Organic compound and organic layer and application thereof, organic electroluminescent device and display or lighting device

Abstract

The invention discloses an organic compound, an organic layer, application of the organic compound and the organic layer, an organic electroluminescent device and a display or lighting device. The structural formula of the organic compound is shown as a formula I: # imgabs0 #, r is selected from a substituted or unsubstituted straight chain or branched chain alkyl group with 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 60 carbon atoms, a substituted or unsubstituted heteroalkyl group with 1 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkyl group with 1 to 60 carbon atoms, a substituted or unsubstituted aryl group with 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group with 3 to 60 carbon atoms; and n is 0-16. When the organic compound is applied to the organic electroluminescent device, the current efficiency and luminous efficiency of the device can be improved, the service life of the device can be prolonged, the working voltage of the device is reduced, and the organic compound has excellent color purity.

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescent materials, and particularly relates to an organic compound, an organic layer and its application, an organic electroluminescent device, and a display or lighting device. Background Art

[0002] Organic Light-Emitting Diode (OLED for short) has attracted much attention because of its characteristics of being thin and capable of emitting high brightness light at a low driving voltage, and being able to emit multi-color light by selecting luminescent materials. Since the organic thin film element was revealed by C.W. Tang of Eastman Kodak Company to be able to emit high brightness light, a large number of researchers in the OLED industry have done a lot of research and promotion on its application. Organic thin film light-emitting devices are widely used in various main display screens, etc., and their practical application has made great progress. Although the research on organic electroluminescent devices has progressed very rapidly, there are still many problems to be solved. For example, aspects such as the current efficiency, driving voltage, operating voltage, luminous efficiency, and service life of the devices still need to be improved.

[0003] How to design and synthesize new materials with higher purity and efficiency for electron transport / hole blocking, luminescent host materials, and doping materials, etc. For organic electroluminescent devices, the luminous quantum efficiency of the devices is a comprehensive reflection of various factors and is also an important indicator for measuring the quality of the devices. At present, some organic electroluminescent materials have been commercially applied due to their excellent performance, but there is still a need for electron transport materials, hole transport materials, host materials, and doping materials with high mobility. Summary of the Invention

[0004] The purpose of the present application is to provide an organic compound, an organic layer and its application, an organic electroluminescent device, and a display or lighting device, which can significantly improve the current efficiency, luminous efficiency and service life of the organic electroluminescent device, reduce the operating voltage of the device, and at the same time have excellent color purity.

[0005] To achieve the above purpose, the technical solution of the present application provides an organic compound, and its structural formula is shown as Formula I:

[0006] In the said Formula I, R is selected from a substituted or unsubstituted straight-chain or branched C1-C60 alkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C60 heteroalkyl group, a substituted or unsubstituted C1-C60 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; n is 0 to 16.

[0007] In some embodiments of the present application, R is a group L-EA, and the structural formula of the organic compound is shown in Formula II: In Formula II, L is selected from a single bond, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; EA is an electron-withdrawing group, and the electron-withdrawing group is selected from an aromatic electron-withdrawing group derivative containing a nitrogen atom, an electron-withdrawing group derivative containing a fluorine atom, a cyano derivative, a phosphine oxide group derivative, or a sulfoxide derivative; n is 1 to 4.

[0008] In some embodiments of the present application, the electron-withdrawing group is selected from the following groups:

[0009] or Ar6-CN

[0010] wherein, Ar6, Ar 61 , Ar 62 , Ar 63 , Ar7, Ar8, Ar9 and Ar 10 are independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group.

[0011] In some embodiments of the present application, the substituent of L is selected from the following substituted or unsubstituted groups: a C1-C30 straight-chain alkyl group, a C1-C30 branched-chain alkyl group, a C3-C30 cycloalkyl group, a C6-C60 aryl group, a C3-C60 heteroaryl group.

[0012] In some embodiments of the present application, n is 1 or 2; L is selected from a single bond, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a triphenylene group, a phenanthryl group, or a phenanthryl derivative;

[0013] The electron-withdrawing group is and Ar8, Ar9 and Ar 10 are independently selected from the following substituted or unsubstituted groups: a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorene, a triphenylene group, a phenanthryl group, or a phenanthryl derivative;

[0014] More specifically, Ar8, Ar9 and Ar10 respectively include: an aryl group substituted by a C1-C10 alkyl group, and the aryl group includes a phenyl group, a naphthyl group, a biphenyl group, 2-phenylnaphthalene, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorene, a triphenylene group, a phenanthryl group, or a combination thereof; the fluorenyl group is preferably a dimethyl-substituted fluorenyl group.

[0015] More specifically, for Ar8, Ar9, and Ar10, the aryl groups can be substituents of one another. For example, they include phenyl, naphthyl, biphenyl, 2-phenylnaphthalene, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorene, triphenylenyl, phenanthryl, or combinations thereof; they can be combined with one another, and can be secondary combinations, tertiary combinations, or quaternary combinations. A secondary combination is preferred. For example, it can be a phenyl group substituted with a naphthyl group, etc.

[0016] In some embodiments of the present application, the organic compound represented by Formula II is represented by any one of the structural formulas of Formulas 1 to 24: wherein Ar8 and Ar 10 are each independently selected from one or more of phenyl, naphthyl, biphenyl, benzofuran, or dibenzofuranyl.

[0017] In some embodiments of the present application, the organic compound represented by Formula II is Compounds 25 to 35.

[0018] In some embodiments of the present application, R is a group The structural formula of the organic compound is as shown in Formula III:

[0019] In Formula III, L is selected from a single bond, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; Ar 11 and Ar 12 are independently selected from a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group, or Ar 11 and Ar 12 form a ring by bonding; n is 1 to 4.

[0020] In some embodiments of the present application, its structural formula is as shown in Formula IV or Formula V:

[0021]

[0022] In Formulas IV and V, Ar 13 ~Ar 16 are independently selected from one of the following structures:

[0023]

[0024] n is 1 or 2.

[0025] In some embodiments of the present application, the organic compound represented by Formula IV is represented by any one of the structural formulas of Formulas 36 to 39; the organic compound represented by Formula V is represented by any one of the following structural formulas of Formulas 40 to 50.

[0026] In some embodiments of the present application, R is a group The structural formula of the organic compound is shown in Formula VI:

[0027] In Formula VI, L is selected from a single bond, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; Ar3 is selected from a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group.

[0028] In some embodiments of the present application, L and Ar3 are independently selected from the following substituted or unsubstituted groups:

[0029] In some embodiments of the present application, the organic compound shown in Formula VI is represented by any one of the structural formulas of Formula 51 to Formula 67.

[0030] The present application also provides an organic compound, the structural formula of which is shown in Formula VII:

[0031]

[0032] In Formula VII, R1 is selected from none, a substituted or unsubstituted straight-chain or branched C1-C60 alkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C60 heteroalkyl group, a substituted or unsubstituted C1-C60 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; CyA, CyB, Ar4, and Ar5 are independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group; wherein at least one of R1, CyA, CyB, Ar4, and Ar5 contains the structural formula of any one of the foregoing items.

[0033] In some embodiments of the present application, at least one of R1, Ar4, and Ar5 contains the structural formula of any one of the foregoing items.

[0034] In some embodiments of the present application, the organic compound shown in Formula VII is represented by any one of the structural formulas of Formula 68 to Formula 77.

[0035] The present application also provides an organic layer including the organic compound of any one of the foregoing items.

[0036] The present application also provides the use of the organic compound of any one of the foregoing items and / or the foregoing organic layer in an organic electroluminescent device.

[0037] The present application also provides an organic electroluminescent device, comprising a first electrode, a second electrode and the aforementioned organic layer, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer or an electron transport layer.

[0038] The present application also provides a display or lighting device, comprising the aforementioned organic electroluminescent device.

[0039] Compared with the prior art, when the organic compound containing an oxaspirofluorene group in the present application is used as an electron transport layer material, it can significantly improve the current efficiency and lifetime of the organic electroluminescent device and reduce the driving voltage; when used as a hole transport material and / or a host material and / or a guest doping material, it can reduce the operating voltage of the organic electroluminescent device, improve the luminous efficiency and lifetime, and at the same time, device data shows that it has excellent color purity when used as a host material. BRIEF DESCRIPTION OF THE DRAWINGS

[0040] The following drawings detail the exemplary embodiments disclosed in the present application. Wherein the same reference numerals represent similar structures in several views of the drawings. Those of ordinary skill in the art will understand that these embodiments are non-limiting, exemplary embodiments, and the drawings are only for illustrative and descriptive purposes and are not intended to limit the scope of the present application. Embodiments in other ways may also equally achieve the inventive concept in the present application. It should be understood that the drawings are not drawn to scale. Wherein:

[0041] Figure 1 is a schematic structural diagram of the organic electroluminescent device in Device Example 1;

[0042] Figure 2 is a schematic structural diagram of the organic electroluminescent device in Device Example 11;

[0043] Figure 3 is a schematic structural diagram of the organic electroluminescent device in Device Example 23;

[0044] Figure 4 is a schematic structural diagram of the organic electroluminescent device in Device Example 31. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0045] The following description provides specific application scenarios and requirements of the present application, aiming to enable those skilled in the art to manufacture and use the content in the present application. For those skilled in the art, various local modifications to the disclosed embodiments are obvious, and without departing from the spirit and scope of the present application, the general principles defined here can be applied to other embodiments and applications. Therefore, the present application is not limited to the disclosed embodiments, but has the broadest scope consistent with the claims.

[0046] At present, for electron transport materials, electron-withdrawing atoms or groups are mainly introduced into aromatic rings. For example, nitrogen atoms, cyano groups, and various large aromatic planar groups are introduced. However, the problems are that after introducing various electron-withdrawing groups, the synthesis of the materials becomes more difficult. In addition, the planarity of the molecules increases, resulting in poor solubility of the materials. Hole transport materials are generally modified and improved based on triarylamine or carbazole, but there are still problems such as low hole transport mobility and short service life of the materials. As the materials for the light-emitting layer, the host material and the doping material need to have high stability and the ability to balance electrons and holes, but the current materials have not fully solved the above problems.

[0047] To solve the problems of the prior art, the inventor introduces a new fragment into the molecular structure. Specifically, when providing a compound containing the following groups as a molecular electron transport material, hole transport material, host material, and doping material, it is surprisingly found that this solution can better balance various optical properties (such as one or more of luminous quantum efficiency, high mobility, stability, hole ability, etc.) and physical and chemical properties (solubility, etc.).

[0048] Through a large amount of exploration and research, the inventor of the present application has obtained an organic compound, which includes an oxaspirofluorene group in the main body part. The non-planar structure of this basic core part combined with its electronic characteristics enables it to better balance optical properties and physical and chemical properties. When this organic compound is used as an electron transport material, hole transport material, host material, and doping material, it can significantly improve the current efficiency and luminous efficiency of the device, reduce the working voltage of the device, and extend the service life of the device.

[0049] Examples of the substituents that appear in the present application are described below, but the substituents are not limited thereto:

[0050] Substituted or unsubstituted: It means substituted by one or more substituents selected from the following: deuterium, halogen group, cyano group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, silyl group, boron group, linear or branched or cyclic alkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamino group, aralkylamino group, heteroarylamino group, arylamino group, arylphosphino group, heterocyclic group, or unsubstituted; or substituted by a substituent connecting two or more of the above-exemplified substituents, or unsubstituted. For example, the "substituent connecting two or more substituents" may include a biphenyl group, that is, the biphenyl group may be an aryl group or a substituent connecting two phenyl groups. The linear or branched or cyclic alkyl group is preferably a C1-C30 alkyl group, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, methyl-substituted isobutyl, methyl-substituted tert-butyl, etc.

[0051] Aryl: There is no particular limitation. The aryl group can be a monocyclic aryl group or a polycyclic aryl group. In some embodiments, the monocyclic aryl group includes, but is not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, etc. The polycyclic aryl group includes, but is not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, etc. The fluorenyl group can be substituted, such as 9,9'-dimethylfluorenyl, fluorenyl, etc. In addition, two of the substituents can combine with each other to form a spiro ring structure, such as 9,9'-spirobifluorenyl, etc.

[0052] The above description of the aryl group can be applied to the arylene group, with the difference that the arylene group is divalent.

[0053] The above description of the aryl group can be applied to the aryl group in aryloxy, arylthio, arylsulfonyl, arylphosphino, aralkyl, aralkylamino, aralkenyl, alkylaryl, arylamino, and arylheteroarylamino.

[0054] Heterocyclic group: Contains one or more of B, N, O, P, S, Si, and Se as heteroatoms. The heterocyclic group includes, but is not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, dioxazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, oxazinyl, thiazinyl, dioxacyclohexenyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, dibenzothienyl, dibenzofuryl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indacarbazolyl, phenazinyl, imidazopyridyl, phenazinyl, phenanthridinyl, phenanthroline, phenothiazinyl, imidazopyridyl, imidazophenanthridinyl, benzimidazoquinazolinyl, benzimidazophenanthridinyl, spiro[fluorene-9,9'-xanthene], binaphthyl, dinaphthofuryl, naphthobenzofuryl, dinaphthothienyl, naphthobenzothienyl, triphenylphosphine oxide, triphenylborane, etc.

[0055] The above description of the heterocyclic group can be applied to the heteroaryl group, with the difference that the heteroaryl group is aromatic.

[0056] The above description of the heterocyclic group can be applied to the heteroaryl group in heteroaryl, heteroarylamino, and arylheteroarylamino.

[0057] The above description of the heterocyclic group can be applied to the heteroarylene group, with the difference that the heteroarylene group is divalent.

[0058] Alkyl: It can be linear, branched or cyclic, and there is no particular limitation on the number of carbon atoms. In some embodiments, the alkyl group includes, but is not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, etc.

[0059] The above description of the alkyl group can be used for the alkyl group in alkylthio, alkylsulfonyl, aralkyl, aralkylamino, alkylaryl and alkylamino.

[0060] One aspect of the present application provides an organic compound having a structural formula shown in Formula I:

[0061] In Formula I, R is selected from a substituted or unsubstituted linear or branched C1-C60 alkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C60 heteroalkyl group, a substituted or unsubstituted C1-C60 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; n is 0 to 16.

[0062] It should be noted that in Formula I, the substitution of R is not limited to a single benzene ring and the substitution position is also not restricted. That is to say, R can substitute a single benzene ring, or can substitute at least two benzene rings simultaneously. At the same time, the substitution of R can occur at any substitutable position on the benzene ring. The substitution of R can occur at one substitutable position on the benzene ring, or can occur at least two substitutable positions on the benzene ring simultaneously. In short, R can perform arbitrary substitution on the entire oxaspirofluorene group.

[0063] In some embodiments, R is the group L-EA, and the structural formula of the organic compound is shown in Formula II: L-EA can perform arbitrary substitution on the entire oxaspirofluorene group.

[0064] In the formula II, n can be 1 to 4, preferably 1 or 2; L is selected from a single bond, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group. Preferably, the L is selected from a single bond, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a triphenylenyl group, a phenanthryl group or a phenanthryl derivative. More preferably, the L is a single bond or a phenyl group.

[0065] In the formula II, EA is an electron-withdrawing group (Electron acceptor), and the electron-withdrawing group is selected from an aromatic electron-withdrawing group derivative containing a nitrogen atom, an electron-withdrawing group derivative containing a fluorine atom, a cyano derivative, a phosphine oxide group derivative or a sulfoxide derivative.

[0066] In some preferred embodiments, the electron-withdrawing group is selected from the following groups:

[0067]

[0068] Among them, Ar6, Ar 61 , Ar 62 , Ar 63 , Ar7, Ar8, Ar9 and Ar 10 are independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group. Further preferably, the Ar6, Ar 61 , Ar 62 , Ar 63 , Ar7, Ar8, Ar9 and Ar 10 are independently selected from a phenyl group, a naphthyl group, a biphenyl group, 2-phenylnaphthalene, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a triphenylenyl group, a phenanthryl group or a phenanthryl derivative. More preferably, Ar6, Ar 61 , Ar 62 , Ar 63 , Ar7, Ar8, Ar9 and Ar 10 are independently selected from a phenyl group, a naphthyl group, a biphenyl group, 2-phenylnaphthalene, a dibenzofuranyl group, a triphenylenyl group, a phenanthryl group or a phenanthryl derivative.

[0069] In some more preferred embodiments, the electron-withdrawing group is a quinazolinyl group or a s-triazinyl group and Ar8, Ar9 and Ar 10 are independently selected from a phenyl group, a naphthyl group, a biphenyl group, 2-phenylnaphthalene, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a triphenylenyl group, a phenanthryl group or a phenanthryl derivative. Most preferably, the electron-withdrawing group is a s-triazinyl group, and the structural formula of the organic compound is as follows:

[0070]

[0071] In some preferred embodiments, the organic compound represented by Formula II is represented by any one of the following structural formulas 1 to 24:

[0072]

[0073]

[0074] In the above structural formulas, Ar8 and Ar 10 are each independently selected from one or more of phenyl, naphthyl, biphenyl, dibenzofuranyl.

[0075] In some preferred embodiments, the organic compound represented by Formula II is the following compound:

[0076]

[0077]

[0078] In some more preferred embodiments, the organic compound represented by Formula II has the following structural formula:

[0079]

[0080] When the basic core group of the present application is combined with a specific electron-withdrawing group, when the organic compound represented by Formula II is applied to an electron transport material, the operating voltage of the device can be significantly reduced, and the current efficiency and lifetime of the device can be improved.

[0081] In some embodiments, in Formula I, R is a group At this time, the structural formula of the organic compound is as shown in Formula III:

[0082]

[0083] In Formula III, L is selected from a single bond, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; Ar 11 and Ar 12 are independently selected from a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group, or Ar 11 and Ar 12 are bonded to form a ring; n is 1 to 4.

[0084] In some embodiments, the structural formula of the organic compound is as shown in Formula IV or Formula V:

[0085]

[0086] In the formulas IV and V, Ar 13 ~Ar 16 are independently selected from one of the following structures:

[0087]

[0088] n is 1 or 2.

[0089] In some preferred embodiments, the organic compound represented by the formula IV is represented by any one of the following structural formulas 36 to 39:

[0090]

[0091] In the formulas 36 to 39, Ar 14 is selected from

[0092] In some preferred embodiments, the organic compound represented by the formula V is represented by any one of the following structural formulas 40 to 50:

[0093]

[0094]

[0095] In the formulas 40 to 50, Ar 16 is selected from

[0096] In some more preferred embodiments, the organic compound represented by the formula III has the following structural formula:

[0097]

[0098] When the organic compound represented by the formula III is applied to a hole transport material, it can significantly reduce the operating voltage of the device, improve the luminous efficiency, and extend the service life.

[0099] In some embodiments, in the formula I, R is a group and can arbitrarily substitute the entire oxaspirofluorene group; at this time, the structural formula of the organic compound is as shown in the formula VI:

[0100]

[0101] In the formula VI, L is selected from a single bond, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; Ar3 is selected from a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group.

[0102] In some preferred embodiments, L and Ar3 are independently selected from the following substituted or unsubstituted groups:

[0103]

[0104] In some preferred embodiments, the organic compound represented by Formula VI is represented by any one of the structural formulas of Formulas 51 to 67 as follows:

[0105]

[0106] When the organic compound represented by Formula VI is used as the host material of the light-emitting layer, it can significantly reduce the operating voltage of the device, improve the light-emitting efficiency, and at the same time extend the lifespan of the device.

[0107] In some embodiments, the structural formula of the organic compound is as shown in Formula VII:

[0108]

[0109] In Formula VII, at least one of R1, CyA, CyB, Ar4, and Ar5 contains the structural formula of Formula I. Preferably, at least one of R1, Ar4, and Ar5 contains the structural formula of Formula I. For the substitution conditions of each substituent in the structural formula of Formula I, reference can be made to the foregoing content and will not be elaborated here. R1 can be connected to any substitution position of the benzene ring in the main structure of Formula VII. R1 is selected from none, substituted or unsubstituted straight-chain or branched C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl; CyA, CyB, Ar4, and Ar5 are independently selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl.

[0110] In some preferred embodiments, the organic compound represented by Formula VII is represented by any one of the structural formulas of Formulas 68 to 77 as follows:

[0111]

[0112] When the organic compound represented by Formula VII is used as the doping material of the light-emitting layer, it can significantly reduce the operating voltage of the device, improve the light-emitting efficiency, and extend the lifespan of the device.

[0113] On the other hand, the present application provides an organic layer, which comprises any one of the aforementioned organic compounds. Any one of the aforementioned organic compounds and this organic layer can be applied to an organic electroluminescent device. The organic electroluminescent device can be an organic photovoltaic device, an organic light-emitting device, an organic solar cell, an electronic paper, an organic photoreceptor, or an organic thin-film transistor, etc.

[0114] The present application further provides an organic electroluminescent device, which comprises a first electrode, a second electrode, and the aforementioned organic layer. As an example, the first electrode is an anode, the second electrode is a cathode, and the cathode can be one or more layers. The organic layer is located between the first electrode and the second electrode. The organic layer can be a single-layer structure or a multi-layer series structure laminated with two or more organic layers. The organic layer is at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, or an electron transport layer.

[0115] In some specific embodiments, the structure of the organic electroluminescent device can be selected from one of the following:

[0116] (1) The organic electroluminescent device comprises an anode, a hole injection layer, a first hole transport layer, a light-emitting layer, a first electron transport layer, and a cathode stacked in sequence, that is, anode / hole injection layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode. Hereinafter, the device structure will be expressed in this simplified manner.

[0117] (2) anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode.

[0118] (3) anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / cathode.

[0119] (4) anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / electron injection layer / cathode.

[0120] (5) anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / multi-layer cathode.

[0121] (6) anode / hole injection layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / cathode.

[0122] (7) anode / hole injection layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / second electron transport layer / cathode.

[0123] (8) Anode / hole injection layer / second hole transport layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / cathode.

[0124] (9) Anode / hole injection layer / second hole transport layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / second electron transport layer / cathode.

[0125] (10) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode.

[0126] (11) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode.

[0127] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode.

[0128] The light-emitting direction of the organic electroluminescent device can be emitted from the anode side or the cathode side. In some specific embodiments, when it is emitted from the cathode side, a covering layer needs to be added on the cathode side, and the specific structure is as follows:

[0129] 1) Anode / hole injection layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode / covering layer.

[0130] 2) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode / covering layer.

[0131] 3) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / cathode / covering layer.

[0132] 4) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / electron injection layer / cathode / covering layer.

[0133] 5) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / multi-layer cathode / covering layer.

[0134] 6) Anode / hole injection layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / cathode / covering layer.

[0135] 7) Anode / Hole Injection Layer / First Hole Transport Layer / First Light Emitting Layer / Carrier Generation Layer / First Hole Transport Layer / Second Light Emitting Layer / First Electron Transport Layer / Second Electron Transport Layer / Cathode / Cover Layer.

[0136] 8) Anode / Hole Injection Layer / Second Hole Transport Layer / First Hole Transport Layer / First Light Emitting Layer / Carrier Generation Layer / First Hole Transport Layer / Second Light Emitting Layer / First Electron Transport Layer / Cathode / Cover Layer.

[0137] 9) Anode / Hole Injection Layer / Second Hole Transport Layer / First Hole Transport Layer / First Light Emitting Layer / Carrier Generation Layer / First Hole Transport Layer / Second Light Emitting Layer / First Electron Transport Layer / Second Electron Transport Layer / Cathode / Cover Layer.

[0138] 10) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode / Cover Layer.

[0139] 11) Anode / Hole Injection Layer / First Hole Transport Layer / Second Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Cathode / Cover Layer.

[0140] 12) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Cathode / Cover Layer.

[0141] Some specific functional layers in the organic electroluminescent device will be described below.

[0142] Substrate:

[0143] The substrate is generally located below the anode. The substrate can be plastic or glass, and can be rigid or bendable. A driving unit is provided on the substrate, which can drive the corresponding pixels to emit light.

[0144] Anode:

[0145] Organic EL (Organic Electro-Luminescence) elements usually have requirements for good conductivity, flat surface, and no cracks on the anode. At the same time, there are also certain requirements for the work function, mainly to be able to match the hole injection layer and play the hole injection effect.

[0146] When the top-emission mode (light emission from the cathode side) is adopted, the anode uses a metal compound with a work function of 4.2 eV or more, such as indium tin oxide alloy, tin oxide, indium zinc oxide, gold, silver, platinum, copper, carbon nanotubes, carbon nanowires, graphene, etc. The thickness is 10 nm to 200 nm, preferably 10 nm to 50 nm for use. A reflective electrode is provided below the anode (close to the substrate end). The reflective electrode is generally made of a metal or a metal alloy. For example, silver metal, copper metal, aluminum metal, gold metal or an alloy of these metals with other metals. The reflectivity of the reflective electrode is relatively high, and the required reflectivity is more than 90%. The thickness is usually used in the range of 100 nm to 500 nm, preferably in the range of 80 nm to 150 nm.

[0147] When the bottom-emission mode (light emission from the cathode substrate side) is adopted, the anode uses a metal compound with a work function of 4.2 eV or more, such as indium tin oxide alloy, tin oxide, indium zinc oxide, gold, silver, platinum, copper, carbon nanotubes, carbon nanowires, graphene, etc. The thickness is 10 nm to 1 μm, preferably 50 nm to 200 nm.

[0148] The anode can be fabricated by forming a thin film of the electrode material using methods such as evaporation, sputtering, coating, etc.

[0149] Hole injection layer:

[0150] The thickness of the hole injection layer is generally 3 nm to 20 nm. The hole injection layer uses a P-type material and a hole transport material in combination. The purpose of using the P-type material is to receive holes from the anode and transfer them to the hole transport material. The weight ratio of the P-type material in the hole injection layer is generally 0.5% to 10%. When the weight ratio is 0.5% to 3%, the absolute value of the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the P-type material and the highest occupied molecular orbital (HOMO) energy level of the HTL material shall not be greater than 0.3 eV. When the weight ratio is 3% to 5%, the absolute value of the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the P-type material and the highest occupied molecular orbital (HOMO) energy level of the HTL material shall not be greater than 0.5 eV. When the weight ratio is 5% to 10%, the absolute value of the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the P-type material and the highest occupied molecular orbital (HOMO) energy level of the HTL material shall not be greater than 1 eV.

[0151] The P-type material can be a metal oxide, such as molybdenum oxide, vanadium oxide, tungsten oxide, etc.; it can also be an organic compound, such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-tris(cyanomethylene))tris(2,3,5,6-tetrafluorobenzyl) (PD1, CAS No.: 1224447-88-4), tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), and is not limited thereto. The hole transport material paired with the P-type material can be selected from the materials of the second hole transport layer, and can be the same as or different from the materials of the second hole transport layer.

[0152] Second hole transport layer:

[0153] The thickness of the second hole transport layer is generally 40 nm to 150 nm. Arylamine compounds are often used, and aryl monoamines or aromatic polyamines can be used. The hole transport material is required to have a high hole mobility, be able to reduce the driving voltage, and have a glass transition temperature exceeding 100 °C to avoid crystallization at high temperatures.

[0154] First hole transport layer:

[0155] The thickness of the first hole transport layer is generally 3 nm to 220 nm. When there is no second hole transport layer, the thickness of the first hole transport layer is generally 40 nm to 150 nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 3 nm to 120 nm. Generally, for red, green, blue, yellow light, etc., thickness adjustment is required according to the "microcavity effect", and different thicknesses are selected.

[0156] Taking the top-emitting light-emitting device as an example, the formula of the microcavity is as follows:

[0157]

[0158] where n i , d i respectively represent the refractive index coefficient and thickness of the i-th layer, m is an integer, which is the mode number of the microcavity, and the more common values are 1 or 2; θ1 and θ2 respectively represent the phase shifts of light generated at the anode interface and the cathode interface.

[0159] Red light, green light, blue light, or light of other colors have their optimal thicknesses due to different wavelengths. Taking the modulus of 2 as an example, for red light, when there is no second hole transport layer, the thickness of the first hole transport layer is generally 160 nm to 220 nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 8 nm to 120 nm. For green light, when there is no second hole transport layer, the thickness of the first hole transport layer is generally 100 nm to 180 nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 30 nm to 70 nm. For blue light, when there is no second hole transport layer, the thickness of the first hole transport layer is generally 80 nm to 130 nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 3 nm to 30 nm. When other colors are selected, there will be different optimal "microcavity adjustment thicknesses"

[0160] Electron blocking layer:

[0161] The electron blocking layer can simultaneously have a hole transport function and an electron blocking function. At the same time, the relatively high triplet excitation energy level of the electron blocking layer can confine the excitons generated in the light-emitting layer in the light-emitting layer, thereby improving the light-emitting efficiency of the device.

[0162] Light-emitting layer:

[0163] The materials of the light-emitting layer generally include a host material and a dopant material. The content of the host material is greater than that of the dopant material. Optionally, the mass percentage of the dopant material in the light-emitting layer is 1% to 20%.

[0164] The dopant material as the light-emitting material can include phosphorescent or fluorescent materials or thermally activated delayed fluorescent materials. Red, green, and blue lights can be selected from the above three dopant materials. For example, the dopant material of the light-emitting layer corresponding to the light-emitting unit with a red light-emitting color and the light-emitting layer corresponding to the light-emitting unit with a green light-emitting color is a phosphorescent material, and the dopant material of the light-emitting layer corresponding to the light-emitting unit with a blue light-emitting color is a fluorescent material.

[0165] Or, for example, the dopant material of the light-emitting layer corresponding to the light-emitting unit with a red light-emitting color and the light-emitting layer corresponding to the light-emitting unit with a green light-emitting color is a phosphorescent material, and the dopant material of the light-emitting layer corresponding to the light-emitting unit with a blue light-emitting color is a phosphorescent material.

[0166] Or, for example, the dopant material of the light-emitting layer corresponding to the light-emitting unit with a red light-emitting color and the light-emitting layer corresponding to the light-emitting unit with a green light-emitting color is a thermally activated delayed fluorescent material, and the dopant material of the light-emitting layer corresponding to the light-emitting unit with a blue light-emitting color is a fluorescent material.

[0167] Alternatively, for example, the host doping material of the light-emitting layer corresponding to the light-emitting unit with a red emission color and the host doping material of the light-emitting layer corresponding to the light-emitting unit with a green emission color are thermally activated delayed fluorescence materials, and the host doping material of the light-emitting layer corresponding to the light-emitting unit with a blue emission color is a phosphorescent material.

[0168] To reduce the power consumption of the organic light-emitting display panel in the organic electroluminescent device, the host doping material can be selected as a host doping material with excellent light-emitting performance. Taking a top-emitting device as an example, optionally, when the emission brightness of the light-emitting unit with a red emission color is 1000 cd / m 2 the current efficiency is greater than 30 cd / A, when the emission brightness of the light-emitting unit with a green emission color is 6000 cd / m 2 the current efficiency is greater than 100 cd / A, when the emission brightness of the light-emitting unit with a fluorescent blue emission color is 1000 cd / m 2 the current efficiency is greater than 5 cd / A as the standard, and when the emission brightness of the light-emitting unit with a phosphorescent blue emission color is 1000 cd / m 2 the current efficiency is greater than 10 cd / A as the standard. When the current efficiency is higher, the power consumption can be reduced.

[0169] It should be noted that as the light-emitting host material, one light-emitting host material or two light-emitting host materials can be selected.

[0170] The first electron transport layer:

[0171] The thickness of the first electron transport layer can generally be 3 nm to 40 nm, 3 nm to 10 nm, 10 nm to 20 nm, 20 nm to 30 nm, 30 nm to 40 nm, or 20 nm to 40 nm, etc. When there is no second electron transport layer, the thickness of the first electron transport layer is generally 20 nm to 50 nm, and when there is a second electron transport layer, the thickness of the first electron transport layer is generally 40 nm to 20 nm. The first electron transport layer is in direct contact with the light-emitting layer. Therefore, similar to the first hole transport layer, electron changes will also occur during electron transport, resulting in increased molecular vibration and molecular deformation. Also, due to the interaction between the excitons in the light-emitting layer and the polarons of the electron transport material, this interaction is likely to generate active free radicals and damage the electron transport material. The electron transport material can be a single compound or a mixture with other metals or metal compounds, such as a mixture with Liq. It can include a mixture of an organic electron transport material and a metal compound, or a mixture of an organic electron transport material and a metal.

[0172] When an organic electron transport material is mixed with a metal compound material, for example, mixed with an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, more specifically, mixed with a lithium metal compound, a calcium metal compound, a magnesium metal compound, a samarium metal compound, a ytterbium metal compound, etc., and more specifically, mixed with lithium 8-hydroxyquinoline, lithium fluoride, magnesium fluoride, ytterbium fluoride, calcium fluoride, etc. When used in combination with a metal compound, the mass ratio of the organic electron transport material can be 20% - 80%, 20% - 40%, 40% - 60%, or 60% - 80%, etc.

[0173] When an organic electron transport material is used in combination with a metal, for example, mixed with an alkali metal, an alkaline earth metal, a rare earth metal, more specifically, mixed with a lithium metal, a magnesium metal, a calcium metal, a ytterbium metal, a samarium metal, etc. When used in combination with a metal, the mass ratio of the organic electron transport material can be 80% - 99%, 80% - 89%, 89% - 99%, 80% - 85%, 85% - 90%, 90% - 95%, or 95% - 99%, etc.

[0174] Second electron transport layer:

[0175] The thickness of the second electron transport layer is generally 10 nm - 40 nm. The material of the second electron transport layer can include a mixture of an organic electron transport material and a metal compound, or a mixture of an organic electron transport material and a metal.

[0176] When an organic electron transport material is mixed with a metal compound material, for example, mixed with an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, more specifically, mixed with a lithium metal compound, a calcium metal compound, a magnesium metal compound, a samarium metal compound, a ytterbium metal compound, etc., and more specifically, mixed with lithium 8-hydroxyquinoline, lithium fluoride, magnesium fluoride, ytterbium fluoride, calcium fluoride, etc. When used in combination with a metal compound, the mass ratio of the organic electron transport material can be 20% - 80%, 20% - 40%, 40% - 60%, or 60% - 80%, etc.

[0177] When an organic electron transport material is used in combination with a metal, for example, mixed with an alkali metal, an alkaline earth metal, a rare earth metal, more specifically, mixed with a lithium metal, a magnesium metal, a calcium metal, a ytterbium metal, a samarium metal, etc. When used in combination with a metal, the mass ratio of the organic electron transport material can be 80% - 99%, 80% - 89%, 89% - 99%, 80% - 85%, 85% - 90%, 90% - 95%, or 95% - 99%, etc.

[0178] Charge generation layer:

[0179] When a single-layer light-emitting layer device is adopted, holes and electrons are injected from the anode and the cathode respectively, and no charge generation layer is required. When a double-layer or multi-layer light-emitting layer is adopted, a charge generation layer is required between the light-emitting layers to achieve the effects of charge generation, injection and transport. The charge generation layer is located between two light-emitting layers and is generally composed of two P / N-type materials. The P-type material is selected from the hole injection materials mentioned above, and the N-type material is a mixture of an organic electron transport material and a metal. The organic electron transport layer material is selected from the second electron transport layer mentioned above, and the metal is selected from alkali metals, alkaline earth metals, and rare earth metals. More specifically, examples include lithium metal, magnesium metal, calcium metal, ytterbium metal, samarium metal, etc. When the organic electron transport material is used in combination with the metal, the mass ratio of the organic electron transport material can be 80% - 99%, 80% - 89%, 89% - 99%, 80% - 85%, 85% - 90%, 90% - 95%, or 95% - 99%, etc.

[0180] Cathode:

[0181] The cathode requires a material with good conductivity and good surface flatness. To improve the electron injection ability, a material with a small work function is usually selected. The cathode material can be a single-layer cathode or a double-layer or multi-layer cathode, and generally metals or metal alloys are used. For a single-layer cathode, silver, copper, aluminum, gold, or alloys of these metals with other metals can be used, such as alloys with rare earth metals, alkali metals, and alkaline earth metals. Examples include magnesium indium alloy, magnesium aluminum alloy, aluminum potassium alloy, aluminum scandium potassium alloy, magnesium silver alloy, silver ytterbium alloy, silver samarium alloy, etc. If the cathode is a double-layer metal, the cathode closer to the light-emitting layer can use alkali metals, alkaline earth metals, rare earth metals, etc., such as lithium, calcium, magnesium, ytterbium, etc., to increase the electron injection ability. The cathode layer far from the light-emitting side is mainly to improve the conductivity and generally can use silver, copper, aluminum, gold, or alloys of these metals with other metals, such as alloys with rare earth metals, alkali metals, and alkaline earth metals. Examples include magnesium indium alloy, magnesium aluminum alloy, aluminum potassium alloy, aluminum scandium potassium alloy, magnesium silver alloy, silver ytterbium alloy, silver samarium alloy, etc. The cathode can also form a thin film by methods such as evaporation and sputtering.

[0182] When the light comes out from the anode side, the cathode is required to be non-transparent, and a cathode with a thickness greater than 100 nm can be evaporated. When the light comes out from the cathode side, the cathode is required to be transparent, and the transmittance at this time should be greater than 40%, and the thickness is 10 nm - 20 nm.

[0183] Cover layer:

[0184] For a single-layer cover layer, the refractive index n and the absorption coefficient need to meet the following conditions:

[0185] The refractive index n(450 - 650nm) between wavelengths of 450 to 650nm > 1.8, and the extinction coefficient between wavelengths of 450 to 650nm is below 0.1; the extinction coefficient at 380nm is greater than 0.2; the difference in refractive index between 450nm and 530nm, n(450nm) - n(530nm) < 0.5, more preferably n(450nm) - n(530nm) < 0.3; the difference in refractive index between 510nm and 620nm, n(510nm) - n(620nm) < 0.4, more preferably the difference in refractive index between 510nm and 620nm, n(510nm) - n(620nm) < 0.2.

[0186] Materials that can meet the requirements of the refractive index n of the cover layer can further achieve high luminous efficiency of the device, while achieving a more balanced effect of the light extraction efficiency and viewing angle of red, green, and blue light.

[0187] In some specific embodiments, the thickness of the cover layer is 50nm to 90nm, such as 50nm, 55nm, 57nm, 59nm, 62nm, 64nm, 67nm, 68nm, 70nm, 75nm, 77nm, 79nm, 80nm, 82nm, 85nm, 88nm, 90nm, etc.

[0188] After the cover layer is formed on the side of the semi - transparent cathode of the OLED display panel away from the substrate, the light transmittance of the stack formed by the cover layer and the semi - transparent cathode for light between 450nm and 650nm ≥ 65%, such as 68%, 69%, 73%, 77%, 79%, 83%, 88%, 93%, etc.

[0189] When using two layers of cover layers, the refractive index n and the absorption coefficient need to meet the following conditions:

[0190] For the cover layer closer to the cathode side (the first cover layer), the refractive index n(450 - 650nm) between wavelengths of 450 to 650nm < 1.8, and the extinction coefficient between wavelengths of 450 to 650nm is below 0.1; the maximum coefficient at any wavelength directly between 250nm and 350nm wavelengths is greater than 0.3, optimally greater than 0.6.

[0191] For the cover layer farther from the cathode side (the second cover layer), the refractive index n(450 - 650nm) between wavelengths of 450 to 650nm > 1.8, and the extinction coefficient between wavelengths of 450 to 650nm is below 0.1; the extinction coefficient at 380nm is greater than 0.1, more optimally greater than 0.2.

[0192] The difference in refractive index between 450 nm and 530 nm, n(450 nm) - n(530 nm) < 0.5, and more preferably, the difference in refractive index between 450 nm and 530 nm, n(450 nm) - n(530 nm) < 0.3;

[0193] The difference in refractive index between 510 nm and 620 nm, n(510 nm) - n(620 nm) < 0.4, and more preferably, the difference in refractive index between 450 nm and 530 nm, n(450 nm) - n(530 nm) < 0.2.

[0194] The total thickness of the double-layer covering layer is 50 nm to 90 nm, for example: 50 nm, 55 nm, 57 nm, 59 nm, 62 nm, 64 nm, 67 nm, 68 nm, 70 nm, 75 nm, 77 nm, 79 nm, 80 nm, 82 nm, 85 nm, 88 nm, 90 nm, etc.

[0195] The thickness of the covering layer (the first covering layer) near the cathode side is 5 nm to 40 nm, for example: 5 nm, 7 nm, 10 nm, 12 nm, 15 nm, 18 nm, 20 nm, 22 nm, 25 nm, 27 nm, 30 nm, 32 nm, 34 nm, 36 nm, 38 nm, 40 nm, etc.

[0196] The thickness of the covering layer (the second covering layer) far from the cathode side is 35 nm to 85 nm, for example: 35 nm, 40 nm, 43 nm, 45 nm, 48 nm, 50 nm, 55 nm, 57 nm, 59 nm, 62 nm, 64 nm, 67 nm, 68 nm, 70 nm, 75 nm, 77 nm, 79 nm, 80 nm, 82 nm, 85 nm, etc.

[0197] On the other hand, the present application also provides a display or lighting device, including the above-mentioned organic electroluminescent device.

[0198] Next, the technical solutions of the present application will be clearly and completely described in conjunction with the embodiments of the present application. Unless otherwise specified, the reagents and raw materials used can be purchased through commercial channels. The experimental methods without specific conditions in the following embodiments are usually determined according to national standards. If there is no corresponding national standard, they are determined according to general international standards, conventional methods and conditions, or according to the conditions recommended by the manufacturer, or according to the product instructions. Unless otherwise stated, all parts are parts by weight and all percentages are percentages by weight.

[0199] The synthesis of the compounds of the present application can be carried out using known methods. For example, cross-coupling reactions using transition metals such as nickel and palladium, or C-C and C-N coupling formation reactions using transition metals such as magnesium or zinc can be used. Considering the mild reaction conditions and excellent selectivity of various functional groups, the Suzuki and Buchwald reactions are preferred. The starting materials and solvents of the following examples were purchased from Jiangsu March Optoelectronics Co., Ltd., and some commonly used OLED intermediate products were purchased from domestic OLED intermediate manufacturers; various palladium catalysts, ligands, etc. were purchased from sigma Aldrich. 1 1H NMR data was measured using a JEOL (400 MHz) nuclear magnetic resonance spectrometer; HPLC data was measured using a Shimadzu LC 20AD high-performance liquid chromatograph; LC-MS (liquid chromatography-mass spectrometry) was tested on an H-class + SQD2 model instrument of Waters Corporation.

[0200] Example 1

[0201] Synthesis of Compound 1-1

[0202] Synthesis route:

[0203]

[0204] Synthesis method: Under an argon atmosphere, 42.7 g (101 mmol) of Compound 1-A, 35.3 g (100 mmol) of Compound 1-B, 787 mg (1 mmol%) of XPhos Pd G3 (CAS No. 1445085-55-1), 50 mL (300 mmol) of 1.5 M potassium phosphate, and 1000 mL of tetrahydrofuran (THF) were added to a reaction vessel, and the mixture was refluxed with heating and stirred for 12 hours. After the reaction was completed, it was cooled to room temperature, 800 mL of water was added, and a large amount of solid precipitated. The mixture was filtered, and the filter cake was washed with water three times and dried in vacuo to obtain the crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 51.8 g of Compound 1-1, with a yield of 79% and an HPLC purity of 99.9%. LC-MS (liquid chromatography-mass spectrometry): M / Z 655.23 (M+).

[0205] Example 2

[0206] Synthesis of Compound 2-1

[0207] Synthesis route:

[0208]

[0209] Synthesis method: Refer to Example 1. Except that Compound 1-B was replaced with Compound 2-B, other conditions were the same as those in Example 1. The yield was 76%, and the HPLC purity was 99.9%. LC-MS: M / Z 705.24 (M+).

[0210] Example 3

[0211] Synthesis of Compound 3-1

[0212] Synthesis route:

[0213]

[0214] Synthesis method: Refer to Example 1. Except that Compound 1-A and Compound 1-B were replaced with Compound 3-A and Compound 3-B respectively, other conditions were the same as those in Example 1. The yield was 76%, and the HPLC purity was 99.9%. LC-MS: M / Z705.24 (M+).

[0215] Example 4

[0216] Synthesis of Compound 4-1

[0217] Synthesis route:

[0218]

[0219] Synthesis method: Refer to Example 1. Except that Compound 1-B was replaced with Compound 4-B, other conditions were the same as those in Example 1. The yield was 77%, and the HPLC purity was 99.9%. LC-MS: M / Z 705.82 (M+).

[0220] Example 5

[0221] Synthesis of Compound 5-1

[0222] Synthesis route:

[0223]

[0224] Synthesis method: Refer to Example 1. Except that Compound 1-B was replaced with Compound 5-B, other conditions were the same as those in Example 1. The yield was 72%, and the HPLC purity was 99.9%. LC-MS: M / Z 678.79 (M+). "

[0225] Example 6

[0226] Synthesis of Compound 6-1

[0227] Synthesis route:

[0228]

[0229] Synthesis method: Refer to Example 1. Except that Compound 1-A and Compound 1-B are replaced with Compound 6-A and Compound 3-B respectively, other conditions are the same as those in Example 1. The yield is 76%, and the HPLC purity is 99.9%. LC-MS: M / Z 810.27 (M+).

[0230] Example 7

[0231] Synthesis of Compound 7-1

[0232] Synthesis route:

[0233]

[0234] Synthesis method: Refer to Example 1. Except that Compound 1-A and Compound 1-B are replaced with 6-A and 7-B respectively, other conditions are the same as those in Example 1. The yield is 70%, and the HPLC purity is 99.9%. LC-MS: M / Z 962.34 (M+).

[0235] Example 8

[0236] Synthesis of Compound 1-2

[0237] Synthesis route:

[0238]

[0239] Synthesis method: Refer to Example 1. Except that Compound 1-B is replaced with 8-B, other conditions are the same as those in Example 1. The yield is 75%, and the HPLC purity is 99.9%. LC-MS: M / Z 745.84 (M+).

[0240] Example 9

[0241] Synthesis of Compound 1-3

[0242] Synthesis route:

[0243]

[0244] Synthesis method: Refer to Example 1. Except that Compound 1-B is replaced with 9-B, other conditions are the same as those in Example 1. The yield is 73%, and the HPLC purity is 99.9%. LC-MS: M / Z 731.26 (M+).

[0245] Example 10

[0246] Synthesis of Compound 10-1

[0247] Synthesis route:

[0248]

[0249] Synthesis method: Refer to Example 1. Except for replacing compound 1-B with 10-B, the other steps were the same as in Example 1. The yield was 76%, and the HPLC purity was 99.9%. LC-MS: M / Z 871.28 (M+).

[0250] Embodiment 11

[0251] Synthesis of compound 40-1

[0252] Synthesis route:

[0253]

[0254] Synthesis method:

[0255] 1) Synthesis of Intermediate 40-1A

[0256] Under an argon atmosphere, a reaction vessel was charged with 50.3 g (100 mmol) of compound 11-A, 20.9 g (100 mmol) of compound 11-B, 23.4 g (240 mmol) of sodium tert-butoxide, 575 mg (1 mmol%) of bis(dibenzylideneacetonepalladium), 348 mg (1.2 mmol%) of tri-tert-butylphosphine tetrafluoroborate, and 1000 mL of xylene. The mixture was heated and stirred at 140°C for 15 hours. The reaction mixture was cooled to room temperature, 1000 mL of water was added, and the mixture was filtered. The filter cake was washed with copious amounts of water and dried under vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 48.6 g of intermediate 40-1A, with a yield of 77% and an HPLC purity of 99.6%. LC MS: M / Z 631.25 (M+).

[0257] 2) Synthesis of Compound 40-1

[0258] Refer to the synthesis method of Intermediate 40-1A. The synthesis method was identical to Intermediate 40-1, except that Compound 11-A and Compound 11-B were replaced with Intermediate 40-1A and Compound 11-C, respectively. The yield was 74%, the HPLC purity was 99.9%, and the LC MS showed M / Z 797.29 (M+).

[0259] Example 12

[0260] Synthesis of compound 41-1

[0261] Synthesis route:

[0262]

[0263] Synthesis method: Except for replacing compound 11-A with compound 3-A, other procedures can refer to Example 11. The yield is 55%, the HPLC purity is 99.9%, LC MS: M / Z 721.26 (M+).

[0264] Example 13

[0265] Synthesis of Compound 42-1

[0266] Synthesis route:

[0267]

[0268] Synthesis method: Except for replacing compound 11-A, compound 11-B and compound 11-C with compound 13-A, compound 13-B and compound 13-C respectively, other procedures can refer to Example 11. The yield is 51%, the HPLC purity is 99.9%, LCMS: M / Z 681.23 (M+).

[0269] Example 14

[0270] Synthesis of Compound 43-1

[0271] Synthesis route:

[0272]

[0273] Synthesis method: Except for replacing compound 11-A, compound 11-B and compound 11-C with compound 1-A, compound 14-B and compound 13-C respectively, other procedures can refer to Example 11. The yield is 54%, the HPLC purity is 99.9%, LCMS: M / Z 667.25 (M+).

[0274] Example 15

[0275] Synthesis of Compound 43-2

[0276] Synthesis route:

[0277]

[0278] Synthesis method: Except for replacing compound 11-A, compound 11-B and compound 11-C with compound 1-A, compound 15-B and compound 13-C respectively, other procedures are the same as those in Example 11. LC MS: M / Z 756.28 (M+). HPLC purity: 99.9%, total yield: 51%.

[0279] Example 16

[0280] Synthesis of Compound 44-1

[0281] Synthetic route:

[0282]

[0283] Synthetic method: Except for replacing compound 11-B and compound 11-C with compound 14-B and compound 13-C respectively, the synthesis is the same as that of Example 11. LC MS: M / Z 743.28 (M+). HPLC purity is 99.9%, and the total yield is 59%.

[0284] Example 17

[0285] Synthesis of compound 45-1

[0286] Synthetic route:

[0287]

[0288] Synthetic method: Except for replacing compound 11-A, compound 11-B and compound 11-C with compound 3-A, compound 17-B and compound 17-C respectively, the synthesis is the same as that of Example 11. LC MS: M / Z 873.32 (M+). HPLC purity is 99.9%, and the total yield is 54%.

[0289] Example 18

[0290] Synthesis of compound 46-1

[0291] Synthetic route:

[0292]

[0293] Synthetic method: Except for replacing compound 11-A, compound 11-B and compound 11-C with compound 3-A, compound 18-B and compound 18-C respectively, the synthesis is the same as that of Example 11. LC MS: M / Z 833.29 (M+). HPLC purity: 99.9%, total yield: 50%.

[0294] Example 19

[0295] Synthesis of compound 47-1

[0296] Synthetic route:

[0297]

[0298] Synthesis method: Except for replacing compound 11-A, compound 11-B, and compound 11-C with compound 6-A, compound 19-B, and compound 19-C respectively, the synthesis is the same as that in Example 11. LC MS: M / Z 682.26 (M+). HPLC purity: 99.9%, total yield: 57%.

[0299] Example 20

[0300] Synthesis of compound 48-1

[0301] Synthesis route

[0302]

[0303] Synthesis method: Except for replacing compound 11-A, compound 11-B, and compound 11-C with compound 20-A, compound 19-B, and compound 20-C respectively, the synthesis is the same as that in Example 11. LC MS: M / Z 682.26 (M+). HPLC purity: 99.9%, total yield: 57%.

[0304] Example 21

[0305] Synthesis of compound 51

[0306] Synthesis route:

[0307]

[0308] Synthesis method:

[0309] 1) Synthesis of intermediate 51-1A

[0310] Under an argon atmosphere, 25.7 g (100 mmol) of compound 21-A, 17.2 g (100 mmol) of compound 21-B, 787 mg (1 mmol%) of XPhos Pd G3, 50 mL (300 mmol) of 1.5 M potassium phosphate, and 1000 mL of tetrahydrofuran (THF) were added to a reaction vessel, and the mixture was refluxed with heating and stirring for 12 hours. After cooling to room temperature, 800 mL of water was added, and a large amount of solid precipitated. The mixture was filtered, and the filter cake was washed with water three times and dried in vacuo. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 24.7 g of compound 51-1A. Yield: 81%, HPLC purity: 99.5%. LC-MS: M / Z 304.13 (M+).

[0311] 2) Synthesis of intermediate 51-1B

[0312] Add 200 mL of DMF to the reaction vessel, then add 17.8 g (100 mmol) of compound NBS and 30.4 g (100 mmol) of intermediate 51-1A. Stir at room temperature for 4 hours. Add 500 mL of water, and a large amount of solid precipitates. Filter, wash the filter cake with water 3 times, and dry it under vacuum. The crude product is purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 24.7 g of intermediate 51-1B, yield: 91%, HPLC purity: 99.7%. LC-MS: M / Z 382.04 (M+).

[0313] 3) Synthesis of compound 51

[0314] Under an argon atmosphere, add 38.2 g (100 mmol) of intermediate 51-1B, 39.2 g (100 mmol) of compound 21-C, 787 mg (1 mmol%) of XPhos Pd G3, 50 mL (300 mmol) of 1.5 M potassium phosphate, and 1000 mL of tetrahydrofuran (THF) to the reaction vessel. Reflux and stir for 12 hours. Cool to room temperature, add 800 mL of water, and a large amount of solid precipitates. Filter, wash the filter cake with water 3 times, and dry it under vacuum. The crude product is purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 48.2 g of compound 51, yield: 74%, HPLC purity: 99.9%. LC-MS: M / Z 650.22 (M+).

[0315] Example 22

[0316] Synthesis of compound 52

[0317] Synthesis route:

[0318]

[0319] Synthesis method: Except for replacing compound 21-B and compound 21-C with compound 22-B and compound 22-C respectively, the synthesis is the same as that in Example 21. LC MS: M / Z 676.24 (M+). HPLC purity: 99.9%, total yield: 54.5%.

[0320] Example 23

[0321] Synthesis of compound 53

[0322] Synthesis route:

[0323]

[0324] Synthesis method: The synthesis is the same as that of Example 21, except that compound 21-B and compound 21-C are replaced with compound 23-B and compound 23-C respectively. LC MS: M / Z 690.22 (M+). HPLC purity: 99.9%, total yield: 51%.

[0325] Example 24

[0326] Synthesis of Compound 24

[0327] Synthesis route:

[0328]

[0329] Synthesis method: The synthesis is the same as that of Example 21, except that compound 21-B and compound 21-C are replaced with compound 24-B and compound 23-C respectively. LC MS: M / Z 700.24 (M+). HPLC purity: 99.9%, total yield: 53%.

[0330] Example 25

[0331] Synthesis of Compound 55

[0332] Synthesis route:

[0333]

[0334] Synthesis method: The synthesis is the same as that of Example 21, except that compound 21-B and compound 21-C are replaced with compound 25-B and compound 23-C respectively. LC MS: M / Z 838.29 (M+). HPLC purity: 99.9%, total yield: 51%.

[0335] Example 26

[0336] Synthesis of Compound 56

[0337] Synthesis route:

[0338]

[0339] Synthesis method: The synthesis is the same as that of Example 21, except that compound 21-B and compound 21-C are replaced with compound 26-B and compound 22-C respectively. LC MS: M / Z 740.24 (M+). HPLC purity: 99.9%, total yield: 52%.

[0340] Example 27

[0341] Synthesis of Compound 57

[0342] Synthesis route:

[0343]

[0344] Synthesis method: Except that compound 21-B and compound 21-C are replaced with compound 27-B and compound 27-C respectively, the synthesis is the same as that of Example 21. LC MS: M / Z 816.27 (M+). HPLC purity: 99.9%, total yield: 50%.

[0345] Example 28

[0346] Synthesis of Compound 60

[0347] Synthesis route:

[0348]

[0349] Synthesis method: Except that compound 21-B and compound 21-C are replaced with 28-B and 28-C respectively, the synthesis is the same as that of Example 21. LC MS: M / Z 752.27 (M+). HPLC purity: 99.9%, total yield: 50%.

[0350] Example 29

[0351] Synthesis of Compound 61

[0352] Synthesis route:

[0353]

[0354] Synthesis method: Except that compound 21-B and compound 21-C are replaced with 29-B and 23-C respectively, the synthesis is the same as that of Example 21. LC MS: M / Z 776.27 (M+). HPLC purity: 99.9%, total yield: 53%.

[0355] Example 30

[0356] Synthesis of Compound 62

[0357] Synthesis route:

[0358]

[0359] Synthesis method: Except that compound 21-B and compound 21-C are replaced with 30-B and 30-C respectively, the synthesis is the same as that of Example 21. LC MS: M / Z 914.32 (M+). HPLC purity: 99.9%, total yield: 52%.

[0360] Example 31

[0361] Synthesis of Compound 68

[0362] Synthesis route:

[0363]

[0364] Synthesis method:

[0365] 1) Synthesis of Intermediate 68-1

[0366] Under an argon atmosphere, a reaction vessel was charged with 69.4 g (101 mmol) of compound 31-A, 21.3 g (100 mmol) of compound 31-B, 787 mg (1 mmol%) of XPhos Pd G3, 50 mL (300 mmol) of 1.5 M potassium phosphate, and 1000 mL of tetrahydrofuran (THF). The mixture was stirred under reflux for 12 hours. After cooling to room temperature, 800 mL of water was added. A large amount of solid precipitated and was filtered. The filter cake was washed three times with water and dried under vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 67.1 g of compound 68-1, with a yield of 70% and a purity of 99.3% by HPLC. LC-MS: M / Z 957.50 (M+).

[0367] 2) Synthesis of Compound 68

[0368] Under an argon atmosphere, a reaction vessel was charged with 95.7 g (100 mmol) of compound 68-1, 39.2 g (100 mmol) of compound 31-C, 23.4 g (240 mmol) of sodium tert-butoxide, 575 mg (1 mmol%) of bisdibenzylideneacetonepalladium, 348 mg (1.2 mmol%) of tri-tert-butylphosphine tetrafluoroborate, and 1000 mL of xylene. The mixture was heated and stirred at 140°C for 15 hours. The reaction mixture was cooled to room temperature, 1000 mL of water was added, and the mixture was filtered. The filter cake was washed with a large amount of water and dried under vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 88.9 g of compound 68 with an HPLC purity of 99.9% and a yield of 67%. LC MS: M / Z 1269.64 (M+).

[0369] Embodiment 32

[0370] Synthesis of compound 69

[0371] Synthesis route:

[0372]

[0373] Synthesis method: Except for replacing compound 68-1 and compound 31-C with 32-A and 31-B respectively, the synthesis of compound 68 in Example 31 is the same. LC MS: M / Z 1137.54 (M+). HPLC purity: 99.9%, yield: 65%.

[0374] Example 33

[0375] Synthesis of Compound 70

[0376] Synthesis route:

[0377]

[0378] Synthesis method: Except for replacing compound 32-A and compound 31-B with compound 33-A and compound 33-B respectively, the synthesis of Example 32 is the same. LC MS: M / Z 1137.54 (M+). HPLC purity: 99.9%, yield: 69%.

[0379] Example 34

[0380] Synthesis of Compound 71

[0381] Synthesis route:

[0382]

[0383] Synthesis method: Except for replacing compound 32-A and compound 31-B with compound 34-A and compound 34-B respectively, the synthesis of Example 32 is the same. LC MS: M / Z 1137.54 (M+). HPLC purity: 99.9%, yield: 66%.

[0384] Example 35

[0385] Synthesis of Compound 72

[0386] Synthesis route:

[0387]

[0388] Synthesis method: Except for replacing compound 32-A and compound 31-B with compound 35-A and compound 35-B respectively, the synthesis of Example 32 is the same. LC MS: M / Z 1137.54 (M+). HPLC purity: 99.9%, yield: 61%.

[0389] Example 36

[0390] Synthesis of Compound 73

[0391] Synthesis route:

[0392]

[0393] Synthesis method: Except that compound 31-A, compound 31-B, and compound 31-C are replaced with compound 36-A, compound 36-B, and compound 36-C respectively, the synthesis is the same as that of Example 31. LC MS: M / Z 1325.61 (M+). HPLC purity: 99.9%, total yield: 51%.

[0394] Example 37

[0395] Synthesis of Compound 74

[0396] Synthesis route:

[0397]

[0398] Synthesis method: Except that compound 31-A, compound 31-B, and compound 31-C are replaced with compound 37-A, compound 37-B, and compound 37-C respectively, the synthesis is the same as that of Example 31. LC MS: M / Z 1325.61 (M+). HPLC purity: 99.9%, total yield: 49%.

[0399] Example 38

[0400] Synthesis of Compound 75

[0401] Synthesis route:

[0402]

[0403] Synthesis method: Except that compound 31-A, compound 31-B, and compound 31-C are replaced with compound 38-A, compound 38-B, and compound 38-C respectively, the synthesis is the same as that of Example 31. LC MS: M / Z 1269.55 (M+). HPLC purity: 99.9%, total yield: 51%.

[0404] Example 39

[0405] Synthesis of Compound 76

[0406] Synthesis route:

[0407]

[0408] Synthesis method: Except that compound 31-A, compound 31-B and compound 31-C are replaced with compound 39-A, compound 39-B and compound 39-C respectively, the synthesis is the same as that of Example 31. LC MS: M / Z 1233.63 (M+). HPLC purity: 99.9%, total yield: 56%.

[0409] Example 40

[0410] Synthesis of Compound 77

[0411] Synthesis route:

[0412]

[0413] Synthesis method: Except that compound 32-A and compound 31-B are replaced with compound 40-A and compound 40-C respectively, the synthesis is the same as that of Example 32. LC MS: M / Z 1101.54 (M+). HPLC purity: 99.9%, yield 77%.

[0414] Preparation of Organic Electroluminescent Device

[0415] The organic electroluminescent device is prepared using the compound of the present application as the electron transport material. Other compounds involved, in addition to the compound of the present application, are as follows:

[0416]

[0417] Device Example 1

[0418] The basic structural model of the organic electroluminescent device prepared in this example is:

[0419] ITO / HAT-CN(10nm) / TAPC(40nm) / TCTA(10nm) / RH-1:RD(Ir complex)=94:6(40nm) / Compound 1-1(30nm) / LiF(1nm) / Al(80nm).

[0420] Reference Figure 1 , the method for preparing the organic electroluminescent device in this example includes:

[0421] (1) The transparent anode ITO (indium tin oxide) glass substrate (surface resistivity of 10 Ω / sq) is ultrasonically cleaned successively with acetone, ethanol and distilled water, and then treated with ozone plasma for 15 minutes. The transparent anode ITO (indium tin oxide) glass substrate includes an ITO glass substrate 101 and an anode 102 located on the ITO glass substrate 101.

[0422] (2) After installing the transparent anode ITO glass substrate 100 on the substrate holder of the vacuum vapor deposition equipment, the system pressure is controlled at 10 -6 Torr, and then successively deposit HAT-CN with a thickness of 10 nm, TAPC with a thickness of 40 nm, and TCTA with a thickness of 10 nm on the transparent anode ITO glass substrate 100 to form a hole injection layer 103, a hole transport layer 104, and an electron blocking layer 105 respectively.

[0423] (3) Deposit a light-emitting layer (EML) 106 with a thickness of 40 nm on the TCTA. The composition of the light-emitting layer 106 includes RH-1 and RD with a mass ratio of 94:6.

[0424] (4) Deposit the compound 1-1 of the present application with a thickness of 30 nm on the light-emitting layer 106 as an electron transport layer (ETL) 107.

[0425] (5) Deposit LiF with a thickness of 1 nm on the electron transport layer 107 as an electron injection layer 108.

[0426] (6) Deposit Al with a thickness of 80 nm on the electron injection layer 108 as a cathode 109, and encapsulate the device with a glass encapsulation cover 110.

[0427] Device Examples 2-10

[0428] Except that when forming the electron transport layer 107, compounds 2-1, 3-1, 4-1, 5-1, 6-1, 7-1, 1-2, 1-3, and 10-1 are used to replace the compound 1-1 respectively, the organic electroluminescent device is fabricated by the same method as in Device Example 1.

[0429] Device Comparative Example 1

[0430] Except that when forming the electron transport layer 107, the compound ETL-1 is used to replace the compound 1-1, the organic electroluminescent device is fabricated by the same method as in Device Example 1.

[0431] The above-prepared organic electroluminescent devices are tested by a computer-controlled Keithley 2400 test system, and the operating voltage and current efficiency are calculated.

[0432] The operating voltage refers to the voltage when the OLED is in normal operation. According to the usage environment, it can be expressed in terms of current or brightness. When expressed in terms of current, the general operating environment is 5 mA / cm 2 ~20 mA / cm 2 , preferably 10 mA / cm 2 , 15 mA / cm 2 . When 10 mA / cm 2Taking [time] as an example, the operating voltage can be described as the voltage at 10 mA / cm 2 Under the condition of 2 . When expressed in terms of luminance, the general operating environment is 500 nit to 20,000 nit, and the environments for red, green, and blue light are generally different. The operating voltage at this time is described as the voltage at a certain luminance. The lower the voltage, the lower the power consumption. The test current of this application is 10 mA / cm 2 .

[0433] The LT95 device lifetime under dark conditions was obtained using a Fluorstar lifetime measurement system equipped with a power supply and a photodiode as the detection unit. The LT95 device lifetime refers to the time required for the luminance at the initial luminance to decrease to 95% of the initial luminance. The longer the time, the longer the device lifetime.

[0434] Each group of device examples and device comparative example 1 devices were produced and tested in the same batch. The operating voltage, current efficiency, and LT95 lifetime of the devices in device comparative example 1 were all recorded as 1, and the ratios of the corresponding indicators of device examples 1 to 10 and device comparative example 1 were calculated respectively, obtaining the relative operating voltage, relative current efficiency, and relative lifetime shown in Table 1.

[0435] Table 1 Test results of device examples 1 to 10 and device comparative example 1

[0436] Device ETL Material Relative Operating Voltage Relative Current Efficiency Relative Lifetime Device Comparative Example 1 ETL-1 1 1 1 Device Example 1 Compound 1-1 0.931 1.135 1.234 Device Example 2 Compound 2-1 0.953 1.346 1.354 Device Example 3 Compound 3-1 0.946 1.278 1.678 Device Example 4 Compound 4-1 0.957 1.356 1.653 Device Example 5 Compound 5-1 0.964 1.431 1.590 Device Example 6 Compound 6-1 0.931 1.268 1.435 Device Example 7 Compound 7-1 0.945 1.359 1.532 Device Example 8 Compound 8-1 0.921 1.468 1.368 Device Example 9 Compound 9-1 0.976 1.367 1.374 Device Example 10 Compound 10-1 0.961 1.389 1.382

[0437] Except for the different ETLs, the other structures of device examples 1 to 10 and device comparative example 1 are the same. Based on the performance of the device prepared with ETL-1 as the electron transport material in device comparative example 1 as a reference, for the device prepared with the compound of this application as the electron transport material, its operating voltage decreased significantly, and the current efficiency and lifetime were significantly improved.

[0438] The following uses the compound of this application as the hole transport material to prepare an organic electroluminescent device. Except for the compound of this application, the other compounds involved are as follows:

[0439]

[0440] Device example 11

[0441] The basic structure model of the organic electroluminescent device prepared in this example is:

[0442] ITO(150 nm) / T-1:T-2 = 3:97(10 nm) / T-2(100 nm) / Compound 40-1(10 nm) / T-3:T-4 = 95:5(40 nm) / T-5(10 nm) / T-6:LiQ = 4:6(30 nm) / Mg:Ag = 1:9(80 nm).

[0443] Reference Figure 2 , the method for preparing an organic light-emitting device in this embodiment includes:

[0444] (1) On a substrate 100 made of glass, a 150-nm-thick transparent anode ITO film layer is formed to obtain a first electrode as the anode 110.

[0445] (2) By means of vacuum evaporation, a mixed material of compound T-1 and compound T-2 is evaporated on the surface of the anode 110 as the hole injection layer 120, with a mixing ratio of 3:97 (mass ratio) and a thickness of 10 nm.

[0446] (3) 100 nm of compound T-2 is evaporated on the hole injection layer 120 to obtain the first hole transport layer 130.

[0447] (4) 10 nm of compound 40-1 is evaporated on the first hole transport layer 130 to obtain the second hole transport layer 140.

[0448] (5) On the second hole transport layer 140, compound T-3 and compound T-4 are co-evaporated at a mass ratio of 95:5 to form an organic light-emitting layer 150 with a thickness of 40 nm.

[0449] (6) On the organic light-emitting layer 140, compound T-5 is evaporated in sequence to form a hole blocking layer 160 (with a thickness of 10 nm), and a mixed material of compound T-6 and LiQ with a mixing ratio of 4:6 (mass ratio) is evaporated to form an electron transport layer 170 (with a thickness of 30 nm).

[0450] (7) Magnesium (Mg) and silver (Ag) are mixed at an evaporation rate of 1:9 and vacuum-evaporated on the electron transport layer 170 as the second electrode 180, completing the preparation of the organic light-emitting device.

[0451] Device Examples 12 - 20

[0452] Except that when forming the second hole transport layer 140, compound 41-1, 42-1, 43-1, 43-2, 44-1, 45-1, 46-1, 47-1, and 48-1 are used to replace compound 40-1 respectively, an organic light-emitting device is fabricated using the same method as in Device Example 11.

[0453] Device Comparative Examples 2 - 3

[0454] Except that when forming the second hole transport layer 140, compound HT-1 and compound HT-2 are used to replace compound 40-1 respectively, an organic light-emitting device is fabricated using the same method as in Device Example 11.

[0455] The above-prepared organic electroluminescent devices were tested by a computer-controlled Keithley 2400 test system, and the operating voltage and luminous efficiency were calculated. The device lifetime under dark conditions was obtained using a Fluorida lifetime measurement system equipped with a power supply and a photodiode as the detection unit. The specific test conditions for each performance can be referred to the foregoing.

[0456] The devices in each group of device examples and each group of device comparative examples were produced and tested in the same batch. The operating voltage, luminous efficiency, and lifetime of the devices in device comparative example 2 were all recorded as 1, and the ratios of the corresponding indexes of device examples 11 to 20 to those of device comparative example 3 were calculated respectively, obtaining the relative operating voltage, relative luminous efficiency, and relative lifetime shown in Table 2.

[0457] Table 2 Test results of device examples 11 to 20 and device comparative examples 2 to 3

[0458]

[0459]

[0460] According to the results in Table 2, it can be seen that compared with the organic electroluminescent devices prepared in comparative examples 2 to 3, the operating voltages of the organic electroluminescent devices prepared using the compound of the present application as the second hole transport material are all reduced, the luminous efficiencies are all improved, and the lifetime is significantly improved.

[0461] Hereinafter, the compound of the present application is used as the blue light host material to prepare an organic electroluminescent device. Except for the compound of the present application, the other compounds involved are as follows:

[0462]

[0463] Device example 21

[0464] The basic structural model of the organic electroluminescent device prepared in this example is:

[0465] ITO (150 nm) / F4-TCNQ (10 nm) / NPB (110 nm) / EB-01 (10 nm) / Compound 51:BD-1 = 100:3 (10 nm) / ET-01:LiQ = 1:1 (30 nm) / Yb (15 Å) / Mg:Ag = 1:9 (11 nm) / CP-1 (65 nm).

[0466] Reference Figure 3 , the method for preparing the organic electroluminescent device in this example includes:

[0467] (1) A transparent anode ITO film layer (thickness 150 nm) was formed on the glass substrate 10 to obtain the first electrode as the anode 11.

[0468] (2) By vacuum evaporation, compound F4-TCNQ is evaporated on the surface of the anode 11 to form a hole injection layer 12 with a thickness of 10 nm, and compound NPB is vacuum-deposited on the hole injection layer 12 to form a hole transport layer (HTL) 13 with a thickness of 110 nm.

[0469] (3) Compound EB-01 with a thickness of 10 nm is evaporated on the hole injection layer 13 to obtain an electron blocking layer 14.

[0470] (4) On the electron blocking layer 14, compound 51 is used as the host, and BD-1 is doped simultaneously according to a film thickness ratio of 100:3 to form a light-emitting layer (EML) 15 with a thickness of 10 nm.

[0471] (5) On the light-emitting layer 15, ET-01 and LiQ are deposited with a film thickness ratio of 1:1 to form an electron transport layer (ETL) 16 with a thickness of 30 nm, and Yb is deposited on the electron transport layer to form an electron injection layer (EIL) 17 with a thickness of 15 Å.

[0472] (6) Magnesium (Mg) and silver (Ag) are vacuum-deposited on the electron injection layer 17 with a film thickness ratio of 1:9 to form a cathode 18 with a thickness of 11 nm.

[0473] (7) CP-1 with a thickness of 65 nm is deposited on the above-mentioned cathode 18 as an organic capping layer (CPL) 19, and the preparation of the organic electroluminescent device is completed.

[0474] Device Examples 22 - 30

[0475] Except that when forming the light-emitting layer 15, compound 52, 53, 54, 55, 56, 57, 60, 61, and 62 are used to replace compound 51 respectively, the organic electroluminescent device is fabricated by the same method as in Device Example 21.

[0476] Device Comparative Examples 4 - 5

[0477] Except that when forming the light-emitting layer 15, compound BH-1 and compound BH-2 are used to replace compound 51 of this application respectively, the organic electroluminescent device is fabricated by the same method as in Device Example 21.

[0478] The above-prepared organic electroluminescent devices are tested by a computer-controlled Keithley 2400 test system, and the operating voltage and luminous efficiency are calculated. The device lifetime under dark conditions is obtained using a Fluorida lifetime measurement system equipped with a power supply and a photodiode as the detection unit. The specific test conditions for each performance can be referred to the foregoing.

[0479] Each group of device examples and each group of device comparative examples are produced and tested in the same batch. The operating voltage, luminous efficiency, and lifespan of the devices in device comparative example 4 are each recorded as 1, and the ratios of the corresponding indicators of device examples 22 to 30 to those of device comparative example 5 are calculated respectively to obtain the relative operating voltage, relative luminous efficiency, and relative lifespan shown in Table 3.

[0480] The color purity is tested using an existing color purity testing method.

[0481] Table 3 Test results of device examples 22 - 30 and device comparative examples 4 - 5

[0482] Device EML Relative Operating Voltage Relative Luminescence Efficiency Relative Lifetime CIE-x CIE-y Device Comparative Example 4 BH-1 1 1 1 0.14 0.05 Device Comparative Example 5 BH-2 1.078 0.989 1.049 0.14 0.05 Device Example 21 51 0.963 1.147 1.326 0.14 0.05 Device Example 22 52 0.951 1.196 1.289 0.14 0.05 Device Example 23 53 0.980 1.129 1.241 0.14 0.05 Device Example 24 54 0.931 1.146 1.157 0.14 0.05 Device Example 25 55 0.937 1.157 1.331 0.14 0.05 Device Example 26 56 0.935 1.147 1.313 0.14 0.05 Device Example 27 57 0.964 1.150 1.270 0.14 0.05 Device Example 28 60 0.946 1.169 1.107 0.14 0.05 Device Example 29 61 0.958 1.131 1.227 0.14 0.05 Device Example 30 62 0.954 1.174 1.139 0.14 0.05

[0483] According to the results in Table 3, when used as the light-emitting layer of an organic electroluminescent device, compared with the devices formed by the commercial products used in device comparative examples 4 - 5, the devices using the compounds in device examples 21 - 30 have a reduced voltage, increased luminous efficiency, and improved device lifespan, and exhibit a color purity comparable to that of commercial products.

[0484] The following uses the compound of the present application as a blue light doping material to prepare an organic electroluminescent device. Other compounds involved, in addition to the compound of the present application, are as follows:

[0485]

[0486] Device example 31

[0487] The basic structural model of the organic electroluminescent device prepared in this example is:

[0488] ITO / D - 1:D - 2 = 3:97(10nm) / D - 2:D - 3 = 5:1(120nm) / BH - 3: Compound 68 = 98:2(20nm) / D - 4:LiQ = 4:6(40nm) / KI:Yb = 8:2(1nm) / Ag:Mg = 90:10(10nm).

[0489] Reference Figure 4 , the method for preparing the organic electroluminescent device in this example includes:

[0490] (1) A glass substrate 1 (a product of Corning Inc.) with a formed ITO (anode 2) of 15 Ω / cm 2 is cut into a size of 50 mm × 50 mm × 0.75 mm, ultrasonically treated with acetone, isopropyl alcohol, and pure water for 15 minutes each, and then cleaned by exposing to ultraviolet light and ozone for 30 minutes. Then, the obtained glass substrate 1 is mounted on a vacuum deposition device.

[0491] (2) HT3 was vacuum deposited on the anode 2 to form a hole injection layer 3 with a thickness of 120 nm, and HT47 was vacuum deposited on the hole injection layer 3 to form a hole transport layer 4 with a thickness of 10 nm.

[0492] (3) Compound BH-3 (host) and compound 68 (dopant) were vacuum deposited on the hole transport layer at a weight ratio of 98:2 to form a light-emitting layer 5 with a thickness of 20 nm.

[0493] (4) ET1 was vacuum deposited on the light-emitting layer 5 to form an electron transport layer 6 with a thickness of 40 nm, and KI and Yb were vacuum deposited on the electron transport layer 6 at a weight ratio of 8:2 to form an electron injection layer 7 with a thickness of 1 nm. Ag and Mg were vacuum deposited on the electron injection layer 7 at a weight ratio of 90:10 to form a cathode 8 with a thickness of 10 nm, thus completing the preparation of the organic electroluminescent device.

[0494] Device Examples 32 - 40

[0495] Except that when forming the light-emitting layer 5, compound 69, 70, 71, 72, 73, 74, 75, 76, and 77 were used to replace compound 68 respectively, the organic electroluminescent device was fabricated by the same method as in Device Example 31.

[0496] Device Comparative Examples 6 - 7

[0497] Except that when forming the light-emitting layer 5, compound BD-2 and compound BD-3 were used to replace compound 68 respectively, the organic electroluminescent device was fabricated by the same method as in Device Example 31.

[0498] The above-prepared organic electroluminescent devices were tested by a computer-controlled Keithley 2400 test system, and the operating voltage and luminous efficiency were calculated. The device lifetime under dark conditions was obtained using a Fluorstar lifetime measurement system equipped with a power supply and a photodiode as the detection unit. The specific test conditions for each performance can be referred to the foregoing.

[0499] Each group of device examples and each group of device comparative examples were produced and tested in the same batch. The operating voltage, luminous efficiency, and lifetime of the devices in Device Comparative Example 6 were all recorded as 1 respectively, and the ratios of the corresponding indexes of Device Examples 31 - 40 to those of Device Comparative Example 7 were calculated respectively, obtaining the relative operating voltage, relative luminous efficiency, and relative lifetime as shown in Table 4.

[0500] Table 4 Test Results of Device Examples 31 - 40 and Device Comparative Examples 6 - 7

[0501] Device Doping Material Relative Operating Voltage Relative Luminescence Efficiency Relative Lifetime Device Comparative Example 6 BD-2 1 1 1 Device Comparative Example 7 BD-3 0.975 1.257 1.316 Device Example 31 Compound 68 0.958 1.385 1.478 Device Example 32 Compound 69 0.923 1.456 1.489 Device Example 33 Compound 70 0.928 1.389 1.599 Device Example 34 Compound 71 0.936 1.573 1.642 Device Example 35 Compound 72 0.957 1.489 1.473 Device Example 36 Compound 73 0.933 1.432 1.651 Device Example 37 Compound 74 0.955 1.376 1.542 Device Example 38 Compound 75 0.948 1.487 1.458 Device Example 39 Compound 76 0.937 1.398 1.581 Device Example 40 Compound 77 0.949 1.431 1.573

[0502] As can be seen from the results in Table 4, compared with the devices formed by using the commercial products used in Device Comparative Examples 6-7 as the doping materials and the compounds used in Device Examples 31-40, the operating voltages are all reduced, and the luminous efficiency and lifespan are both improved.

[0503] The above description of the embodiments is to enable those of ordinary skill in the art to understand and apply the present application. It is obvious that those skilled in the art can easily make various modifications to these embodiments and apply the general principles described herein to other embodiments without creative efforts. Therefore, the present application is not limited to the embodiments herein, and the improvements and modifications made by those skilled in the art within the scope and spirit of the present application without departing from the content disclosed in the present application are within the scope of the present application.

Claims

1. An organic compound, characterized in that, Its structural formula is shown in Formula I: In the said Formula I, R is selected from a substituted or unsubstituted straight-chain or branched C1-C60 alkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C60 heteroalkyl group, a substituted or unsubstituted C1-C60 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; n is from 0 to 16.

2. The organic compound according to claim 1, wherein R is the group L-EA, and the structural formula of the said organic compound is shown in Formula II: In the said Formula II, L is selected from a single bond, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; EA is an electron-withdrawing group, and the said electron-withdrawing group is selected from aromatic electron-withdrawing group derivatives containing a nitrogen atom, electron-withdrawing group derivatives containing a fluorine atom, cyano derivatives, phosphine oxide group derivatives, or sulfoxide derivatives; n is from 1 to 4.

3. The organic compound according to claim 2, characterized in that, The said electron-withdrawing group is selected from the following groups: Among them, Ar6, Ar 61 , Ar 62 , Ar 63 , Ar7, Ar8, Ar9 and Ar 10 are independently selected from substituted or unsubstituted C6-C60 aryl groups and substituted or unsubstituted C3-C60 heteroaryl groups.

4. The organic compound according to claim 2, characterized in that, The substituents of the said L are selected from the following substituted or unsubstituted groups: C1-C30 straight-chain alkyl groups, C1-C30 branched-chain alkyl groups, C3-C30 cycloalkyl groups, C6-C60 aryl groups, C3-C60 heteroaryl groups.

5. The organic compound according to claim 3, wherein n is 1 or 2; L is selected from a single bond, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, triphenylene, phenanthryl, or phenanthryl derivatives; The electron-withdrawing group is and Ar8, Ar9 and Ar 10 are independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorene, triphenylene, phenanthryl or phenanthryl derivatives; More specifically, the Ar8, Ar9 and Ar 10 respectively include: aryl groups substituted by C1-C10 alkyl groups, the aryl groups including phenyl, naphthyl, biphenyl, 2-phenylnaphthalene, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorene, triphenylene, phenanthryl or combinations thereof; the fluorenyl group is preferably dimethyl-substituted fluorene; More specifically, the Ar8, Ar9 and Ar 10 , the aryl groups may be substituents of each other. For example, they include phenyl, naphthyl, biphenyl, 2-phenylnaphthalene, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorene, triphenylene, phenanthryl or combinations thereof; they may be combined with each other, and may be secondary combinations, tertiary combinations, or quaternary combinations. Secondary combinations are preferred. For example, it may be phenyl substituted with naphthyl and so on.

6. The organic compound according to claim 5, characterized in that, The organic compound shown in the said Formula II is represented by any one of the following structural formulas from Formula 1 to Formula 24: wherein Ar8 and Ar 10 are each independently selected from one or more of phenyl, naphthyl, biphenyl or dibenzofuranyl.

7. The organic compound according to claim 6, characterized in that, The organic compound shown in the said Formula II is the following compound:

8. The organic compound according to claim 1, characterized in that, R is a group The structural formula of the organic compound is as shown in Formula III: In the said Formula III, L is selected from a single bond, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; Ar 11 and Ar 12 are independently selected from substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl, or Ar 11 and Ar 12 are bonded to form a ring; n is from 1 to 4.

9. The organic compound according to claim 8, characterized in that, Its structural formula is shown in Formula IV or Formula V: In the formulas IV and V, Ar 13 ~Ar 16 are independently selected from one of the following structures: n is 1 or 2.

10. The organic compound according to claim 9, wherein The organic compound shown in the said Formula IV is represented by any one of the following structural formulas from Formula 36 to Formula 39: In Formulas 36 to 39, Ar 14 is selected from The organic compound shown in the said Formula V is represented by any one of the following structural formulas from Formula 40 to Formula 50: In Formulas 40 to 50, Ar 16 is selected from 11. The organic compound according to claim 1, characterized in that, R is a group The structural formula of the organic compound is as shown in Formula VI: In the said Formula VI, L is selected from a single bond, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; Ar3 is selected from a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group.

12. The organic compound according to claim 11, wherein The said L and Ar3 are independently selected from the following substituted or unsubstituted groups:

13. The organic compound according to claim 12, wherein, The organic compound shown in the said Formula VI is represented by any one of the following structural formulas from Formula 51 to Formula 67:

14. An organic compound, characterized in that, Its structural formula is shown in Formula VII: In the said Formula VII, R1 is selected from none, a substituted or unsubstituted straight-chain or branched C1-C60 alkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C60 heteroalkyl group, a substituted or unsubstituted C1-C60 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; CyA, CyB, Ar4, and Ar5 are independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group; Among them, at least one of R1, CyA, CyB, Ar4 and Ar5 contains the structural formula of any one of claims 1 to 5.

15. The organic compound according to claim 14, wherein, At least one of R1, Ar4 and Ar5 contains the structural formula of any one of claims 1 to 5.

16. The organic compound according to claim 15, wherein the organic compound represented by formula VII is represented by any one of the following structural formulas 68 to 77:

17. An organic layer, characterized in that, Comprising the organic compound according to any one of claims 1 to 16.

18. Use of the organic compound according to any one of claims 1 to 16 and / or the organic layer according to claim 17 in an organic electroluminescent device.

19. An organic electroluminescent device, characterized in that, Comprising a first electrode, a second electrode and the organic layer according to claim 17, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer or an electron transport layer.

20. A display or lighting device, characterized in that, Comprising the organic electroluminescent device according to claim 19.

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