Nucleation inhibition material and organic electroluminescent device thereof

Abstract

The invention provides a nucleation inhibition material and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The organic light-emitting device comprises a first electrode, an organic matter layer and a second electrode, the organic matter layer is located between the first electrode and the second electrode, the organic light-emitting device further comprises a nucleation inhibition layer, the nucleation inhibition layer is located on the side face of the second electrode, and the nucleation inhibition layer contains anthracene compounds shown in the formula 1. The nucleation inhibition material shows relatively poor surface adsorption energy to the metal electrode material, and deposition of the metal electrode material can be effectively inhibited, so that relatively high light transmittance is obtained, selective deposition of a metal electrode material coating is realized, and application of cathode patterning is facilitated. Therefore, the material is a nucleation inhibition material with good performance.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescent materials, in particular to a nucleation inhibiting material and an organic electroluminescent device thereof. BACKGROUND

[0002] An organic light emitting diode (OLED) is also known as an organic electroluminescent device. Compared with traditional display technologies, the OLED has the advantages of self-illumination, wide viewing angle, ultra-thin, ultra-light, low power consumption, high contrast, fast response speed, flexible display, etc., and shows great application prospects in the fields of OLED display and lighting.

[0003] The light emitting principle of the organic electroluminescent device is that under the action of an applied electric field, the electrons injected from the cathode and the holes injected from the anode recombine in the light emitting layer to form excitons, and the released energy is transferred to the organic light emitting material to make it transition from the ground state to the excited state. When the excited molecule jumps from the less stable excited state to the ground state by radiation, the light emitting phenomenon occurs.

[0004] The OLED usually adopts a sandwich structure, i.e. the organic functional layer is sandwiched between the anode and the cathode on both sides of the device. The OLED structure gradually develops from the original single-layer device structure to the multi-layer device structure, from the original deposition of the organic layer between the two electrodes to a more complex structure. Although the structure of the device becomes more complex, the functions of each layer are more and more clear.

[0005] According to the different light emitting directions, the OLED device can be divided into two types of bottom emission device and top emission device. The light of the bottom emission device emits from the transparent anode, while the light of the top emission device emits from the transparent or semi-transparent cathode. Compared with the bottom emission device, the light emitting direction of the top emission device is on the cathode side, which is not affected by the thin film transistor (TFT), has a high aperture ratio, so that the device can achieve a higher pixel density, and the color vividness is also higher. For the top emission device, the cathode is required to be a transparent or semi-transparent metal film layer, which not only requires the electrode to have good conductivity, but also requires the cathode to have good light transmission. The quality of the light transmission is not only related to the properties of the cathode material itself, but also closely related to the thickness of the film layer. In order to achieve good light transmission effect, the cathode usually has a thin film layer.

[0006] In addition to organic functional layers such as hole injection layers, hole transport layers, light-emitting layers, hole blocking layers, electron transport layers, and electron injection layers, OLEDs can also incorporate nucleation suppression layers on the sides of the transmission electrodes. The function of the nucleation suppression layer is to inhibit metal deposition on its thin surface, ensuring that the conductive coating is primarily deposited in other areas of the device. This design helps control the distribution of the conductive coating, preventing its formation in unwanted areas and thus optimizing the overall device performance. Based on this property, the nucleation suppression layer plays a crucial role in cathode patterning technology, enabling cathode patterning and providing important technical support for device manufacturing.

[0007] However, current devices are not ideal for inhibiting metal deposition on their surfaces due to the nucleation inhibition layers at the cathode, which hinders the application of cathode patterning. Therefore, it is crucial to study materials and devices that can improve the nucleation inhibition effect. Summary of the Invention

[0008] To address the problems existing in the prior art, the present invention provides a nucleation inhibition material and its organic electroluminescent device.

[0009] This invention provides an organic electroluminescent device, comprising a first electrode, an organic layer, and a second electrode, wherein the organic layer is located between the first and second electrodes, and further comprising a nucleation inhibition layer located on the side of the second electrode, the nucleation inhibition layer containing an anthracene compound as shown in Formula 1.

[0010]

[0011] Wherein, the R 11 ~R 20 The two groups in the middle are used to bond with L1 and L2, and the groups that bond with L1 or L2 are single bonds;

[0012] The R 11 ~R 20 The term is not used to bond with L1 or L2. It is an independent group selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, and substituted or unsubstituted C2-C30 heteroaryl.

[0013] The L1 to L2 are independently selected from one of the following: single bond, substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C6 to C30 fused polycyclic aromatic hydrocarbon, and substituted or unsubstituted C2 to C30 heteroarylene.

[0014] The Ar1 is selected from one of the following groups.

[0015]

[0016] The R1 to R2 are independently selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C6 to C30 fused polycyclic, substituted or unsubstituted C2 to C30 heteroaryl, or two adjacent R1 and R2 are bonded to each other to form a substituted or unsubstituted ring;

[0017] The n1 is selected from integers from 0 to 5, the n2 is selected from integers from 0 to 3, and the n3 is selected from integers from 0 to 4;

[0018] The Ar2 is selected from the following groups.

[0019] The R 01 ~R 03 The independent group is selected from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, and substituted or unsubstituted C2-C30 heteroaryl.

[0020] The present invention also provides a nucleation inhibition material, represented by an anthracene compound as shown in Formula 1.

[0021] The present invention also provides a nucleation inhibition layer containing anthracene compounds represented by Formula 1.

[0022] The present invention also provides the application of the anthracene compounds shown in Formula 1 as nucleation inhibition materials.

[0023] The present invention also provides the use of the anthracene compounds shown in Formula 1 in the fabrication of nucleation inhibition layers.

[0024] Beneficial effects: The nucleation inhibition material of this invention exhibits relatively poor surface adsorption energy on metal electrode materials, effectively inhibiting the deposition of metal electrode materials and thus achieving high light transmittance. This enables selective deposition of the metal electrode material coating, which is beneficial for cathode patterning applications. Therefore, it is a high-performance nucleation inhibition material. Detailed Implementation

[0025] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art will fall within the scope of protection claimed in this application.

[0026] In the compounds described herein, any atom not specified as a particular isotope includes any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances. In this invention, "H," "hydrogen," and "hydrogen atom" refer to isotopes with different numbers of neutrons, including protium, deuterium, and tritium.

[0027] In this specification, the halogens mentioned include fluorine, chlorine, bromine, and iodine.

[0028] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring.

[0029] For example, Can represent Can represent Can represent And so on.

[0030] In this specification, "the formation of a ring by bonding two adjacent groups" refers to the formation of a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by bonding adjacent groups together and optionally aromatizing them. The hydrocarbon ring can be an aliphatic or aromatic hydrocarbon ring. The heterocycle can be an aliphatic or aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated or unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated or unsaturated aliphatic heterocycle. The hydrocarbon ring and heterocycle can be monocyclic or polycyclic groups. Furthermore, the ring formed by the bonding of adjacent groups can be connected to another ring to form a spirostructure. See the example below:

[0031]

[0032] In this specification, the rings formed by the linkage can be three-membered, four-membered, five-membered, six-membered, seven-membered, eight-membered, fused rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but are not limited to these.

[0033] In this specification, "integers selected from 0 to M" means that the value is selected from any one of the integers from 0 to M, including 0, 1, 2...M-2, M-1, M. For example, "n1 is selected from integers from 0 to 5" means that n1 is selected from 0, 1, 2, 3, 4, or 5. And so on.

[0034] In this specification, "unsubstituted ZZ group" in "substituted or unsubstituted ZZ group" means that the hydrogen atom of the "ZZ group" is not substituted by a substituent. For example, "unsubstituted aryl group" in "substituted or unsubstituted C6-C60 aryl group" means that the hydrogen atom of the "aryl group" is not substituted by a substituent. And so on.

[0035] In this specification, "CXX~CYY" in "substituted or unsubstituted CXX~CYY ZZ group" indicates the number of carbon atoms in the unsubstituted "ZZ group". When the "ZZ group" has a substituent, the number of carbon atoms in the substituent is not included. For example, "C6~C60" in "substituted or unsubstituted C6~C60 aryl group" indicates the number of carbon atoms in the unsubstituted "aryl group". When the "aryl group" has a substituent, the number of carbon atoms in the substituent is not included. And so on.

[0036] In this specification, the term "substituted or unsubstituted" means that at least one hydrogen atom on a group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different. The position of the hydrogen atoms replaced by the substituents can be arbitrary. The substituents represented by "substituted or unsubstituted" include the following groups: deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted C3-C15 heterocyclic groups, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic groups, substituted or unsubstituted C2-C30 heteroaryl, etc. Preferred groups include: deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornel, camphene, isocamphene, fentanyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene. Substituents include benzo[a]yl, fluoranyl, peryl, benzo[a]phenanthryl, benzo[a]cyclopropane, benzo[a]cyclobutane, benzo[a]cyclobutenyl, dihydroindyl, indyl, tetrahydronaphthyl, dihydronaphthyl, benzo[a]cycloheptyl, fluorenyl, benzo[a]fluorenyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, etc. Furthermore, each of the above substituents can be substituted or unsubstituted, and two adjacent substituents can bond to form a ring.

[0037] In this specification, alkyl refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. Alkyl groups include straight-chain alkyl groups and branched-chain alkyl groups. Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, etc. Chain alkyl groups containing three or more carbon atoms include their isomers; for example, propyl includes n-propyl and isopropyl, butyl includes n-butyl, sec-butyl, isobutyl, and tert-butyl, and so on. The number of carbon atoms in the alkyl group is 1 to 30, preferably 1 to 20, more preferably 1 to 15, and even more preferably 1 to 10.

[0038] In this specification, cycloalkyl refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule. Cycloalkyl includes monocyclic, polycyclic, and bridged cycloalkyl groups. Examples of cycloalkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornane, camphene, etc. The number of carbon atoms in the cycloalkyl group is 3 to 30, preferably 3 to 20, more preferably 3 to 15, and even more preferably 3 to 10.

[0039] In this specification, "silyl group" refers to -Si(R t )3 groups, wherein each R t The same or different groups are selected from the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic aromatic hydrocarbons, substituted or unsubstituted C2-C60 heteroaryl, etc. Preferably, each R tThe same or different groups are selected from the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted adamantyl, substituted or unsubstituted norborneol. Alkyl groups, substituted or unsubstituted phenyl groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted dihydroindyl groups, substituted or unsubstituted indyl groups, substituted or unsubstituted tetrahydronaphthyl groups, substituted or unsubstituted dihydronaphthyl groups, substituted or unsubstituted benzocyclobutyl groups, substituted or unsubstituted benzocyclobutenyl groups, substituted or unsubstituted benzocyclopropyl groups, substituted or unsubstituted pyridyl groups, substituted or unsubstituted pyrimidinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyridazinyl groups, etc., but not limited to these. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, etc., but not limited to these.

[0040] In this specification, aryl refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. The aryl group includes monocyclic aryl, polycyclic aryl, fused-ring aryl, or combinations thereof. Examples of the aryl group may include phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, naphthyl, phenanthryl, anthraceneyl, triphenylene, pyrene, perylene, etc. Aryl, fluoranyl, fluorenyl, benzo[a]fluorenyl, spiroanthracene fluorenyl, etc., but not limited to these. The number of carbon atoms in the aryl group is 6 to 60, preferably 6 to 30, more preferably 6 to 25, more preferably 6 to 18, and even more preferably 6 to 12.

[0041] In this specification, the fused polycyclic group refers to a monovalent group comprising at least two rings, wherein at least one aromatic ring and at least one non-aromatic ring are fused together. Examples of the fused polycyclic group may include, but are not limited to, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, benzocycloheptenyl, etc. The fused polycyclic group has 6 to 60 carbon atoms, preferably 6 to 30, more preferably 6 to 25, more preferably 6 to 18, and even more preferably 6 to 12.

[0042] In this specification, the term "heteroaryl" refers to a group obtained by replacing one or more carbon atoms of an aryl group with heteroatoms. These heteroatoms include, but are not limited to, atoms such as oxygen, sulfur, nitrogen, phosphorus, boron, and silicon. The heteroaryl comprises monocyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of heteroaryl include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxazolyl, benzothiazolyl, benzimidazolyl, benzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, indolyl, carbazoleyl, benzocarbazoleyl, spirofluoreneoxanthraceneyl, spirofluorenethionanthraceneyl, spirofluoreneazanthraceneyl, etc., but are not limited to these. The number of carbon atoms in the heteroaryl can be 2 to 60, preferably 2 to 30, more preferably 2 to 25, and even more preferably 3 to 18.

[0043] In this specification, the term "arylene" refers to the collective term for divalent groups remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic compound molecule. The arylene includes monocyclic arylene, polycyclic arylene, fused-ring arylene, or combinations thereof. Examples of arylene may include phenylene, biphenylene, terphenylene, tetraphenylene, pentaphenylene, naphthylene, phenanthrene, anthracene, triphenylene, pyrene, fluoranthracene, perylene, etc. The aryl group may contain, but is not limited to, fluoreneyl, benzo[a]fluoreneyl, spiroanthracene fluoreneyl, etc. The number of carbon atoms in the aryl group is 6 to 60, preferably 6 to 30, more preferably 6 to 25, more preferably 6 to 18, and even more preferably 6 to 10.

[0044] In this specification, the term "hybridized polycyclic group" refers to a divalent group comprising at least two rings, wherein at least one aromatic ring and at least one non-aromatic ring are fused together. Examples of such fused polycyclic groups may include, but are not limited to, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, and benzocycloheptenyl. The number of carbon atoms in the fused polycyclic group is 6 to 60, preferably 6 to 30, more preferably 6 to 25, more preferably 6 to 18, and even more preferably 6 to 12.

[0045] In this specification, the term "heteroaryl" refers to a divalent group in which at least one carbon atom is replaced by a heteroatom. The heteroatom is selected from, but is not limited to, oxygen, sulfur, nitrogen, phosphorus, boron, silicon, etc. The heteroaryl includes monocyclic heteroaryl, polycyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of the heteroaryl include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolineyl, isoquinolineyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, indolyl, carbazoyl, benzocarbazoyl, etc., but are not limited to these. The number of carbon atoms in the heteroaryl is 2 to 60, preferably 2 to 30, more preferably 2 to 25, and even more preferably 2 to 18.

[0046] This invention provides an organic electroluminescent device, comprising a first electrode, an organic layer, and a second electrode, wherein the organic layer is located between the first and second electrodes, and further comprising a nucleation inhibition layer located on the side of the second electrode, the nucleation inhibition layer containing an anthracene compound as shown in Formula 1.

[0047]

[0048] Wherein, the R 11 ~R 20 The two groups in the middle are used to bond with L1 and L2, and the groups that bond with L1 or L2 are single bonds;

[0049] The R 11 ~R 20 The term is not used to bond with L1 or L2. It is an independent group selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, and substituted or unsubstituted C2-C30 heteroaryl.

[0050] The L1 to L2 are independently selected from one of the following: single bond, substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C6 to C30 fused polycyclic aromatic hydrocarbon, and substituted or unsubstituted C2 to C30 heteroarylene.

[0051] The Ar1 is selected from one of the following groups.

[0052]

[0053] The R1 to R2 are independently selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C6 to C30 fused polycyclic, substituted or unsubstituted C2 to C30 heteroaryl, or two adjacent R1 and R2 are bonded to each other to form a substituted or unsubstituted ring;

[0054] The n1 is selected from integers from 0 to 5, the n2 is selected from integers from 0 to 3, and the n3 is selected from integers from 0 to 4;

[0055] The Ar2 is selected from the following groups.

[0056] The R 01 ~R 03 The independent group is selected from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, and substituted or unsubstituted C2-C30 heteroaryl.

[0057] Preferably, the anthracene compound represented by Formula 1 is selected from one of Formulas 1-1 to 1-23.

[0058]

[0059]

[0060] Preferably, the Ar1 is selected from one of the following groups:

[0061]

[0062]

[0063] R1 to R2 are independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C6 to C30 fused polycyclic, and substituted or unsubstituted C2 to C30 heteroaryl.

[0064] The R nThe same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl;

[0065] The n1 is selected from integers from 0 to 5, the n2 is selected from integers from 0 to 3, the n3 is selected from integers from 0 to 4, the n4 is selected from integers from 0 to 7, the n5 is selected from integers from 0 to 9, the n6 is selected from integers from 0 to 6, the n7 is selected from integers from 0 to 2, the n8 is selected from integers from 0 to 8, and the n9 is selected from integers from 0 to 10.

[0066] Preferably, R1 to R2 are independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted One of the following: substituted anthraquinone, substituted or unsubstituted pyrene, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, and substituted or unsubstituted quinoxalinyl;

[0067] The R nThe same or different from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracene The following is a list of compounds: alkyl, substituted or unsubstituted pyrene, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, and substituted or unsubstituted quinoxalinyl.

[0068] Preferably, the R in 01 ~R 03 Independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene. One of the following: alkyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted triphenylene, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, and substituted or unsubstituted isoquinolinyl.

[0069] Preferably, the Selected from one of the following groups,

[0070]

[0071]

[0072] The R3s, whether identical or different, are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R3s bonded together to form a substituted or unsubstituted ring.

[0073] The m1 is selected from integers from 0 to 5.

[0074] Preferably, the same or different R3s are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted One of the following: substituted anthraquinone, substituted or unsubstituted pyrene, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, and substituted or unsubstituted quinoxalinyl.

[0075] Preferably, L1 to L2 are independently selected from one or a combination of single bonds, groups shown below, and other similar groups.

[0076]

[0077] The X, whether the same or different, is selected from C(R4) or N. The R4, whether the same or different, is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R4s bonded together to form a substituted or unsubstituted ring.

[0078] Preferably, L1 to L2 are independently selected from one or a combination of single bonds, groups shown below, and other similar groups.

[0079]

[0080] The same or different R4 is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, and substituted or unsubstituted C2-C30 heteroaryl.

[0081] The R g The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl;

[0082] The g1 is selected from integers from 0 to 4, the g2 is selected from integers from 0 to 2, the g3 is selected from integers from 0 to 3, the g4 is selected from integers from 0 to 6, the g5 is selected from integers from 0 to 8, the g6 is selected from integers from 0 to 10, and the g7 is selected from integers from 0 to 5.

[0083] Preferably, the R4 is the same or different from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tritert-butylsilyl, substituted or unsubstituted dimethylethylsilyl, substituted or unsubstituted dimethylisopropylsilyl, substituted or unsubstituted dimethyltert-butylsilyl, substituted or unsubstituted tricyclopentylsilyl, substituted or unsubstituted Substituted tricyclohexylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted tripyridylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexyl, substituted Or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted anthraquinone, substituted or unsubstituted pyrene, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted One of the following: indene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, and substituted or unsubstituted quinoxalinyl;

[0084] The R gThe same or different from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracene The following is a list of compounds: alkyl, substituted or unsubstituted pyrene, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, and substituted or unsubstituted quinoxalinyl.

[0085] Preferably, the R 11 ~R 20 The following are not used for bonding with L1 or L2: independent molecules selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted benzocyclopropane. Substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted fluoranthyl, substituted or unsubstituted perylyl, substituted or unsubstituted One of the following: benzo[a]phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, or substituted or unsubstituted quinoxalinyl.

[0086] Preferably, the R 19 R 20 When not used in conjunction with L1 or L2, the individual components are selected independently from substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracene, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted fluoranthyl, substituted or unsubstituted perylene, substituted or unsubstituted One of the following: benzo[a]phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, or substituted or unsubstituted quinoxalinyl.

[0087] Preferably, the anthracene compound of Formula 1 is selected from at least one of the following structures:

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129] The above lists some specific chemical structures of anthracene compounds of Formula 1 of the present invention, but the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in Formula 1 with substituents as defined above should be included.

[0130] Preferably, the nucleation inhibition layer is located between the organic layer and the second electrode or on the side of the second electrode away from the organic layer, and the nucleation inhibition layer contains anthracene compounds represented by Formula 1 of the present invention.

[0131] Preferably, the nucleation inhibition layer is located between the organic layer and the second electrode, and the nucleation inhibition layer contains anthracene compounds represented by Formula 1 of the present invention.

[0132] Preferably, the nucleation inhibition layer is located on the side of the second electrode away from the organic layer, and the nucleation inhibition layer contains anthracene compounds represented by Formula 1 of the present invention.

[0133] Preferably, the first electrode is an anode, the second electrode is a cathode, the nucleation inhibition layer is located between the organic layer and the cathode or on the side of the cathode away from the organic layer, and the nucleation inhibition layer contains anthracene compounds represented by Formula 1 of the present invention.

[0134] Preferably, the first electrode is a cathode, the second electrode is an anode, the nucleation inhibition layer is located between the organic layer and the anode or on the side of the anode away from the organic layer, and the nucleation inhibition layer contains anthracene compounds represented by Formula 1 of the present invention.

[0135] The nucleation inhibition layer of the present invention has a surface that exhibits a relatively low affinity for the deposition of conductive materials, thereby inhibiting the deposition of conductive materials on its surface and achieving selective deposition of conductive materials.

[0136] Preferably, the cathode has a first portion and a second portion on the side away from the organic layer, with a nucleation inhibition layer disposed on the first portion and a conductive coating disposed on the second portion. Preferably, the anode has a first portion and a second portion on the side away from the organic layer, with a nucleation inhibition layer disposed on the first portion and a conductive coating disposed on the second portion.

[0137] The first portion corresponds to the emitting region of the organic electroluminescent device, and the second portion corresponds to the non-emitting region of the organic electroluminescent device.

[0138] The ratio of the first part to the second part is 5:95 to 95:5; preferably, the ratio of the first part to the second part is 10:90 to 90:10; preferably, the ratio of the first part to the second part is 20:80 to 80:20; most preferably, the ratio of the first part to the second part is 30:70 to 70:30.

[0139] The present invention also provides a nucleation inhibition material, represented by an anthracene compound as shown in Formula 1.

[0140] The present invention also provides a nucleation inhibition layer containing anthracene compounds represented by Formula 1.

[0141] The present invention also provides the application of the anthracene compounds shown in Formula 1 as nucleation inhibition materials.

[0142] The present invention also provides the use of the anthracene compounds shown in Formula 1 in the fabrication of nucleation inhibition layers.

[0143] Preferably, the nucleation inhibition material or nucleation inhibition layer refers to the nucleation inhibition material or nucleation inhibition layer in an organic electroluminescent device.

[0144] The functional layer of the organic electroluminescent device of the present invention may further include at least one of the following functional layers: hole injection layer, hole transport layer, light-emitting auxiliary layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, charge generation layer, capping layer, etc., but is not limited thereto. Any functional layer having hole injection and / or transport properties, electron injection and / or transport properties, light-emitting properties, charge generation properties, or light extraction properties should be included. Each functional layer may be composed of a single thin film or multiple thin films, and each thin film may be composed of only one material or multiple materials.

[0145] The organic electroluminescent device described in this invention can be a top-emitting device, a bottom-emitting device, or a double-sided emitting device.

[0146] This invention does not impose any particular limitation on the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below:

[0147] In this specification, the nucleation inhibition layer inhibits metal deposition on its thin-film surface, thereby ensuring that the conductive coating is mainly deposited in other areas of the device. This design helps control the distribution of the conductive coating, avoiding the formation of conductive coating in unwanted areas, and thus optimizing the overall performance of the device. The nucleation inhibition layer needs to exhibit relatively poor surface adsorption energy to the metal electrode material, enabling it to inhibit metal deposition on its thin-film surface and thus have high transmittance. The nucleation inhibition material includes, but is not limited to, the following materials: anthracene compounds, pyrene compounds, triarylamine compounds, heterocyclic compounds, fluorine-containing compounds, rare earth metal oxides, etc., but is not limited to these. Preferably, anthracene compounds of Formula 1 of this invention are used. The film thickness of the nucleation inhibition layer is 1 nm to 200 nm, preferably 1 nm to 150 nm, preferably 1 nm to 100 nm, preferably 1 nm to 80 nm, preferably 1 nm to 50 nm, and more preferably 1 nm to 30 nm.

[0148] In this specification, the conductive coating refers to the anode, cathode, and auxiliary electrode in an organic electroluminescent device.

[0149] In this specification, the auxiliary electrode is located outside the cathode and serves to reduce the film resistance and associated current-resistance (IR) drop of the transmission electrode, allowing current to be carried more effectively to various regions of the device. The auxiliary electrode includes, but is not limited to, the materials described below, metals or their alloys, multilayer materials, etc. Specific examples may include magnesium (Mg), silver (Ag), ytterbium (Yb), zinc (Zn), cadmium (Cd), magnesium:silver (Mg:Ag), etc., but are not limited to these. The film thickness of the auxiliary electrode is 1 nm to 1 μm, preferably 1 nm to 800 nm, preferably 1 nm to 500 nm, preferably 1 nm to 300 nm, preferably 1 nm to 150 nm, preferably 1 nm to 100 nm, preferably 1 nm to 80 nm, and more preferably 5 nm to 50 nm.

[0150] In this specification, the anode needs to be a material with a high work function in order to inject holes into the organic layer. The anode includes, but is not limited to, the materials described below: metals or their alloys, metal oxides, multilayer materials, etc. Specific examples may include silver (Ag), platinum (Pt), aluminum (Al), nickel (Ni), copper (Cu), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), indium tin oxide (ITO), etc., but are not limited to these. The film thickness of the anode is 1 nm to 1 μm, preferably 10 nm to 500 nm, more preferably 50 nm to 200 nm.

[0151] In this specification, the cathode needs to have a low work function in order to inject electrons into the organic layer. The cathode includes, but is not limited to, the materials described below, metals or their alloys, multilayer materials, etc. Specific examples may include magnesium (Mg), silver (Ag), magnesium:silver (Mg:Ag), magnesium:ytterbium (Mg:Yb), aluminum (Al), gold (Au), etc., but are not limited to these. The film thickness of the cathode is 1 nm to 500 nm, preferably 1 nm to 200 nm, and more preferably 5 nm to 50 nm.

[0152] In this specification, the hole injection layer serves to reduce the interfacial barrier between the anode and hole transport, and to enhance the hole injection capability. The hole injection material includes, but is not limited to, the following: metal oxides, phthalocyanine compounds, aromatic amine compounds, low-molecular-weight organic compounds such as conjugated organic materials containing polycyanides, and high-molecular-weight materials. Specific examples include silver oxide (AgO), copper phthalocyanine (CuPc), 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 4,4',4”-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), etc., but is not limited to these. The hole injection layer thickness is 0.1 nm to 1 μm, preferably 1 nm to 800 nm, and more preferably 1 nm to 500 nm.

[0153] In this specification, the hole transport layer is used to improve the hole transport efficiency in the device and to block electrons within the light-emitting layer. The hole transport layer includes, but is not limited to, the materials described below, such as aromatic amine derivatives, carbazole derivatives, and polymers. Specific examples may include, but are not limited to, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 2,2,7,7-tetra(diphenylamino)-9,9-spirodifluorene (Spiro-TAD), 1,3,5-tris(9-carbazolyl)benzene (TCB), 4,4',4”-tris(carbazol-9-yl)triphenylamine (TCTA), poly(4-vinyltriphenylamine) (PVTPA), etc. The hole transport layer film thickness is 1 nm to 1 μm, preferably 1 nm to 800 nm, and more preferably 5 nm to 500 nm.

[0154] In this specification, the light-emitting layer may contain one or more materials, and may contain a host material and a dopant material. The doping ratio of the host material and the dopant material may vary depending on the materials used, typically the doping ratio of the dopant material is 0.01% to 20%, preferably 0.1% to 15%, more preferably 1% to 10%. The thickness of the light-emitting layer is 1 nm to 500 nm, preferably 1 nm to 200 nm, and more preferably 5 nm to 100 nm.

[0155] The host material of the light-emitting layer can be one material or two or more materials. Host materials include, but are not limited to, the following: heterocyclic compounds, aromatic amine compounds, fused aromatic ring derivatives, metal complexes, silicon-containing compounds, etc. Specific examples may include 4,4-bis(9-carbazole)biphenyl (CBP), 3,3'-bis(N-carbazole)-1,1'-biphenyl (mCBP), 2,7-bis(carbazole-9-yl)-9,9-spirodifluorene (Spiro-2CBP), 3,3'-bis( Dibenzothiophene-4-yl)-1,1'-biphenyl (m-BPDBT), 9,10-di-2-naphthane (AND), 9,10-di(naphth-1-yl)anthracene, 1,4-bis(9-phenyl-9H-fluorene-9-yl)benzene (pDPFB), tris(8-hydroxyquinoline)aluminum (Alq3), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9Hcarbazole (CzSi), etc., but not limited to these.

[0156] Doped materials include, but are not limited to, the following: metal complexes, aromatic amine derivatives, styrene amine compounds, fused aromatic compounds, heterocyclic compounds, etc. Specific examples of doped materials may include: bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium (FIrPic), bis(2-phenylpyridinium)iridium acetylacetonate (Ir(ppy)2(acac)), tris(2-phenylpyridinium)iridium (Ir(ppy)3), bis(1-phenyl-isoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)), tris(1-phenyl-isoquinoline)iridium (Ir(piq)3), bis[9,9-dimethyl-2-(2-quinolinyl)-9H-fluoren-3-yl](2,4-pentanedione)iridium (Ir(flq)2(acac)), N... 1 N 1 N 6 N 6 Tetraphenylpyrene-1,6-diamine, 2,5,8,11-tetra-tert-butylperylene (TBPe), 1,4-bis(4-(9H-carbazole-9-yl)styryl)benzene (BCzSB), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), coumarin 545T, 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM), etc., but not limited to these.

[0157] In this specification, the hole blocking layer serves to block holes within the light-emitting layer, thereby increasing the binding rate of electrons and holes. The hole blocking layer material may include imidazole derivatives, phenanthroline derivatives, triazole derivatives, rare earth complexes, oxazole derivatives, triazine derivatives, etc., such as 4,7-diphenyl-1,10-phenanthroline (Bphen), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), etc., but is not limited to these. The hole blocking layer film thickness is 0.01 nm to 500 nm, preferably 0.1 nm to 200 nm, and more preferably 0.1 nm to 100 nm.

[0158] In this specification, the electron transport layer serves to improve the electron transport efficiency in the device and block holes within the light-emitting layer. The electron transport layer includes, but is not limited to, the materials described below, such as metal complexes and heteroaromatic compounds. Specific examples may include, but are not limited to, aluminum 8-hydroxyquinoline (Alq3), 2,5-di-(4-naphthyl)-1,3,4-oxadiazole (BND), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), and 1,3,5-tris[(3-pyridyl)-phenyl]benzene (TmPyPB), but are not limited to these. The electron transport layer has a film thickness of 1 nm to 1 μm, preferably 1 nm to 800 nm, and more preferably 5 nm to 500 nm.

[0159] In this specification, the electron injection layer serves to reduce the interfacial barrier between the cathode and electron transport, thereby enhancing the electron injection capability. The electron injection layer material includes, but is not limited to, the materials described below, such as metals, metal compounds, and metal oxides. Specific examples may include lithium (Li), lithium fluoride (LiF), lithium 8-hydroxyquinoline (Liq), lithium oxide (Li₂O), cesium carbonate (Cs₂CO₃), etc., but are not limited to these. The electron injection layer film thickness is 0.01 nm to 200 nm, preferably 0.1 nm to 100 nm, and more preferably 0.1 nm to 50 nm.

[0160] There are no particular limitations on the preparation method of each thin film in the organic electroluminescent device of the present invention. Vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, etc. can be used, but are not limited to these methods.

[0161] The organic electroluminescent device of this invention is mainly used in the fields of information display technology and lighting. In terms of information display, it is widely used in various information displays, such as mobile phones, tablet computers, flat-screen TVs, smartwatches, VR, in-vehicle systems, digital cameras, wearable devices, etc.

[0162] Synthesis Examples

[0163] Raw materials and reagents: This invention does not impose any particular limitations on the raw materials or reagents used in the following synthesis examples. They can be commercially available products or prepared using methods well-known to those skilled in the art. All raw materials and reagents used in this invention are of reagent purity.

[0164] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0165] There are no particular limitations on the preparation method of the anthracene compounds of Formula 1 of the present invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-carbon coupling reaction, carbon-nitrogen coupling reaction, etc. The anthracene compounds of Formula 1 of the present invention can be prepared, for example, by the synthetic route shown below.

[0166] Synthesis Route 1:

[0167] Synthesis Route 2:

[0168]

[0169] The Xn is a halogen, for example, the same or different Xn are selected from Cl, Br, I.

[0170] Synthesis Example 1:

[0171]

[0172] Under nitrogen protection, a-6 (45.77 g, 120.00 mmol), pinacol diborate (30.47 g, 120.00 mmol), potassium carbonate (24.88 g, 180.00 mmol), tetrakis(triphenylphosphine)palladium (1.39 g, 1.20 mmol), and 800 mL of dimethylformamide were added to a reaction flask. The mixture was stirred under reflux for 6.0 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and the mixture was recrystallized from toluene / ethanol at a ratio of 6:1 to obtain A-6 (40.62 g, 79%) with an HPLC purity of ≥99.75%.

[0173] Under nitrogen protection, A-6 (34.27 g, 80.00 mmol), b-6 (23.33 g, 80.00 mmol), potassium carbonate (16.59 g, 120.00 mmol), tetraphenylphosphine palladium (924 mg, 0.80 mmol), and 500 mL of toluene / ethanol / water (3:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5.0 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, washed with ethanol, and then recrystallized from toluene to obtain B-6 (31.61 g, 77%) with an HPLC purity of ≥99.79%.

[0174] Under nitrogen protection, B-6 (25.66 g, 50.00 mmol), pinacol diborate (12.70 g, 50.00 mmol), potassium acetate (7.36 g, 75.00 mmol), Pd(dppf)Cl2 (366 mg, 0.50 mmol), and 500 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred under reflux for 5.5 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and the mixture was recrystallized from toluene to give C-6 (24.19 g, 80%) with an HPLC purity of ≥99.85%.

[0175] Under nitrogen protection, C-6 (18.14 g, 30.00 mmol), d-6 (6.99 g, 30.00 mmol), potassium carbonate (6.22 g, 45.00 mmol), Pd2(dba)3 (275 mg, 0.30 mmol), tri-tert-butylphosphine (121 mg, 0.60 mmol), and 200 mL of tetrahydrofuran were added to a reaction flask. The mixture was stirred under reflux for 6.5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with a small amount of toluene, and then recrystallized from the filter cake with toluene to give compound 6 (14.76 g, 78%), with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 630.2751 (theoretical value: 630.2743). Theoretical elemental content (%) C 47 H 38 Si: C, 89.48; H, 6.07. Measured elemental content (%): C, 89.45; H, 6.09.

[0176] Synthesis Example 2:

[0177]

[0178] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-41, yielding compound 41 (9.54 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 402.1809 (theoretical value: 402.1804). Theoretical elemental content (%) C 29 H 26 Si: C, 86.51; H, 6.51. Measured elemental content (%): C, 86.49; H, 6.54.

[0179] Synthesis Example 3:

[0180]

[0181] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of a-41 to obtain compound 53 (11.11 g), with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 474.2190 (theoretical value: 474.2199). Theoretical elemental content (%) C 32 H 34 Si2: C, 80.95; H, 7.22. Measured elemental content (%): C, 80.92; H, 7.26.

[0182] Synthesis Example 4:

[0183]

[0184] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, b-6 with an equimolar amount of b-85, and d-6 with an equimolar amount of d-41, yielding compound 85 (10.77 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 478.2125 (theoretical value: 478.2117). Theoretical elemental content (%) C 35 H 30 Si: C, 87.82; H, 6.32. Measured elemental content (%): C, 87.84; H, 6.28.

[0185] Synthesis Example 5:

[0186]

[0187] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41 to obtain compound 89 (11.35 g), with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 478.2111 (theoretical value: 478.2117). Theoretical elemental content (%) C 35 H 30 Si: C, 87.82; H, 6.32. Measured elemental content (%): C, 87.80; H, 6.35.

[0188] Synthesis Example 6:

[0189]

[0190] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-95, yielding compound 95 (10.88 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 483.2438 (theoretical value: 483.2431). Theoretical elemental content (%) C 35 H 25D5Si: C, 86.90; H, 7.29. Measured elemental content (%): C, 86.93; H, 7.25.

[0191] Synthesis Example 7:

[0192]

[0193] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-101, yielding compound 101 (12.73 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 550.2504 (theoretical value: 550.2512). Theoretical elemental content (%) C 38 H 38 Si2: C, 82.85; H, 6.95. Measured elemental content (%): C, 82.81; H, 6.97.

[0194] Synthesis Example 8:

[0195]

[0196] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-102, yielding compound 102 (12.56 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 550.2505 (theoretical value: 550.2512). Theoretical elemental content (%) C 38 H 38 Si2: C, 82.85; H, 6.95. Measured elemental content (%): C, 82.82; H, 6.99.

[0197] Synthesis Example 9:

[0198]

[0199] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-119, yielding compound 119 (12.51 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 534.2751 (theoretical value: 534.2743). Theoretical elemental content (%) C 39 H 38 Si: C, 87.59; H, 7.16. Measured elemental content (%): C, 87.56; H, 7.18.

[0200] Synthesis Example 10:

[0201]

[0202] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-127, yielding compound 127 (11.18 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 496.2014 (theoretical value: 496.2023). Theoretical elemental content (%) C 35 H 29 FSi: C, 84.64; H, 5.89. Measured elemental content (%): C, 84.67; H, 5.87.

[0203] Synthesis Example 11:

[0204]

[0205] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and b-6 was replaced with an equimolar amount of b-138, yielding compound 138 (13.47 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 590.3361 (theoretical value: 590.3369). Theoretical elemental content (%) C 43 H 46 Si: C, 87.40; H, 7.85. Measured elemental content (%): C, 87.44; H, 7.83.

[0206] Synthesis Example 12:

[0207]

[0208] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of d-101, and d-6 was replaced with an equimolar amount of d-41, yielding compound 145 (11.35 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 478.2122 (theoretical value: 478.2117). Theoretical elemental content (%) C 35 H 30 Si: C, 87.82; H, 6.32. Measured elemental content (%): C, 87.79; H, 6.33.

[0209] Synthesis Example 13:

[0210]

[0211] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of d-102, and d-6 was replaced with an equimolar amount of d-161 to obtain compound 161 (12.98 g), with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 554.2437 (theoretical value: 554.2430). Theoretical elemental content (%) C41 H 34 Si: C, 88.76; H, 6.18. Measured elemental content (%): C, 88.79; H, 6.16.

[0212] Synthesis Example 14:

[0213]

[0214] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of d-101, and d-6 was replaced with an equimolar amount of d-197 to obtain compound 197 (11.33 g), with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 503.2077 (theoretical value: 503.2069). Theoretical elemental content (%) C 36 H 29 NSi: C, 85.84; H, 5.80; N, 2.78. Measured elemental content (%): C, 85.82; H, 5.83; N, 2.76.

[0215] Synthesis Example 15:

[0216]

[0217] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-209, yielding compound 209 (12.82 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 554.2422 (theoretical value: 554.2430). Theoretical elemental content (%) C 41 H 34 Si: C, 88.76; H, 6.18. Measured elemental content (%): C, 88.79; H, 6.16.

[0218] Synthesis Example 16:

[0219]

[0220] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-226, yielding compound 226 (12.65 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 554.2439 (theoretical value: 554.2430). Theoretical elemental content (%) C 41 H 34 Si: C, 88.76; H, 6.18. Measured elemental content (%): C, 88.78; H, 6.14.

[0221] Synthesis Example 17:

[0222]

[0223] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-241, and d-6 was replaced with an equimolar amount of d-41, yielding compound 241 (13.92 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 626.2834 (theoretical value: 626.2825). Theoretical elemental content (%) C 44 H 42 Si2: C, 84.29; H, 6.75. Measured elemental content (%): C, 84.25; H, 6.77.

[0224] Synthesis Example 18:

[0225]

[0226] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-261 to obtain compound 261 (10.19 g), with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 452.1953 (theoretical value: 452.1960). Theoretical elemental content (%) C 33 H 28 Si: C, 87.56; H, 6.23. Measured elemental content (%): C, 87.54; H, 6.26.

[0227] Synthesis Example 19:

[0228]

[0229] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-263, yielding compound 263 (10.05 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 452.1954 (theoretical value: 452.1960). Theoretical elemental content (%) C 33 H 28 Si: C, 87.56; H, 6.23. Measured elemental content (%): C, 87.53; H, 6.25.

[0230] Synthesis Example 20:

[0231]

[0232] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-269, yielding compound 269 (11.90 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 528.2279 (theoretical value: 528.2273). Theoretical elemental content (%) C 39 H 32 Si: C, 88.59; H, 6.10. Measured elemental content (%): C, 88.56; H, 6.12.

[0233] Synthesis Example 21:

[0234]

[0235] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of d-101, and d-6 was replaced with an equimolar amount of d-310, yielding compound 310 (14.15 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 604.2579 (theoretical value: 604.2586). Theoretical elemental content (%) C 45 H 36 Si: C, 89.36; H, 6.00. Measured elemental content (%): C, 89.34; H, 6.04.

[0236] Synthesis Example 22:

[0237]

[0238] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-342, yielding compound 342 (11.46 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 502.2124 (theoretical value: 502.2117). Theoretical elemental content (%) C 37 H 30 Si: C, 88.40; H, 6.02. Measured elemental content (%): C, 88.44; H, 6.00.

[0239] Synthesis Example 23:

[0240]

[0241] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-343, yielding compound 343 (11.61 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 502.2123 (theoretical value: 502.2117). Theoretical elemental content (%) C 37 H30 Si: C, 88.40; H, 6.02. Measured elemental content (%): C, 88.43; H, 6.00.

[0242] Synthesis Example 24:

[0243]

[0244] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-355, yielding compound 355 (12.85 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 578.2439 (theoretical value: 578.2430). Theoretical elemental content (%) C 43 H 34 Si: C, 89.23; H, 5.92. Measured elemental content (%): C, 89.21; H, 5.95.

[0245] Synthesis Example 25:

[0246]

[0247] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-409, yielding compound 409 (12.44 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 552.2264 (theoretical value: 552.2273). Theoretical elemental content (%) C 41 H 32 Si: C, 89.08; H, 5.84. Measured elemental content (%): C, 89.05; H, 5.88.

[0248] Synthesis Example 26:

[0249]

[0250] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-461, yielding compound 461 (13.20 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 602.2439 (theoretical value: 602.2430). Theoretical elemental content (%) C 45 H 34 Si: C, 89.66; H, 5.68. Measured elemental content (%): C, 89.69; H, 5.64.

[0251] Synthesis Example 27:

[0252]

[0253] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-508, yielding compound 508 (15.48 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 678.2750 (theoretical value: 678.2743). Theoretical elemental content (%) C 51 H 38 Si: C, 90.22; H, 5.64. Measured elemental content (%): C, 90.25; H, 5.60.

[0254] Synthesis Example 28:

[0255]

[0256] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-537, yielding compound 537 (12.11 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 552.2265 (theoretical value: 552.2273). Theoretical elemental content (%) C 41 H 32 Si: C, 89.08; H, 5.84. Measured elemental content (%): C, 89.05; H, 5.88.

[0257] Synthesis Example 29:

[0258]

[0259] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-569, yielding compound 569 (13.32 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 576.2281 (theoretical value: 576.2273). Theoretical elemental content (%) C 43 H 32 Si: C, 89.54; H, 5.59. Measured elemental content (%): C, 89.57; H, 5.56.

[0260] Synthesis Example 30:

[0261]

[0262] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-581, yielding compound 581 (13.54 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 578.2439 (theoretical value: 578.2430). Theoretical elemental content (%) C 43 H 34 Si: C, 89.23; H, 5.92. Measured elemental content (%): C, 89.21; H, 5.95.

[0263] Synthesis Example 31:

[0264]

[0265] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-606, yielding compound 606 (15.43 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 650.2816 (theoretical value: 650.2825). Theoretical elemental content (%) C 46 H 42 Si2: C, 84.87; H, 6.50. Measured elemental content (%): C, 84.83; H, 6.53.

[0266] Synthesis Example 32:

[0267]

[0268] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-637, yielding compound 637 (11.83 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 518.2436 (theoretical value: 518.2430). Theoretical elemental content (%) C 38 H 34 Si: C, 87.98; H, 6.61. Measured elemental content (%): C, 87.95; H, 6.63.

[0269] Synthesis Example 33:

[0270]

[0271] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-679, yielding compound 679 (13.38 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 594.2751 (theoretical value: 594.2743). Theoretical elemental content (%) C 44 H38 Si: C, 88.84; H, 6.44. Measured elemental content (%): C, 88.87; H, 6.40.

[0272] Synthesis Example 34:

[0273]

[0274] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-686, yielding compound 686 (13.14 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 568.2594 (theoretical value: 568.2586). Theoretical elemental content (%) C 42 H 36 Si: C, 88.68; H, 6.38. Measured elemental content (%): C, 88.65; H, 6.40.

[0275] Synthesis Example 35:

[0276]

[0277] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-744, yielding compound 744 (12.28 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 524.2347 (theoretical value: 524.2356). Theoretical elemental content (%) C 36 H 36 Si2: C, 82.38; H, 6.91. Measured elemental content (%): C, 82.35; H, 6.93.

[0278] Synthesis Example 36:

[0279]

[0280] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-748, yielding compound 748 (12.44 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 524.2348 (theoretical value: 524.2356). Theoretical elemental content (%) C 36 H 36 Si2: C, 82.38; H, 6.91. Measured elemental content (%): C, 82.36; H, 6.94.

[0281] Synthesis Example 37:

[0282]

[0283] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-774, yielding compound 774 (12.76 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 574.2521 (theoretical value: 574.2512). Theoretical elemental content (%) C 40 H 38 Si2: C, 83.57; H, 6.66. Measured elemental content (%): C, 83.54; H, 6.68.

[0284] Synthesis Example 38:

[0285]

[0286] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-780, and d-6 was replaced with an equimolar amount of d-41, yielding compound 780 (12.01 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 526.2125 (theoretical value: 526.2117). Theoretical elemental content (%) C 39 H 30 Si: C, 88.93; H, 5.74. Measured elemental content (%): C, 88.97; H, 5.71.

[0287] Synthesis Example 39:

[0288]

[0289] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-785, and d-6 was replaced with an equimolar amount of d-41, yielding compound 785 (13.78 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 588.2267 (theoretical value: 588.2273). Theoretical elemental content (%) C 44 H 32 Si: C, 89.75; H, 5.48. Measured elemental content (%): C, 89.78; H, 5.46.

[0290] Synthesis Example 40:

[0291]

[0292] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-785, and d-6 was replaced with an equimolar amount of a-785, yielding compound 795 (18.81 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 846.3146 (theoretical value: 846.3138). Theoretical elemental content (%) C 62 H 46 Si2: C, 87.90; H, 5.47. Measured elemental content (%): C, 87.94; H, 5.44.

[0293] Synthesis Example 41:

[0294]

[0295] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-785, and d-6 was replaced with an equimolar amount of d-261, yielding compound 801 (14.57 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 638.2424 (theoretical value: 638.2430). Theoretical elemental content (%) C 48 H 34 Si: C, 90.24; H, 5.36. Measured elemental content (%): C, 90.27; H, 5.34.

[0296] Synthesis Example 42:

[0297]

[0298] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-785, and d-6 was replaced with an equimolar amount of d-637, yielding compound 837 (15.44 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 704.2891 (theoretical value: 704.2899). Theoretical elemental content (%) C 53 H 40 Si: C, 90.30; H, 5.72. Measured elemental content (%): C, 90.34; H, 5.70.

[0299] Synthesis Example 43:

[0300]

[0301] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-869, yielding compound 869 (11.21 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 518.2441 (theoretical value: 518.2430). Theoretical elemental content (%) C 38 H34 Si: C, 87.98; H, 6.61. Measured elemental content (%): C, 87.95; H, 6.65.

[0302] Synthesis Example 44:

[0303]

[0304] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-957, yielding compound 957 (10.07 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 479.2059 (theoretical value: 479.2069). Theoretical elemental content (%) C 34 H 29 Si: C, 85.13; H, 6.09; N, 2.92. Measured elemental content (%): C, 85.11; H, 6.06; N, 2.95.

[0305] Synthesis Example 45:

[0306]

[0307] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-41, and d-6 was replaced with an equimolar amount of d-984, yielding compound 984 (10.99 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 530.2185 (theoretical value: 530.2178). Theoretical elemental content (%) C 37 H 30 N₂Si: C, 83.73; H, 5.70; N, 5.28. Measured elemental content (%): C, 83.75; H, 5.73; N, 5.24.

[0308] Synthesis Example 46:

[0309]

[0310] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of d-6, b-6 with an equimolar amount of b-1009, and d-6 with an equimolar amount of a-41, yielding compound 1009 (12.48 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 554.2436 (theoretical value: 554.2430). Theoretical elemental content (%) C 41 H 34 Si: C, 88.76; H, 6.18. Measured elemental content (%): C, 88.79; H, 6.14.

[0311] Synthesis Example 47:

[0312]

[0313] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of d-101, b-6 with an equimolar amount of b-1062, and d-6 with an equimolar amount of a-41, yielding compound 1062 (15.61 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 702.3131 (theoretical value: 702.3138). Theoretical elemental content (%) C 50 H 46 Si2: C, 85.42; H, 6.59. Measured elemental content (%): C, 85.45; H, 6.54.

[0314] Synthesis Example 48:

[0315]

[0316] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of d-1126, b-6 with an equimolar amount of b-1009, and d-6 with an equimolar amount of a-41, yielding compound 1126 (13.25 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 604.2580 (theoretical value: 604.2586). Theoretical elemental content (%) C 45 H 36 Si: C, 89.36; H, 6.00. Measured elemental content (%): C, 89.32; H, 6.03.

[0317] Synthesis Example 49:

[0318]

[0319] Following the same preparation method as in Synthesis Example 1, a-6 was replaced with an equimolar amount of a-1409, b-6 with an equimolar amount of b-1409, and d-6 with an equimolar amount of a-41, yielding compound 1409 (15.10 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 670.3051 (theoretical value: 670.3056). Theoretical elemental content (%) C 50 H 42 Si: C, 89.50; H, 6.31. Measured elemental content (%): C, 89.54; H, 6.29.

[0320] Transmittance measurement

[0321] The measuring instrument was the UV-2202PC ultraviolet-visible spectrophotometer from Shanghai Xipu Instrument Co., Ltd.

[0322] Example 1:

[0323] Compound 6 of the present invention was vacuum-deposited onto a glass substrate using a vacuum evaporation apparatus to a thickness of 20 nm; then Mg was deposited at a deposition rate of [missing information]. A reference layer thickness of approximately 50 nm was obtained over a period of approximately 250 s. The transmittance of the glass plate at 550 nm was then measured.

[0324] Examples 2-49:

[0325] In Example 1, compound 6 was replaced with compounds 41, 53, 85, 89, 95, 101, 102, 119, 127, 138, 145, 161, 197, 209, 226, 241, 261, 263, 269, 310, 342, 343, 355, 409, 461, and 5, respectively. Compounds 537, 569, 581, 606, 637, 679, 686, 744, 748, 774, 780, 785, 795, 801, 837, 869, 957, 984, 1009, 1062, 1126, and 1409 were used to obtain corresponding glass plates, and the transmittance of the above glass plates at 550 nm was measured respectively.

[0326] Comparative Examples 1-3:

[0327] The compound 6 in Example 1 was replaced with R-1, R-2, and R-3 respectively to obtain corresponding glass plates, and the transmittance of the glass plates at 550 nm was measured respectively.

[0328]

[0329] The transmittance at 550 nm measured in Examples 1 to 49 and Comparative Examples 1 to 3 of the present invention is shown in Table 1.

[0330] Table 1

[0331]

[0332]

[0333]

[0334] As can be seen from Table 1, compared with the comparative example, the sample containing the anthracene compound film of Formula 1 has a higher transmittance at 550 nm, indicating that there is a relatively small amount of magnesium coating on the surface of the nucleation inhibition layer of the present invention. Therefore, the nucleation inhibition layer material in the device of the present invention can effectively inhibit the deposition of magnesium, realize the selective deposition of magnesium coating, and is beneficial to the application of cathode patterning.

[0335] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. An organic electroluminescent device, comprising a first electrode, an organic layer, and a second electrode, wherein the organic layer is located between the first electrode and the second electrode, characterized in that, It also includes a nucleation inhibition layer located on the side of the second electrode, the nucleation inhibition layer containing an anthracene compound as shown in Formula 1. Wherein, the R 11 ~R 20 The two groups in the middle are used to bond with L1 and L2, and the groups that bond with L1 or L2 are single bonds; The R 11 ~R 20 The term is not used to bond with L1 or L2. It is an independent group selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, and substituted or unsubstituted C2-C30 heteroaryl. The L1 to L2 are independently selected from one of the following: single bond, substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C6 to C30 fused polycyclic aromatic hydrocarbon, and substituted or unsubstituted C2 to C30 heteroarylene. The Ar1 is selected from one of the following groups. The R1 to R2 are independently selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C6 to C30 fused polycyclic, substituted or unsubstituted C2 to C30 heteroaryl, or two adjacent R1 and R2 are bonded to each other to form a substituted or unsubstituted ring; The n1 is selected from integers from 0 to 5, the n2 is selected from integers from 0 to 3, and the n3 is selected from integers from 0 to 4; The Ar2 is selected from the following groups. The R 01 ~R 03 The independent group is selected from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, and substituted or unsubstituted C2-C30 heteroaryl.

2. The organic electroluminescent device according to claim 1, characterized in that, The Ar1 is selected from one of the following groups. R1 to R2 are independently selected from one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C6 to C30 fused polycyclic, and substituted or unsubstituted C2 to C30 heteroaryl. The R n The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl; The n1 is selected from integers from 0 to 5, the n2 is selected from integers from 0 to 3, the n3 is selected from integers from 0 to 4, the n4 is selected from integers from 0 to 7, the n5 is selected from integers from 0 to 9, the n6 is selected from integers from 0 to 6, the n7 is selected from integers from 0 to 2, the n8 is selected from integers from 0 to 8, and the n9 is selected from integers from 0 to 10.

3. The organic electroluminescent device according to claim 1, characterized in that, The R in 01 ~R 03 Independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene. One of the following: alkyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted triphenylene, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, and substituted or unsubstituted isoquinolinyl.

4. The organic electroluminescent device according to claim 1, characterized in that, The Selected from one of the following groups, The R3s, whether identical or different, are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R3s bonded together to form a substituted or unsubstituted ring. The m1 is selected from integers from 0 to 5.

5. The organic electroluminescent device according to claim 1, characterized in that, The L1 to L2 are independently selected from one or a combination of single-bonded groups, as shown below. The X, whether the same or different, is selected from C(R4) or N. The R4, whether the same or different, is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R4s bonded together to form a substituted or unsubstituted ring.

6. The organic electroluminescent device according to claim 1, characterized in that, The L1 to L2 are independently selected from one or a combination of single-bonded groups, as shown below. The same or different R4 is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, and substituted or unsubstituted C2-C30 heteroaryl. The R g The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl; The g1 is selected from integers from 0 to 4, the g2 is selected from integers from 0 to 2, the g3 is selected from integers from 0 to 3, the g4 is selected from integers from 0 to 6, the g5 is selected from integers from 0 to 8, the g6 is selected from integers from 0 to 10, and the g7 is selected from integers from 0 to 5.

7. The organic electroluminescent device according to claim 1, characterized in that, The R 11 ~R 20 The following are not used for bonding with L1 or L2: independent molecules selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted benzocyclopropane. Substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted fluoranthyl, substituted or unsubstituted perylyl, substituted or unsubstituted One of the following: benzo[a]phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, or substituted or unsubstituted quinoxalinyl.

8. The organic electroluminescent device according to claim 1, characterized in that, The anthracene compounds of Formula 1 are selected from at least one of the structures shown below.

9. The organic electroluminescent device according to claim 1, characterized in that, The nucleation inhibition layer is located between the organic layer and the second electrode, or on the side of the second electrode away from the organic layer.

10. A nucleation inhibition material, characterized in that, Represented by an anthracene compound of Formula 1 as described in any one of claims 1-9.

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