (25nm) / TCTA (15nm) / P1 (20nm) / TPBi (40nm) / LiF (1nm) / Al (100nm).

[0274] The compounds used in the application examples are shown below:

[0275]

[0276] The resulting organic electroluminescent device was tested using the following method, with a turn-on voltage and a current density of 10 mA / cm². 2 The device performance (current efficiency, luminous efficiency), electroluminescence peak, and CIE1931 (x, y) chromaticity coordinates are shown below. Detailed electroluminescence performance data of the device are listed in Table 1.

[0277] • Brightness: Measured using a spectrophotometer (CS-2000, Konica Minolta Holdings, Inc.).

[0278] • Current efficiency (L / J): L / J is the ratio of luminance to current density. Current and voltage are measured using a SOURCEMEASURE UNIT 236 (Keithley Instruments Inc.), and luminance is measured using a spectrophotometer. The current density is calculated based on the current value and the emitting area, thus yielding the L / J ratio.

[0279] Luminous efficiency (lm / W) is obtained using the following formula:

[0280] • Electroluminescence peak: Measured by a spectrophotometer (CS-2000, Konica Minolta Holdings, Inc.).

[0281] • CIE1931 (x, y) chromaticity coordinates: measured by a spectrophotometer (CS-2000, Konica Minolta Holdings, Inc.).

[0282] Examples 1-8

[0283] The organic electroluminescent device was fabricated and measured in the same manner as in Comparative Example 1, except for the doping material used in the light-emitting layer. The device structure is as follows:

[0284] ITO / HATCN(5nm) / TPAC(25nm) / TCTA(15nm) / B-Host: B-Dopant(40:2,20nm) / TPBi(40nm) / LiF(1nm) / Al(100nm).

[0285] The structure of the B-Host compound used in the application examples is shown below, and the specific doping material B-Dopant used is shown in Table 1.

[0286]

[0287] Detailed electroluminescence performance data of the device are shown in Table 1.

[0288] Table 1

[0289]

[0290] As can be seen from Table 1, the device in the embodiment has the characteristics of low turn-on voltage, high blue light purity, and high luminous efficiency.

[0291] Therefore, the tetraphenylethylene derivative of the present invention can realize a display device with low power consumption and high blue light purity.

[0292] Industrial applications

[0293] The organic electroluminescent device of the present invention can be used as a planar light source, such as a flat panel display of a wall-mounted television, a backlight of a copier / printer, or a light source, display panel, or indicator light of a measuring instrument.

[0294] The foregoing has only described in detail a few embodiments and / or examples of the present invention. However, those skilled in the art can readily make modifications and changes to these exemplary embodiments and / or examples without substantially departing from the novel teachings and effects of the present invention. All such modifications are also included within the scope of the present invention.

Claims

1. A tetraphenyl ethylene derivative, characterized by, The structural general formula is as follows: In formula (1), R1~R4are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an alkyl group having a carbon number of 1~20, an alkenyl group having a carbon number of 2~20, an alkynyl group having a carbon number of 2~20, a cyclic alkyl group having a ring-forming carbon number of 3~10, an alkoxy group having a carbon number of 1~30; Ar1is selected from the following groups: Ar2and Ar3are each independently selected from an aryl group having 6 to 30 ring carbon atoms; m and n are each independently 0 or 1; In formula (2), In formula (2-1), R 11 ~R 12 each independently is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an alkyl group having a carbon number of 1 to 20, an alkenyl group having a carbon number of 2 to 20, an alkynyl group having a carbon number of 2 to 20, a cyclic alkyl group having a carbon number of 3 to 10 forming a ring, an alkoxy group having a carbon number of 1 to 30; Ar 11 and Ar 12 each independently is selected from aryl having 6 to 18 ring carbon atoms; In formula (2-2), R 21 ~R 22 each independently is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an alkyl group having a carbon number of 1 to 20, an alkenyl group having a carbon number of 2 to 20, an alkynyl group having a carbon number of 2 to 20, a cyclic alkyl group having a carbon number of 3 to 10 forming a ring, an alkoxy group having a carbon number of 1 to 30; Ar 21 and Ar 22 each independently is selected from aryl having 6 to 18 ring carbon atoms; In formula (2-3), R 31 ~R 32 each independently is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an alkyl group having a carbon number of 1 to 20, an alkenyl group having a carbon number of 2 to 20, an alkynyl group having a carbon number of 2 to 20, a cyclic alkyl group having a carbon number of 3 to 10 forming a ring, an alkoxy group having a carbon number of 1 to 30; Ar 31 and Ar 32 each independently is selected from aryl having 6 to 18 ring carbon atoms; In formula (2-4), R 41 selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an alkyl group having a carbon number of 1 to 20, an alkenyl group having a carbon number of 2 to 20, an alkynyl group having a carbon number of 2 to 20, a cyclic alkyl group having a carbon number of 3 to 10 forming a ring, an alkoxy group having a carbon number of 1 to 30; Ar 41 and Ar 42 each independently is selected from aryl having 6 to 18 ring carbon atoms; In formula (2-5), R 51 ~R 52 a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an alkyl group having a carbon number of 1 to 20, an alkenyl group having a carbon number of 2 to 20, an alkynyl group having a carbon number of 2 to 20, a cyclic alkyl group having a carbon number of 3 to 10 forming a ring, an alkoxy group having a carbon number of 1 to 30; Ar 51 and Ar 52 each independently is selected from aryl having 6 to 18 ring carbon atoms; X1is selected from an O atom and an S atom; In formula (1), formula (2), The halogen atom is selected from fluorine, chlorine, and bromine; The alkyl group having a carbon number of 1~20 is selected from a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an s-butyl group, an iso-butyl group, a t-butyl group, an n-pentyl group, a 2-pentyl group, a 3-pentyl group, a 2,2-dimethylpropyl group, a 1,1,3,3-tetramethylpentyl group, an n-hexyl group, a 1-methylhexyl group, a 1,1,3,3,5,5-hexamethylhexyl group, an n-heptyl group, an iso-heptyl group, a 1,1,3,3-tetramethylbutyl group, a 1-methylheptyl group, a 3-methylheptyl group, an n-octyl group, a 2-ethylhexyl group, an n-nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, and an octadecyl group; The alkenyl group having a carbon number of 2~20 is selected from an ethenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butadienyl group, a 1-methylethenyl group, a 1-methylpropenyl group, a 1,1-dimethylpropenyl group, a 2-methylpropenyl group, and a 1,2-dimethylpropenyl group; The alkynyl group having a carbon number of 2~20 is selected from an ethynyl group, a propynyl group, and a 3-pentynyl group; The cyclic alkyl group having a ring-forming carbon number of 3~10 is selected from a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, and a cyclooctyl group; The alkoxy group having a carbon number of 1~30 is selected from a methoxy group, an ethoxy group, a propoxy group, an iso-propoxy group, a butoxy group, an iso-hexyloxy group, a 2-butoxy group, a t-butoxy group, a pentyloxy group, and a hexyloxy group; The aryl group having 6 to 30 ring carbon atoms is selected from a phenyl group, a biphenyl group, a terphenyl group, a benzophenyl group, a naphthyl group, an anthryl group, a phenalenyl group, a phenanthryl group, a fluorenyl group, a pyrenyl group, and a chrysenyl group.

2. The tetraphenyl ethylene derivative according to claim 1, characterized in that, In formula (1), n is 1, m is 0, and Ar2is selected from a phenyl group, a biphenyl group, and a naphthyl group.

3. The tetraphenyl ethylene derivative according to claim 1, characterized in that, In formula (2-1), R 11 12 is a hydrogen atom, Ar 11 and Ar 12 is a phenyl group, a naphthyl group, and a biphenyl group;​ In formula (2-2), R 21 22 is a hydrogen atom, Ar 21 and Ar 22 is a phenyl group, a naphthyl group, and a biphenyl group;​ In formula (2-3), R 31 32 is a hydrogen atom, Ar 31 32 is a phenyl group, a naphthyl group, and a biphenyl group.​​ In formula (2-4), R 41 is a hydrogen atom, Ar 41 and Ar 42 is a phenyl group, a naphthyl group, and a biphenyl group; In formula (2-5), R 51 52 is a hydrogen atom, Ar 51 and Ar 52 is a phenyl group, a naphthyl group and a biphenyl group, and X1is selected from an O atom.​ 4. An organic electroluminescent device, characterized by comprising The organic electroluminescence device comprises an anode, a cathode, and an organic layer between the anode and the cathode, wherein at least one of the organic layers is a light-emitting layer, and the light-emitting layer is a tetraphenyl ethylene derivative or a mixture containing a tetraphenyl ethylene derivative.

5. The organic electroluminescent device according to claim 4, characterized in that The organic electroluminescence device is any one of a fluorescent or phosphorescent single-color light-emitting device, and a fluorescent-phosphorescent hybrid white light-emitting device.

6. The organic electroluminescent device according to any one of claims 4 to 5, wherein ​ 7. The organic electroluminescent device according to any one of claims 4 to 5, wherein The organic electroluminescent device is any one of a simple light emitting device having a single light emitting unit and a series light emitting device having two or more light emitting units.

8. The organic electroluminescent device according to any one of claims 4 to 5, wherein The organic electroluminescent device is applied to a flat display device, a special-shaped display device, a curved display device, a flexible display device, and an illumination device.

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