Organic light-emitting device

Abstract

The invention provides an organic electroluminescent device, and relates to the technical field of organic electroluminescence. According to the organic light-emitting device, the compound in the formula 1 serves as a nucleation inhibition layer material, has weak metal adsorption capacity and good film-forming property, can inhibit metal electrode materials from being deposited on the surface of the nucleation inhibition layer material, effectively improves the light transmittance of the organic light-emitting device, and further improves the performance of the organic light-emitting device. The nucleation inhibition layer material disclosed by the invention has a very good application prospect.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescence, and in particular to an organic electroluminescence device. Background Art

[0002] Organic light-emitting diodes (OLEDs), also known as organic electroluminescent devices, have the characteristics of being light, thin, energy-saving, self-luminous, having a wide viewing angle, fast response speed, and flexible display. Its working principle is that under the action of an external electric field, electrons and holes are injected from the cathode and anode respectively, transmitted through the organic layer to the light-emitting layer, and recombined in the light-emitting layer to form excitons, and the excitons transition to emit light.

[0003] OLEDs are generally classified as bottom-emitting or top-emitting devices, depending on the relative direction of light emitted by the device. Bottom-emitting devices emit light from the anode toward the base substrate, while top-emitting devices emit light toward the cathode. In top-emitting devices, the cathode is often made of a relatively thin, transparent or semi-transparent conductive material to reduce light attenuation. However, the reduction in transparent electrode thickness is accompanied by an increase in its sheet resistance, resulting in a higher current-resistance (IR) drop during use, which is detrimental to the performance and efficiency of the OLED.

[0004] Cathode patterning technology is currently used to solve the IR voltage drop loss problem in the cathode layer of OLEDs. Cathode patterning technology is mostly implemented using a mask, and selective deposition is performed through technologies such as physical vapor deposition (PVD) and chemical vapor deposition (CVD). This involves nucleation inhibitory materials and metal electrode materials. The role of nucleation inhibitory materials is to effectively inhibit the deposition of metal electrode materials, thereby achieving cathode patterning. However, the current single type of nucleation inhibitory materials and unsatisfactory effects are still important issues that need to be addressed. Therefore, it is necessary to develop new and efficient nucleation inhibitory materials. Summary of the Invention

[0005] In view of the problems existing in the prior art, the present invention provides an organic electroluminescent device.

[0006] The present invention provides an organic electroluminescent device, comprising a first electrode, an organic layer, a second electrode, and a nucleation inhibition layer, wherein the organic layer is located between the first electrode and the second electrode, the nucleation inhibition layer is located outside the second electrode or between the organic layer and the second electrode, and the nucleation inhibition layer comprises a compound represented by Formula 1.

[0007]

[0008] Wherein, the X is selected from O or S;

[0009] The z are the same or different and are selected from CR1 or N, and the z bonded to L1 and L2 are selected from C atoms;

[0010] The R1s are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or two adjacent R1s are bonded to form a substituted or unsubstituted ring;

[0011] The Ar1 is selected from one of the following groups:

[0012]

[0013] The v's are the same or different and are selected from CR3 or N, and at least one v is selected from N;

[0014] The R3 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R3 are bonded to form a substituted or unsubstituted ring;

[0015] The Y is the same or different and is selected from one of O, S, and NR4;

[0016] Said a is the same or different and is selected from CR5 or N;

[0017] The R2 and R4 are the same or different and are selected from one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring;

[0018] The R5 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or two adjacent R5 are bonded to form a substituted or unsubstituted ring;

[0019] Ar2 is selected from a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C20 alicyclic group and a C6-C30 aromatic ring sub-condensed ring group;

[0020] The R a 、R b 、R c the same or different ones selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0021] The L1 and L2 are the same or different and are selected from one or a combination of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, and a substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused sub-ring group.

[0022] The present invention also provides use of the compound represented by Formula 1 as a nucleation inhibition layer material in an organic electroluminescent device.

[0023] The present invention also provides the use of the compound represented by formula 1 in preparing a nucleation inhibition layer in an organic electroluminescent device.

[0024] Beneficial effects: The compound of formula 1 in the organic electroluminescent device of the present invention, as a nucleation inhibition layer material, has weak metal adsorption ability and good film-forming properties, can inhibit the deposition of metal electrode materials on its surface, effectively improve the transmittance of the organic electroluminescent device, and thus improve the performance of the organic electroluminescent device. DETAILED DESCRIPTION

[0025] The present invention is further illustrated below with reference to specific examples. It should be understood that these examples are only used to illustrate the present invention and are not used to limit the scope of the present invention. After reading the present invention, modifications of various equivalent forms of the present invention made by those skilled in the art all fall within the scope of protection claimed in this application.

[0026] In the compounds of the present invention, any atom not designated as a particular isotope encompasses any stable isotope of that atom and includes the atom at both its natural isotopic abundance and unnatural abundance.

[0027] The halogens described in the present invention include fluorine, chlorine, bromine and iodine.

[0028] In the present invention, the term "unsubstituted ZZ group" in the context of a "substituted or unsubstituted ZZ group" means that the hydrogen atoms of the ZZ group are not replaced by a substituent. For example, the term "unsubstituted aryl group" in the context of a "substituted or unsubstituted C6-C60 aryl group" means that the hydrogen atoms of the aryl group are not replaced by a substituent. The same applies analogously.

[0029] In the present invention, "CXX-CYY" in a "substituted or unsubstituted ZZ group of CXX-CYY" represents the number of carbon atoms in the unsubstituted "ZZ group." If the "ZZ group" has a substituent, the number of carbon atoms in the substituent is not included. For example, "C6-C60" in a "substituted or unsubstituted C6-C60 aryl group" represents the number of carbon atoms in the unsubstituted "aryl group." If the "aryl group" has a substituent, the number of carbon atoms in the substituent is not included. "C3-C25" in a "substituted or unsubstituted fused ring group of a C3-C25 alicyclic ring and a C6-C30 aromatic ring" represents the number of carbon atoms in the unsubstituted "alicyclic ring." If the "alicyclic ring" has a substituent, the number of carbon atoms in the substituent is not included; "C6-C30" represents the number of carbon atoms in the unsubstituted "aromatic ring." If the "aromatic ring" has a substituent, the number of carbon atoms in the substituent is not included. And so on.

[0030] In the present invention, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically any of the corresponding optional sites of the rings. For example, Can represent Can represent And so on.

[0031] In the present invention, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the aromatic ring. For example, Can represent Can represent Can represent And so on.

[0032] In the present invention, "two adjacent groups are bonded to form a ring" means that the adjacent groups are bonded to each other and optionally aromatized to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle can include an aliphatic heterocycle or an aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated aliphatic heterocycle or an unsaturated aliphatic heterocycle. The hydrocarbon ring and the heterocycle can be monocyclic or polycyclic groups. In addition, the ring formed by the bonding of adjacent groups can be connected to another ring to form a spiro structure. Specific examples are shown below:

[0033]

[0034]

[0035] In the present invention, the ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a condensed ring, a spiro ring, etc., for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but is not limited thereto.

[0036] The term "substituted" as used herein refers to the replacement of at least one hydrogen atom in a group with a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the substituents may be the same or different. The position of the hydrogen atoms replaced by the substituents may be arbitrary. The substituent represented by the "substituted" in the above-mentioned "substituted or unsubstituted" includes the following groups, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1~C15 alkoxy, substituted or unsubstituted C6~C20 aryloxy, substituted or unsubstituted C2~C15 heterocyclic group, substituted or unsubstituted C1~C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3~C15 cycloalkyl, substituted or unsubstituted C6~C20 aryl, substituted or unsubstituted C2~C20 heteroaryl, substituted or unsubstituted C3~C15 alicyclic and C6~C20 aromatic ring fused ring group, substituted or unsubstituted C3~C15 alicyclic and C2~C20 heteroaromatic ring fused ring group, etc. Preferred are the following groups: deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, bornyl, isobornyl, fenchyl, silyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, phenanthrenyl, triphenylene, anthracenyl, pyrenyl, benzothiophene, dihydroisobenzofuranyl, dihydrobenzofuranyl, dihydrobenzothiophene, dihydroisobenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, etc. In addition, each of the above substituents can be substituted or unsubstituted. Two adjacent substituents can be bonded to form a ring.

[0037] The alkyl group described in the present invention refers to a hydrocarbon group formed by removing a hydrogen atom from an alkane molecule. The alkyl group can be a straight-chain alkyl group or a branched-chain alkyl group. When the number of carbon atoms in the chain alkyl group described in the present invention is three or more, its isomers are included. For example, the propyl group includes n-propyl and isopropyl; the butyl group includes n-butyl, isobutyl, sec-butyl, tert-butyl, and so on. Examples of the alkyl group include, but are not limited to, the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited thereto. The number of carbon atoms in the alkyl group is C1 to C30, preferably C1 to C25, preferably C1 to C20, preferably C1 to C15, and more preferably C1 to C10.

[0038] The silyl group of the present invention refers to -Si(R k )3 groups, wherein each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic fused ring group. Preferably, each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The number of carbon atoms in the alkyl group is preferably C1-C20, preferably C1-C15, more preferably C1-C10, and most preferably C1-C8. The number of carbon atoms in the cycloalkyl group is preferably C3-C20, preferably C3-C15, more preferably C3-C10, and most preferably C3-C7. Preferably, each R kThe same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, 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 heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyl-tert-butylsilyl, tricyclopentanylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, and the like, but are not limited thereto.

[0039] The cycloalkyl group described herein refers to a hydrocarbon group formed by removing a hydrogen atom from a cycloalkane molecule. These cycloalkyl groups include monocyclic cycloalkyl groups, polycyclic cycloalkyl groups, and bridged cycloalkyl groups. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, bornyl, fenchyl, and isobornyl groups, but are not limited thereto. The cycloalkyl group has a carbon number of C3-C30, preferably C3-C25, preferably C3-C20, preferably C3-C15, and more preferably C3-C10.

[0040] The aryl group described in the present invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic compound molecule. The aryl group includes a monocyclic aryl group, a polycyclic aryl group, a condensed ring aryl group or a combination thereof. Examples of the aryl group include, but are not limited to, the following groups: phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, anthracenyl, triphenylene, fluorenyl, benzofluorenyl, spirobifluorenyl, spiroanthrafluorenyl, pyrenyl, The number of carbon atoms in the aryl group is C6 to C60, preferably C6 to C30, preferably C6 to C25, and more preferably C6 to C20.

[0041] The heteroaryl group of the present invention refers to a monovalent group in which at least one carbon atom in the aryl group is replaced by a heteroatom. The heteroatom is selected from, but is not limited to, O, S, N, Si, B, P, etc. Examples of heteroaryl groups include, but are not limited to, benzofuranyl, naphthofuranyl, phenanthrofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothiophenyl, naphthiophenyl, phenanthrothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, indolyl, naphthoindolyl, carbazolyl, benzocarbazolyl, spirofluorenylxanthenyl, spirofluorenylthioanthenyl, spirofluorenylazaanthenyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, phenoxazinyl, phenothiazinyl, dihydroacridinyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, etc., but are not limited to these. The number of carbon atoms in the heteroaryl group is C2 to C60, preferably C2 to C30, preferably C2 to C25, and more preferably C3 to C20.

[0042] The fused cyclic group of an alicyclic ring and an aromatic ring described in the present invention refers to a general term for a monovalent group remaining after an alicyclic ring and an aromatic ring are fused together and one hydrogen atom is removed. Examples of the fused cyclic group of an alicyclic ring and an aromatic ring include, but are not limited to, the following groups: benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, benzocycloheptenyl, etc., but are not limited thereto. The number of carbon atoms in the alicyclic ring is C3 to C30, preferably C3 to C25, preferably C3 to C20, preferably C3 to C15, more preferably C3 to C10, and more preferably C3 to C8. The number of carbon atoms in the aromatic ring is C6 to C60, preferably C6 to C30, preferably C6 to C25, preferably C6 to C18, more preferably C6 to C12, and more preferably C6 to C10.

[0043] The arylene group described in the present invention refers to the general term for a divalent group remaining after removing two hydrogen atoms from the aromatic carbon nucleus of an aromatic compound molecule. The arylene group includes a monocyclic arylene group, a polycyclic arylene group, a condensed ring arylene group, or a combination thereof. Examples of the arylene group include, but are not limited to, the following groups: phenylene, biphenylene, terphenylene, naphthylene, phenanthrenylene, fluorenylene, benzofluorenylene, dibenzofluorenylene, naphthylenefluorenylene, spirobifluorenylene, etc., but are not limited thereto. The number of carbon atoms in the arylene group is C6 to C30, preferably C6 to C25, preferably C6 to C20, and more preferably C6 to C18.

[0044] The heteroarylene group described in the present invention refers to a divalent group in which at least one carbon atom in the arylene group is replaced by a heteroatom. The heteroatom is selected from, but not limited to, O, S, N, Si, B, P, etc. The heteroarylene group includes a monocyclic heteroarylene group, a polycyclic heteroarylene group, a condensed-ring heteroarylene group, or a combination thereof. Examples of the heteroarylene group include, but are not limited to, the following groups: pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, quinolinylene, quinazolinylene, naphthyridinylene, etc., but are not limited thereto. The number of carbon atoms in the heteroarylene group is C2 to C30, preferably C2 to C25, and preferably C2 to C20.

[0045] The sub-condensed cyclic group of an alicyclic ring and an aromatic ring described in the present invention refers to a general term for a divalent group remaining after the alicyclic ring and the aromatic ring are fused together and two hydrogen atoms are removed. Examples of the sub-condensed cyclic group of an alicyclic ring and an aromatic ring include, but are not limited to, the following groups: benzocyclopropanediylene, benzocyclobutanediylene, indenylene, indenylene, tetrahydronaphthylene, dihydronaphthylene, benzocycloheptylene, benzocyclobutenylene, benzocycloheptenylene, etc., but are not limited thereto. The number of carbon atoms of the alicyclic ring is C3 to C30, preferably C3 to C25, preferably C3 to C20, preferably C3 to C15, and more preferably C3 to C8. The number of carbon atoms of the aromatic ring is C6 to C60, preferably C6 to C30, preferably C6 to C20, preferably C6 to C18, and preferably C6 to C10.

[0046] The present invention provides an organic electroluminescent device, comprising a first electrode, an organic layer, a second electrode, and a nucleation inhibition layer, wherein the organic layer is located between the first electrode and the second electrode, the nucleation inhibition layer is located outside the second electrode or between the organic layer and the second electrode, and the nucleation inhibition layer comprises a compound represented by Formula 1.

[0047]

[0048] Wherein, the X is selected from O or S;

[0049] The z are the same or different and are selected from CR1 or N, and the z bonded to L1 and L2 are selected from C atoms;

[0050] The R1s are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or two adjacent R1s are bonded to form a substituted or unsubstituted ring;

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

[0052]

[0053] The v's are the same or different and are selected from CR3 or N, and at least one v is selected from N;

[0054] The R3 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R3 are bonded to form a substituted or unsubstituted ring;

[0055] The Y is the same or different and is selected from one of O, S, and NR4;

[0056] Said a is the same or different and is selected from CR5 or N;

[0057] The R2 and R4 are the same or different and are selected from one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring;

[0058] The R5 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or two adjacent R5 are bonded to form a substituted or unsubstituted ring;

[0059] Ar2 is selected from a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C20 alicyclic group and a C6-C30 aromatic ring sub-condensed ring group;

[0060] The R a 、R b 、R cthe same or different ones selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0061] The L1 and L2 are the same or different and are selected from one or a combination of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, and a substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused sub-ring group.

[0062] Preferably, the compound of formula 1 is selected from one of the following formulas 1-1 or 1-2,

[0063]

[0064] Preferably, the One selected from the following groups,

[0065]

[0066]

[0067] The R1s are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, or one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylmethyl Silyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R1 are bonded to form a substituted or unsubstituted ring;

[0068] The n1 is selected from 0, 1, 2 or 3; the n2 is selected from 0, 1, 2, 3 or 4; the n3 is selected from 0, 1 or 2; the n4 is selected from 0 or 1; the n5 is selected from 0, 1, 2, 3, 4 or 5; the n6 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0069] Preferably, the One selected from the following groups,

[0070]

[0071]

[0072] The R1 is the same or different and is selected from hydrogen, deuterium, cyano, halogen, nitro, or one of the following groups which are substituted or unsubstituted with one or more deuteriums: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butyl, methyl silyl ... Butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R1 are bonded to form a substituted or unsubstituted benzene ring;

[0073] The n1 is selected from 0, 1, 2 or 3; the n2 is selected from 0, 1, 2, 3 or 4; and the n3 is selected from 0, 1 or 2.

[0074] Preferably, the Ar1 is selected from one of the following groups:

[0075]

[0076]

[0077] The Y is the same or different and is selected from one of O, S, and NR4;

[0078] Said R2 and R4 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, or one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisosilyl, methylsilyl, methylisosilyl ... Propylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl;

[0079] The R6 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylmethyl Silyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R6 are bonded to form a substituted or unsubstituted ring;

[0080] Said b1 is selected from 0, 1, 2, 3 or 4; said b2 is selected from 0, 1, 2 or 3; said b3 is selected from 0, 1 or 2; said b4 is selected from 0 or 1; said b5 is selected from 0, 1, 2, 3, 4, 5 or 6; said b6 is selected from 0, 1, 2, 3, 4 or 5; said b7 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said b8 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0081] Preferably, the "substituted or unsubstituted" substituents in R2, R4, and R6 are selected from hydrogen, deuterium, cyano, halogen, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropyl Silyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl.

[0082] Preferably, the Ar2 is selected from one of the groups shown below,

[0083]

[0084] The R dThe same or different R is selected from one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R d bonded to form a substituted or unsubstituted ring;

[0085] The R f 、R g The same or different R is selected from one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or adjacent R f 、R g bonded to form a substituted or unsubstituted ring;

[0086] The ring Q is selected from substituted or unsubstituted C3 to C15 alicyclic rings;

[0087] The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2, 3, 4, 5 or 6; the m3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the m4 is selected from 0, 1, 2, 3, 4 or 5; the m5 is selected from 0, 1, 2 or 3; the m6 is selected from 0, 1 or 2.

[0088] Preferably, the Ar2 is selected from one of the groups shown below,

[0089]

[0090]

[0091] The R d1 the same or different selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent Rd1 bonded to form a substituted or unsubstituted ring;

[0092] The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2, 3, 4, 5 or 6; the m3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the m4 is selected from 0, 1, 2, 3, 4 or 5; the m5 is selected from 0, 1, 2 or 3; the m6 is selected from 0, 1 or 2; the m7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the m8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.

[0093] Preferably, the R d1 the same or different selected from hydrogen, deuterium, cyano, halogen, nitro, one of the following groups which are substituted or unsubstituted with one or more deuteriums: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylmethyl Silyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R d1 Bonded to form a substituted or unsubstituted benzene ring.

[0094] Preferably, the One selected from the following groups,

[0095]

[0096]

[0097] Preferably, L1 and L2 are the same or different and are selected from a single bond or one or a combination of the following groups:

[0098]

[0099] The e are the same or different and are selected from CR8 or N;

[0100] Said T1 is selected from O, S, NR h One of the following; the T2 is selected from CR i or N;

[0101] The T3 is selected from O, S, CR j R k NR m One of the following;

[0102] The R8 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or two adjacent R8 are bonded to form a substituted or unsubstituted ring;

[0103] The R i 、R h 、R m the same or different ones selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring;

[0104] The R j 、R k The same or different ones are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or adjacent R j 、R k The bonds form a substituted or unsubstituted ring.

[0105] Preferably, L1 and L2 are the same or different and are selected from a single bond or one of the following groups:

[0106]

[0107] The R9 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylmethyl Silyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R9 are bonded to form a substituted or unsubstituted ring;

[0108] The t1 is selected from 0, 1, 2, 3 or 4; the t2 is selected from 0, 1, 2, 3, 4, 5 or 6; the t3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the t4 is selected from 0, 1, 2 or 3; the t5 is selected from 0, 1 or 2; the t6 is selected from 0 or 1; the t7 is selected from 0, 1, 2, 3, 4 or 5; the t8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the t9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0109] Preferably, the "substituted or unsubstituted" substituent in R9 is selected from hydrogen, deuterium, cyano, halogen, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilane alkyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl.

[0110] Preferably, the compound of formula 1 is selected from one of the structures shown below:

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143] Some specific chemical structures of the compounds of Formula 1 of the present invention are listed above, but the present invention is not limited to these listed chemical structures. All compounds based on the structure shown in Formula 1 and having substituents as defined above should be included.

[0144] Preferably, the nucleation inhibition layer is located outside the second electrode, and the nucleation inhibition layer comprises the compound represented by Formula 1.

[0145] Preferably, the first electrode is an anode, the second electrode is a cathode, the nucleation inhibition layer is located on the outside of the cathode, and the nucleation inhibition layer comprises the compound shown in Formula 1. Preferably, the cathode has a first portion and a second portion, the nucleation inhibition layer is provided on the first portion of the cathode, and a conductive coating is provided on the second portion of the cathode, and the nucleation inhibition layer comprises the compound shown in Formula 1.

[0146] Preferably, the first electrode is a cathode, the second electrode is an anode, the nucleation inhibition layer is located on the outside of the anode, and the nucleation inhibition layer comprises the compound shown in Formula 1. Preferably, the anode has a first portion and a second portion, the nucleation inhibition layer is provided on the first portion of the anode, and a conductive coating is provided on the second portion of the anode, and the nucleation inhibition layer comprises the compound shown in Formula 1.

[0147] Preferably, the first portion corresponds to the emission region of the organic light-emitting device, and the second portion corresponds to the non-emitting region of the organic light-emitting device. Preferably, the ratio of the first portion to the second portion is 5:95 to 95:5; preferably, the ratio of the first portion to the second portion is 10:90 to 90:10; preferably, the ratio of the first portion to the second portion is 20:80 to 80:20; most preferably, the ratio of the first portion to the second portion is 30:70 to 70:30.

[0148] Preferably, the organic layer is located between the first electrode and the second electrode, the nucleation inhibition layer is located between the organic layer and the second electrode, and the nucleation inhibition layer comprises the compound represented by Formula 1.

[0149] Preferably, the first electrode is an anode, the second electrode is a cathode, the organic layer is located between the anode and the cathode, the nucleation inhibition layer is located between the organic layer and the cathode, and the nucleation inhibition layer comprises the compound shown in Formula 1.

[0150] Preferably, the first electrode is a cathode, the second electrode is an anode, the organic layer is located between the cathode and the anode, the nucleation inhibition layer is located between the organic layer and the anode, and the nucleation inhibition layer comprises the compound shown in Formula 1.

[0151] The nucleation-suppression 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 the surface. The presence of the nucleation-suppression layer helps control the distribution of the conductive material, allowing it to selectively deposit in certain areas of the device, thereby optimizing the overall performance of the device.

[0152] Preferably, the organic electroluminescent device is a top-emitting device, a bottom-emitting device or a double-sided emitting device.

[0153] The present invention also provides use of the compound represented by Formula 1 as a nucleation inhibition layer material in an organic electroluminescent device.

[0154] The present invention also provides the use of the compound represented by formula 1 in preparing a nucleation inhibition layer in an organic electroluminescent device.

[0155] The organic functional layer of the organic electroluminescent device of the present invention may include a hole injection layer, a hole transport layer, a luminescence-assisting layer, an electron blocking layer, a luminescent layer, a hole blocking layer, an electron transport layer, an electron injection layer, a capping layer, a nucleation inhibition layer, etc. The organic functional layer may be formed by a single layer structure or a multilayer structure of the above organic layers, and each organic functional layer may also contain one or more materials.

[0156] The present invention does not particularly limit the materials of the thin films in the organic electroluminescent device, and materials known in the art can be used. The following is an introduction to the organic functional layers of the organic electroluminescent device and the electrodes on both sides of the device:

[0157] The anode of the present invention preferably comprises a material having a relatively large work function, including, but not limited to, metals, their oxides, and metal alloys. Specific examples include, but are not limited to, silver (Ag), zinc (Zn), indium tin oxide (ITO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), and polypyrrole.

[0158] The hole injection layer of the present invention is preferably a material with good hole injection ability. The hole injection layer material includes, but is not limited to, arylamine derivatives, quinacridone compounds, anthraquinone compounds, etc. Specific examples may include, but are not limited to, 4,4',4"-tris(N-(1-naphthyl)-N-phenylamino)triphenylamine (1-TNATA), 4,4',4"-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), etc.

[0159] The hole transport layer of the present invention is preferably a material with high hole mobility. The hole transport material includes carbazole derivatives, triarylamine derivatives, biphenyl diamine derivatives, etc., but is not limited thereto. Specific examples may include N, N'-diphenyl-N, N'-(1-naphthyl)-1, 1'-biphenyl-4, 4'-diamine (NPB), N4, N4'-di(biphenyl-4-yl)-N4, N4'-diphenylbiphenyl-4, 4'-diamine (TPD-10), 4, 4'-cyclohexylbis[N, N-di(4-methylphenyl)aniline] (TAPC), 4, 4', 4"-tris(carbazole-9-yl)triphenylamine (TCTA), etc., but are not limited thereto.

[0160] The electron blocking layer of the present invention preferably has a material capable of blocking electrons. Electron blocking materials include, but are not limited to, aromatic amine derivatives, carbazole derivatives, and the like. Specific examples include, but are not limited to, N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPD), N,N-di([1,1'-biphenyl]-4-)-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine, and the like.

[0161] The light-emitting layer of the present invention comprises a host material and a guest material. The host material includes, but is not limited to, heterocyclic compounds, aromatic amine compounds, and the like. Specific examples include, but are not limited to, 4,4'-bis(carbazol-9-yl)biphenyl (CBP) and 9,10-di(2-naphthyl)anthracene (ADN). The guest material includes, but is not limited to, boron complexes and metal complexes. Specific examples include, but are not limited to, tris(2-phenylpyridine)iridium (Ir(ppy)3), tris(1-phenyl-isoquinoline)iridium (Ir(piq)3), and 2,5,8,11-tetra-tert-butylperylene (TBPe).

[0162] The hole-blocking layer of the present invention preferably comprises a material with a strong hole-blocking capability, including, but not limited to, metal complexes and heteroaromatic compounds. Specific examples include, but are not limited to, bis(2-methyl-8-hydroxyquinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq) and 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi).

[0163] The electron transport layer of the present invention preferably comprises a material with strong electron-withdrawing ability, including, but not limited to, imidazole derivatives and triazine derivatives. Specific examples include, but are not limited to, 8-hydroxyquinoline aluminum (Alq3), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), and 4,4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)biphenyl (BTB).

[0164] The electron injection layer of the present invention is preferably made of a material with good electron injection capability, including, but not limited to, metals and their compounds. Specific examples include, but are not limited to, ytterbium (Yb), lithium fluoride (LiF), lithium 8-hydroxyquinoline (LiQ), and lithium oxide (Li2O).

[0165] The cathode of the present invention preferably has a relatively small work function material, including metals and their oxides, metal alloys, etc., but is not limited thereto. Specific examples may include aluminum (Al), lithium (Li), magnesium (Mg), magnesium-silver alloy (Mg / Ag), etc., but are not limited thereto.

[0166] The cover layer material of the present invention preferably has excellent light extraction properties, including, but not limited to, aromatic amine derivatives, metal compounds, and carbazole derivatives. Specific examples include, but are not limited to, tris(8-hydroxyquinolinolato)aluminum (Alq3) and 4,4'-bis(carbazol-9-yl)biphenyl (CBP).

[0167] The nucleation inhibition material is preferably an organic material, including, but not limited to, small molecule organic materials and organic polymers. Specific examples include, but not limited to, polycyclic aromatic compounds. The compound of formula 1 of the present invention is preferred.

[0168] The conductive material described herein is located outside the electrodes, including auxiliary electrodes, and can effectively reduce sheet resistance and, therefore, the IR drop associated with the cathode. Specific examples include metals and their alloys, including, but not limited to, zinc (Zn), magnesium (Mg), ytterbium (Yb), and magnesium-silver alloys (Mg / Ag).

[0169] The substrate of the present invention is used to support the organic layer / substrate-free base substrate material and can be flexible or rigid. It includes inorganic substrate materials, semiconductor substrate materials, etc. Specific examples include, but are not limited to, silicon, glass, metal, polymer, sapphire, etc.

[0170] There is no particular limitation on the method for preparing the thin films in the organic electroluminescent device of the present invention, and vacuum evaporation, sputtering, spin coating, spray coating, screen printing, laser transfer, etc. may be used, but are not limited thereto.

[0171] The organic electroluminescent device of the present invention is mainly used in the fields of panel display, lighting, organic solar cells, organic thin film transistors, flexible OLEDs, etc., but is not limited thereto.

[0172] The present invention is described in more detail with reference to the following examples. However, the following examples are only provided to illustrate the present description, and the scope of the present description is not limited to these examples.

[0173] Synthesis Example

[0174] Raw materials and reagents: The present invention has no particular limitations on the raw materials or reagents used in the following synthetic 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 the present invention are of reagent grade.

[0175] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube organic element analyzer (Elementar, Germany).

[0176] There is no particular limitation on the preparation method of the compound represented by Formula 1 of the present invention, and conventional methods known to those skilled in the art can be used. For example, carbon-carbon coupling reaction, etc. The compound represented by Formula 1 of the present invention can be prepared using the synthetic route shown below.

[0177] Synthesis Route 1:

[0178]

[0179] Synthesis route 2:

[0180]

[0181] The X n is halogen, the X n The same or different ones are selected from Cl, Br, I;

[0182] Said Q is selected from *-B(OH)2 or

[0183] Ar1, Ar2, L1, L2, R a 、R b 、R c The limitations of , X, and z are the same as those above.

[0184] Synthesis Example 1: Preparation of Intermediate b-156

[0185]

[0186] Preparation of intermediate a-156: Under nitrogen, a reaction flask was charged with d-156 (61.06 g, 200.00 mmol), pinacol diboron (50.79 g, 200.00 mmol), KCO (41.46 g, 300.00 mmol), Pd(PPh) (2.31 g, 2.00 mmol), and 1400 mL of dimethylformamide. The mixture was stirred at reflux for 4.5 h. After completion of the reaction, 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 (5:1) to afford b-156 (52.85 g, 75% yield). HPLC purity ≥99.87%. Mass spectrum: m / z: 352.2039 (theoretical value: 352.2030).

[0187] According to the synthesis steps of intermediate b-156, the raw materials are replaced accordingly to obtain the intermediates shown in the following table:

[0188]

[0189]

[0190] Synthesis Example 2: Preparation of Intermediate c-197

[0191]

[0192] Preparation of intermediate c-197: Under nitrogen, e-197 (46.13 g, 200.00 mmol), pinacol diboron (50.79 g, 200.00 mmol), KCO (41.46 g, 300.00 mmol), Pd(PPh) (2.31 g, 2.00 mmol), and 1400 mL of dimethylformamide were added to a reaction flask. The mixture was stirred at reflux for 4.5 h. After completion of the reaction, 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 (5:1) to obtain c-197 (45.75 g, 71% yield). HPLC purity ≥99.83%. Mass spectrum: m / z: 322.1471 (theoretical value: 322.1489).

[0193] According to the synthesis steps of intermediate c-197, the raw materials are replaced accordingly to obtain the intermediates shown in the following table:

[0194]

[0195] Synthesis Example 3: Preparation of Compound 14

[0196]

[0197] Preparation of intermediate A-14: Under nitrogen, a-14 (33.78 g, 120.00 mmol), b-14 (33.15 g, 120.00 mmol), K2CO3 (27.64 g, 200.00 mmol), Pd(PPh3)4 (1.39 g, 1.20 mmol), and 750 mL of toluene / ethanol / water (3:2:1) were added to a reaction flask. The mixture was stirred at reflux for 6 h. After completion of the reaction, the mixture was cooled to room temperature, filtered, and rinsed with ethanol. The resulting solid was then recrystallized from toluene to obtain A-14 (32.85 g, 78% yield). HPLC purity was ≥99.80%. Mass spectrum: m / z: 350.0886 (theoretical value: 350.0894).

[0198] Preparation of Compound 1: Under nitrogen, A-14 (17.55 g, 50.00 mmol), c-14 (16.06 g, 50.00 mmol), K2CO3 (10.37 g, 75.00 mmol), Pd2(dba)3 (0.46 g, 0.50 mmol), P(t-Bu)3 (0.20 g, 1.00 mmol), and 500 mL of tetrahydrofuran were added to a reaction flask. The mixture was stirred at reflux for 5.5 h. After the reaction, the mixture was cooled to room temperature and filtered to obtain a filter cake. The filter cake was rinsed with a small amount of toluene and then recrystallized from toluene to obtain Compound 14 (19.11 g, 75% yield). HPLC purity ≥99.94%. Mass spectrum m / z: 509.1824 (theoretical value: 509.1811). Theoretical element content (%): C 34 H 27 NO2Si: C, 80.12; H, 5.34; N, 2.75. Measured element content (%): C, 80.14; H, 5.35; N, 2.71.

[0199] Synthesis Example 4: Preparation of Compound 51

[0200]

[0201] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 and c-14 were replaced with equimolar amounts of b-51 and c-51, respectively, to obtain compound 51 (22.62 g) with HPLC purity ≥ 99.95%. Mass spectrum m / z: 619.1952 (theoretical value: 619.1968). Theoretical element content (%) C 43 H 29 NO2Si: C, 83.33; H, 4.72; N, 2.26. Measured element content (%): C, 83.30; H, 4.73; N, 2.23.

[0202] Synthesis Example 5: Preparation of Compound 67

[0203]

[0204] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14 and c-14 were replaced with equimolar amounts of a-67 and c-67, respectively, to obtain compound 67 (21.38 g) with HPLC purity ≥ 99.91%. Mass spectrum m / z: 585.2136 (theoretical value: 585.2124). Theoretical element content (%) C 40 H 31 NO2Si: C, 82.02; H, 5.33; N, 2.39. Measured element content (%): C, 82.00; H, 5.36; N, 2.37.

[0205] Synthesis Example 6: Preparation of Compound 121

[0206]

[0207] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14 and b-14 were replaced with equimolar amounts of a-121 and b-121, respectively, to obtain compound 121 (20.50 g) with HPLC purity ≥ 99.96%. Mass spectrum m / z: 585.2113 (theoretical value: 585.2124). Theoretical element content (%) C 40 H 31 NO2Si: C, 82.02; H, 5.33; N, 2.39. Measured element content (%): C, 82.04; H, 5.35; N, 2.36.

[0208] Synthesis Example 7: Preparation of Compound 128

[0209]

[0210] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14 and b-14 were replaced with equimolar amounts of a-67 and b-121, respectively, to obtain compound 128 (21.67 g) with HPLC purity ≥ 99.93%. Mass spectrum m / z: 585.2136 (theoretical value: 585.2124). Theoretical element content (%) C 40 H 31 NO2Si: C, 82.02; H, 5.33; N, 2.39. Measured element content (%): C, 82.03; H, 5.37; N, 2.35.

[0211] Synthesis Example 8: Preparation of Compound 134

[0212]

[0213] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 were replaced with equimolar amounts of b-121 to obtain compound 134 (21.09 g) with HPLC purity ≥ 99.96%. Mass spectrum m / z: 585.2137 (theoretical value: 585.2124). Theoretical element content (%) C 40 H 31 NO2Si: C, 82.02; H, 5.33; N, 2.39. Measured element content (%): C, 82.00; H, 5.36; N, 2.38.

[0214] Synthesis Example 9: Preparation of Compound 146

[0215]

[0216] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14 and b-14 were replaced with equimolar amounts of a-146 and b-146, respectively, to obtain compound 146 (22.85 g) with HPLC purity ≥ 99.92%. Mass spectrum m / z: 585.2139 (theoretical value: 585.2124). Theoretical element content (%) C 40 H 31 NO2Si: C, 82.02; H, 5.33; N, 2.39. Measured element content (%): C, 82.01; H, 5.35; N, 2.35.

[0217] Synthesis Example 10: Preparation of Compound 156

[0218]

[0219] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-67, b-156, and c-156, respectively, to obtain compound 156 (20.21 g) with HPLC purity ≥ 99.97%. Mass spectrum m / z: 585.2112 (theoretical value: 585.2124). Theoretical element content (%): C 40 H 31 NO2Si: C, 82.02; H, 5.33; N, 2.39. Measured element content (%): C, 82.00; H, 5.31; N, 2.38.

[0220] Synthesis Example 11: Preparation of Compound 197

[0221]

[0222] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 and c-14 were replaced with equimolar amounts of b-121 and c-197, respectively, to obtain compound 197 (21.71 g) with HPLC purity ≥ 99.95%. Mass spectrum m / z: 586.2066 (theoretical value: 586.2077). Theoretical element content (%) C 39 H 30 N2O2Si: C, 79.83; H, 5.15; N, 4.77. Measured element content (%): C, 79.80; H, 5.17; N, 4.75.

[0223] Synthesis Example 12: Preparation of Compound 202

[0224]

[0225] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-67, b-121, and c-202, respectively, to obtain compound 202 (20.71 g) with HPLC purity ≥ 99.92%. Mass spectrum m / z: 559.1954 (theoretical value: 559.1968). Theoretical element content (%): C 38 H 29 NO2Si: C, 81.54; H, 5.22; N, 2.50. Measured element content (%): C, 81.52; H, 5.20; N, 2.54

[0226] Synthesis Example 13: Preparation of Compound 209

[0227]

[0228] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 and c-14 were replaced with equimolar amounts of b-121 and c-209, respectively, to obtain compound 209 (21.97 g) with HPLC purity ≥ 99.94%. Mass spectrum m / z: 585.2132 (theoretical value: 585.2124). Theoretical element content (%) C 40 H 31 NO2Si: C, 82.02; H, 5.33; N, 2.39. Measured element content (%): C, 82.03; H, 5.31; N, 2.36.

[0229] Synthesis Example 14: Preparation of Compound 228

[0230]

[0231] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 and c-14 were replaced with equimolar amounts of b-228 and c-228, respectively, to obtain compound 228 (20.65 g) with HPLC purity ≥ 99.95%. Mass spectrum m / z: 565.2426 (theoretical value: 565.2437). Theoretical element content (%) C 38 H 35 NO2Si: C, 80.67; H, 6.24; N, 2.48. Measured element content (%): C, 80.64; H, 6.23; N, 2.44.

[0232] Synthesis Example 15: Preparation of Compound 232

[0233]

[0234] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-67, b-121, and c-232, respectively, to obtain compound 232 (21.09 g) with HPLC purity ≥ 99.97%. Mass spectrum m / z: 585.2135 (theoretical value: 585.2124). Theoretical element content (%): C 40 H 31 NO2Si: C, 82.02; H, 5.33; N, 2.39. Measured element content (%): C, 82.03H, 5.30; N, 2.37.

[0235] Synthesis Example 16: Preparation of Compound 249

[0236]

[0237] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-67, b-249, and c-51, respectively, to obtain compound 249 (21.38 g) with HPLC purity ≥ 99.93%. Mass spectrum m / z: 585.2137 (theoretical value: 585.2124). Theoretical element content (%): C 40 H 31 NO2Si: C, 82.02; H, 5.33; N, 2.39. Measured element content (%): C, 82.00; H, 5.32; N, 2.38.

[0238] Synthesis Example 17: Preparation of Compound 254

[0239]

[0240] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 were replaced with equimolar amounts of b-254 to obtain compound 254 (20.43 g) with HPLC purity ≥ 99.94%. Mass spectrum m / z: 559.1959 (theoretical value: 559.1968). Theoretical element content (%) C 38 H 29 NO2Si: C, 81.54; H, 5.22; N, 2.50. Measured element content (%): C, 81.51; H, 5.21; N, 2.54.

[0241] Synthesis Example 18: Preparation of Compound 262

[0242]

[0243] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 were replaced with equimolar amounts of b-262 to obtain compound 262 (22.53 g) with HPLC purity ≥ 99.93%. Mass spectrum m / z: 625.2425 (theoretical value: 625.2437). Theoretical element content (%) C 43 H 35 NO2Si: C, 82.52; H, 5.64; N, 2.24. Measured element content (%): C, 82.50; H, 5.63; N, 2.27.

[0244] Synthesis Example 19: Preparation of Compound 276

[0245]

[0246] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 were replaced with equimolar amounts of b-276 to obtain compound 276 (23.53 g) with HPLC purity ≥ 99.96%. Mass spectrum m / z: 635.2274 (theoretical value: 635.2281). Theoretical element content (%) C 44 H 33 NO2Si: C, 83.12; H, 5.23; N, 2.20. Measured element content (%): C, 83.10; H, 5.21; N, 2.23.

[0247] Synthesis Example 20: Preparation of Compound 289

[0248]

[0249] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 were replaced with equimolar amounts of b-289 to obtain compound 289 (25.04 g) with HPLC purity ≥ 99.92%. Mass spectrum m / z: 685.2446 (theoretical value: 685.2437). Theoretical element content (%) C 48 H 35 NO2Si: C, 84.05; H, 5.14; N, 2.04. Measured element content (%): C, 84.02; H, 5.13; N, 2.07.

[0250] Synthesis Example 21: Preparation of Compound 290

[0251]

[0252] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 were replaced with equimolar amounts of b-290 to obtain compound 290 (21.71 g) with HPLC purity ≥ 99.97%. Mass spectrum m / z: 586.2097 (theoretical value: 586.2077). Theoretical element content (%) C 39 H 30 N2O2Si: C, 79.83; H, 5.15; N, 4.77. Measured element content (%): C, 79.85; H, 5.16; N, 4.74.

[0253] Synthesis Example 22: Preparation of Compound 306

[0254]

[0255] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 and c-14 were replaced with equimolar amounts of b-121 and c-306, respectively, to obtain compound 306 (21.67 g) with HPLC purity ≥ 99.92%. Mass spectrum m / z: 601.1883 (theoretical value: 601.1896). Theoretical element content (%) C 40 H 31 NOSSi: C, 79.83; H, 5.19; N, 2.33. Measured element content (%): C, 79.85; H, 5.16; N, 2.35.

[0256] Synthesis Example 23: Preparation of Compound 346

[0257]

[0258] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-346, b-346, and c-346, respectively, to obtain compound 346 (22.17 g) with HPLC purity ≥ 99.95%. Mass spectrum m / z: 615.2785 (theoretical value: 615.2774). Theoretical element content (%): C 40 H 17 D 14 NOSSi: C, 78.00; H, 7.36; N, 2.27. Measured element content (%): C, 78.03; H, 7.34; N, 2.26.

[0259] Synthesis Example 24: Preparation of Compound 431

[0260]

[0261] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 and c-14 were replaced with equimolar amounts of b-121 and c-431, respectively, to obtain compound 431 (24.45 g) with HPLC purity ≥ 99.94%. Mass spectrum m / z: 660.2586 (theoretical value: 660.2597). Theoretical element content (%) C 46 H 36 N2OSi: C, 83.60; H, 5.49; N, 4.24. Measured element content (%): C, 83.62; H, 5.46; N, 4.25.

[0262] Synthesis Example 25: Preparation of Compound 526

[0263]

[0264] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 and c-14 were replaced with equimolar amounts of b-121 and c-526, respectively, to obtain compound 526 (23.24 g) with HPLC purity ≥ 99.98%. Mass spectrum m / z: 595.2324 (theoretical value: 595.2331). Theoretical element content (%) C 42 H 33 NOSi: C, 84.67; H, 5.58; N, 2.35. Measured element content (%): C, 84.65; H, 5.57; N, 2.38.

[0265] Synthesis Example 26: Preparation of Compound 557

[0266]

[0267] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 and c-14 were replaced with equimolar amounts of b-557 and c-557, respectively, to obtain compound 557 (23.21 g) with HPLC purity ≥ 99.95%. Mass spectrum m / z: 635.2656 (theoretical value: 635.2644). Theoretical element content (%) C 45 H 37 NOSi: C, 85.00; H, 5.87; N, 2.20. Measured element content (%): C, 85.02; H, 5.86; N, 2.22.

[0268] Synthesis Example 27: Preparation of Compound 624

[0269]

[0270] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 and c-14 were replaced with equimolar amounts of b-121 and c-624, respectively, to obtain compound 624 (21.45 g) with HPLC purity ≥ 99.97%. Mass spectrum m / z: 595.2343 (theoretical value: 595.2331). Theoretical element content (%) C 42 H 33 NOSi: C, 84.67; H, 5.58; N, 2.35. Measured element content (%): C, 84.66; H, 5.59; N, 2.33.

[0271] Synthesis Example 28: Preparation of Compound 673

[0272]

[0273] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 and c-14 were replaced with equimolar amounts of b-121 and c-673, respectively, to obtain compound 673 (22.08 g) with HPLC purity ≥ 99.98%. Mass spectrum m / z: 596.2276 (theoretical value: 596.2284). Theoretical element content (%) C 41 H 32 N2OSi: C, 82.51; H, 5.40; N, 4.69. Measured element content (%): C, 82.53; H, 5.41; N, 4.65.

[0274] Synthesis Example 29: Preparation of Compound 712

[0275]

[0276] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 and c-14 were replaced with equimolar amounts of b-121 and c-712, respectively, to obtain compound 712 (21.78 g) with HPLC purity ≥ 99.93%. Mass spectrum m / z: 596.2296 (theoretical value: 596.2284). Theoretical element content (%) C 41 H 32 N2OSi: C, 82.51; H, 5.40; N, 4.69. Measured element content (%): C, 82.54; H, 5.42; N, 4.66.

[0277] Synthesis Example 30: Preparation of Compound 749

[0278]

[0279] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 and c-14 were replaced with equimolar amounts of b-121 and c-749, respectively, to obtain compound 749 (23.71 g) with HPLC purity ≥ 99.96%. Mass spectrum m / z: 623.2381 (theoretical value: 623.2393). Theoretical element content (%) C 42 H 33 N3OSi: C, 80.87; H, 5.33; N, 6.74. Measured element content (%): C, 80.85; H, 5.30; N, 6.77.

[0280] Synthesis Example 31: Preparation of Compound 791

[0281]

[0282] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-67, b-121, and c-791, respectively, to obtain compound 791 (22.42 g) with HPLC purity ≥ 99.92%. Mass spectrum m / z: 622.2427 (theoretical value: 622.2440). Theoretical element content (%): C 43 H 34 N2OSi: C, 82.92; H, 5.50; N, 4.50. Measured element content (%): C, 82.90; H, 5.51; N, 4.52.

[0283] Synthesis Example 32: Preparation of Compound 822

[0284]

[0285] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 and c-14 were replaced with equimolar amounts of b-121 and c-822, respectively, to obtain compound 822 (23.32 g) with HPLC purity ≥ 99.97%. Mass spectrum m / z: 621.2476 (theoretical value: 621.2488). Theoretical element content (%) C 44 H 35 NOSi: C, 84.99; H, 5.67; N, 2.25. Measured element content (%): C, 84.97; H, 5.68; N, 2.26.

[0286] Synthesis Example 33: Preparation of Compound 828

[0287]

[0288] According to the preparation method of Synthesis Example 3, equimolar amounts of b-14 and c-14 were replaced with equimolar amounts of b-121 and c-828, respectively, to obtain compound 828 (20.19 g) with HPLC purity ≥ 99.95%. Mass spectrum m / z: 545.2166 (theoretical value: 545.2175). Theoretical element content (%) C 38 H 31 NOSi: C, 83.63; H, 5.73; N, 2.57. Measured element content (%): C, 83.60; H, 5.75; N, 2.55.

[0289] Synthesis Example 34: Preparation of Compound 836

[0290]

[0291] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-836, b-836, and c-836, respectively, to obtain compound 836 (24.64 g) with HPLC purity ≥ 99.92%. Mass spectrum m / z: 623.2658 (theoretical value: 623.2644). Theoretical element content (%): C 44 H 37 NOSi: C, 84.71; H, 5.98; N, 2.25. Measured element content (%): C, 84.73; H, 5.97; N, 2.28.

[0292] Synthesis Example 35: Preparation of Compound 871

[0293]

[0294] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-871, b-871, and c-871, respectively, to obtain compound 871 (21.27 g) with HPLC purity ≥ 99.97%. Mass spectrum m / z: 582.2167 (theoretical value: 582.2159). Theoretical element content (%): C 36 H 34 N2O2Si2: C, 74.19; H, 5.88; N, 4.81. Measured element content (%): C, 74.17; H, 5.86; N, 4.85.

[0295] Synthesis Example 36: Preparation of Compound 879

[0296]

[0297] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14 and b-14 were replaced with equimolar amounts of a-879 and b-121, respectively, to obtain compound 879 (20.80 g) with HPLC purity ≥ 99.94%. Mass spectrum m / z: 585.2137 (theoretical value: 585.2124). Theoretical element content (%) C 40 H 31 NO2Si: C, 82.02; H, 5.33; N, 2.39. Measured element content (%): C, 82.00; H, 5.35; N, 2.35.

[0298] Synthesis Example 37: Preparation of Compound 958

[0299]

[0300] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-958, b-121, and c-306, respectively, to obtain compound 958 (22.27 g) with HPLC purity ≥ 99.98%. Mass spectrum m / z: 601.1884 (theoretical value: 601.1896). Theoretical element content (%): C 40 H 31 NOSSi: C, 79.83; H, 5.19; N, 2.33. Measured element content (%): C, 79.85; H, 5.18; N, 2.36.

[0301] Synthesis Example 38: Preparation of Compound 1038

[0302]

[0303] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-1038, b-121, and c-1038, respectively, to obtain compound 1038 (21.45 g) with HPLC purity ≥ 99.95%. Mass spectrum m / z: 595.2324 (theoretical value: 595.2331). Theoretical element content (%): C 42 H 33 NOSi: C, 84.67; H, 5.58; N, 2.35. Measured element content (%): C, 84.66; H, 5.56; N, 2.37.

[0304] Synthesis Example 39: Preparation of Compound 1112

[0305]

[0306] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14 and c-14 were replaced with equimolar amounts of a-1112 and c-1112, respectively, to obtain compound 1112 (23.33 g) with HPLC purity ≥ 99.98%. Mass spectrum m / z: 613.2559 (theoretical value: 613.2549). Theoretical element content (%) C 41 H 35 N3OSi: C, 80.23; H, 5.75; N, 6.85. Measured element content (%): C, 80.25; H, 5.74; N, 6.88.

[0307] Synthesis Example 40: Preparation of Compound 1169

[0308]

[0309] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-871, b-121, and c-1169, respectively, to obtain compound 1169 (21.56 g) with HPLC purity ≥ 99.94%. Mass spectrum m / z: 545.2163 (theoretical value: 545.2175). Theoretical element content (%): C 38 H 31 NOSi: C, 83.63; H, 5.73; N, 2.57. Measured element content (%): C, 83.62; H, 5.70; N, 2.59.

[0310] Synthesis Example 41: Preparation of Compound 1181

[0311]

[0312] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14 and b-14 were replaced with equimolar amounts of a-1181 and b-121, respectively, to obtain compound 1181 (21.37 g) with HPLC purity ≥ 99.98%. Mass spectrum m / z: 601.1888 (theoretical value: 601.1896). Theoretical element content (%) C 40 H 31 NOSSi: C, 79.83; H, 5.19; N, 2.33. Measured element content (%): C, 79.81; H, 5.17; N, 2.36.

[0313] Synthesis Example 42: Preparation of Compound 1359

[0314]

[0315] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-1181, b-1359, and c-1359, respectively, to obtain compound 1359 (24.16 g) with HPLC purity ≥ 99.95%. Mass spectrum m / z: 661.2268 (theoretical value: 661.2259). Theoretical element content (%): C 46 H 35 NSSi: C, 83.47; H, 5.33; N, 2.12. Measured element content (%): C, 83.45; H, 5.34; N, 2.15.

[0316] Synthesis Example 43: Preparation of Compound 1417

[0317]

[0318] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-1181, b-121, and c-1417, respectively, to obtain compound 1417 (22.59 g) with HPLC purity ≥ 99.97%. Mass spectrum m / z: 586.1887 (theoretical value: 586.1899). Theoretical element content (%): C 39 H 30 N2SSi: C, 79.82; H, 5.15; N, 4.77. Measured element content (%): C, 79.85; H, 5.13; N, 4.79.

[0319] Synthesis Example 44: Preparation of Compound 1471

[0320]

[0321] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-1471, b-121, and c-1471, respectively, to obtain compound 1471 (21.07 g) with HPLC purity ≥ 99.96%. Mass spectrum m / z: 561.1958 (theoretical value: 561.1946). Theoretical element content (%): C 38 H 31 NSSi: C, 81.24; H, 5.56; N, 2.49. Measured element content (%): C, 81.25; H, 5.58; N, 2.46.

[0322] Synthesis Example 45: Preparation of Compound 1502

[0323]

[0324] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14 and b-14 were replaced with equimolar amounts of a-1502 and b-121, respectively, to obtain compound 1502 (21.67 g) with HPLC purity ≥ 99.93%. Mass spectrum m / z: 601.1882 (theoretical value: 601.1896). Theoretical element content (%) C 40 H 31 NOSSi: C, 79.83; H, 5.19; N, 2.33. Measured element content (%): C, 79.85; H, 5.17; N, 2.34.

[0325] Synthesis Example 46: Preparation of Compound 1587

[0326]

[0327] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-1587, b-121, and c-1587, respectively, to obtain compound 1587 (22.03 g) with HPLC purity ≥ 99.98%. Mass spectrum m / z: 611.2120 (theoretical value: 611.2103). Theoretical element content (%): C 42 H 33 NSSi: C, 82.44; H, 5.44; N, 2.29. Measured element content (%): C, 82.42; H, 5.45; N, 2.26.

[0328] Synthesis Example 47: Preparation of Compound 1635

[0329]

[0330] According to the preparation method of Synthesis Example 3, equimolar amounts of a-14, b-14, and c-14 were replaced with equimolar amounts of a-1635, b-121, and c-1635, respectively, to obtain compound 1635 (21.39 g) with HPLC purity ≥ 99.94%. Mass spectrum m / z: 562.1888 (theoretical value: 562.1899). Theoretical element content (%): C 37 H 30 N2SSi: C, 78.96; H, 5.37; N, 4.98. Measured element content (%): C, 78.95; H, 5.35; N, 4.99.

[0331] Density functional theory (DFT) calculations

[0332] In order to further study the nucleation inhibition effect of the compound of formula 1 of the present invention, density functional theory (DFT) calculations were performed using CP2K software. According to the formula: ad =(E total -(E suface +E adsorbate )) / n is used to calculate the surface adsorption performance of the compound of the present invention on metal electrode materials. The specific results are shown in Table 1 below. (The E ad represents the surface adsorption energy; the E total Represents the total energy of the adsorption system; the E surface represents the surface energy of the adsorption substrate; the E adsorbate represents the metal cluster energy; n represents the number of atoms contained in the calculated cluster)

[0333] The comparative compound R-1 is as follows:

[0334]

[0335] Table 1 Surface adsorption energy data

[0336]

[0337]

[0338] It can be seen from Table 1 that, compared with the comparative compound R-1, the compound of formula 1 of the present invention has weaker metal adsorption capacity, can inhibit the deposition of metal electrode materials on its surface, and is suitable as a nucleation inhibition layer material.

[0339] Device Examples

[0340] Optical transmittance test instrument: UV-visible spectrophotometer (manufacturer: Shanghai Xipu Instrument Co., Ltd., model: UV-2202PC)

[0341] Example 1: Preparation of Sample 1

[0342] A series of samples were prepared by depositing a nucleation suppression layer of compound 14 about 20 nm thick on a glass substrate. The surface of the nucleation suppression coating was then subjected to an open mask deposition of magnesium. Each sample was subjected to an average evaporation rate of about The magnesium vapor flux was measured using a deposition time of approximately 240 seconds to obtain a reference magnesium layer thickness of approximately 60 nm. Optical transmittance measurements were then used to determine the relative amount of magnesium deposited on the surface of the nucleation-inhibiting coating. When calculating the optical transmittance measurement, any loss or absorption of light due to the presence of the glass substrate and the nucleation-inhibiting coating was subtracted from the measured transmittance (measured at a wavelength of approximately 550 nm).

[0343] Examples 2 to 45: Preparation of samples 2 to 45

[0344] The compound 14 in the nucleation inhibition layer of Example 1 was replaced by compound 51, compound 67, compound 121, compound 128, compound 134, compound 146, compound 156, compound 197, compound 202, compound 209, compound 228, compound 232, compound 249, compound 254, compound 262, compound 276, compound 289, compound 290, compound 306, compound 346, compound 431, compound 526, compound 557, compound 624, compound 673, compound 712, compound 749, compound 791, compound 822, compound 828, compound 836, compound 871, compound 879, compound 958, compound 1038, compound 1112, compound 1169, compound 1181, compound 1359, compound 1417, compound 1471, compound 1502, compound 1587, and compound 1635. The other steps are the same to obtain samples 2 to 45.

[0345] Comparative Example 1: Preparation of Comparative Sample 1

[0346] The compound 14 in the nucleation inhibition layer of Example 1 was replaced with R-1, and the other steps were the same to obtain comparative sample 1.

[0347]

[0348] The optical transmittance test results of the samples prepared in Examples 1 to 45 of the present invention and Comparative Example 1 are shown in Table 2.

[0349] Table 2 Optical transmittance test data

[0350]

[0351]

[0352] As can be seen from Table 2, compared with Comparative Example 1, the sample containing the compound of Formula 1 of the present invention has a higher optical transmittance, indicating that the compound of Formula 1 of the present invention, as a nucleation inhibition layer material, can effectively inhibit the deposition of magnesium on its surface and improve the transmittance of the sample.

[0353] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. An organic electroluminescent device comprising a first electrode, an organic layer, a second electrode, and a nucleation inhibition layer, wherein the organic layer is located between the first electrode and the second electrode, and the nucleation inhibition layer is located outside the second electrode or between the organic layer and the second electrode, characterized in that: The nucleation inhibition layer comprises a compound represented by Formula 1, Wherein, the X is selected from O or S; The z are the same or different and are selected from CR1 or N, and the z bonded to L1 and L2 are selected from C atoms; The R1s are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or two adjacent R1s are bonded to form a substituted or unsubstituted ring; The Ar1 is selected from one of the following groups: The v's are the same or different and are selected from CR3 or N, and at least one v is selected from N; The R3 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R3 are bonded to form a substituted or unsubstituted ring; The Y is the same or different and is selected from one of O, S, and NR4; Said a is the same or different and is selected from CR5 or N; The R2 and R4 are the same or different and are selected from one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring; The R5 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or two adjacent R5 are bonded to form a substituted or unsubstituted ring; Ar2 is selected from a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C20 alicyclic group and a C6-C30 aromatic ring sub-condensed ring group; The R a 、R b 、R c the same or different ones selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; The L1 and L2 are the same or different and are selected from one or a combination of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, and a substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused sub-ring group.

2. The organic electroluminescent device according to claim 1, wherein The compound of formula 1 is selected from one of the following formulas 1-1 or 1-2, 3. The organic electroluminescent device according to claim 1, wherein described One selected from the following groups, The R1s are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, or one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylmethyl Silyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R1 are bonded to form a substituted or unsubstituted ring; The n1 is selected from 0, 1, 2 or 3; the n2 is selected from 0, 1, 2, 3 or 4; the n3 is selected from 0, 1 or 2; the n4 is selected from 0 or 1; the n5 is selected from 0, 1, 2, 3, 4 or 5; the n6 is selected from 0, 1, 2, 3, 4, 5 or 6.

4. The organic electroluminescent device according to claim 1, wherein The Ar1 is selected from one of the following groups: The Y is the same or different and is selected from one of O, S, and NR4; Said R2 and R4 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, or one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisosilyl, methylsilyl, methylisosilyl ... Propylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl; The R6 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylmethyl Silyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R6 are bonded to form a substituted or unsubstituted ring; Said b1 is selected from 0, 1, 2, 3 or 4; said b2 is selected from 0, 1, 2 or 3; said b3 is selected from 0, 1 or 2; said b4 is selected from 0 or 1; said b5 is selected from 0, 1, 2, 3, 4, 5 or 6; said b6 is selected from 0, 1, 2, 3, 4 or 5; said b7 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said b8 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

5. The organic electroluminescent device according to claim 1, wherein The Ar2 is selected from one of the following groups: The R d The same or different R is selected from one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R d bonded to form a substituted or unsubstituted ring; The R f 、R g The same or different R is selected from one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or adjacent R f 、R g bonded to form a substituted or unsubstituted ring; The ring Q is selected from substituted or unsubstituted C3 to C15 alicyclic rings; The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2, 3, 4, 5 or 6; the m3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the m4 is selected from 0, 1, 2, 3, 4 or 5; the m5 is selected from 0, 1, 2 or 3; the m6 is selected from 0, 1 or 2.

6. The organic electroluminescent device according to claim 1, characterized in that described One selected from the following groups, 7. The organic electroluminescent device according to claim 1, wherein The L1 and L2 are the same or different and are selected from a single bond or one or a combination of the following groups: The e are the same or different and are selected from CR8 or N; Said T1 is selected from O, S, NR h One of the following; the T2 is selected from CR i or N; The T3 is selected from O, S, CR j R k NR m One of the following; The R8 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, or two adjacent R8 are bonded to form a substituted or unsubstituted ring; The R i 、R h 、R m the same or different ones selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring; The R j 、R k The same or different ones are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or adjacent R j 、R k The bonds form a substituted or unsubstituted ring.

8. The organic electroluminescent device according to claim 1, wherein The compound of formula 1 is selected from one of the structures shown below:

9. The organic electroluminescent device according to claim 1, characterized in that: The nucleation inhibition layer is located on the outer side of the second electrode, and the nucleation inhibition layer includes a compound represented by Formula 1.

10. Use of the compound represented by formula 1 according to any one of claims 1 to 8 as a nucleation inhibition layer material in an organic electroluminescent device.

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