Organic compound and organic electroluminescent device comprising same, and electronic apparatus
By using a compound in which phenanthroline is linked to a terpyridine derivative at the 4-position as a charge generation layer material, the lifespan and efficiency issues of organic electroluminescent devices in large-area displays were solved, achieving a reduction in driving voltage and an improvement in luminous efficiency.
Patent Information
- Application Number
- PCT/CN2025/089086
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-07-26
- Filing Date
- 2025-04-15
- Publication Date
- 2026-01-29
AI Technical Summary
Existing organic electroluminescent devices suffer from lifespan and efficiency issues in large-area displays. As voltage increases, improved materials are needed to enhance performance.
Compounds with specific structures of phenanthroline linked to terpyridine derivatives at the 4-position are used as charge generation layer materials, providing a large conjugated plane and high bond energy, improving the solid-state stacking stability between molecules, and enhancing charge generation efficiency through metal complexation.
Lowering the driving voltage improves luminous efficiency and extends the lifespan of organic electroluminescent devices.
Smart Images

Figure CN2025089086_29012026_PF_FP_ABST
Abstract
Description
Organic compounds, organic electroluminescent devices and electronic apparatuses comprising the same
[0001] Cross-reference to Related Applications
[0002] This application claims priority to Chinese Patent Application No. 2024110187249, filed on July 26, 2024, the contents of which are incorporated herein in their entirety as part of this application. TECHNICAL FIELD
[0003] The present application relates to the technical field of organic electroluminescence, in particular, to an organic compound, an organic electroluminescent device comprising the same and an electronic apparatus. BACKGROUND
[0004] At present, organic electroluminescent devices are considered as the next generation display and lighting technology due to their active light-emitting, high current efficiency, low power consumption, lightness, thinness, fast response speed, large viewing angle and other advantages. An organic electroluminescent device generally includes a cathode and an anode arranged opposite to each other, and a functional layer arranged between the cathode and the anode. When a voltage is applied to the cathode and the anode, an electric field is generated between the two electrodes. Under the action of the electric field, electrons on the cathode side move to the electroluminescent layer, and holes on the anode side also move to the electroluminescent layer. The electrons and holes combine to form excitons in the electroluminescent layer. The excitons in the excited state release energy to the outside, and then the electroluminescent layer emits light.
[0005] The organic electroluminescent device can be of various structures, such as a single-layer structure and a stacked structure. A single-layer organic electroluminescent device includes only one light-emitting unit between the cathode and the anode, and a stacked organic electroluminescent device is stacked by multiple light-emitting units. A light-emitting unit generally includes at least one light-emitting layer, one hole transport layer and one electron transport layer. On this basis, the light-emitting unit can further include a hole injection layer, an electron injection layer, a hole blocking layer and an electron blocking layer. There is a charge generation layer (CGL) between adjacent light-emitting units for the generation and movement of charges. The CGL is constructed in the form of p-n, including an n-type charge generation layer (n-CGL) and a p-type charge generation layer (p-CGL). Among them, the p-type material mainly generates holes, and the n-type material is doped with a low work function metal through an electron transport layer material to generate electrons.
[0006] The most important problems in the existing organic electroluminescent devices are the lifetime and the efficiency. With the large-area display, the voltage also increases. Therefore, it is necessary to continue to develop new materials to further improve the performance of the organic electroluminescent device. SUMMARY
[0007] To solve the above problems, the present application aims to provide an organic compound, an organic electroluminescence device including the same, and an electronic device, which can be used in an organic electroluminescence device to improve the performance of the device.
[0008] The first aspect of the present application provides an organic compound having a structure represented by Formula 1:
[0009] wherein L is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted pyrenylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted pyrimidylene, a substituted or unsubstituted pyrazinylene, a substituted or unsubstituted quinolyne, a substituted or unsubstituted isoquinolyne, a substituted or unsubstituted quinazolyne, a substituted or unsubstituted quinoxalyne, a substituted or unsubstituted dibenzofurylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted carbazolylyene;
[0010] the substituents in L are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group with a carbon number of 1 to 5, a trideuteromethyl group with a carbon number of 1 to 5, a haloalkyl group with a carbon number of 1 to 5, an aryl group with a carbon number of 6 to 12, or a heteroaryl group with a carbon number of 3 to 12;
[0011] Ar1and Ar2are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group with a carbon number of 1 to 10, a haloalkyl group with a carbon number of 1 to 10, a deuterated alkyl group with a carbon number of 1 to 10, a trialkylsilyl group with a carbon number of 3 to 12, an alkenyl group with a carbon number of 2 to 10, a cycloalkyl group with a carbon number of 3 to 10, a substituted or unsubstituted aryl group with a carbon number of 6 to 30, or a substituted or unsubstituted heteroaryl group with a carbon number of 3 to 30;
[0012] the substituents in Ar1and Ar2are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group with a carbon number of 1 to 10, an alkyl group with a carbon number of 1 to 10, a deuterated alkyl group with a carbon number of 1 to 10, a trialkylsilyl group with a carbon number of 3 to 12, an alkenyl group with a carbon number of 2 to 10, an aryl group with a carbon number of 6 to 20, or a heteroaryl group with a carbon number of 3 to 20;
[0013] each R is the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group with a carbon number of 1 to 10, a haloalkyl group with a carbon number of 1 to 10, a deuterated alkyl group with a carbon number of 1 to 10, a cycloalkyl group with a carbon number of 3 to 10, a substituted or unsubstituted aryl group with a carbon number of 6 to 20, or a substituted or unsubstituted heteroaryl group with a carbon number of 3 to 20;
[0014] the substituents in R are the same or different, and each independently selected from deuterium, a halogen group, a cyano group, an alkyl group with a carbon number of 1-10, a haloalkyl group with a carbon number of 1-10, a deuterated alkyl group with a carbon number of 1-10, a cycloalkyl group with a carbon number of 3-10, an aryl group with a carbon number of 6-12, or a heteroaryl group with a carbon number of 3-12;
[0015] m is the number of R, and m is selected from 0, 1, 2, 3, 4, or 5, and when m is greater than 1, any two R are the same or different.
[0016] The second aspect of the present application provides an organic electroluminescent device, comprising an anode and a cathode oppositely arranged, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound according to the first aspect.
[0017] The third aspect of the present application provides an electronic device comprising the organic electroluminescent device according to the second aspect of the present application.
[0018] The purpose of the present application is to provide a compound in which a phenanthroline is connected to a terpyridine derivative at the 4-position, the structure provided by the present application has a large conjugated plane, the bond energy between atoms is high, which is conducive to the solid-state stacking between molecules, and good thermodynamic stability is exhibited. And the structure provided by the present application has a fast charge transport capacity, thereby reducing the driving voltage. At the same time, the structure provided by the present application can effectively form a complex with metal, and when used as a charge generation layer material, it can improve the efficiency of charge generation, thereby improving the luminous efficiency and prolonging the service life of the organic electroluminescent device.
[0019] Other features and advantages of the present application will be described in detail in the subsequent specific embodiments. BRIEF DESCRIPTION OF DRAWINGS
[0020] The accompanying drawings are included to provide a further understanding of the present application, and constitute a part of the specification, and together with the following specific embodiments, serve to explain the present application, but do not constitute a limitation on the present application.
[0021] Figure 1 is a structural schematic diagram of an organic electroluminescent device according to an embodiment of the present application.
[0022] Figure 2 is a structural schematic diagram of an organic electroluminescent device according to another embodiment of the present application.
[0023] Figure 3 is a structural schematic diagram of an electronic device according to an embodiment of the present application.
[0024] Reference Signs100, anode200, cathode300, functional layer310, hole injection layer321, hole transport layer322, electron blocking layer330, organic light emitting layer340, electron transport layer350, electron injection layer411, first hole transport layer412, first hole adjustment layer413, first organic light emitting layer414, first electron transport layer421, n-type charge generation layer422, p-type charge generation layer431, second hole transport layer432, second hole adjustment layer433, second organic light emitting layer434, second electron transport layer410, first light emitting unit420, charge generation layer430, second light emitting unit500, electronic device DETAILED DESCRIPTION
[0025] Example embodiments now will be described more fully hereinafter with reference to the accompanying drawings; however, the example embodiments can be implemented in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the example embodiments to those skilled in the art. The described features, structures, or characteristics can be combined in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application. However, embodiments can be practiced without the specific details.
[0026] In a first aspect, the present application provides an organic compound having a structure represented by Formula 1:
[0027] wherein L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted quinoxalinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted carbazolylene group;
[0028] the substituents in L are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a trideuteromethyl group having 1 to 5 carbon atoms, a halogenated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms;
[0029] Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, alkenyl with 2 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms;
[0030] The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, haloalkyl with 1 to 10 carbon atoms, alkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, alkenyl with 2 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms;
[0031] Each R may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 20 carbon atoms;
[0032] The substituents in R may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, or heteroaryl with 3 to 12 carbon atoms;
[0033] m is the number of R, and m is selected from 0, 1, 2, 3, 4 or 5. When m is greater than 1, any two R are the same or different.
[0034] In this application, the descriptive phrases "each independently selected from" and "separately independently selected from" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, " wherein each q is independently 0, 1, 2, or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, chlorine, and the meaning is that: formula Q-1 represents that there are q substituents R" on the benzene ring, each R" can be the same or different, and each R" is selected independently; formula Q-2 represents that there are q substituents R" on each benzene ring of the biphenyl, the number of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and each R" is selected independently.
[0035] In the present application, the term "substituted or unsubstituted" means that the functional group described after the term can have or not have a substituent (hereinafter, the substituent will be collectively referred to as Rcfor the convenience of description). For example, "substituted or unsubstituted aryl" means aryl having a substituent Rc, or non-substituted aryl. The above-mentioned substituent Rc, for example, can be deuterium, a halogen group, a cyano group, an alkyl group, a trialkylsilyl group, a haloalkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, and the like. The number of substituents can be one or more.
[0036] In the present application, a group can be a monovalent group or a polyvalent group formed by substitution.
[0037] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group means the total number of carbon atoms.
[0038] In the present application, an aryl group means an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (for example, phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond, a monocyclic aryl group and a fused ring aryl group connected by a carbon-carbon bond, two or more fused ring aryl groups connected by a carbon-carbon bond. That is, unless otherwise specified, two or more aromatic groups connected by a carbon-carbon bond can also be regarded as an aryl group in the present application. Among them, the fused ring aryl group can include, for example, a bicyclic fused aryl group (for example, naphthyl), a tricyclic fused aryl group (for example, phenanthryl, fluorenyl, anthryl), and the like. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in the present application, biphenyl, terphenyl, and the like are aryl groups. Examples of the aryl group can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthene, chrysenyl, triphenylenyl, pyridinyl, quinolinyl, isoquinolinyl, indolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, and the like. In the present application, the aryl group can be substituted or unsubstituted.
[0039] In the present application, the aryl group can be substituted or unsubstituted.
[0040] In the present application, substituted aryl group means that one or more than two hydrogen atoms in aryl group is substituted with a group such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, trialkylsilyl group, alkyl group, cycloalkyl group, haloalkyl group, deuterated alkyl group, and the like. Specific examples of aryl group-substituted heteroaryl group include, but are not limited to, phenyl-substituted dibenzofuranyl group, phenyl-substituted dibenzothiophenyl group, phenyl-substituted pyridyl group, and the like. It should be understood that the number of carbon atoms of substituted aryl group refers to the total number of carbon atoms of aryl group and substituents on aryl group, for example, substituted aryl group having 18 carbon atoms means that the total number of carbon atoms of aryl group and substituents is 18.
[0041] In the present application, heteroaryl group means a monovalent aromatic ring or its derivative comprising at least one heteroatom in the ring, and the heteroatom can be one or more of B, O, N, P, Si, Se, and S. Heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems connected by a carbon-carbon bond in conjugation, and any of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl group can include thienyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidinyl group, triazinyl group, acridinyl group, pyridazinyl group, pyrazinyl group, quinolyl group, quinazolinyl group, quinoxalinyl group, phenoxazinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, thienothiophenyl group, benzofuranyl group, phenanthrolinyl group, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, silafluorenyl group, dibenzofuranyl group, and N-phenylcarbazolyl group, N-pyridylcarbazolyl group, N-methylcarbazolyl group, and the like, but is not limited thereto. In the present application, the term "heteroaryl group" refers to a divalent group formed by further losing one hydrogen atom from the heteroaryl group.
[0042] In the present application, substituted heteroaryl group means that one or more than two hydrogen atoms in heteroaryl group is substituted with a group such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, trialkylsilyl group, alkyl group, cycloalkyl group, haloalkyl group, deuterated alkyl group, and the like. Specific examples of aryl group-substituted heteroaryl group include, but are not limited to, phenyl-substituted dibenzofuranyl group, phenyl-substituted dibenzothiophenyl group, phenyl-substituted pyridyl group, and the like. It should be understood that the number of carbon atoms of substituted heteroaryl group refers to the total number of carbon atoms of heteroaryl group and substituents on heteroaryl group.
[0043] In the present application, the number of carbon atoms of aryl group as a substituent can be 6 to 20, for example, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, and specific examples of aryl group as a substituent include, but are not limited to, phenyl group, biphenyl group, naphthyl group, anthryl group, Base.
[0044] In the present application, the number of carbon atoms of a heteroaryl group as a substituent group can be 3 to 20, for example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, and specific examples of the heteroaryl group as a substituent group include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolyl, quinazolinyl, quinoxalinyl, isoquinolyl.
[0045] In the present application, an alkyl group having 1 to 10 carbon atoms can include a straight chain alkyl group having 1 to 10 carbon atoms and a branched chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, and the like.
[0046] In the present application, a halogen group can be, for example, fluorine, chlorine, bromine, iodine.
[0047] In the present application, specific examples of a haloalkyl group include, but are not limited to, trifluoromethyl.
[0048] In the present application, specific examples of a deuterated alkyl group include, but are not limited to, trideuteromethyl.
[0049] In the present application, specific examples of an alkenyl group include, but are not limited to, ethenyl, propenyl.
[0050] In the present application, specific examples of a cycloalkyl group include, but are not limited to, cyclohexyl, cyclopentyl, adamantyl.
[0051] In the present application, is a chemical bond to be connected to other groups.
[0052] In the present application, an indefinite position connection bond refers to a single bond extending from a ring system which indicates that one end of the connection bond can be connected to any position in the ring system through which the bond passes, and the other end is connected to the rest of the molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions in the molecule through two indefinite position connection bonds that pass through the bicyclic ring, and the meaning represented thereby includes any possible connection mode as shown in formulae (f-1) to (f-10):
[0053] For example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through an indeterminate linking bond extending from the middle of one side benzene ring, and the meaning represented thereby includes any possible connection mode as shown in formula (X'-1) to formula (X'-4):
[0054] In some embodiments of the present application, L in formula 1 is selected from the group consisting of:
[0055] In some embodiments of the present application, L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted quinoxalinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, or a substituted or unsubstituted carbazolylene group.
[0056] Optionally, the substituents in L are the same or different, and each is independently selected from deuterium, fluorine, cyano, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl.
[0057] In some embodiments of the present application, L is selected from a single bond, or a substituted or unsubstituted group V; wherein the unsubstituted group V is selected from the following groups:
[0058] The substituted group V has one or more than two substituents, which are the same or different, and each is independently selected from deuterium, fluorine, cyano, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl, and when the number of substituents on group V is more than 1, each substituent is the same or different.
[0059] In some embodiments of the present application, L is selected from a single bond, or the following group:
[0060] In some embodiments of the present application, L is selected from a single bond, or the following group:
[0061] In some embodiments of the application, Ar1and Ar2are the same or different and each is independently selected from the group consisting of deuterium, fluorine, cyano, alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 5 carbon atoms, deuterated alkyl of 1 to 5 carbon atoms, trialkylsilyl of 3 to 6 carbon atoms, alkenyl of 2 to 5 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, substituted or unsubstituted aryl of 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl of 3 to 18 carbon atoms. For example, Ar1and Ar2are the same or different and each is independently selected from the group consisting of deuterium, fluorine, cyano, alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 5 carbon atoms, deuterated alkyl of 1 to 5 carbon atoms, trialkylsilyl of 3 to 6 carbon atoms, alkenyl of 2 to 5 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, substituted or unsubstituted aryl of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms, and substituted or unsubstituted heteroaryl of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
[0062] Optionally, the substituents in Ar1and Ar2are the same or different and each is independently selected from the group consisting of deuterium, fluorine, cyano, haloalkyl of 1 to 5 carbon atoms, alkyl of 1 to 5 carbon atoms, deuterated alkyl of 1 to 5 carbon atoms, trialkylsilyl of 3 to 6 carbon atoms, alkenyl of 2 to 5 carbon atoms, aryl of 6 to 12 carbon atoms, and heteroaryl of 3 to 12 carbon atoms.
[0063] In some embodiments of the application, Ar1and Ar2are the same or different and each is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, ethenyl, propenyl, cyclohexyl, cyclopentyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.
[0064] Optionally, the substituents in Ar1and Ar2are the same or different and each is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, ethenyl, propenyl, cyclohexyl, cyclopentyl, adamantyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl.
[0065] In some embodiments of the application, Ar1and Ar2are the same or different and each is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, ethenyl, propenyl, cyclopentyl, cyclohexyl, or the following group of radicals:
[0066] In some embodiments of the application, Ar1and Ar2are the same or different and each is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, ethenyl, propenyl, cyclopentyl, cyclohexyl, or the following group of radicals:
[0067] In some embodiments of the application, Ar1and Ar2in formula 1 are selected from the group consisting of: In some embodiments of the application, Ar1and Ar2in formula 1 are selected from the group consisting of:
[0068] In some embodiments of the application, Ar1and Ar2in formula 1 are selected from the group consisting of: In some embodiments of the application, Ar1and Ar2in formula 1 are selected from the group consisting of:
[0069] In some embodiments of the application, each R is the same or different and each is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolyl, substituted or unsubstituted quinoxalyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.
[0070] Optionally, the substituents in R are the same or different and each is independently selected from the group consisting of deuterium, fluorine, cyano, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl.
[0071] In particular, the organic compound is selected from the group consisting of the following compounds:
[0072] In a second aspect, the present application provides an organic electroluminescence device, comprising an anode and a cathode oppositely arranged, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound of the present application.
[0073] Optionally, the functional layer comprises an electron transport layer, and the electron transport layer comprises the organic compound of the present application.
[0074] In an embodiment of the present application, the structure of the organic electroluminescence device is shown in Figure 1, comprising an anode 100 and a cathode 200 oppositely arranged, and a functional layer 300 arranged between the anode 100 and the cathode 200; the functional layer 300 comprises a hole injection layer 310, a hole transport layer 321, an electron blocking layer 322, a light-emitting layer 330, an electron transport layer 340 and an electron injection layer 350, and the electron transport layer 340 comprises the organic compound of the present application.
[0075] In the present application, the anode 100 comprises the following anode materials, which are preferably materials with large work function (work function) that facilitate hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metal and oxide such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, but not limited thereto. Optionally, a transparent electrode comprising indium tin oxide (ITO) as an anode is included.
[0076] In the present application, the hole injection layer 310 can be selected from diphenylamine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in the present application. The material of the hole injection layer 310 is selected, for example, from the following compounds or any combination thereof:
[0077] In an embodiment of the present application, the hole injection layer 310 is composed of HT-1 and P-dopant.
[0078] In some embodiments of the present application, the hole transport material can be selected from triarylamine compounds or other types of compounds, which can be selected by those skilled in the art with reference to the prior art. For example, the material of the hole transport layer is selected from the group consisting of the following compounds.
[0079] In an embodiment of the present application, the material of the hole transport layer 321 comprises HT-1.
[0080] In an embodiment of the present application, the electron blocking layer 322 comprises one or more electron blocking materials, which can be selected from carbazole polymers or other types of compounds, without special limitation in the present application. For example, in some embodiments of the present application, the electron blocking layer 322 is compound EB-1
[0081] Optionally, the organic light emitting layer material can be composed of a single light emitting material, or can comprise a host material and a guest material. Optionally, the organic light emitting layer 330 is composed of a host material and a guest material, the holes injected into the organic light emitting layer 330 and the electrons injected into the organic light emitting layer 330 can recombine to form excitons in the organic light emitting layer 330, the excitons transfer energy to the host material, the host material transfers energy to the guest material, and the guest material can emit light.
[0082] Optionally, the host material of the organic light emitting layer 330 can comprise a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. The host material of the organic light emitting layer 330 can be a single host material, or can be a mixed host material. In an embodiment of the present application, the host material of the organic light emitting layer 330 is BH
[0083] In a specific embodiment of the present application, the guest material of the organic light emitting layer 330 is BD
[0084] In the present application, the electron injection layer 350 can comprise inorganic materials such as alkali metal sulfides, alkali metal halides, or can comprise complexes of alkali metals and organic materials. In an embodiment of the present application, the electron injection layer 350 comprises Yb.
[0085] Optionally, the electron transport layer 340 can be a single layer structure, or can be a multi-layer structure, which can comprise one or more electron transport materials, which can generally comprise metal complexes or / and nitrogen-containing heterocyclic derivatives, wherein the metal complex material can be selected from LiQ, Alq3, etc. In an embodiment of the present application, the electron transport layer 340 is composed of a compound of the present application and LiQ.
[0086] In the present application, the cathode 200 comprises a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; or a multi-layered material such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver is included as the cathode.
[0087] Further, the present application also provides another organic electroluminescent device as shown in Figure 2, which comprises an anode and a cathode, and a functional layer disposed between the anode and the cathode, the functional layer comprising a first light-emitting unit, a second light-emitting unit, and a charge generation layer; the charge generation layer comprising the organic compound described in the present application. The organic electroluminescent device shown in Figure 2 is also referred to as a stacked organic electroluminescent device hereinafter.
[0088] The stacked organic electroluminescent device shown in Figure 2 comprises an anode 100, a cathode 200, a hole injection layer 310, an electron injection layer 350, a first light-emitting unit 410, a second light-emitting unit 430, and a charge generation layer 420. The first light-emitting unit 410, the second light-emitting unit 430, and the charge generation layer 420 are located between the cathode 100 and the anode 200, the charge generation layer 420 is located between the first light-emitting unit 410 and the second light-emitting unit 430, and the charge generation layer 420 comprises the organic compound described in the present application.
[0089] In an embodiment of the present application, the first light-emitting unit 410 comprises a first hole transport layer 411, a first hole adjustment layer 412, a first organic light-emitting layer 413, and a first electron transport layer 414; and the second light-emitting unit 430 comprises a second hole transport layer 431, a second hole adjustment layer 432, a second organic light-emitting layer 433, and a second electron transport layer 434.
[0090] In an embodiment of the present application, the charge generation layer 420 comprises an n-type charge generation layer (n-CGL) 421 and a p-type charge generation layer (p-CGL) 422, the n-type charge generation layer 421 provides electrons to the first electron transport layer 414 of the first light-emitting unit 410, and the p-type charge generation layer 422 provides holes to the second hole transport layer 431 of the second light-emitting unit 430. In an embodiment of the present application, the n-type charge generation layer comprises the organic compound described in the present application.
[0091] In an embodiment of the present application, the n-type charge generation layer is composed of the organic compound described in the present application and a metal-doped material. Optionally, the metal-doped material is Li, Ca, Ag, Cs, or Yb.
[0092] In one embodiment of the present application, the p-CGL layer comprises HT-1 and P-dopant.
[0093] In the present application, the anode 100 comprises an anode material, which optionally comprises indium tin oxide (ITO).
[0094] In one embodiment of the present application, the hole injection layer 310 is composed of HT-1 and P-dopant.
[0095] In one embodiment of the present application, the material of the first hole transport layer 411 and the second hole transport layer 431 comprises HT-1.
[0096] In one embodiment of the present application, the material of the first hole adjustment layer 412 and the second hole adjustment layer 432 comprises HT-2.
[0097] In the present application, the first organic light-emitting layer of the first light-emitting unit; and the second organic light-emitting layer of the second light-emitting unit, each can comprise the same or different host material and the same or different guest material.
[0098] In one specific embodiment of the present application, the host material of the first organic light-emitting layer 413 and the second organic light-emitting layer 433 is RH
[0099] In one specific embodiment of the present application, the guest material of the first organic light-emitting layer 413 and the second organic light-emitting layer 433 is RD
[0100] In one specific embodiment of the present application, the material of the first electron transport layer 414 and the second electron transport layer 434 comprises ET-1 and LiQ.
[0101] In one embodiment of the present application, the electron injection layer 350 comprises Yb.
[0102] In one specific embodiment of the present application, the cathode 200 comprises a cathode material, which comprises magnesium (Mg) and silver (Ag).
[0103] In a third aspect, the present application provides an electronic device comprising the organic electroluminescent device of the second aspect of the present application.
[0104] According to one embodiment, an electronic device provided is an electronic device 500 including the organic electroluminescent device described above, as shown in FIG. 3. The electronic device 500 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, for example, but not limited to, a computer screen, a cell phone screen, a television, electronic paper, an emergency lighting device, an optical module, and the like.
[0105] The synthesis method of the organic compound of the present application will be specifically described below in connection with the synthesis examples, but the present application is not limited thereto in any respect. The synthesis method of the organic compound of the present application will be specifically described below in connection with the synthesis examples, but the present application is not limited thereto in any respect.
[0106] The compounds of which the synthesis method is not mentioned in the present application are all raw material products obtained through commercial channels.
[0107] Synthesis Example
[0108] 1. Synthesis of Intermediate IMA-1
[0109] To 4-chloro-2,9-dimethyl-1,10-phenanthroline (9.7 g, 40 mmol) and 4-chlorobenzeneboronic acid (7.5 g, 48 mmol) dissolved in 80 mL of toluene, were added tetrakis(triphenylphosphine)palladium (0.46 g, 0.4 mmol), K2CO3(11 g, 80 mmol), 10 mL of ethanol, and 10 mL of water. After heating under reflux for 8 h under a nitrogen atmosphere, the reaction mixture was cooled to room temperature, extracted with water and dichloromethane, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained solid was chromatographed using ethyl acetate: n-heptane = 1:9 (v / v) to obtain intermediate IMA-1 (9.3 g, yield: 73%).
[0110] The intermediates IMA-X (X is 2 to 20) shown in Table 1 were synthesized in the same manner as in the case of intermediate IMA-1, except that raw material 1 was used instead of 4-bromo-1,10-phenanthroline and raw material 2 was used instead of 4-chlorobenzeneboronic acid, wherein the main raw materials used, the synthesized intermediates, and their yields are shown in Table 1.
[0111] Table 1
[0112] 2. Synthesis of Intermediate IM B-X
[0113] Intermediate IM B-1 (4.1 g, 10 mmol) and 4'-chloro-4,2':6',4"-terpyridine (2.68 g, 10 mmol) were added to a 100 mL three-necked flask, and 32 mL of toluene, 4 mL of ethanol, 4 mL of water, tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol), and K2CO3 (2.8 g, 20 mmol) were added. Under a nitrogen atmosphere, it was heated to reflux for 6 h. After cooling to room temperature, 50 mL of water was added, stirred for 30 min, and then the solid was collected by suction filtration, and the filter cake was washed with 50 mL of ethanol three times. The obtained solid was recrystallized with dichloromethane: ethyl acetate = 1:2 to obtain compound 2 (3.8 g, yield: 74%). Mass (m / z) = 516.21 [M+H]
[0114] The intermediates IM B-X (X is 2 to 20) shown in Table 2 were synthesized in the same manner as the intermediate IM B-1, except that the intermediate IM A-X was used instead of IMA-1, wherein the main raw materials used, the synthesized intermediates, and their yields are shown in Table 2.
[0115] Table 2
[0116] Synthesis Example 1: Synthesis of compound 2
[0117] IM B-1 (4.1 g, 10 mmol) and 4'-chloro-4,2':6',4"-terpyridine (2.68 g, 10 mmol) were added to a 100 mL three-necked flask, and 32 mL of toluene, 4 mL of ethanol, 4 mL of water, tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol), and K2CO3 (2.8 g, 20 mmol) were added. Under a nitrogen atmosphere, it was heated to reflux for 6 h. After cooling to room temperature, 50 mL of water was added, stirred for 30 min, and then the solid was collected by suction filtration, and the filter cake was washed with 50 mL of ethanol three times. The obtained solid was recrystallized with dichloromethane: ethyl acetate = 1:2 to obtain compound 2 (3.8 g, yield: 74%). Mass (m / z) = 516.21 [M+H] + .
[0118] The compounds shown in Table 3 were synthesized in the same manner as compound 2, except that the intermediate IM B-X was used instead of IM B-1, wherein the main raw materials used, the synthesized compounds, and their yields and mass spectra are shown in Table 3.
[0119] Table 3
[0120] NMR data of compound 2:
[0121] 1 H-NMR (CDC13, 400 MHz): 8.73 (d, 4H), 8.26-8.22 (m, 3H), 8.04-7.79 (m, 10H), 7.54 (s, IH), 7.41 (d, IH), 2.72 (d, 6H).
[0122] NMR data of compound 28:
[0123] 1 H-NMR (CDC13, 400 MHz): 8.73 (d, 4H), 8.26-8.22 (m, 3H), 8.04-7.79 (m, 10H), 7.54 (s, IH), 7.41 (d, IH), 2.72 (d, 6H).
[0124] Example 1: Blue organic electroluminescent device
[0125] The anode was prepared by cutting ITO / Ag / ITO with thicknesses of 1500 A / 100 A / 1500 A in order of 40 mm (length) x 40 mm (width) x 0.7 mm (thickness), and using a photolithography process to prepare an experimental substrate having an anode and an insulating layer pattern, and using ultraviolet, ozone, and O2:N2 plasma to perform surface treatment to increase the work function of the anode, and using an organic solvent to clean the surface of the experimental substrate to remove impurities and oil on the surface of the experimental substrate. Compound HT-1 and P-dopant were co-evaporated on the experimental substrate at a rate ratio of 97%:3% to form a hole injection layer with a thickness of 100 A.
[0126] Compound HT-1 was evaporated on the hole injection layer to form a hole transport layer with a thickness of 100 A.
[0127] Compound EB-1 was evaporated on the hole transport layer to form an electron blocking layer with a thickness of 100 A. Compound BH and compound BD were co-evaporated on the electron blocking layer at a rate ratio of 98%:2% to form an organic light-emitting layer with a thickness of 100 A.
[0128] Compound 2 and LiQ were co-evaporated on the organic light-emitting layer at a rate ratio of 50%:50% to form an electron transport layer with a thickness of 100 A.
[0129] Compound 2 and LiQ were co-evaporated on the organic light-emitting layer at a rate ratio of 50%:50% to form an electron transport layer with a thickness of 100 A. Compound 2 and LiQ were co-evaporated on the organic light-emitting layer at a rate ratio of 50%:50% to form an electron transport layer with a thickness of 100 A.
[0130] Compound 2 and LiQ were co-evaporated on the organic light-emitting layer at a rate ratio of 50%:50% to form an electron transport layer with a thickness of 100 A.
[0131] Yb was evaporated on the electron transport layer to form an electron injection layer with a thickness of 20 A. Then, magnesium (Mg) and silver (Ag) were co-evaporated on the electron injection layer at a rate ratio of 10%:90% to form a cathode with a thickness of 200 A.
[0132] Finally, compound CP-1 was evaporated on the cathode to form a cathode cover layer with a thickness of 20 A, thereby completing the preparation of the blue organic electroluminescent device.
[0133] Examples 2-10:
[0134] The organic electroluminescent device was prepared by the same method as in Example 1, except that compound 2 was replaced by the compounds in Table 4 below when forming the electron transport layer.
[0135] Comparative Examples 1-3
[0136] The organic electroluminescent device was prepared by the same method as in Example 1, except that compound 2 was replaced by compounds A, B, and C when forming the electron transport layer.
[0137] The main materials used in the above examples and comparative examples are shown in the following structures.
[0138] The blue organic electroluminescent devices prepared in Examples 1-10 and Comparative Examples 1-3 were tested for performance, specifically the IVL performance of the devices was tested under the condition of 10 mA / cm 2 The T 95 The device lifetime was tested under the condition of 15 mA / cm 2 The test results are shown in Table 4 below:
[0139] Table 4
[0140] As can be seen from Table 4 above, the luminous efficiency of Examples 1-10 using the compound of the present application as the electron transport layer material is at least 15.4% higher than that of Comparative Examples 1-3, and the device lifetime is at least 17.7% higher. It can be seen that using the organic compound of the present application in the electron transport layer of an organic electroluminescent device can reduce the device voltage and improve the luminous efficiency and T 95 lifetime of the organic electroluminescent device.
[0141] To further illustrate the application of the compound of the present application as a charge generation layer in a stacked organic electroluminescent device, the performance of the material of the present application was studied by constructing a stacked device.
[0142] Example 11: Red Stacked Organic Electroluminescent Device
[0143] The anode was prepared by the following process: the ITO / Ag / ITO experimental substrate with thicknesses of 1500 A / 1500 A / 1500 A, respectively, was surface treated by UV, ozone and O2:N2 plasma to increase the work function of the anode, and the experimental substrate surface was cleaned by organic solvent to remove impurities and oil on the experimental substrate surface.
[0144] Compound HT-1 and P-dopant were co-evaporated on the experimental substrate at a rate ratio of 97%:3% to form a hole injection layer with a thickness of 100 A.
[0145] Compound HT-1 was evaporated on the hole injection layer to form a first hole transport layer with a thickness of 100 A.
[0146] Compound HT-2 was evaporated on the first hole transport layer to form a first hole adjustment layer with a thickness of 100 A. Compound RH and compound RD were co-evaporated on the first hole adjustment layer at a rate ratio of 98%:2% to form a first organic light-emitting layer with a thickness of 100 A.
[0147] Compound ET-1 and LiQ were co-evaporated on the first organic light-emitting layer at a rate ratio of 50%:50% to form a first electron transport layer with a thickness of 100 A.
[0148] The above is a first light-emitting unit Compound 2 and Yb were co-evaporated on the first electron transport layer at a rate ratio of 99%:1% to form an n-type charge generation layer with a thickness of 100 A, and then compound HT-1 and P-dopant were co-evaporated thereon at a rate ratio of 95%:5% to form a p-type charge generation layer with a thickness of 100 A.
[0149] The above is a charge generation layer
[0150] Compound HT-1 was vacuum evaporated on the p-type charge generation layer to form a second hole transport layer with a thickness of 100 A. Compound HT-2 was vacuum evaporated on the second hole transport layer to form a second hole adjustment layer with a thickness of 100 A.
[0151] Compound 2 and Yb were co-evaporated on the first electron transport layer at a rate ratio of 99%:1% to form an n-type charge generation layer with a thickness of 100 A, and then compound HT-1 and P-dopant were co-evaporated thereon at a rate ratio of 95%:5% to form a p-type charge generation layer with a thickness of 100 A.
[0152] Compound HT-1 was vacuum evaporated on the p-type charge generation layer to form a second hole transport layer with a thickness of 100 A.
[0153] Compound HT-2 was vacuum evaporated on the second hole transport layer to form a second hole adjustment layer with a thickness of 100 A. Compound 2 and Yb were co-evaporated on the first electron transport layer at a rate ratio of 99%:1% to form an n-type charge generation layer with a thickness of 100 A, and then compound HT-1 and P-dopant were co-evaporated thereon at a rate ratio of 95%:5% to form a p-type charge generation layer with a thickness of 100 A.
[0154] On the second hole adjusting layer, compound RH and compound RD are co-evaporated at a rate ratio of 98%:2% to form a second organic light emitting layer with a thickness of 30 A.
[0155] On the second organic light emitting layer, compound ET-1 and LiQ are co-evaporated at a rate ratio of 50%:50% to form a second electron transport layer with a thickness of 30 A.
[0156] The above is the second light emitting unit
[0157] On the second electron transport layer, Yb is evaporated to form an electron injection layer with a thickness of 30 A; then, on the electron injection layer, magnesium (Mg) and silver (Ag) are co-evaporated at a rate ratio of 10%:90% to form a cathode with a thickness of 200 A.
[0158] Finally, on the cathode, compound CP-1 is evaporated to form a cathode cover layer with a thickness of 30 A, thus completing the preparation of the red stacked organic electroluminescent device.
[0159] Examples 12-31:
[0160] The organic electroluminescent device is prepared by using the same method as in Example 6, except that in the preparation of the n-type charge generation layer, the compound 2 in Example 11 is replaced by the compounds in Table 5.
[0161] Comparative Examples 4-6
[0162] The organic electroluminescent device is prepared by using the same method as in Example 6, except that in the preparation of the n-type charge generation layer, the compound 2 in Example 11 is replaced by compounds D, E, and F.
[0163] In the preparation of the organic electroluminescent device, the main material structures used in the above examples and comparative examples are shown as follows.
[0164] The red stacked organic electroluminescent devices prepared in Examples 11-31 and Comparative Examples 4-6 are tested for performance, specifically the IVL performance of the devices is tested under the condition of 10 mA / cm 2 The T 95 The device lifetime is tested under the condition of 20 mA / cm 2 The test results are shown in the following Table 5.
[0165] Table 5
[0166] As can be seen from Table 5, the compounds of Examples 11-31 are used as n-type charge generation layer materials, compared with Comparative Examples 4-6, the luminous efficiency (Cd / A) is increased by at least 11.4%, the device T 95 The lifetime is increased by at least 14.9%.
[0167] It can be seen that the organic compound of the present application is used as an n-type charge generation layer of an organic electroluminescent device, which can significantly improve the luminous efficiency and device lifetime of the organic electroluminescent device.
[0168] The preferred embodiments of the present application are described in detail above, but the present application is not limited to the specific details of the above-described embodiments, and various simple modifications can be made to the technical solutions of the present application within the technical concept of the present application, and these simple modifications all belong to the protection scope of the present application.
Claims
1. Organic compound, characterized in that, The organic compound has a structure shown in Formula 1: L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted quinoxalinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted carbazolylene group; the substituents in L are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a trideuteromethyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms; Ar1and Ar2are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; the substituents in Ar1and Ar2are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms; each R is the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms; the substituents in R are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms; m is the number of R, and m is selected from 0, 1, 2, 3, 4, or 5, and when m is greater than 1, any two R are the same or different.
2. The organic compound according to claim 1, wherein L is selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted pyrenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted pyrimidylene, substituted or unsubstituted pyrazinylene, substituted or unsubstituted quinolyiene, substituted or unsubstituted isoquinolyiene, substituted or unsubstituted quinazolyiene, substituted or unsubstituted quinoxalyiene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted carbazolyiene; Optionally, the substituents in L are the same or different, and each is independently selected from deuterium, fluorine, cyano, a C1-5 alkyl group, a C1-5 haloalkyl group, a C1-5 deuterated alkyl group, a C3-6 trialkylsilyl group, a C2-5 alkenyl group, a C3-10 cycloalkyl group, a C6-20 substituted or unsubstituted aryl group, or a C3-12 substituted or unsubstituted heteroaryl group.
3. The organic compound according to claim 1, wherein L is selected from the group consisting of a single bond or the following groups:
4. The organic compound according to claim 1, wherein Ar1and Ar2are the same or different, and each is independently selected from deuterium, fluorine, cyano, a C1-5 alkyl group, a C1-5 haloalkyl group, a C1-5 deuterated alkyl group, a C3-6 trialkylsilyl group, a C2-5 alkenyl group, a C3-10 cycloalkyl group, a C6-20 substituted or unsubstituted aryl group, or a C3-12 substituted or unsubstituted heteroaryl group. Optionally, the substituents in Ar1and Ar2are the same or different, and each is independently selected from deuterium, fluorine, cyano, a C1-5 haloalkyl group, a C1-5 alkyl group, a C1-5 deuterated alkyl group, a C3-6 trialkylsilyl group, a C2-5 alkenyl group, a C6-12 aryl group, or a C3-12 heteroaryl group.
5. The organic compound according to claim 1, wherein Ar1and Ar2are the same or different, and each is independently selected from deuterium, fluorine, cyano, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a trideuteromethyl group, a trimethylsilyl group, a vinyl group, a propenyl group, a cyclohexyl group, a cyclopentyl group, an adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolyl group, a substituted or unsubstituted quinoxalyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group. Optionally, the substituents in Ar1and Ar2are the same or different, and each is independently selected from deuterium, fluorine, cyano, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a trideuteromethyl group, a trimethylsilyl group, a vinyl group, a propenyl group, a cyclohexyl group, a cyclopentyl group, an adamantyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.
6. The organic compound according to claim 1, wherein Ar1and Ar2are the same or different and each independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, ethenyl, propenyl, cyclopentyl, cyclohexyl, or the following groups:
7. The organic compound according to claim 1, wherein each R is the same or different, and each is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in R are the same or different, and each is independently selected from the group consisting of deuterium, fluorine, cyano, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl.
8. The organic compound according to claim 1, wherein from the group consisting of: consisting of:
9. The organic compound according to claim 1, wherein The organic compound is selected from the group consisting of:
10. An organic electroluminescent device comprising an anode and a cathode, and a functional layer provided between the anode and the cathode; characterized in that, the functional layer comprises the organic compound according to any one of claims 1 to 9; Optionally, the functional layer comprises an electron transport layer, and the electron transport layer comprises the organic compound according to any one of claims 1 to 9. Optionally, the functional layer comprises a first light-emitting unit, a second light-emitting unit, and a charge generation layer; and the charge generation layer comprises the organic compound according to any one of claims 1 to 9. 11.An electronic device comprising the organic electroluminescent device according to claim 10.
Citation Information
Patent Citations
Compound, display panel and display device
CN110128424A
Novel compound and organic light-emitting element including same
CN110177778A
Compound, electron transport material and organic electroluminescent device
CN113321649A
Compound containing phenanthroline as well as preparation method and application thereof
CN117720534A
Compound, organic el element, display device and lighting device
WO2023058644A1