CN113429397B - Compound, display panel and display device - Google Patents

Compound, display panel and display device Download PDF

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CN113429397B
CN113429397B CN202110732914.7A CN202110732914A CN113429397B CN 113429397 B CN113429397 B CN 113429397B CN 202110732914 A CN202110732914 A CN 202110732914A CN 113429397 B CN113429397 B CN 113429397B
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CN113429397A (en
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高威
代文朋
冉佺
张磊
翟露
朱红岩
黄轩
匡立莲
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Wuhan Tianma Microelectronics Co Ltd
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Wuhan Tianma Microelectronics Co Ltd
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Abstract

The invention discloses a compound, a display panel and a display device. The compound has a structure shown as the following formula, wherein L 11 、L 12 、R 11 、R 12 、R 1 To R 8 M, n, p and q are each as defined herein. The compound provided by the invention can be used for display panels and display devices.
Figure DDA0003139658440000011

Description

Compound, display panel and display device
Technical Field
The invention belongs to the technical field of organic light emitting, and particularly relates to a compound, a display panel and a display device.
Background
An Organic Light Emitting Diode (OLED) is a self-emitting device that generates electroluminescence by using an organic thin film layer. Specifically, under the drive of an external electric field, the OLED device injects holes and electrons into an anode and a cathode respectively; the hole and the electron respectively migrate to the light emitting layer and combine in the organic light emitting material to generate an exciton; the excitons in the excited state may release energy in the form of light back to a stable ground state, generating visible light. As a new generation of display technology, the OLED display panel has the advantages of being ultra-thin, self-luminous, wide in viewing angle, fast in response, high in luminous efficiency, good in temperature adaptability, simple in production process, low in driving voltage, low in energy consumption and the like, and thus has been widely applied to the industries of flat panel display, flexible display, solid state lighting, vehicle-mounted display and the like.
Although OLED display panels have been widely used commercially, there is still much room for improvement in luminous efficiency. The light emitting efficiency of the OLED display panel is greatly affected by the organic material used, in addition to being related to the device structure. Therefore, in order to further enhance the market competitiveness of OLED display panels and display devices, there is still a need to provide a compound that can improve the efficiency of OLED devices.
Disclosure of Invention
The invention provides a compound, a display panel comprising the compound and a display device, aiming at improving the luminous efficiency of an OLED device in the display panel and the display device and further enabling the OLED device to have lower working voltage and longer service life.
In order to achieve the above object, a first aspect of the present invention provides a compound having a structure represented by formula (1),
Figure BDA0003139658420000011
in the formula (1), L 11 、L 12 、R 11 、R 12 、R 1 To R 8 M, n, p and q are each as defined herein.
A second aspect of the invention provides a display panel comprising an organic light emitting device comprising an anode, a cathode and an organic film layer comprising a light emitting layer between said anode and cathode, wherein the organic film layer comprises at least one compound according to the invention.
A third aspect of the invention provides a display device comprising a display panel according to the invention.
The compound has a core unit with a dibenzodiazepine eight-membered ring-diketone structure, is an electron accepting unit and has better electron transport capability. Further, by carrying out appropriate substituent (such as a first group with electron donating capability and/or a second group with electron accepting capability) substitution on the core unit, the polarity and carrier (hole and electron) transmission characteristics of the whole molecule can be effectively adjusted, so that the exciton recombination zone of the light-emitting layer of the OLED device can be adjusted, and the light-emitting efficiency and the service life of the device are improved. Meanwhile, the connecting substituent on the core unit can also realize the adjustment of HOMO and LUMO energy levels of molecules, so that the energy levels of the compounds and the compounds of adjacent layers are matched, and the injection barrier of holes and/or electrons is reduced, thereby preventing the accumulation of current carriers in an interlayer interface region, improving the luminous efficiency and reducing the working voltage of the device.
Alternatively, substitution of the first group having electron donating ability on the core unit having electron accepting ability can achieve appropriate HOMO and LUMO levels while facilitating transport of holes and electrons, thereby obtaining a compound having good electron and hole ambipolar transport ability. The compound also has higher triplet state energy level, is suitable for being used as a light-emitting host material in a light-emitting layer, and can prevent the backflow of triplet state energy from a light-emitting object material to the light-emitting host material, so that triplet state excitons are limited in the light-emitting layer to the maximum extent, the exciton utilization rate can be improved, and the light-emitting efficiency of an OLED device is improved. In addition, the compounds may also have large HOMO and LUMO energy level differences. The energy level difference of the luminescent host material is larger than that of the luminescent object material, so that the energy transfer from the luminescent host material to the luminescent object material and the direct capture of current carriers on the luminescent object material are facilitated, and the further improvement of the luminescent efficiency is facilitated.
Alternatively, by performing substitution with the second group having an electron accepting ability on the core unit, or by simultaneously performing substitution with the second group having an electron accepting ability and the first group having an electron donating ability, it is possible to make the compound have an appropriate HOMO level and a deeper LUMO level, achieve a stronger electron transporting ability, and also effectively block holes. And the compound also has a higher triplet energy level, and can block excitons in the light-emitting layer. Therefore, these compounds are suitable as electron transport materials or hole blocking materials in OLED devices. The compound can reduce the working voltage of the device and improve the luminous efficiency of the device.
The compound of the invention has higher glass transition temperature Tg, so the molecular stability is better. The compound has poor planarity on the spatial configuration and weak intermolecular force, so the compound has good film forming property and is beneficial to forming a stable and uniform amorphous film in the thermal vacuum evaporation process. In addition, the device adopting the compound can reduce the stacking and crystallization phenomena among molecules in use, ensure excellent film stability, and effectively inhibit the phenomenon of aggregation luminescence quenching in a luminescent layer, thereby improving the luminescent efficiency and prolonging the service life of the device.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the embodiments of the present invention will be briefly described below, and it is obvious that the drawings described below are only some embodiments of the present invention, and it is obvious for those skilled in the art that other drawings can be obtained according to the drawings without creative efforts.
Fig. 1 is a schematic structural diagram of an OLED device according to an embodiment of the present invention.
Fig. 2 is a schematic diagram of a display device according to an embodiment of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantageous technical effects of the present invention more clear, the present invention is further described in detail with reference to the following embodiments. It should be understood that the embodiments described in this specification are only for the purpose of explaining the present invention and are not intended to limit the present invention.
The above summary of the present invention is not intended to describe each disclosed embodiment or every implementation of the present invention. The following description more particularly exemplifies illustrative embodiments. At various points throughout this application, guidance is provided through a list of embodiments that can be used in various combinations. In each instance, the list is merely a representative group and should not be construed as exhaustive.
In the description herein, the terms "above", "below" and "including" mean "two or more" unless otherwise specified.
The terms "preferred" and "preferably" refer to embodiments of the invention that may provide certain benefits under certain circumstances. However, other embodiments may also be preferred, under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, and is not intended to exclude other embodiments from the scope of the disclosure.
Groupings of alternative elements or embodiments disclosed herein are not to be construed as limitations. Each group member may be employed and claimed individually or in any combination with other members of the group or other elements found herein. It is contemplated that one or more members of a group may be included in or deleted from the group for reasons of convenience and/or patentability. When any such inclusion or deletion occurs, the specification is considered herein to contain the modified group and thus satisfy the written description of all markush groups used in the claims.
When a compound or a chemical structural feature (e.g., aryl) is referred to as "substituted," the feature may have one or more substituents, unless otherwise specified. The term "substituent" has the broadest meaning known to those of ordinary skill in the art and includes such fragments (moieity): which occupies the position normally occupied by one or more hydrogen atoms attached to the parent compound or chemical structural feature. In some embodiments, the substituent may be a common organic moiety known in the art, which may have a molecular weight (e.g., the sum of the atomic masses of the atoms of the substituent) of 15 to 50g/mol, 15 to 100g/mol, 15 to 200g/mol, or 15 to 500 g/mol. Some substituents include F, Cl, Br, I, NO 2 、C 1-12 H 3-25 、C 1- 12 H 1-25 O、C 1-12 H 1-25 O 2 、C 1-12 H 3-26 N、C 1-12 H 1-26 NO、C 1-12 H 3-27 N 2 、C 1-12 F 3-25 Substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted C3-C10 heteroaryl, and the like.
The term "alkyl" includes not only straight-chain or branched-chain saturated hydrocarbon groups such as methyl, ethyl, propyl (e.g., n-propyl, isopropyl), butyl (e.g., n-butyl, isobutyl, sec-butyl, tert-butyl), pentyl (e.g., n-pentyl, isopentyl, neopentyl) and the like, but also alkyl substituents bearing other substituents known in the art, such as hydroxyl, alkylsulfonyl, halogen atoms, cyano, nitro, amino, carboxyl and the like. Thus, "alkyl" includes ether groups, haloalkyl groups, nitroalkyl groups, carboxyalkyl groups, hydroxyalkyl groups, sulfoalkyl groups, and the like. In various embodiments, the C1-C10 alkyl groups, i.e., alkyl groups, can contain 1-10 carbon atoms.
The term "halo" or "halogen" refers to fluorine, chlorine, bromine and iodine, such as fluorine.
The term "alkoxy" refers to-O-alkyl. Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy (e.g., n-propoxy, isopropoxy), butoxy (e.g., n-butoxy, isobutoxy, sec-butoxy, tert-butoxy), and the like.
The term "alkylthio" refers to-S-alkyl. Examples of alkylthio include, but are not limited to, methylthio, ethylthio, propylthio (e.g., n-propylthio, isopropylthio), butylthio (e.g., n-butylthio, isobutylthio, sec-butylthio, tert-butylthio), and the like.
The term "cycloalkyl" refers to a non-aromatic carbocyclic group, including cyclized alkyl, alkenyl, and alkynyl groups. Cycloalkyl groups can be monocyclic (e.g., cyclohexyl) or polycyclic (e.g., fused, bridged, and/or spiro rings). Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl. In various embodiments, the cycloalkyl group, which is a cycloalkyl group having from about 3 to about 10 carbon atoms for forming a ring, is a C3 to C10 cycloalkyl group.
The term "silyl" refers to-Si- (alkyl) 3 . Examples of silane groups include, but are not limited to, trimethylsilyl, triethylsilyl, dimethylethylsilyl, diethylmethylsilyl, and the like.
The term "aryl" refers to a closed aromatic ring or ring system. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, indenyl, anthryl, phenanthryl, pyrenyl, spirobifluorenyl, and similar aryl groups. In various embodiments, the C6-C30 aryl group can contain 6-30 carbon atoms for forming a ring.
The term "heteroaryl" refers to an aryl in which one or more of the atoms in the ring is an element other than carbon (e.g., N, O, S, Si, etc.). In some embodiments, the heteroaryl group of C2-C30 can include 1-8 or 1-5 ring heteroatoms (e.g., N, O, S, Si, etc.) as a whole. Examples of heteroaryl groups include, but are not limited to, pyrrolyl, furanyl, thienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazolyl (e.g., 1,2, 3-triazolyl, 1,3, 4-triazolyl, 1,2, 5-triazolyl), triazinyl (e.g., 1,3, 5-triazinyl), indolyl, isoindolyl, carbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, indolocarbazolyl, phenylindolocarbazolyl, phenanthrolinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, quinolinyl, isoquinolinyl, acridinyl, isobenzofuranyl, and similar heteroaryl groups. In various embodiments, the heteroaryl group of C2-C30 may contain 2-30 carbon atoms for forming a ring.
Throughout this specification, substituents of compounds are disclosed in groups or ranges. It is expressly intended that such description include each individual sub-combination of members of these groups and ranges. For example, the term "alkyl of C1-C6" is expressly contemplated to disclose separately C1, C2, C3, C4, C5, C6, C1-C6, C1-C5, C1-C4, C1-C3, C1-C2, C2-C6, C2-C5, C2-C4, C2-C3, C3-C6, C3-C5, C3-C4, C4-C6, C4-C5, and C5-C6 alkyl. As other examples, integers ranging from 6 to 30 are expressly contemplated to disclose individually 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, and 30; integers in the range of 1 to 20 are expressly contemplated to disclose 1,2,3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 and 20 individually. Accordingly, other groups or ranges are expressly contemplated.
As used herein, the expression that a single bond is taken through a ring or ring system means that a single bond may be attached at any accessible position on the ring or ring system. The occurrence of "#" indicates the connection location.
In an embodiment of the first aspect, the present invention provides a compound having a structure represented by formula (1),
Figure BDA0003139658420000051
in the formula (1), L 11 And L 12 Each independently selected from substituted or unsubstituted aryl of C6-C30, substituted or unsubstituted heteroaryl of C2-C20, and substituted or unsubstituted adamantyl.
R 11 And R 12 Each independently selected from the first group or the second group. The first group is selected from groups having electron donating ability. Preferably, the first group is selected from substituted or unsubstituted carbazolyl groups and derivatives thereof, substituted or unsubstituted acridinyl groups and derivatives thereof, substituted or unsubstituted arylamino groups and derivatives thereof, and substituted or unsubstituted dibenzo B and G hetero six membered ring unit-containing groups, wherein the aryl groups in the arylamino groups are independently selected from substituted or unsubstituted C6-C30 aryl groups, and G independently represents O, S or N. The second group is selected from groups having electron accepting capability. Preferably, the second group is selected from the group consisting of substituted or unsubstituted nitrogen heteroatom-containing heteroaryl, cyano-substituted aryl, cyano-substituted heteroaryl, substituted or unsubstituted arylboronyl, substituted or unsubstituted arylketonyl, substituted or unsubstituted heteroarylketonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted arylphosphonoxy and derivatives thereof, substituted or unsubstituted phthaloylamino and derivatives thereof, substituted or unsubstituted naphthalimide and derivatives thereof, substituted or unsubstituted perylene imide and derivatives thereof.
m and n each independently represent 0, 1,2 or 3. p and q each independently represent 0, 1,2 or 3. m + p is more than or equal to 1. n + q is not less than 1. If m is 0, then (R) 11 ) p -directly linked to N by a single bond. If p is 0, then no R is present 11 And (4) substituting the group. Similarly, if n is 0, then this represents (R) 12 ) q -directly linked to N by a single bond. If q is 0, then no R is present 12 And (4) substituting the group.
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 And R 8 Each independently represents hydrogen, halogen, cyano, isocyanoThe aryl group comprises a base group, a substituted or unsubstituted silane group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C1-C10 alkylthio group, a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C2-C30 heteroaryl group.
In any embodiment, m represents 0, 1 or 2. In some embodiments, m represents 1. And p + q is not less than 1. As an example, p represents 0 and q represents 1,2 or 3. Alternatively, p represents 0 and q represents 1. As another example, p represents 1,2 or 3, and q represents 0, 1,2 or 3. In these examples, R 11 Radical passing through L 11 The group is connected to the core unit, which can improve the stability of the molecule. Alternatively, p represents 1 and q represents 0 or 1.
In any embodiment, L 11 Can be independently selected from substituted or unsubstituted aryl groups of C6-C30. Alternatively, L 11 Can be independently selected from substituted or unsubstituted aryl groups of C6-C20. Yet alternatively, L 11 Can be independently selected from substituted or unsubstituted aryl groups of C6-C14. In some embodiments, L 11 Can be independently selected from phenyl, naphthyl, phenanthryl, anthryl, biphenyl, triphenylene, pyrenyl, spirobifluorenyl,
Figure BDA0003139658420000061
Perylene, indenyl, azulenyl. Examples of biphenyl groups include biphenyl, terphenyl, and the like. Alternatively, L 11 Can be independently selected from phenyl, naphthyl, phenanthryl, anthracyl, biphenyl, triphenylene. Yet alternatively, L 11 Can be independently selected from phenyl, naphthyl, anthryl and biphenyl. Further optionally, L 11 Represents phenyl or biphenyl. Especially alternatively, L 11 Represents a phenyl group.
In some embodiments, (R) 11 ) p -(L 11 ) m - # may represent
Figure BDA0003139658420000062
Wherein p is as defined herein. As specific examples include
Figure BDA0003139658420000063
Or
Figure BDA0003139658420000064
p represents 0 or 1. In some embodiments. p represents 1.
In some embodiments, (R) 11 ) p -(L 11 ) m - # may represent
Figure BDA0003139658420000065
Or
Figure BDA0003139658420000066
Wherein p is as defined herein. Specific examples include the structures shown below, wherein p represents 0 or 1. In some embodiments. p represents 1.
Figure BDA0003139658420000067
In some embodiments, (R) 11 ) p -(L 11 ) m - # may represent
Figure BDA0003139658420000068
Or
Figure BDA0003139658420000069
Wherein p is as defined herein. As a specific example may include
Figure BDA00031396584200000610
Or
Figure BDA00031396584200000611
Wherein p represents 0 or 1. In some embodiments, p represents 1.
In some embodiments, (R) 11 ) p -(L 11 ) m - # may represent any of the following structures, wherein p is as defined herein.
Figure BDA0003139658420000071
As a specific example may include
Figure BDA0003139658420000072
p represents 0 or 1. In some embodiments, p represents 1.
In any embodiment, L 11 Can be independently selected from substituted or unsubstituted C2-C20 heteroaryl. Alternatively, L 11 Can be independently selected from substituted or unsubstituted C4-C12 heteroaryl. In some embodiments, L 11 May be independently selected from pyrrolyl, furanyl, oxazolyl, isoxazolyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, oxadiazolyl, imidazolyl, pyrazolyl, triazole, pyridazinyl, pyrazinyl, pyridyl, pyrimidinyl, triazinyl, pyronyl, indolyl, quinolyl, isoquinolyl, acridinyl, purinyl, pteridinyl, benzofuranyl, benzothienyl, benzimidazolyl, benzothiazolyl, coumarinyl, cinnoline, quinoxalyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenanthrolinyl, phenothiazinyl, phenoxazinyl. Alternatively, L 11 Represents a pyridyl group.
In some embodiments, (R) 11 ) p -(L 11 ) m - # may represent
Figure BDA0003139658420000073
Or
Figure BDA0003139658420000074
Wherein p is as defined herein. As a specific example may include
Figure BDA0003139658420000075
p represents 0 or 1. In some embodiments, p represents 1.
In any embodiment, L 11 May be independently selected from substituted or unsubstituted adamantyl groups. Adamantyl is a non-conjugated rigid structure, introduced in the moleculeThe inclusion of adamantyl groups allows for high triplet energy levels. The compound can be suitable for a blue light emitting host material or a green light emitting host material. In addition, the adamantyl group is introduced on the core unit, so that the compound can obtain better thermal stability; and the solubility of molecules can be improved, and the cleaning of a Mask (Mask) in a mass production stage is facilitated.
In any embodiment, n represents 0, 1 or 2. In some embodiments, n represents 1. And p + q is not less than 1. As an example, q represents 0 and p represents 1,2 or 3. Alternatively, q represents 0 and p represents 1. As another example, q represents 1,2 or 3 and p represents 0, 1,2 or 3. In these examples, R 12 Radical passing through L 12 The group is connected to the core unit, which can improve the stability of the molecule. Alternatively, q represents 1 and p represents 0 or 1.
In any embodiment, L 12 Can be independently selected from substituted or unsubstituted aryl groups of C6-C30. Alternatively, L 12 Can be independently selected from substituted or unsubstituted aryl groups of C6-C20. Yet alternatively, L 12 Can be independently selected from substituted or unsubstituted aryl groups of C6-C14. In some embodiments, L 12 Can be independently selected from phenyl, naphthyl, phenanthryl, anthryl, biphenyl, triphenylene, pyrenyl, spirobifluorenyl,
Figure BDA0003139658420000076
Perylene, indenyl, azulenyl. Examples of biphenyls include biphenyl, terphenyl, and the like. Alternatively, L 12 Can be independently selected from phenyl, naphthyl, phenanthryl, anthracyl, biphenyl, triphenylene. Yet alternatively, L 12 Can be independently selected from phenyl, naphthyl, anthryl and biphenyl. Further optionally, L 12 Represents phenyl or biphenyl. Especially alternatively, L 12 Represents a phenyl group.
In some embodiments, (R) 12 ) q -(L 12 ) n - # may represent
Figure BDA0003139658420000081
Wherein q is as defined herein. As specific examples include
Figure BDA0003139658420000082
Or
Figure BDA0003139658420000083
q represents 0 or 1. In some embodiments. q represents 1.
In some embodiments, (R) 12 ) q -(L 12 ) n - # may represent
Figure BDA0003139658420000084
Or
Figure BDA0003139658420000085
Wherein q is as defined herein. Specific examples include the structures shown below, wherein q represents 0 or 1. In some embodiments. q represents 1.
Figure BDA0003139658420000086
In some embodiments, (R) 12 ) q -(L 12 ) n - # may represent
Figure BDA0003139658420000087
Or
Figure BDA0003139658420000088
Wherein q is as defined herein. As a specific example may include
Figure BDA0003139658420000089
Wherein q represents 0 or 1. In some embodiments, q represents 1.
In some embodiments, (R) 12 ) q -(L 12 ) n - # may represent any of the following structures, wherein q is as defined herein.
Figure BDA00031396584200000810
As a specific example may include
Figure BDA00031396584200000811
q represents 0 or 1. In some embodiments, q represents 1.
In any embodiment, L 12 Can be independently selected from substituted or unsubstituted heteroaryl of C2-C20. Alternatively, L 12 Can be independently selected from substituted or unsubstituted C4-C12 heteroaryl. In some embodiments, L 12 May be independently selected from pyrrolyl, furanyl, oxazolyl, isoxazolyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, oxadiazolyl, imidazolyl, pyrazolyl, triazole, pyridazinyl, pyrazinyl, pyridyl, pyrimidinyl, triazinyl, pyronyl, indolyl, quinolyl, isoquinolyl, acridinyl, purinyl, pteridinyl, benzofuranyl, benzothienyl, benzimidazolyl, benzothiazolyl, coumarinyl, cinnoline, quinoxalyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenanthrolinyl, phenothiazinyl, phenoxazinyl. Alternatively, L 12 Represents a pyridyl group.
In some embodiments, (R) 12 ) q -(L 12 ) n - # may represent
Figure BDA0003139658420000091
Or
Figure BDA0003139658420000092
Wherein q is as defined herein. As a specific example may include
Figure BDA0003139658420000093
q represents 0 or 1. In some embodiments, q represents 1.
In any embodiment, L 12 May be independently selected from substituted or unsubstituted adamantyl groups. Adamantyl is a non-conjugated rigid structure, and high triplet state energy level can be realized by introducing adamantyl into molecules. The compound can be suitable for blue light emitting main body material or green light emitting main body materialAnd (5) feeding. In addition, the adamantyl group is introduced on the core unit, so that the compound can obtain better thermal stability; and the solubility of molecules can be improved, and the cleaning of a Mask (Mask) in a mass production stage is facilitated.
In any embodiment, L 11 And L 12 May be the same or different. When m is greater than or equal to 2, more than 2L 11 May be the same or different. When n is more than or equal to 2, more than 2L 12 May be the same or different. Alternatively, L 11 And L 12 Each independently represents phenyl, biphenyl, naphthyl or anthryl. In some embodiments, L 11 And L 12 The same is true.
In any embodiment, m represents 1, p represents 0 or 1, n represents 1, q represents 0 or 1, and p + q.gtoreq.1. Alternatively, p and q are both 1. Alternatively, p is 1 and q is 0; alternatively, p is 0 and q is 1.
In some embodiments, the compound has a structure represented by formula (1-1), formula (1-2), or formula (1-3). In the formulae, R 11 、R 12 、R 1 To R 8 P and q are each as defined herein. Alternatively, the compound has a structure represented by formula (1-1), or formula (1-2).
Figure BDA0003139658420000094
Figure BDA0003139658420000101
In any embodiment, R 11 And R 12 May be the same or different. When p is more than or equal to 2, more than 2R 11 May be the same or different and may be independently selected from the first group or the second group. When q is not less than 2, the number of R is not less than 2 12 May be the same or different and may be independently selected from the first group or the second group. Can be adjusted according to actual requirements 11 、R 12 、R 11 And L 11 And R 12 And L 12 Are designed differently to give the compounds the desired HOMO and LUMO energy levels, andelectron transport ability and hole transport ability.
In some embodiments, R 11 And R 12 Each independently selected from the first group. Alternatively, p and q are both 1. Alternatively, p is 1 and q is 0; alternatively, p is 0 and q is 1. The substitution of the first group with electron donating ability on the core unit with electron accepting ability can realize appropriate HOMO and LUMO levels while facilitating the transport of holes and electrons, thereby obtaining a compound with good electron and hole ambipolar transport ability. The compound also has higher triplet state energy level, is suitable for being used as a light-emitting host material in a light-emitting layer, and can prevent the backflow of triplet state energy from a light-emitting object material to the light-emitting host material, so that triplet state excitons are limited in the light-emitting layer to the maximum extent, the exciton utilization rate can be improved, and the light-emitting efficiency of an OLED device is improved. In addition, the compounds may also have large HOMO and LUMO energy level differences. The energy level difference of the luminescent host material is larger than that of the luminescent object material, so that the energy transfer from the luminescent host material to the luminescent object material and the direct capture of current carriers on the luminescent object material are facilitated, and the further improvement of the luminescent efficiency is facilitated.
In some embodiments, R 11 And R 12 Each independently selected from the second group. Alternatively, p and q are both 1. Alternatively, p is 1 and q is 0; alternatively, p is 0 and q is 1. The substitution of the second group with the electron accepting capability on the core unit with the electron accepting capability can enable the compound to have a proper HOMO energy level and a deeper LUMO energy level, realize stronger electron transfer capability, and simultaneously effectively block holes. And the compound also has a higher triplet energy level, and can block excitons in the light-emitting layer. Therefore, these compounds are suitable as electron transport materials or hole blocking materials in OLED devices. The compound can reduce the working voltage of the device and improve the luminous efficiency of the device.
In some embodiments, R 11 And R 12 One selected from the first group and the other selected from the second group. Alternatively, p and q are both 1. In the presence of electron-receiving capabilityThe core unit is substituted by a first group with electron donating ability and a second group with electron accepting ability, and the HOMO and LUMO energy levels of the compound can be adjusted according to actual requirements, so that the compound has required electron transport ability and hole transport ability, and the energy level of the compound is more matched with the energy level of the material of the adjacent layer of the OLED device. Alternatively, the compound may have an appropriate HOMO level and a deeper LUMO level, achieving a stronger electron transport capability, while effectively blocking holes. These compounds are suitable as electron transport materials or hole blocking materials in OLED devices. The compound also has a higher triplet energy level, and can block excitons in the light-emitting layer. Therefore, the compound can reduce the working voltage of the device and improve the luminous efficiency of the device.
In any embodiment, the first group can be selected from substituted or unsubstituted carbazolyl groups and derivatives thereof. Examples thereof may include substituted or unsubstituted carbazolyl groups shown below and derivative groups thereof.
Figure BDA0003139658420000111
When present, R a 、R b And R c Each independently represents a cyano group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, or a substituted or unsubstituted C6-C40 aryl group. In some embodiments, the C1-C20 alkyl group, C1-C20 alkoxy group, and C6-C40 aryl group can each be selected from those described herein.
Alternatively, R a When present, represents cyano, methyl, isopropyl, t-butyl, methoxy, or phenyl. In some embodiments, R a When present, represents methyl, isopropyl, or tert-butyl.
Alternatively, R b When present, represents cyano, methyl, isopropyl, tert-butyl, methoxy, or phenyl. In some embodiments, R b When present, represents methyl, isopropyl, or tert-butyl.
Alternatively, R c At the time of appearanceRepresents cyano, methyl, isopropyl, tert-butyl, methoxy, or phenyl. In some embodiments, R c When present, represents methyl, isopropyl, or tert-butyl.
When present, R A And R B Each independently represents a cyano group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C40 aryl group, a substituted or unsubstituted C4-C40 heteroaryl group, or a substituted or unsubstituted arylamino group. In some embodiments, the C1-C20 alkyl group, C1-C20 alkoxy group, C6-C40 aryl group, C4-C40 heteroaryl and arylamino groups, respectively, can be selected from those described herein.
Alternatively, R A When present, represents cyano, methyl, isopropyl, tert-butyl, methoxy, phenyl, pyridyl, or diphenylamino. Yet alternatively, R A When present, represents methyl, isopropyl, tert-butyl, methoxy, or phenyl. In some embodiments, R A When present, represents methyl, isopropyl, or tert-butyl.
Alternatively, R B When present, represents cyano, methyl, isopropyl, tert-butyl, methoxy, phenyl, pyridyl, or diphenylamino. Yet alternatively, R B When present, represents methyl, isopropyl, tert-butyl, methoxy, or phenyl. In some embodiments, R B When present, represents methyl, isopropyl, or tert-butyl.
When present, X independently represents O, S, N (Z), C (Z) 2 、Si(Z) 2 Wherein Z independently represents hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, or a substituted or unsubstituted C6-C40 aryl group. In some embodiments, the C1-C20 alkyl group, C1-C20 alkoxy group, and C6-C40 aryl group can each be selected from those described herein.
In some embodiments, X independently represents O.
In some embodiments, X independently represents S.
In some embodiments, X independently represents n (z). Such as n (ph). Herein, Ph represents phenyl. Further examples are N (biphenyl). As another example, N (naphthyl).
In some embodiments, X independently represents C (Z) 2 . E.g. C (Ph) 2 . Further example is C (CH) 3 ) 2 。
In some embodiments, X independently represents Si (Z) 2 . For example Si (Ph) 2 。
When present, α represents 0, 1 or 2. Beta represents 0, 1 or 2.γ represents 0, 1 or 2. In some embodiments, when two or more of α, β, and γ occur simultaneously, one or more of them represents 0. In some embodiments, two or more of α, β, and γ all represent 0 when they occur simultaneously.
In some embodiments, the first group is selected from
Figure BDA0003139658420000131
R A And R B As defined herein, α represents 0 or 1 and β represents 0 or 1, respectively. Specific examples may include the following structures:
Figure BDA0003139658420000132
in some embodiments, the first group is selected from the group shown below, wherein X, R A And R B As defined herein, α represents 0 or 1 and β represents 0 or 1. For example, α represents 0 and β represents 0.
Figure BDA0003139658420000133
Specific examples may include groups shown below,
Figure BDA0003139658420000134
alternatively, the first group is selected from
Figure BDA0003139658420000135
In some embodiments, the first group is selected from carbazolyl derivative groups shown below, wherein X is as defined herein,
Figure BDA0003139658420000141
in some embodiments, the first group is selected from the group shown below,
Figure BDA0003139658420000142
in any embodiment, the first group may be selected from substituted or unsubstituted acridinyl and derivatives thereof. Examples thereof include substituted or unsubstituted acridinyl and derivative groups thereof as shown below,
Figure BDA0003139658420000151
in each of the above structural formulae, R a 、R b 、R c X, α, β and γ are each as defined herein.
When present, Y independently represents O, S, N (Z), C (Z) 2 、Si(Z) 2 Wherein Z is as defined herein.
In some embodiments, Y independently represents O.
In some embodiments, Y independently represents S.
In some embodiments, Y independently represents n (z). Such as n (ph). Further examples are N (biphenyl). As another example, N (naphthyl).
In some embodiments, Y independently represents C (Z) 2 . For example C (Ph) 2 . Further example is C (CH) 3 ) 2 。
In some embodiments, Y independently represents Si (Z) 2 . For example Si (Ph) 2 。
In some embodiments, the first group can be selected from
Figure BDA0003139658420000152
R a And R b As defined herein, α represents 0 or 1 and β represents 0 or 1, respectively. Examples may include, but are not limited to:
Figure BDA0003139658420000153
in some embodiments, the first group can be selected from the group shown below,
Figure BDA0003139658420000154
specific examples may include, but are not limited to:
Figure BDA0003139658420000161
in any embodiment, the first group may be selected from substituted or unsubstituted arylamino groups and derivatives thereof, wherein the aryl groups in the arylamino groups are independently selected from substituted or unsubstituted C6-C30 aryl groups. In some embodiments, the aryl group of C6 to C30 may be selected from those described herein. In some embodiments, the aryl groups in the arylamino groups are independently selected from substituted or unsubstituted phenyl, or substituted or unsubstituted naphthyl.
In some embodiments, the first group can be selected from substituted or unsubstituted arylamino groups and derivatives thereof,
Figure BDA0003139658420000162
Figure BDA0003139658420000171
in each of the above structural formulae, R a 、R b 、R c Alpha, beta and gammaEach as defined herein. Optionally, two aryl groups in each arylamino group and derivatives thereof may be linked.
In some embodiments, the first group can be selected from the group consisting of,
Figure BDA0003139658420000172
in some embodiments, the first group can be selected from the group consisting of,
Figure BDA0003139658420000173
in any embodiment, the first group can be selected from substituted or unsubstituted dibenzo B-and G-containing heterosix-membered ring units (e.g., a substituted or unsubstituted dibenzo B-and G-containing heterocyclic ring unit
Figure BDA0003139658420000174
) Wherein G independently represents O, S or N. In some embodiments, the first group may be selected from dibenzo B and G heterosix-membered ring unit-containing groups as shown below,
Figure BDA0003139658420000175
in any embodiment, the second group may be selected from substituted or unsubstituted nitrogen heteroatom-containing heteroaryl groups.
In some embodiments, the electron accepting group may be selected from nitrogen heteroatom-containing heteroaryl groups as shown below,
Figure BDA0003139658420000181
when present, R is independently selected from hydrogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C4-C8 cycloalkyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C4-C40 heteroaryl. In some embodiments, the aforementioned C1-C20 alkyl, C1-C20 alkoxy, C4-C8 cycloalkyl, C6-C40 aryl, C4-C40 heteroaryl can each be selected from those described herein. In some embodiments, R represents phenyl.
Alternatively, the second group may be selected from the group shown below,
Figure BDA0003139658420000182
in some embodiments, the second group may be selected from nitrogen heteroatom-containing heteroaryl groups as shown below,
Figure BDA0003139658420000183
alternatively, the second group may be selected from:
Figure BDA0003139658420000184
in some embodiments, the second group may be selected from nitrogen heteroatom-containing heteroaryl groups as shown below,
Figure BDA0003139658420000191
alternatively, the second group is selected from the group shown below,
Figure BDA0003139658420000192
further optionally, the second group is selected from
Figure BDA0003139658420000193
In some embodiments, the second group may be selected from
Figure BDA0003139658420000194
Wherein R is as defined hereinAnd (4) defining. In some embodiments, R represents phenyl.
In some embodiments, the second group may be selected from
Figure BDA0003139658420000195
(e.g. using
Figure BDA0003139658420000196
) Wherein R is as defined herein. In some embodiments, R represents phenyl.
In some embodiments, the second group may be selected from nitrogen heteroatom-containing heteroaryl groups as shown below.
Figure BDA0003139658420000197
Alternatively, the second group may be selected from
Figure BDA0003139658420000198
In some embodiments, the second group may be selected from
Figure BDA0003139658420000201
Alternatively, the second group may be selected from:
Figure BDA0003139658420000202
in some embodiments, the second group may be selected from nitrogen heteroatom-containing heteroaryl groups as shown below.
Figure BDA0003139658420000203
Alternatively, the second group may be selected from
Figure BDA0003139658420000204
In some embodiments, the second group may be selected from nitrogen heteroatom-containing heteroaryl groups as shown below.
Figure BDA0003139658420000205
In some embodiments, the second group may be selected from nitrogen heteroatom-containing heteroaryl groups as shown below.
Figure BDA0003139658420000206
Alternatively, the second group may be selected from nitrogen heteroatom-containing heteroaryl groups as shown below,
Figure BDA0003139658420000211
in any embodiment, the second group may be selected from cyano.
In any embodiment, the second group may be selected from cyano-substituted aryl groups. In some embodiments, the aryl group can be those described herein, such as phenyl, naphthyl, and the like. In some embodiments, the second group may be selected from cyano-substituted aryl groups as shown below,
Figure BDA0003139658420000212
alternatively, the second group is selected from the group shown below,
Figure BDA0003139658420000213
in any embodiment, the second group may be selected from cyano-substituted heteroaryl. Heteroaryl groups may be those described herein, such as pyridyl and the like. In some embodiments, the second group is selected from cyano-substituted heteroaryl groups as shown below,
Figure BDA0003139658420000214
alternatively, the second group is selected from
Figure BDA0003139658420000215
In any embodiment, the second group may be selected from arylboron. In some embodiments, the second group is selected from the arylboron groups shown below,
Figure BDA0003139658420000221
in any embodiment, the second group may be selected from aryl ketone groups. In some embodiments, the second group is selected from the group of aryl ketones shown below,
Figure BDA0003139658420000222
when present, R' independently represents hydrogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C4-C8 cycloalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl. In some embodiments, the aforementioned C1-C20 alkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, C4-C8 cycloalkyl, C6-C40 aryl, and C4-C40 heteroaryl can be respectively selected from those described herein. In some embodiments, R' independently represents phenyl.
Alternatively, the second group is selected from the group of aryl ketones shown below,
Figure BDA0003139658420000223
in any embodiment, the second group may be selected from heteroAryl ketone group. Optionally selected from:
Figure BDA0003139658420000224
further selected from
Figure BDA0003139658420000225
In any embodiment, the second group may be selected from aryl sulfone-based groups. In some embodiments, the second group is selected from aryl sulfone-based groups as shown below,
Figure BDA0003139658420000231
alternatively, the second group may be selected from aryl sulfone groups as shown below,
Figure BDA0003139658420000232
further alternatively, the second group may be selected from aryl sulfone groups as shown below,
Figure BDA0003139658420000233
in any embodiment, the second group can be selected from substituted or unsubstituted arylphosphoxy groups and derivatives thereof. Alternatively, the second group is selected from
Figure BDA0003139658420000234
R' is as defined herein, for example represents phenyl. Further optionally, the second group is selected from
Figure BDA0003139658420000235
In any embodiment, the second group may be selected from substituted or unsubstituted phthalamide groups and derivatives thereof. Is optionally selected from
Figure BDA0003139658420000236
R' is as defined herein, for example represents phenyl. Further optionally, the second group is selected from
Figure BDA0003139658420000237
In any embodiment, the second group may be selected from substituted or unsubstituted naphthalene dimethylamides and derivatives thereof. Is optionally selected from
Figure BDA0003139658420000241
R' is as defined herein, for example represents phenyl. Further alternatively, the second group is selected from
Figure BDA0003139658420000242
In any embodiment, the second group can be selected from substituted or unsubstituted perylene imide groups and derivatives thereof. Optionally selected from the groups shown below, R' is as defined herein, for example representing phenyl.
Figure BDA0003139658420000243
Further alternatively, the second group is selected from
Figure BDA0003139658420000244
In any embodiment, R 1 Represents hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy. Alternatively, the halogen, the C1-C10 alkyl group, and the C1-C10 alkoxy group can each be selected from those described herein. In some embodiments, R 1 Represents hydrogen, halogen, cyano, methyl, isopropyl, tert-butyl, or methoxy. In some embodiments, R 1 Represents hydrogen or fluorine.
In any embodiment, R 2 Represents hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstitutedSubstituted C1-C10 alkoxy. Alternatively, the halogen, the C1-C10 alkyl group, and the C1-C10 alkoxy group can each be selected from those described herein. In some embodiments, R 2 Represents hydrogen, halogen, cyano, methyl, isopropyl, tert-butyl, or methoxy. In some embodiments, R 2 Represents hydrogen or fluorine.
In any embodiment, R 3 Represents hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy. Alternatively, the halogen, the C1-C10 alkyl group, and the C1-C10 alkoxy group can each be selected from those described herein. In some embodiments, R 3 Represents hydrogen, halogen, cyano, methyl, isopropyl, tert-butyl, or methoxy. In some embodiments, R 3 Represents hydrogen or fluorine.
In any embodiment, R 4 Represents hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy. Alternatively, the halogen, the C1-C10 alkyl group, and the C1-C10 alkoxy group can each be selected from those described herein. In some embodiments, R 4 Represents hydrogen, halogen, cyano, methyl, isopropyl, tert-butyl, or methoxy. In some embodiments, R 4 Represents hydrogen or fluorine.
In any embodiment, R 5 Represents hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy. Alternatively, the halogen, the C1-C10 alkyl group, and the C1-C10 alkoxy group can each be selected from those described herein. In some embodiments, R 5 Represents hydrogen, halogen, cyano, methyl, isopropyl, tert-butyl, or methoxy. In some embodiments, R 5 Represents hydrogen or fluorine.
In any embodiment, R 6 Represents hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy. Alternatively, the halogen, the C1-C10 alkyl group, and the C1-C10 alkoxy group can each be selected from those described herein. In some embodiments, R 6 Represents hydrogen, halogen, cyano, methyl, isopropyl, tert-butyl, or methoxy. In some embodiments, R 6 Represents hydrogen or fluorine.
In any embodiment, R 7 Represents hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy. Alternatively, the halogen, the C1-C10 alkyl group, and the C1-C10 alkoxy group can each be selected from those described herein. In some embodiments, R 7 Represents hydrogen, halogen, cyano, methyl, isopropyl, tert-butyl, or methoxy. In some embodiments, R 7 Represents hydrogen or fluorine.
In any embodiment, R 8 Represents hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C1-C10 alkoxy. Alternatively, the halogen, the C1-C10 alkyl group, and the C1-C10 alkoxy group can each be selected from those described herein. In some embodiments, R 8 Represents hydrogen, halogen, cyano, methyl, isopropyl, tert-butyl or methoxy. In some embodiments, R 8 Represents hydrogen or fluorine.
In some embodiments, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 And R 8 One or more of which is fluorine. The fluorine atom is taken as a substituent group, so that the energy level of the compound can be adjusted, and the polarity and the carrier transmission performance of the compound are further improved; and the stability of the compound can be enhanced, and the service life of the device can be prolonged. Especially in organic light emitting diodes, C-H … F interaction can give rise to the typical pi-stacking arrangement, thereby enhancing charge mobility.
In some embodiments of the invention, m, n, p and q are all 1; l is 11 And L 12 Is selected from phenyl or biphenyl, and L 11 And L 12 The same; r 11 And R 12 Are each selected from a first group, and R 11 And R 12 The same; r 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 And R 8 Are all shown asAnd (3) hydrogen. Examples of the compound include any of the following:
Figure BDA0003139658420000251
Figure BDA0003139658420000261
Figure BDA0003139658420000271
Figure BDA0003139658420000281
Figure BDA0003139658420000291
Figure BDA0003139658420000301
Figure BDA0003139658420000311
Figure BDA0003139658420000321
Figure BDA0003139658420000331
Figure BDA0003139658420000341
Figure BDA0003139658420000351
in some embodiments of the invention, m and n are both 1, p is 0, and q is 1; l is 11 Selected from phenyl, biphenyl or naphthyl, L 12 Selected from phenyl or biphenyl; r 12 Selected from the first group; r 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 And R 8 All represent hydrogen. Examples of the compound include any of the following:
Figure BDA0003139658420000361
in some embodiments of the invention, m, n, p and q are all 1; l is 11 And L 12 Is selected from phenyl or biphenyl, and L 11 And L 12 The same; r 11 And R 12 Are each selected from a second group, and R 11 And R 12 The same; r is 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 And R 8 Both represent hydrogen. Examples of the compound include any of H001 to H081.
In some embodiments of the invention, m, n, p and q are all 1; l is 11 And L 12 Is selected from phenyl or biphenyl, and L 11 And L 12 The same; r 11 And R 12 Are each selected from a second group, and R 11 And R 12 Different; r 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 And R 8 Both represent hydrogen. Examples of the compound include any of H082.
In some embodiments of the invention, m and n are both 1, p is 0, and q is 1; l is 11 Selected from phenyl, biphenyl or naphthyl, L 12 Selected from phenyl or biphenyl; r is 12 Selected from the second group; r 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 And R 8 All represent hydrogen. Examples of the compound include any one of H083 to H092.
Figure BDA0003139658420000362
Figure BDA0003139658420000371
Figure BDA0003139658420000381
Figure BDA0003139658420000391
Figure BDA0003139658420000401
Figure BDA0003139658420000411
Figure BDA0003139658420000421
Figure BDA0003139658420000431
In some embodiments of the invention, m, n, p and q are all 1; l is 11 And L 12 Is selected from pyridyl, and L 11 And L 12 The same; r 11 And R 12 Are each selected from a second group, and R 11 And R 12 The same; r 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 And R 8 All represent hydrogen. Examples of the compound include any of H093.
Figure BDA0003139658420000432
In some embodiments of the invention, m, n, p and q are all 1; l is a radical of an alcohol 11 And L 12 Is selected from phenyl or biphenyl, and L 11 And L 12 The same; r 11 And R 12 One selected from the first group and the other selected from the second group; r 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 And R 8 All represent hydrogen. Examples of the compound include any of the following,
Figure BDA0003139658420000433
Figure BDA0003139658420000441
it is understood that the compound of the invention can be any L described herein 11 、L 12 、R 11 、R 12 、R 1 To R 8 M, n, p and q, and are not limited to those listed.
The present invention next provides a display panel. The display panel includes an organic light emitting device including an anode, a cathode, and an organic film layer between the anode and the cathode, the organic film layer including an emission layer (EML). Other functional layers may also be included in the organic film layer. For example, the other functional layers may include one or more of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), and a Capping layer (Capping layer). The organic film layer contains more than one compound of the invention.
The compound can obtain required HOMO and LUMO energy levels and required hole and/or electron transport capacity by carrying out different group substitution on the core unit, and can be further applied to different functional materials in an organic film layer, such as a light-emitting host material, a hole transport material, an electron blocking material, a cap layer material and the like. When the compounds of the present invention are applied in any one of the functional layers, the materials of the other functional layers may be selected from materials known in the art, respectively.
In some embodiments, in the compound, R 11 And R 12 Each independently selected from the first group. These compounds are suitable for use in luminescent layer materials. The light-emitting layer includes 1 or more compounds of the present invention.
At present, the light emitting layer in the OLED basically uses a host-guest light emitting system structure, i.e., a light emitting host material is doped with a light emitting guest material. The light color of the OLED can be regulated and controlled by matching the light-emitting host material and the light-emitting guest material, and the efficiency of the device is improved. In some embodiments, the luminescent host material comprises a compound of the present invention. Preferably, as the compound of the light emitting host material, the HOMO level may be-5.0 ± 0.3 eV. Further, the LUMO level of the compound may be-1.1 + -0.3 eV. In these embodiments, the light-emitting guest material may be a fluorescent light-emitting material, a thermally activated delayed fluorescent material, or a phosphorescent light-emitting material, and may be a blue light-emitting material, a green light-emitting material, a red light-emitting material, or the like. In some embodiments, the emissive guest material is a phosphorescent emissive material. Further optionally, the emissive guest material is a green phosphorescent emissive material. Those skilled in the art can select the combination according to the light emitting principle and different light emitting colors.
Alternatively, the difference between the HOMO level of the light emitting host material and the HOMO level of the light emitting guest material is less than 0.6eV, or the difference between the LUMO level of the light emitting host material and the LUMO level of the light emitting guest material is less than 0.6 eV. Alternatively, the light-emitting guest material may be a fluorescent light-emitting material, or a thermally activated delayed fluorescent material, the singlet energy level of the light-emitting guest material being smaller than the singlet energy level of the light-emitting host material, and the difference between the singlet energy level of the light-emitting host material and the singlet energy level of the light-emitting guest material being smaller than 1.0 eV. The light-emitting guest material may be a phosphorescent material, a triplet level of the light-emitting guest material is less than a triplet level of the light-emitting host material, and a difference between the triplet level of the light-emitting host material and the triplet level of the light-emitting guest material is less than 1.0 eV.
In some embodiments, in the compound, R 11 And R 12 Each independently selected from the second group. Yet alternatively, R 11 And R 12 One of them represents a first group and the other represents a second group, p.gtoreq.1, q.gtoreq.1. These compounds are suitable for use in hole blocking materials or electron transport materials. Preferably, the LUMO level of the compound may be-1.8 + -0.1 eV. Further, the HOMO energy level of the compound may be-6.0 + -0.4 eV. Thus, in some embodiments, the organic film layer comprises a hole blocking layer between the cathode and the light-emitting layer, the hole blocking layer comprising 1 or more compounds of the invention. In some embodiments, the organic film layer comprises an electron transport layer between the cathode and the light-emitting layer, the electron transport layer comprising 1 or more compounds of the present invention.
In some embodiments, the anode material may include a metal (e.g., copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc., and alloys thereof), a metal oxide (e.g., indium oxide, zinc oxide, indium tin oxide ITO, indium zinc oxide IZO, indium gallium zinc oxide IGZO, etc.), a conductive polymer (e.g., polyaniline, polypyrrole, poly (3-methylthiophene), etc.). In addition to the above materials and combinations thereof that facilitate hole injection, other known materials suitable for use as anodes may be included.
In some embodiments, the cathode can include a metal layer (e.g., aluminum, magnesium, silver, indium, tin, titanium, and the like, and alloys thereof), a multi-layered cathode formed by compounding a metal layer and a layer comprising one or more of a metal oxide and a metal halide (e.g., LiF/Al, LiO) 2 /Al、BaF 2 Al, etc.). In addition to the above materials and combinations thereof that facilitate electron injection, other known materials suitable for use as cathodes are also included.
Fig. 1 illustrates one example of an organic light emitting device. Referring to fig. 1, the organic light emitting device includes a substrate 1, an anode 2, an organic film layer, and a cathode 9 sequentially stacked, wherein the organic film layer includes a hole injection layer 3, a first hole transport layer 4, a second hole transport layer or electron blocking layer 5, a light emitting layer 6, a first electron transport layer or hole blocking layer 7, and a second electron transport layer 8 sequentially stacked in a direction from the anode 2 to the cathode 9. Optionally, an electron injection layer may also be provided between the second electron transport layer 8 and the cathode 9. The arrows in the figure indicate the light direction.
The organic light emitting device may be fabricated using methods known in the art. An exemplary method of fabrication includes: an anode is formed on a transparent or opaque substrate, an organic film layer is formed on the anode, and a cathode is formed on the organic film layer. The substrate may be a hard substrate (e.g., a glass substrate, a hard plastic substrate, etc.), or may be a flexible substrate (e.g., a polyimide substrate, etc.). The organic film layer can be formed by a known film formation method such as evaporation, sputtering, spin coating, dipping, ion plating, or the like. The compound of the present invention can have high solubility in conventional solvents (such as dichloromethane DCM, chloroform, toluene, dimethylformamide DMF, tetrahydrofuran THF, ethanol, etc.), facilitating the preparation of organic layers containing the same. In addition, the organic layer can obtain better film forming uniformity, and reduce or avoid the occurrence of holes.
Next, the present invention provides a display device. The display device comprises a display panel according to the invention. Examples of the display device include, but are not limited to, a mobile phone (as shown in fig. 2, the mobile phone 100 is an example), a computer, a television, a smart watch, a smart car, a VR or AR helmet, and the like, and the present invention is not particularly limited thereto.
Examples
The present disclosure is more particularly described in the following examples that are intended as illustrations only, since various modifications and changes within the scope of the present disclosure will be apparent to those skilled in the art. Unless otherwise indicated, all parts, percentages, and ratios reported in the following examples are on a weight basis, and all reagents used in the examples are commercially available or synthesized according to conventional methods and can be used directly without further treatment, and the equipment used in the examples is commercially available.
Synthesis of Compound (I)
The present invention illustratively provides methods for the preparation of several compounds. Other compounds of the invention may be prepared by reference to this exemplary method. Specific methods for carrying out each synthetic step are readily available to those skilled in the art from relevant scientific literature or standard textbooks in the art, based on the exemplified methods of compound preparation. Unless otherwise specified, commercially available or literature-known compounds are used as starting materials for the synthesis. One skilled in the art of organic synthesis will recognize that the nature and order of the synthetic steps presented may be varied for the purpose of optimizing the production of the compounds described herein.
The processes described herein may be monitored according to any suitable method known in the art. For example, product formation can be by spectroscopic means such as nuclear magnetic resonance spectroscopy (NMR, e.g. of 1 H or 13 C) Infrared spectroscopy (IR), spectrophotometry (e.g. UV visible), Mass Spectrometry (MS) or by chromatography such as High Performance Liquid Chromatography (HPLC), Gas Chromatography (GC), Gel Permeation Chromatography (GPC) or Thin Layer Chromatography (TLC).
(1) Synthesis of intermediate s1
Figure BDA0003139658420000461
To 300mL of water were added s01(10mmol), s02(10mmol), and NaOH (10mmol) to form a suspension; the suspension was heated at 85 ℃ for 1h until the solution became clear. After cooling, water was again added to dilute the solution. Glacial acetic acid is added to the diluted solution to precipitate the solid from the solution, filtered and dried in vacuum to obtain the crude intermediate a. The crude intermediate a was extracted with ethyl acetate, the organic phase was washed with brine, dried over anhydrous sodium sulfate, and the organic solvent was removed by distillation under reduced pressure. 100mL of methanol was added and 5mL of concentrated sulfuric acid was slowly added dropwise. Heated to reflux for 72 h. Distilling under reduced pressure to remove excess methanol, and adding the obtained solid into water; an aqueous solution of NaOH was added to adjust the pH of the solution to 8. Extraction was performed with ethyl acetate and the organic phase was collected. And sequentially washing the organic phase by using 1mol/L NaOH aqueous solution, deionized water and saline solution, drying the organic phase by using anhydrous sodium sulfate, and removing the organic solvent by reduced pressure distillation to obtain an intermediate crude product b. The crude intermediate b was dissolved in 200mL of anhydrous tetrahydrofuran THF, 2 molar equivalents of NaOH in mineral oil were added, and the mixture was heated under reflux for 18 h. The excess THF was distilled off under reduced pressure, the obtained organic phase was washed successively with 1mol/L aqueous HCl, deionized water, brine, and the organic phase was dried over anhydrous sodium sulfate, and the organic solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by column chromatography eluting with n-hexane/ethyl acetate to give the title compound S1(3.4mmol, 34%).
Calculated MALDI-TOF MS m/z: C26H16Br2N2O2: 546.0; measurement values: 545.8
(2) Synthesis of intermediate S2
Figure BDA0003139658420000471
With reference to the synthesis method of S1, the target compound S2(3.2mmol, 32%) was synthesized.
(3) Synthesis of intermediate S3
Figure BDA0003139658420000472
By referring to the synthesis method of S1, S3(2.8mmol, 28%) as a target compound was synthesized.
Example 1: synthesis of Compound M001
Figure BDA0003139658420000473
S1(1.3mmol), S4(3.25mmol), tris (dibenzylideneacetone) dipalladium (0) (0.13mmol), sodium tert-butoxide (0.13mmol), and tri-tert-butylphosphine (0.26mmol) were put in a 250mL three-necked flask, and while stirring, degassing and nitrogen substitution were rapidly repeated 3 times, and 80mL of toluene was added via a syringe. The mixture was heated to reflux under a stream of nitrogen for 24 hours. After the reaction, standing and cooling to room temperature; then, water was added to the reaction solution, followed by extraction with dichloromethane and washing with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain M001(1.12mmol, 86%).
Calculated MALDI-TOF MS m/z: 720.2 parts of C50H32N4O 2; measurement values: 720.3
Calculated values of elemental analysis: c, 83.31; h, 4.47; n, 7.77; o, 4.44; measurement values: c, 83.35; h, 4.48; n, 7.74; and O, 4.42.
1 H NMR(400MHz,CDCl 3 ,ppm):8.09-8.16(m,6H),7.63-7.68(m,10H),7.51-7.53(m,2H),7.37-7.38(m,2H),7.30-7.33(m,10H),7.21-7.23(m,2H)。
Example 2: synthesis of Compound M045
Figure BDA0003139658420000481
S1(1.5mmol), S5(3.75mmol), tris (dibenzylideneacetone) dipalladium (0) (0.15mmol), sodium tert-butoxide (0.15mmol), and tri-tert-butylphosphine (0.30mmol) were put in a 250mL three-necked flask, and while stirring, degassing and nitrogen substitution were rapidly repeated 3 times, and 90mL of toluene was added via a syringe. The mixture was heated to reflux under a stream of nitrogen for 24 hours. After the reaction, standing and cooling to room temperature; then, water was added to the reaction solution, followed by extraction with dichloromethane and washing with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain M045(1.23mmol, 82%).
Calculated MALDI-TOF MS m/z: C74H46N6O2: 1050.4; measurement values: 1050.6
Calculated value of elemental analysis: c, 84.55; h, 4.41; n, 7.99; o, 3.04; measurement values: c, 84.59; h, 4.42; n, 7.96; and O, 3.02.
1 H NMR(400MHz,CDCl 3 ,ppm):8.09-8.13(m,6H),7.64-7.69(m,12H),7.56-7.58(m,2H),7.48-7.52(m,8H),7.37-7.41(m,6H),7.30-7.33(m,10H),7.21-7.23(m,2H)。
Example 3: synthesis of Compound M063
Figure BDA0003139658420000482
S3(1.5mmol), S6(3.75mmol), tris (dibenzylideneacetone) dipalladium (0) (0.15mmol), sodium tert-butoxide (0.15mmol), and tri-tert-butylphosphine (0.30mmol) were put in a 250mL three-necked flask, and while stirring, degassing and nitrogen substitution were rapidly repeated 3 times, and 80mL of toluene was added via a syringe. The mixture was heated to reflux under a stream of nitrogen for 24 hours. After the reaction, standing and cooling to room temperature; then, water was added to the reaction solution, followed by extraction with dichloromethane and washing with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain M063(1.2mmol, 80%).
Calculated MALDI-TOF MS m/z: C48H30N6O2: 722.2; measurement values: 722.4
Calculated values of elemental analysis: c, 79.76; h, 4.18; n, 11.63; o, 4.43; measurement values: c, 79.79; h, 4.20; n, 11.60; o, 4.41.
1 H NMR(400MHz,CDCl 3 ,ppm):8.48-8.50(m,2H),8.44-8.46(m,2H),8.08-8.10(m,4H),7.87(d,2H),7.78(d,2H),7.71(d,2H),7.62-7.64(m,2H),7.49-7.52(m,6H),7.31-7.33(m,4H),7.26-7.27(m,2H),7.22-7.23(m,2H)。
Example 4: synthesis of Compound M081
Figure BDA0003139658420000491
S1(1.0mmol), S7(2.5mmol), tris (dibenzylideneacetone) dipalladium (0) (0.10mmol), sodium tert-butoxide (0.10mmol), and tri-tert-butylphosphine (0.20mmol) were put in a 250mL three-necked flask, and while stirring, degassing and nitrogen substitution were rapidly repeated 3 times, and 70mL of toluene was added via a syringe. The mixture was heated to reflux under a stream of nitrogen for 24 hours. After the reaction, standing and cooling to room temperature; then, water was added to the reaction solution, followed by extraction with dichloromethane and washing with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain M080(0.75mmol, 75%).
Calculated MALDI-TOF MS m/z: C62H42N6O2: 902.3; measurement values: 902.5
Calculated value of elemental analysis: c, 82.46; h, 4.69; n, 9.31; o, 3.54; measurement values: c, 82.49; h, 4.71; n, 9.28; and O, 3.52.
1 H NMR(400MHz,CDCl 3 ,ppm):8.08(d,2H),7.62-7.64(m,2H),7.51-7.52(m,6H),7.31-7.33(m,12H),7.25-7.26(m,4H),7.18-7.22(m,16H)。
Example 5: synthesis of Compound H004
Figure BDA0003139658420000492
Under the protection of nitrogen, weighing compounds S1(2.0mmol), S8(5.0mmol) and [ Pd ] 2 (dba) 3 ]·CHCl 3 (0.2mmol) and HP (tBu) 3 ·BF 4 (0.4mmol) was charged into a 250mL two-necked flask. Into a two-necked flask, 80mL of toluene was charged (N was introduced in advance) 2 Oxygen removal for 15 min), then 1.2mL of 1mol/L K was added dropwise 2 CO 3 Aqueous solution (Advance N) 2 15min deoxygenated), stirred at room temperature overnight. After the reaction, 30mL of deionized water was added and a few drops of 2mol/L HCl solution were added dropwise. Extracting with dichloromethane, collecting organic phase, and extracting with anhydrous Na 2 SO 4 And (5) drying. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to afford H004(1.56mmol, 78%) as a solid.
Calculated MALDI-TOF MS m/z: C56H36N8O2: 852.3; measurement values: 852.5
Calculated values of elemental analysis: c, 78.86; h, 4.25; n, 13.14; o, 3.75; measurement values: c, 78.91; h, 4.26; n, 13.10; and O, 3.73.
1 H NMR(400MHz,CDCl 3 ,ppm):8.32-8.34(m,8H),8.19-8.20(m,4H),8.07-8.09(m,4H),7.61-7.63(m,6H),7.48-7.51(m,12H),7.20-7.22(m,2H)。
Example 6: synthesis of Compound H019
Figure BDA0003139658420000501
Under the protection of nitrogen, weighing compounds S1(1.0mmol), S9(2.5mmol) and [ Pd ] 2 (dba) 3 ]·CHCl 3 (0.1mmol) and HP (tBu) 3 ·BF 4 (0.2mmol) was charged into a 100mL two-necked flask. 40mL of toluene (N was introduced into the two-neck flask in advance) 2 Oxygen removal for 15 min), then 0.6mL of 1mol/L K was added dropwise 2 CO 3 Aqueous solution (Advance N) 2 15min deoxygenated), stirred at room temperature overnight. After the reaction was complete, 20mL of deionized water was added and a few drops of 2mol/L HCl solution were added dropwise. Extracting with dichloromethane, collecting organic phase, and extracting with anhydrous Na 2 SO 4 And (5) drying. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to give H019(0.81mmol, 81%) as a solid.
Calculated MALDI-TOF MS m/z: C48H28N4O4: 724.2; measurement values: 724.3
Calculated value of elemental analysis: c, 79.55; h, 3.89; n, 7.73; o, 8.83; measurement values: c, 79.60; h, 3.90; n, 7.71; o, 8.79.
1 H NMR(400MHz,CDCl 3 ,ppm):8.46(d,2H),8.34-8.35(m,2H),8.07-8.08(m,2H),8.02-8.03(m,2H),7.76-7.78(m,2H),7.67-7.69(m,4H),7.59-7.64(m,8H),7.49-7.52(m,4H),7.21-7.22(m,2H)。
Example 7: synthesis of Compound H045
Figure BDA0003139658420000502
Under the protection of nitrogen, weighing compounds S2(1.5mmol), S10(3.75mmol) and [ Pd ] 2 (dba) 3 ]·CHCl 3 (0.15mmol) and HP (tBu) 3 ·BF 4 (0.3mmol) was charged into a 250mL two-necked flask. Into a two-necked flask, 80mL of toluene was charged (N was introduced in advance) 2 Oxygen removal for 15 min), then 1.5mL of 1mol/L K was added dropwise 2 CO 3 Aqueous solution (Advance N) 2 15min deoxygenated), stirred at room temperature overnight. After the reaction, 45mL of deionized water was added and a few drops of 2mol/L HCl solution were added dropwise. Extracting with dichloromethane, collecting organic phase, and extracting with anhydrous Na 2 SO 4 And (5) drying. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to give H045(1.28mmol, 85%) as a solid.
Calculated MALDI-TOF MS m/z: C40H24N4O2: 592.2; measurement values: 592.3
Calculated values of elemental analysis: c, 81.07; h, 4.08; n, 9.45; o, 5.40; measurement values: c, 81.11; h, 4.10; n, 9.43; and O, 5.36.
1 H NMR(400MHz,CDCl 3 ,ppm):8.08(d,2H),8.05(s,2H),7.81-8.82(m,4H),7.74-7.75(m,4H),7.62-7.63(m,2H),7.48-7.52(m,8H),7.21-7.23(m,2H)。
Example 8: synthesis of Compound M110
Figure BDA0003139658420000511
S1(1.35mmol), pinacol diboron ester S11(3.30mmol), (1, 1' -bis (diphenylphosphino) ferrocene) dichloropalladium (II) (0.10mmol) and potassium acetate (18mmol) were placed in a 100mL three-necked flask, and while stirring, degassing and nitrogen substitution were rapidly repeated 3 times, and 12mL of tetrahydrofuran was added via a syringe. Heating and refluxing the mixed solution at 80 ℃ for 5 hours under stirring; after the reaction was completed, it was cooled to room temperature and 12ml of water was added, extraction was performed with ether, the resulting organic phase was dried over anhydrous sodium sulfate, the solvent was removed by distillation, and purification was performed using column chromatography to obtain intermediate S12(1.1mmol, 81%).
MALDI-TOF MS: C38H40B2N2O6, calculated m/z: 642.3; measurement values: 642.5.
Figure BDA0003139658420000512
under the protection of nitrogen, weighing compounds S12(1.0mmol), S13(2.5mmol) and [ Pd ] 2 (dba) 3 ]·CHCl 3 (0.1mmol) and HP (tBu) 3 ·BF 4 (0.2mmol) was charged into a 250mL two-necked flask. Into a two-necked flask, 80mL of toluene was charged (N was introduced in advance) 2 Oxygen removal for 15 min), then 1.2mL of 1mol/L K was added dropwise 2 CO 3 Aqueous solution (Advance N) 2 15min deoxygenated), stirred at room temperature overnight. After the reaction, 35mL of deionized water was added and a few drops of 2mol/L HCl solution were added dropwise. Extracting with dichloromethane, collecting organic phase, and extracting with anhydrous Na 2 SO 4 And (5) drying. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to give M110 as a solid (0.6mmol, 60%).
Calculated MALDI-TOF MS m/z: C86H56B2N6O2: 1226.5; measurement values: 1226.7
Calculated values of elemental analysis: c, 84.18; h, 4.60; b, 1.76; n, 6.85; o, 2.61; measurement values: c, 84.23; h, 4.61; b, 1.76; n, 6.82; o, 2.58.
1 H NMR(400MHz,CDCl 3 ,ppm):8.08-8.10(m,2H),7.67-7.69(m,4H),7.59-7.62(m,6H),7.52-7.53(m,2H),7.42-7.43(m,4H),7.31-7.34(m,12H),7.27-7.28(m,4H),7.18-7.23(m,6H),7.10-7.14(m,12H)，7.04-7.06(m,4H)。
Example 9: synthesis of compound H072
Figure BDA0003139658420000521
With reference to the synthesis method of S12, S15 was synthesized.
MALDI-TOF MS: C38H40B2N2O6, calcd for m/z: 642.3, respectively; measurement values: 642.4.
Figure BDA0003139658420000522
under the protection of nitrogen, weighing compounds S15(1.0mmol), S16(2.5mmol) and [ Pd ] 2 (dba) 3 ]·CHCl 3 (0.1mmol) and HP (tBu) 3 ·BF 4 (0.2mmol) was charged into a 250mL two-necked flask. Into a two-necked flask, 80mL of toluene was charged (N was introduced in advance) 2 Oxygen removal for 15 min), then 1.2mL of 1mol/L K was added dropwise 2 CO 3 Aqueous solution (Advance N) 2 15min deoxygenated), stirred at room temperature overnight. After the reaction, 35mL of deionized water was added and a few drops of 2mol/L HCl were added dropwise. Extracting with dichloromethane, collecting organic phase, and extracting with anhydrous Na 2 SO 4 And (5) drying treatment. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to give H072(0.72mmol, 72%) as a solid.
Calculated MALDI-TOF MS m/z: C50H30N2O6S2: 818.2; measurement values: 818.5
Calculated values of elemental analysis: c, 73.33; h, 3.69; n, 3.42; o, 11.72; s, 7.83; measurement values: c, 73.37; h, 3.72; n, 3.41; o, 11.69; and S, 7.80.
1H NMR(400MHz,CDCl 3 ,ppm):8.61(s,2H),8.33-8.34(m,2H),8.25-8.26(m,2H),8.15-8.17(m,2H),8.06-8.08(m,4H),7.78-7.81(m,4H),7.69-7.71(m,2H),7.62-7.63(m,2H),7.56-7.58(m,2H)，7.48-7.52(m,6H),7.21-7.22(m,2H)。
Example 10: synthesis of Compound V001
Figure BDA0003139658420000531
Weighing the compounds S1(1.0mmol), S17(1.0mmol) and [ Pd ] under the protection of nitrogen 2 (dba) 3 ]·CHCl 3 (0.05mmol) and HP (tBu) 3 ·BF 4 (0.1mmol) was charged into a 250mL two-necked flask. 50mL of toluene (N was introduced into the flask in advance) 2 Oxygen removal for 15 min), then 0.8mL of 1mol/L K was added dropwise 2 CO 3 Aqueous solution (Advance through N) 2 15min deoxygenated), stirred at room temperature overnight. After the reaction, 30mL of deionized water was added and a few drops of 2mol/L HCl solution were added dropwise. Extracting with dichloromethane, collecting organic phase, and extracting with anhydrous Na 2 SO 4 And (5) drying. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to give S18(0.45mmol, 45%).
Calculated MALDI-TOF MS m/z: C38H23BrN2O3: 634.1; measurement values: 634.5, respectively;
1 H NMR(400MHz,CDCl 3 ,ppm):8.07-8.10(m,3H),8.04-8.05(m,1H),7.95-7.97(d,1H),7.74-7.75(d,1H),7.58-7.63(m,8H),7.49-7.52(m,3H),7.43-7.44(m,3H),7.38-7.39(m,1H)，7.21-7.23(m,2H)。
Figure BDA0003139658420000532
under the protection of nitrogen, weighing compounds S18(1.0mmol), S19(1.25mmol) and [ Pd ] 2 (dba) 3 ]·CHCl 3 (0.08mmol) and HP (tBu) 3 ·BF 4 (0.16mmol) was charged into a 250mL two-necked flask. Into a two-necked flask, 80mL of toluene was charged (N was introduced in advance) 2 Oxygen removal for 15 min), then 1.5mL of 1mol/L K was added dropwise 2 CO 3 Aqueous solution (Advance N) 2 15min deoxygenated), stirred at room temperature overnight. After the reaction, 50mL of deionized water was added and a few drops of 2mol/L HCl solution were added dropwise. Extracting with dichloromethane, collecting organic phase, and extracting with anhydrous Na 2 SO 4 And (5) drying treatment. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to give solid V001(0.81mmol, 81%).
Calculated MALDI-TOF MS m/z: 787.3 parts of C53H33N5O 3; measurement values: 787.5
Calculated values of elemental analysis: c, 80.80; h, 4.22; n, 8.89; o, 6.09; measurement values: c, 80.84; h, 4.24; n, 8.86; o, 6.06.
1 H NMR(400MHz,CDCl 3 ,ppm):8.32-8.35(m,4H),8.19-8.22(m,2H),8.04-8.10(m,4H),7.95-7.96(m,1H),7.74(d,1H),7.58-7.63(m,8H),7.48-7.52(m,9H),7.43-7.44(m,1H),7.38-7.39(m,1H)，7.21-7.22(m,2H)。
(II) testing of Compound Properties
(1) Compound simulation calculation
Optimizing and calculating the distribution conditions of the molecular front line orbitals HOMO and LUMO of the compound of the invention listed in Table 1 by using a Density Functional Theory (DFT) and utilizing a Gaussian 09 program package under the calculation level of B3LYP/6-31G (d); meanwhile, based on the time-density functional theory (TD-DFT), the singlet state energy level S of each compound molecule is calculated in a simulation mode 1 And triplet state energy level T 1 The results are shown in Table 2, where Δ E ST ＝S 1 -T 1 ，E g ＝HOMO-LUMO，E g The absolute value of (a) is taken.
Table 1 Compounds
Figure BDA0003139658420000541
Figure BDA0003139658420000551
Table 2 characterization of the parameters of the compounds
Compound (I) HOMO(eV) LUMO(eV) S 1 (eV) T 1 (eV) E g (eV)
M001 -5.29 -1.33 3.51 3.13 3.96
M004 -5.28 -1.28 3.55 3.18 4.00
M045 -4.84 -1.26 3.20 2.67 3.58
M072 -4.99 -1.33 3.24 3.22 3.66
M101 -4.82 -1.04 3.28 2.88 3.78
M110 -4.79 -1.31 3.02 2.53 3.48
M111 -5.26 -1.14 3.69 3.18 4.12
M112 -5.19 -1.01 3.77 3.02 4.18
H003 -5.82 -1.73 3.61 2.84 4.09
H004 -5.86 -1.86 3.54 2.82 4
H045 -6.12 -1.72 3.90 3.00 4.4
H072 -6.24 -1.85 3.86 2.86 4.39
H086 -6.04 -1.80 3.80 2.91 4.24
V001 -5.60 -1.78 3.45 2.81 3.82
As can be seen from table 2, the compounds of the present invention can give compounds having appropriate HOMO and LUMO energy levels by appropriate substituent substitution on the core unit.
Since the core unit is poweredThe subunit has good electronic transmission capability. Further, by substituting an electron donating group for the core unit, a compound having good electron and hole transporting ability can be obtained (e.g., M001, M004, M045, M072, M101, M110, M111, M112, etc.). These compounds can have appropriate HOMO levels (e.g., -4.79eV to-5.29 eV) and LUMO levels (e.g., -1.01eV to-1.33 eV) while also having appropriate triplet levels (e.g., 2.53eV to 3.22eV, particularly, e.g., 2.67eV to 3.22eV), and thus can be suitably used as hole-type light-emitting host materials in green phosphorescent light-emitting layers. Suitable HOMO and LUMO energy levels facilitate energy level matching of the compounds with adjacent layer compounds, and thus can reduce hole and electron injection barriers, thereby enabling reduction of the driving voltage of the device. The appropriate triplet energy level can prevent the backflow of triplet energy from the light-emitting object material to the light-emitting host material, so that triplet excitons are limited in the light-emitting layer to the maximum extent, the exciton utilization rate can be improved, and the light-emitting efficiency of the OLED device is improved. In addition, the compounds may also have large HOMO and LUMO energy level differences (e.g., E) g ≧ 3.48eV, especially E g Not less than 3.58 eV). The energy level difference of the luminescent host material is larger than that of the luminescent object material, so that the energy transfer from the luminescent host material to the luminescent object material and the direct capture of current carriers on the luminescent object material are facilitated, and the further improvement of the luminescent efficiency is facilitated.
By performing substitution with an electron-accepting group or an electron-accepting group and an electron-donating group on the core unit, a compound having good electron transport ability (e.g., H003, H004, H045, H072, H086, V001) can be obtained. These compounds have appropriate LUMO levels (e.g., -1.72eV to-1.86 eV), and are suitable as electron transport materials or hole blocking materials in OLED devices.
The compound of the invention has poor planarity on spatial configuration and weak intermolecular force, so the compound has good film forming performance, is favorable for forming a stable and uniform amorphous film in the thermal vacuum evaporation process, and can prolong the service life of devices. In addition, when the compound is applied to a light-emitting layer of an OLED device, the phenomenon of aggregated luminescence quenching in the light-emitting layer can be effectively inhibited, so that the light-emitting efficiency can be improved, and the service life of the OLED device can be prolonged.
The following application examples provide illustrative examples for illustrating the practical application of the compounds of the present invention in organic light emitting display panels.
Application example 11
The application example provides an OLED device, the structure of which is shown in fig. 1, and the OLED device includes a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4, a second hole transport layer 5, a light emitting layer 6, a first electron transport layer 7, a second electron transport layer 8, and a cathode 9, which are sequentially stacked, and arrows in fig. 1 represent the light emitting direction of the device.
The preparation method of the OLED device comprises the following steps:
1) the glass substrate 1 was cut into a size of 50mm × 50mm × 0.7mm, ultrasonically cleaned in acetone, isopropyl alcohol, and deionized water, respectively, for 30 minutes, and then cleaned under UV ozone for 30 minutes. Mounting the resulting glass substrate with Indium Tin Oxide (ITO) anode on a vacuum deposition apparatus;
2) evaporating a hole injection layer material (compound a) as a hole injection layer 3 on the ITO anode 2 in a vacuum evaporation mode, wherein the thickness of the hole injection layer material is 10 nm;
3) a hole transport layer material (compound b) was vacuum-evaporated on the hole injection layer 3 as a first hole transport layer 4 with a thickness of 100 nm;
4) a hole transport type material (compound c) was vacuum-evaporated as a second hole transport layer 5 on the first hole transport layer 4 to a thickness of 10 nm;
5) a light-emitting layer 6 is vacuum-evaporated on the second hole transport layer 5, wherein a compound M001 of the invention is used as a first light-emitting host material, a compound d is used as a second light-emitting host material, a compound e is used as a light-emitting guest material, the ratio of M001: d: e is 55:35:10 (mass ratio), and the thickness is 30 nm;
6) an electron transport material (compound f) was vacuum-deposited on the light-emitting layer 6 as a first electron transport layer 7 with a thickness of 10 nm;
7) vacuum evaporating an electron transport material (compound g and compound h in a mass ratio of 1:1) on the first electron transport layer 7 to form a second electron transport layer 8 with a thickness of 30 nm;
8) a silver electrode as a cathode 9 was vacuum-evaporated on the second electron transport layer 8 to a thickness of 15 nm.
The preparation of the OLED devices of application examples 12 to 18 and comparative example 1 is similar to application example 1, except that in step 5) compound M001 is replaced by compounds M004, M045, M072, M101, M110, M111, M112 and comparative compound 1, respectively, as detailed in Table 3.
Figure BDA0003139658420000581
Performance evaluation of OLED devices:
the current of the OLED device under different voltages is tested by a Keithley 2365A digital nano-volt meter, and then the current is divided by the light-emitting area to obtain the current density of the OLED device under different voltages. The luminance and radiant energy flux density of the OLED devices at different voltages were tested using a Konicaminolta CS-2000 spectroradiometer. According to the current density and the brightness of the OLED device under different voltages, the same current density (10 mA/cm) is obtained 2 ) Operating voltage Von and current efficiency CE (10mA/cm 2 ) (in cd/A). The lifetime T95 (at 50 mA/cm) was obtained by measuring the time when the luminance of the organic light emitting device reached 95% of the initial luminance 2 Under the test conditions).
The organic light-emitting device thus produced was applied with a dc voltage, and the results of measuring the light-emitting properties of the device are summarized in table 3.
TABLE 3
Figure BDA0003139658420000591
As can be seen from the data in table 3, the green OLED device prepared based on the organic compound provided by the present invention as a p-type light emitting host material has a lower operating voltage (e.g., 3% lower, even 8% lower), a higher current efficiency (e.g., 14% higher, even 37% higher) and a longer operating lifetime (e.g., 5% higher lifetime of T95) relative to comparative compound 1. The compound provided by the invention realizes high triplet state energy level and proper HOMO energy level through reasonable matching of the core unit and the substituent group, can be matched with an n-type light-emitting main body material to be used as a mixed main body of a green phosphorescent device, and realizes an efficient energy transfer process in a light-emitting layer. In addition, the compound has good hole and electron bipolar transmission capability, can effectively adjust a light-emitting composite region in an OLED device, improves the light-emitting efficiency and the long service life of the OLED device, and reduces the working voltage. The compound of the invention has poor planarity on spatial configuration and weak intermolecular force, so that the compound can ensure excellent film stability, thereby being beneficial to improving the stability of devices in long-time work.
Application example 21
The OLED device was fabricated in a similar manner to application example 1, except that,
5) a luminescent layer 6 is vacuum-evaporated on the second hole transport layer 5, wherein a compound k is used as a luminescent host material, a compound j is used as a luminescent guest material, the doping proportion is 2% (mass ratio), and the thickness is 30 nm;
6) an electron transport type compound H003 was vacuum-deposited on the light-emitting layer 6 as a first electron transport layer 7 (i.e., a hole-blocking layer) to a thickness of 10 nm.
The preparation of OLED devices of application examples 22-26 and comparative example 2 was similar to application example 21 except that compound H1 was replaced in step 6) with compounds H004, H045, H072, H086, V001 and comparative compound 2, respectively, as detailed in Table 4.
Figure BDA0003139658420000601
The organic light-emitting device thus fabricated was evaluated for emission performance according to the above-described OLED device performance evaluation method, and the results are summarized in table 4.
TABLE 4
Figure BDA0003139658420000602
From the data in table 4, it can be seen that the OLED device prepared based on the organic compound provided by the present invention as a hole blocking material has a lower operating voltage (e.g., reduced by more than 4%), a higher current efficiency (e.g., improved by more than 4%, even improved by 10%) and a longer operating lifetime (e.g., improved by more than 4%, even improved by more than 10% of the lifetime of T95) relative to comparative compound 2. The compound provided by the invention realizes high triplet state energy level and proper HOMO energy level through reasonable matching of the core unit and the substituent group, and can realize effective blocking of holes; meanwhile, the compound has good electronic transmission capability, can effectively adjust the composite area of the luminous layer of the OLED device, improves the luminous efficiency and the long service life of the OLED device, and reduces the turn-on voltage. The compound of the invention has poor planarity on spatial configuration and weak intermolecular force, so that the compound can ensure excellent film stability, thereby being beneficial to improving the stability of devices in long-time work.
While the invention has been described with reference to specific embodiments, the invention is not limited thereto, and various equivalent modifications and substitutions can be easily made by those skilled in the art within the technical scope of the invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.

Claims (10)

1. A compound having a structure represented by formula (1),
Figure FDA0003778795880000011
wherein, the first and the second end of the pipe are connected with each other,
(R 11 ) p -(L 11 ) m - # represents any one of the following groups:
Figure FDA0003778795880000012
(R 12 ) q -(L 12 ) n - # represents any one of the following groups:
Figure FDA0003778795880000013
wherein p represents 0 or 1, q represents 0 or 1, and p + q is not less than 1; # denotes the ligation site;
R 11 and R 12 Each independently selected from a first group;
the first group is selected from carbazolyl, acridinyl, arylamino, groups containing dibenzo B and G heterocyclic six-membered ring units, wherein aryl in the arylamino is independently selected from aryl of C6-C30, and G independently represents O, S or N;
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 and R 8 Each independently represents hydrogen, halogen, cyano, isocyano, silyl, alkyl of C1-C10, cycloalkyl of C3-C10, alkoxy of C1-C10, alkylthio of C1-C10, aryl of C6-C30, and heteroaryl of C2-C30.
2. The compound of claim 1, wherein the compound has a structure represented by formula (1-1), formula (1-2), or formula (1-3),
Figure FDA0003778795880000021
wherein p represents 0 or 1, q represents 0 or 1, and p + q.gtoreq.1; # denotes the ligation site.
3. A compound of claim 1, wherein R is 11 And R 12 Each independently selected from the first group.
4. A compound according to any one of claims 1 to 3 wherein the first group is selected from the group consisting of groups shown in group I1, group I2, group I3 and group I4,
group I1: carbazolyl group shown below
Figure FDA0003778795880000022
Figure FDA0003778795880000031
Group I2: acridinyl as shown below
Figure FDA0003778795880000032
Figure FDA0003778795880000041
Group I3: arylamino groups shown below
Figure FDA0003778795880000042
Group I4: groups containing dibenzo B and G hetero six-membered ring units as shown below
Figure FDA0003778795880000043
Wherein R is a 、R b And R c Each independently represents a cyano group, a C1-C20 alkyl group, a C1-C20 alkoxy group, or a C6-C40 aryl group;
R A and R B Each independently represents a cyano group, a C1-C20 alkaneA C1-C20 alkoxy group, a C6-C40 aryl group, a C4-C40 heteroaryl group or an arylamino group;
x and Y independently represent O, S, N (Z), C (Z) 2 、Si(Z) 2 Wherein Z independently represents hydrogen, C1-C20 alkyl, C1-C20 alkoxy, or C6-C40 aryl;
α, β and γ each independently represent 0, 1 or 2;
# denotes the ligation site.
5. The compound of claim 4,
said group I1 comprises carbazolyl groups shown below,
Figure FDA0003778795880000051
Figure FDA0003778795880000061
said group I2 comprising an acridinyl group as shown below,
Figure FDA0003778795880000062
said group I3 comprising arylamino groups shown below,
Figure FDA0003778795880000063
wherein R is A 、R B 、R a And R b Each independently represents a methyl group, an isopropyl group, a tert-butyl group, or a methoxy group; x and Y each independently represent O, S, or N (Ph), wherein Ph represents phenyl; α and β each independently represent 0 or 1; # denotes the ligation site.
6. The method according to any one of claims 1 to 3Characterized in that R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 And R 8 Each independently represents hydrogen or fluorine.
7. The compound of claim 3, wherein the compound is selected from any one of the following:
Figure FDA0003778795880000064
Figure FDA0003778795880000071
Figure FDA0003778795880000081
Figure FDA0003778795880000091
Figure FDA0003778795880000101
Figure FDA0003778795880000111
Figure FDA0003778795880000121
Figure FDA0003778795880000131
Figure FDA0003778795880000141
Figure FDA0003778795880000151
Figure FDA0003778795880000161
Figure FDA0003778795880000171
8. a display panel comprising an organic light emitting device comprising an anode, a cathode and an organic film layer comprising a light emitting layer between the anode and cathode, wherein the organic film layer comprises at least one compound according to any one of claims 1 to 7.
9. A display panel as claimed in claim 8 characterized in that the light-emitting layer comprises at least one compound as claimed in any one of claims 3 or 7.
10. A display device comprising the display panel according to claim 8 or 9.
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