CN114075202B - Nitrogen-containing compound, organic electroluminescent device comprising same and electronic device - Google Patents

Nitrogen-containing compound, organic electroluminescent device comprising same and electronic device Download PDF

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CN114075202B
CN114075202B CN202110608345.5A CN202110608345A CN114075202B CN 114075202 B CN114075202 B CN 114075202B CN 202110608345 A CN202110608345 A CN 202110608345A CN 114075202 B CN114075202 B CN 114075202B
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organic electroluminescent
carbon atoms
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CN114075202A (en
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马天天
呼琳琳
金荣国
杨雷
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Material Science Co Ltd
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Abstract

The application provides a nitrogen-containing compound, an organic electroluminescent device and an electronic device thereof, and belongs to the technical field of organic electroluminescence. The structural general formula of the nitrogen-containing compound is shown as formula 1, and the nitrogen-containing compound can be applied to an organic electroluminescent device, so that the performance of the organic electroluminescent device can be obviously improved.

Description

Nitrogen-containing compound, organic electroluminescent device comprising same and electronic device
Technical Field
The application relates to the technical field of organic electroluminescence, in particular to a nitrogen-containing compound, an organic electroluminescent device and an electronic device containing the same.
Background
As a new generation display technology, the organic electroluminescent material (OLED) has the advantages of ultra-thin, self-luminescence, wide viewing angle, quick response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption and the like, and is widely applied to industries of flat panel display, flexible display, solid-state lighting, vehicle-mounted display and the like.
The organic electroluminescence phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic electroluminescent device using an organic electroluminescent phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. The organic material layer is generally formed in a multi-layered structure composed of different materials to improve brightness, efficiency, and lifetime of the organic electroluminescent device, and may be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the organic light emitting device structure, when a voltage is applied between two electrodes, holes and electrons are injected from an anode and a cathode, respectively, into an organic material layer, excitons are formed when the injected holes meet the electrons, and light is emitted when the excitons return to a ground state. In the conventional organic electroluminescent devices, the life and efficiency are the most important problems, and with the increase of the area of the display, the driving voltage is increased, the luminous efficiency and the power efficiency are also increased, and a certain service life is ensured, so that the organic materials have to solve the efficiency or life problems, and new materials for the organic luminescent devices, which have high efficiency, long life and suitability for mass production, are required to be continuously developed.
It should be noted that the information disclosed in the above background section is only for enhancing understanding of the background of the application and thus may include information that does not form the prior art that is already known to those of ordinary skill in the art.
Disclosure of Invention
The application aims to overcome the defects in the prior art and provide a nitrogen-containing compound, an organic electroluminescent device and an electronic device containing the same, which can improve luminous efficiency and prolong the service life of the device.
In order to achieve the aim of the application, the application adopts the following technical scheme:
according to a first aspect of the present application, there is provided a nitrogen-containing compound having a structural formula shown in formula 1:
wherein ,represents a chemical bond, A, B are the same or different, and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a structure represented by formula 1-1, formula 1-2 or formula 1-3, and at least one of A and B is selected from a structure represented by formula 1-1, formula 1-2 or formula 1-3;
X 1 、X 2 and X3 Identical or different, each independently selected from N or C (R), and X 1 、X 2 and X3 At least one of which is N;
each R, R 1 、R 2 、R 3 、R 4 、R 5 Or R is 6 Each independently selected from hydrogen, deuterium, a halogen group, cyano, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, cycloalkyl having 3 to 10 carbon atoms;
n 1 Represents a substituent R 1 Number n of (n) 1 Selected from 1, 2, 3 or 4, when n 1 When the number is greater than 1, any two R 1 Identical or different, optionally, any two adjacent R 1 Forming a ring;
n 2 represents a substituent R 2 Number n of (n) 2 Selected from 1 or 2, when n 2 When the number is greater than 1, any two R 2 Identical or different, optionally, any two adjacent R 2 Forming a ring;
n 3 represents a substituent R 3 Number n of (n) 3 Selected from 1, 2, 3 or 4, when n 3 When the number is greater than 1, any two R 3 Identical or different, any two adjacent R' s 3 Forming a ring;
n 4 represents a substituent R 4 Number n of (n) 4 Selected from 1, 2 or 3, when n 4 When the number is greater than 1, any two R 4 The same or different;
n 5 represents a substituent R 5 Number n of (n) 5 Selected from 1, 2, 3 or 4, when n 5 When the number is greater than 1, any two R 5 The same or different;
n 6 represents a substituent R 6 Number n of (n) 6 Selected from 1, 2, 3 or 4, when n 6 When the number is greater than 1, any two R 6 The same or different;
L、L 1 、L 2 、L 3 each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 、Ar 2 、Ar 3 、Ar 4 and Ar5 Independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted aryl groups having 3 to 30 carbon atomsSubstituted heteroaryl;
said A, B, L, L 1 、L 2 、L 3 、Ar 1 、Ar 2 、Ar 3 、Ar 4 and Ar5 The substituents in (a) are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, heterocycloalkyl group having 2 to 10 carbon atoms, and alkoxy group having 1 to 10 carbon atoms;
optionally in Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Any two adjacent substituents form a ring.
The nitrogen-containing compound provided by the application adopts a specific fused indolocarbazole parent structure, and combines a triazine group with benzimidazole, so that the nitrogen-containing compound provided by the application has excellent electron injection and transmission characteristics on the premise of keeping a higher T1 value, and is suitable for being used as a main material of a luminescent layer in an OLED device. When the compound is used for a luminescent layer material of an organic electroluminescent device, the electron transmission performance of the device is effectively improved, so that the balance degree of hole and electron injection is enhanced, and the luminescent efficiency and the service life of the device are improved.
According to a second aspect of the present application, there is provided an organic electroluminescent device comprising an anode, a cathode, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the above-mentioned nitrogen-containing compound.
According to a third aspect of the present application, there is provided an electronic device comprising the organic electroluminescent device described above.
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the application as claimed.
Drawings
The accompanying drawings are included to provide a further understanding of the application, and are incorporated in and constitute a part of this specification, illustrate the application and together with the description serve to explain, without limitation, the application.
In the drawings:
fig. 1 is a schematic structural view of an embodiment of an organic electroluminescent device of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the application.
Description of the reference numerals
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320. a hole transport layer; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic electroluminescent layer; 340. a hole blocking layer; 350. an electron transport layer; 360. an electron injection layer; 400. an electronic device.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings denote the same or similar structures, and thus detailed descriptions thereof will be omitted.
The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application. One skilled in the relevant art will recognize, however, that the inventive aspects may be practiced without one or more of the specific details, or with other methods, components, materials, etc. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring the main technical idea of the application.
The application provides a nitrogen-containing compound, which has a structural general formula shown in formula 1:
wherein ,represents a chemical bond, A, B are the same or different, and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a structure represented by formula 1-1, formula 1-2 or formula 1-3, and at least one of A and B is selected from a structure represented by formula 1-1, formula 1-2 or formula 1-3;
X 1 、X 2 and X3 Identical or different, each independently selected from N or C (R), and X 1 、X 2 and X3 At least one of which is N;
each R, R 1 、R 2 、R 3 、R 4 、R 5 Or R is 6 Each independently selected from hydrogen, deuterium, a halogen group, cyano, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, cycloalkyl having 3 to 10 carbon atoms;
n 1 represents a substituent R 1 Number n of (n) 1 Selected from 1, 2, 3 or 4, when n 1 When the number is greater than 1, any two R 1 Identical or different, optionally, any two adjacent R 1 Forming a ring;
n 2 represents a substituent R 2 Number n of (n) 2 Selected from 1 or 2, when n 2 When the number is greater than 1, any two R 2 Identical or different, optionally, any two adjacent R 2 Forming a ring;
n 3 represents a substituent R 3 Number n of (n) 3 Selected from 1, 2, 3 or 4, when n 3 When the number is greater than 1, any two R 3 Identical or different, any two adjacent R' s 3 Forming a ring;
n 4 represents a substituent R 4 Number n of (n) 4 Selected from 1, 2 or 3, when n 4 When the number is greater than 1, any two R 4 The same or different;
n 5 represents a substituent R 5 Number n of (n) 5 Selected from 1, 2, 3 or 4, when n 5 When the number is greater than 1, any two R 5 The same or different;
n 6 represents a substituent R 6 Number n of (n) 6 Selected from 1, 2, 3 or 4, when n 6 When the number is greater than 1, any two R 6 The same or different;
L、L 1 、L 2 、L 3 each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 、Ar 2 、Ar 3 、Ar 4 and Ar5 Each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
said A, B, L, L 1 、L 2 、L 3 、Ar 1 、Ar 2 、Ar 3 、Ar 4 and Ar5 The substituents in (a) are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, heterocycloalkyl group having 2 to 10 carbon atoms, and alkoxy group having 1 to 10 carbon atoms;
optionally in Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Any two adjacent substituents form a ring.
At the bookIn the application, the description that "each is independently selected from" and "each is independently selected from" may be used interchangeably, and should be understood in a broad sense, which refers to that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. For example, " Wherein each q is independently 0, 1, 2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced each other.
In the present application, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl or unsubstituted aryl having a substituent Rc. Wherein Rc, the substituent mentioned above, may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms. In the present application, the "substituted" functional group may be substituted with one or more substituents of Rc described above; when two substituents Rc are attached to the same atom, the two substituents Rc may be present independently or attached to each other to form a ring with the atom; when two adjacent substituents Rc are present on a functional group, the adjacent two substituents Rc may be present independently or fused to the functional group to which they are attached to form a ring.
In the present application, the terms "optional", "optionally" and "optionally" mean that the subsequently described event may, but need not, occur, and that the description includes instances where the event occurs or does not. For example, "optionally, two adjacent substituents are x to form a ring; by "is meant that the two substituents may form a ring but do not necessarily form a ring, including: a scenario in which two adjacent substituents form a ring and a scenario in which two adjacent substituents do not form a ring.
In the present application, "any two adjacent substituents form a ring", and "any two adjacent substituents" may include two substituents on the same atom, and may include two adjacent atoms each having one substituent; wherein when two substituents are present on the same atom, the two substituents may form a saturated or unsaturated ring with the atom to which they are commonly attached; when two adjacent atoms each have a substituent, the two substituents may be fused into a ring. For example, when Ar 2 When there are 2 or more substituents, any adjacent substituent forms a ring, the ring may be saturated or unsaturated and has 5 to 13 carbon atoms, for example: benzene rings, naphthalene rings, cyclopentane, cyclohexane, adamantane, and the like.
In the present application, "optionally, any two adjacent R' s 1 Are connected with each other to form a ring; optionally, any two adjacent R 2 Are connected with each other to form a ring; optionally, any two adjacent R 3 The term "ring-formed by interconnection" refers to any two adjacent R 1 、R 2 Or R is 3 The rings may or may not be formed. For example, when two adjacent R' s 2 When forming a ring, the number of carbon atoms of the ring is 6 to 14, and the ring may be saturated or unsaturated. For example: cyclohexane, cyclopentane, adamantane, benzene ring, naphthalene ring, phenanthrene ring, and the like, but is not limited thereto.
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group refers to all the numbers of carbon atoms. For example, if L is selected from a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms. For example: ar (Ar) 1 Is thatThe number of carbon atoms is 7; l is->The number of carbon atoms is 12.
In the present application, "hetero" means that at least 1 hetero atom such as B, N, O, S, P, si or Se is included in one functional group and the remaining atoms are carbon and hydrogen when no specific definition is provided otherwise. Unsubstituted alkyl groups may be "saturated alkyl groups" without any double or triple bonds.
In the present application, "alkyl" may include a straight chain alkyl group or a branched alkyl group. Alkyl groups may have 1 to 10 carbon atoms, and in the present application, a numerical range such as "1 to 10" refers to each integer in the given range; for example, "1 to 10 carbon atoms" refers to an alkyl group that may contain 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Furthermore, alkyl groups may be substituted or unsubstituted.
Preferably, the alkyl group is selected from alkyl groups having 1 to 5 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and pentyl.
In the present application, cycloalkyl refers to saturated hydrocarbons containing alicyclic structures, including monocyclic and condensed ring structures. Cycloalkyl groups may have 3-10 carbon atoms, a numerical range such as "3 to 10" referring to each integer in the given range; for example, "3 to 10 carbon atoms" refers to cycloalkyl groups that may contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, or 10 carbon atoms. Cycloalkyl groups may be substituted or unsubstituted. Examples of cycloalkyl groups are cyclopentylalkyl, cyclohexenyl, adamantyl.
In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a fused ring aryl group, two or more linked by carbon-carbon bond conjugationA plurality of monocyclic aryl groups, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered as aryl groups of the present application unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. For example, in the present application, biphenyl, terphenyl, etc. are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, tetrabiphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl,A base, etc. The "aryl" groups of the present application may contain from 6 to 30 carbon atoms, in some embodiments from 6 to 25 carbon atoms in the aryl group, in some embodiments from 6 to 20 carbon atoms in the aryl group, in other embodiments from 6 to 18 carbon atoms in the aryl group, and in other embodiments from 6 to 12 carbon atoms in the aryl group. For example, in the present application, the number of carbon atoms of the aryl group may be 6, 12, 13, 14, 15, 18, 20, 24, 25, 30, but of course, the number of carbon atoms may be other numbers, which are not listed here. In the present application, biphenyl may be understood as phenyl-substituted aryl, and also as unsubstituted aryl.
In the present application, the arylene group refers to a divalent group formed by further losing one hydrogen atom from the aryl group.
In the present application, the substituted aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, trialkylsilyl group, alkyl group, cycloalkyl group, alkoxy group, or the like. It is understood that the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and its substituents being 18.
In the present application, specific examples of the aryl group as a substituent include, but are not limited to: phenyl, naphthyl, anthryl, phenanthryl, dimethylfluorenyl, biphenyl, and the like.
In the present application, heteroaryl means a monovalent aromatic ring containing 1, 2, 3, 4 or 5 heteroatoms in the ring or a derivative thereof, and the heteroatoms may be at least one of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation thereto. Wherein thienyl, furyl, phenanthroline and the like are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of a polycyclic ring system type which are conjugated and connected through carbon-carbon bonds. The "heteroaryl" groups of the present application may contain 3 to 30 carbon atoms, in some embodiments the number of carbon atoms in the heteroaryl group may be 3 to 25, in some embodiments the number of carbon atoms in the heteroaryl group may be 5 to 25, in other embodiments the number of carbon atoms in the aryl group may be 5 to 20, and in other embodiments the number of carbon atoms in the aryl group may be 5 to 12. For example, the number of carbon atoms may be 3, 4, 5, 7, 12, 13, 18, 20, 24, 25 or 30, although other numbers are also possible and are not listed here.
In the present application, the heteroarylene group refers to a divalent group formed by further losing one hydrogen atom.
In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, an alkoxy group, or the like. It is understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl.
In the present application, specific examples of heteroaryl groups as substituents include, but are not limited to: pyridyl, carbazolyl, dibenzofuranyl, dibenzothienyl.
In the present application, the halogen group may include fluorine, iodine, bromine, chlorine, and the like.
In the present application, specific examples of the trialkylsilyl group having 3 to 12 carbon atoms include, but are not limited to, trimethylsilyl group, triethylsilyl group and the like.
In the present application, specific examples of the haloalkyl group having 1 to 10 carbon atoms include, but are not limited to, trifluoromethyl.
In the present application, the non-positional connection key means a single bond extending from the ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule.
For example, as shown in formula (f), the naphthyl group represented by formula (f) is attached to the other positions of the molecule via two non-positional linkages extending through the bicyclic ring, which means includes any of the possible linkages shown in formulas (f-1) -formula (f-10).
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by the formula (X') is linked to the other position of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning represented by this linkage includes any possible linkage as shown in the formula (X '-1) -formula (X' -4).
The meaning of the non-positional connection or the non-positional substitution is the same as here, and will not be described in detail later.
In one embodiment of the application, X 1 、X 2 、X 3 Are all N.
In one embodiment of the application, each R, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, pyridyl, trifluoromethyl, biphenyl;
optionally, any two adjacent R 1 Forming benzene ring;
optionally, any two adjacent R 2 Forming benzene ring;
optionally, any two adjacent R 3 Forming a benzene ring.
Optionally, each R, R 1 、R 3 、R 4 、R 5 Are all hydrogen.
In the present application, formula 1-1The group shown is selected from the following structures:
in one embodiment of the application, the L, L 1 、L 2 、L 3 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 12 carbon atoms.
Optionally, the L, L 1 、L 2 、L 3 The substituents in (a) are independently selected from deuterium, halogen group, cyano, alkyl with 1-5 carbon atoms and phenyl.
Specifically, the L, L 1 、L 2 、L 3 and L4 Specific examples of substituents in (a) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
In another embodiment of the present application, the L, L 1 、L 2 、L 3 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazole group.
In one embodiment of the application, the L, L 1 、L 2 、L 3 and L4 The same or different are each independently selected from a single bond or a substituted or unsubstituted group V selected from the group consisting of:
wherein ,represents a chemical bond; the substituted group V has one or more substituents thereon, each of which is independently selected from deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl; when the number of substituents of V is greater than 1, the substituents may be the same or different.
Optionally L, L 1 、L 2 、L 3 Are respectively independentIs selected from the group consisting of single bonds or:
preferably, L is a single bond and unsubstituted phenylene.
In one embodiment of the application, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms.
Optionally, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 The substituents in (2) are independently selected from deuterium, halogen group, cyano, alkyl with 1-5 carbon atoms, cycloalkyl with 5-10 carbon atoms, aryl with 6-12 carbon atoms, haloalkyl with 1-5 carbon atoms and trialkylsilyl with 3-6 carbon atoms;
optionally in Ar 1 Any two adjacent substituents form a saturated or unsaturated ring with 5-13 carbon atoms.
In one embodiment of the application, ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted carbazolyl;
Optionally, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 The substituents in (a) are independently selected fromFrom deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexenyl, adamantyl, phenyl, naphthyl, biphenyl, trifluoromethyl, trimethylsilyl.
Optionally in Ar 1 Any two adjacent substituents form a fluorene ring
Alternatively, ar 2 、Ar 3 、Ar 4 、Ar 5 Each independently selected from unsubstituted phenyl groups.
In another embodiment of the present application, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Each independently selected from the group consisting of substituted or unsubstituted groups W; wherein the unsubstituted group W is selected from the group consisting of:
wherein ,represents a chemical bond; the substituted group W has one or more substituents thereon, each of which is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, cyclohexenyl, adamantyl, phenyl, naphthyl, biphenyl, trifluoromethyl, trimethylsilyl; when the number of substituents of W is greater than 1, each substituent is the same or different.
Optionally, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Selected from the group consisting of:
in one embodiment of the application, each of said A, B is independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms, a structure of formula 1-1, 1-2 or 1-3, and one and only one of A and B is selected from a structure of formula 1-1, 1-2 or 1-3.
Optionally, the substituents in A, B are each independently selected from deuterium, halogen group, cyano group, aryl group with 6-12 carbon atoms, alkyl group with 1-5 carbon atoms, cycloalkyl group with 5-10 carbon atoms, haloalkyl group with 1-5 carbon atoms, and trialkylsilyl group with 3-6 carbon atoms.
Specifically, specific examples of the substituent in A, B include, but are not limited to: the substituents in A, B are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, naphthyl, biphenyl, cyclohexenyl, adamantyl, trifluoromethyl, trimethylsilyl.
In one embodiment of the application, each of said A, B is independently selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted fluorenyl, a structure represented by formula 1-1, 1-2 or 1-3, and one or only one of A and B is selected from the structures represented by 1-1, 1-2 or 1-3.
In another embodiment of the present application, one of said A, B is selected from the structures of formulas 1-1, 1-2 or 1-3 and the other is selected from the following groups:
in one embodiment of the present application, A is a structure represented by formula 1-1, and B is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted fluorenyl.
In one embodiment of the present application, A is a structure represented by formula 1-2, and B is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted fluorenyl.
In one embodiment of the present application, A is a structure represented by formulas 1-3, and B is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted fluorenyl.
In one embodiment of the present application, B is a structure represented by formula 1-1, A is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted fluorenyl.
In one embodiment of the present application, B is a structure represented by formula 1-2, A is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted fluorenyl.
In one embodiment of the present application, B is a structure represented by formulas 1-3, A is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted fluorenyl.
In one embodiment of the application, the formula 1-1 is selected from the group consisting of:
in one embodiment of the application, the formula 1-2 is selected from the group consisting of:
in one embodiment of the application, the formulae 1-3 are selected from the group consisting of:
optionally, the nitrogen-containing compound is selected from the group consisting of:
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the present application also provides an organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the nitrogen-containing compound of the present application.
In one embodiment of the present application, the organic electroluminescent device is a green organic electroluminescent device.
In another embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device.
In one embodiment of the present application, as shown in fig. 1, the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one functional layer 300 interposed between the anode layer and the cathode layer, the functional layer 300 including a hole injection layer 310, a hole transport layer 321, a hole auxiliary layer 322, an organic electroluminescent layer 330, an electron transport layer 350, and an electron injection layer 360.
Optionally, a hole blocking layer 340 may be disposed between the organic electroluminescent layer 330 and the electron transport layer 350. The organic electroluminescent layer 330 may contain the nitrogen-containing compound according to the first aspect of the present application.
Alternatively, the anode 100 includes an anode material that is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide such as ZnO, al or SnO 2 Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. It is preferable to include a transparent electrode containing Indium Tin Oxide (ITO) as an anode.
Alternatively, the hole transport layer 321 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited in the present application. For example, in one embodiment of the present application, hole transport layer 321 consists of HT-01.
Alternatively, the hole auxiliary layer 322 may include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited in the present application. For example, in one embodiment of the present application, hole assist layer 322 is comprised of HT-02.
Alternatively, the organic electroluminescent layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. Alternatively, the organic electroluminescent layer 330 is composed of a host material and a guest material, and holes and electrons injected into the organic electroluminescent layer 330 may be recombined at the organic electroluminescent layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The guest material of the organic electroluminescent layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited in the present application.
In one embodiment of the present application, the host material of the organic electroluminescent layer 330 is the nitrogen-containing compound of the present application, GH-P, and guest material Ir (3 mppy) 3 。
In one embodiment of the present application, the host material of the red organic electroluminescent device, organic electroluminescent layer 330, comprises the host material nitrogen-containing compound of the present application, RH-P and guest material Ir (dmpq) 2 acac。
The electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which are not particularly limited in the present application. For example, in one embodiment of the present application, the electron transport layer 350 may be composed of BCP and LiQ.
Alternatively, the cathode 200 includes a cathode material that is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 /Ca, but is not limited thereto. A metal electrode containing silver and magnesium is preferably included as a cathode.
Optionally, a hole injection layer 310 may also be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, and other materials, which are not particularly limited in the present application. In one embodiment of the present application, hole injection layer 310 may be composed of PtPC.
Optionally, an electron injection layer 360 may also be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, the electron injection layer 360 may include ytterbium (Yb).
The application also provides an electronic device comprising the organic electroluminescent device.
For example, as shown in fig. 2, the electronic device provided by the present application is a first electronic device 400, where the first electronic device 400 includes any one of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device. The electronic device may be a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc. Since the first electronic device 400 has the above-mentioned organic electroluminescent device, the present application has the same beneficial effects and is not described herein.
The present application will be described in detail with reference to examples, but the following description is intended to explain the present application and is not intended to limit the scope of the application in any way.
Synthetic examples
Those skilled in the art will recognize that the chemical reactions described herein can be used to suitably prepare many other compounds of the present application, and that other methods for preparing the compounds of the present application are considered to be within the scope of the present application. For example, the synthesis of those non-exemplified compounds according to the application can be successfully accomplished by modification methods, such as appropriate protection of interfering groups, by use of other known reagents in addition to those described herein, or by some conventional modification of the reaction conditions, by those skilled in the art. In addition, the application discloses the synthesis of the inverse compound.
Synthesis of intermediate a 1-1:
5-bromo-7H-benzo [ C ] carbazole (50.0 g;168.8 mmol), 2- (4-iodophenyl) -1-phenyl-1H-benzimidazole (70.8 g;202.6 mmol), tris (dibenzylideneacetone) dipalladium (3.1 g;3.4 mmol), tri-tert-butylphosphine (1.4 g;6.8 mmol), sodium tert-butoxide (24.3 g;253.2 mmol) and xylene (500 mL) were added to a round-bottomed flask and reacted under nitrogen at 135-140℃for 16 hours; cooling to room temperature, washing the reaction solution with water, separating the reaction solution, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification of the crude product by silica gel column chromatography using dichloromethane/n-heptane as eluent afforded compound intermediate a1-1 (52.4 g; 55%)
Referring to the synthesis of intermediate a1-1, the following intermediate compounds shown in Table 1 were synthesized using reactant A instead of 5-bromo-7H-benzo [ C ] carbazole and reactant B instead of 2- (4-iodophenyl) -1-phenyl-1H-benzimidazole in Table 1:
TABLE 1
Synthesis of intermediate a 1-2:
adding the intermediate a1-1 (71.2 g;126.2 mmol) and dry tetrahydrofuran into a round bottom flask protected by nitrogen, cooling to 75-80 ℃ under stirring, slowly dropwise adding n-hexane solution (70.7 mL;176.7 mmol) of n-butyllithium (2.5M) into the mixed solution, and preserving the heat for 1 hour after the dropwise addition; then keeping the temperature at 75-80 ℃, dropwise adding trimethyl borate (22.3 g;214.6 mmol), slowly heating to room temperature after the dropwise adding, and stirring for 2 hours; the reaction mixture was poured into dilute hydrochloric acid (1M; 252.5mL;252.5 mmol) and stirred at room temperature for 8 hours; extracting the mixed solution with dichloromethane, collecting an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; recrystallization purification of the crude product using a dichloromethane/n-heptane system gave intermediate a1-2 (46.1 g, 69%) as a white solid
Referring to the method for synthesizing intermediate a1-2, using reactant C in Table 2 below instead of intermediate a1-1, the intermediates shown in Table 2 below were synthesized:
TABLE 2
Synthesis of intermediate a 1-3:
intermediate a1-2 (45.5 g;86.0 mmol), 1-bromo-2-nitrobenzene (19.1 g;94.6 mmol), tetrakis triphenylphosphine palladium (2.0 g;1.7 mmol), potassium carbonate (23.8 g;172.0 mmol), tetrabutylammonium bromide (5.5 g;17.2 mmol), toluene (240 mL), ethanol (60 mL) and deionized water (60 mL) were added to a round bottom flask and reacted for 16 hours under nitrogen protection with stirring and heating to 75-80 ℃; the reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; purification of the crude product by column chromatography on silica gel using dichloromethane/n-heptane as eluent afforded intermediate a1-3 (38.1 g, 73%) as a pale yellow solid
Referring to the synthesis of intermediate a1-3, using reactant D in Table 3 below in place of intermediate a1-2 and reactant E in place of 1-bromo-2-nitrobenzene, the intermediates shown in Table 3 below were synthesized:
TABLE 3 Table 3
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Synthesis of intermediate a 1:
intermediate a1-3 (38.04 g;62.7 mmol), triphenylphosphine (41.1 g;156.8 mmol), o-dichlorobenzene (250 mL) were added to the flask, heated to 175℃under nitrogen and stirred for 36 hours; cooling to room temperature, washing the reaction solution with water, separating the solution, washing the organic phase with water, drying with anhydrous magnesium sulfate, and removing the solvent under high temperature and reduced pressure to obtain crude product; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to give intermediate a1 (27.7 g, 77%) as a white solid.
Referring to the synthesis of intermediate a1, the intermediates shown in Table 4 below were synthesized with reactant F in place of intermediates a 1-3:
TABLE 4 Table 4
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Indolocarbazole (43.3 g;168.8 mmol), 1-phenyl-2- (4-chlorophenyl) benzimidazole (61.7 g;202.6 mmol), tris (dibenzylideneacetone) dipalladium (3.1 g;3.4 mmol), tri-tert-butylphosphine (1.4 g;6.8 mmol), sodium tert-butoxide (24.3 g;253.2 mmol) and xylene (500 mL) were added to a round-bottomed flask and reacted under nitrogen at 135-140℃for 16 hours with stirring; cooling to room temperature, washing the reaction solution with water, separating the reaction solution, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification of the crude product by silica gel column chromatography using dichloromethane/n-heptane as eluent afforded solid compound intermediate a8 (43.4 g, 49%)
Referring to the synthesis of intermediate a8, the following intermediate shown in Table 5 was synthesized by substituting reactant G for 1-phenyl-2- (4-chlorophenyl) benzimidazole:
TABLE 5
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Synthesis of intermediate i 1:
2, 4-dichloro-6-phenyl-1, 3, 5-triazine (16.1 g;71.0 mmol), phenylboronic acid (9.1 g;74.6 mmol), tetrakis triphenylphosphine palladium (1.6 g;1.4 mmol), potassium carbonate (19.6 g;142.1 mmol), tetrabutylammonium bromide (4.6 g;14.2 mmol), toluene (160 mL), water (40 mL), ethanol (40 mL) were added to a round-bottomed flask and reacted under nitrogen protection at 105-110℃for 12 hours with stirring; cooling to room temperature, washing the reaction solution with water, separating the reaction solution, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification of the crude product by silica gel column chromatography using dichloromethane/n-heptane as eluent afforded compound intermediate i1 (16.2 g, 85%)
Referring to the synthesis of intermediate I1, the intermediates shown in table 6 below were synthesized using reactant H instead of 2, 4-dichloro-6-phenyl-1, 3, 5-triazine and reactant I instead of phenylboronic acid in table 6 below:
TABLE 6
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Synthesis of intermediate i 21:
3-bromo-N 1 Phenyl benzene-1, 2-diamine (21 g,78 mmol), benzaldehyde (9 g,86 mmol), sodium metabisulfite (15 g,80 mmol) and N, N-Dimethylformamide (DMF) (420 mL) were added to a round bottom flask and reacted at 130℃for 16 hours under nitrogen protection; after the reaction system is cooled to room temperature, the reaction system is cooled toPouring the reaction solution into water for quenching, filtering and collecting brown precipitate to obtain brown solid, washing the solid with diethyl ether and ethyl acetate, and then drying; recrystallizing and purifying the brown solid by using dichloromethane and ethanol to obtain 4-bromo-1, 2-diphenyl-1H-benzo [ d ]]Imidazole (21.2 g; 78%).
Adding magnesium bands (1.9 g;77.0 mmol) and Tetrahydrofuran (THF) (150 ml) into a round-bottomed flask, stirring uniformly under the protection of nitrogen, adding two pieces of iodine to initiate reaction, gradually changing the system from colorless to black, dissolving 4-bromo-1, 2-diphenyl-1H-benzo [ d ] imidazole (24.4 g;70.0 mmol) into 100ml of tetrahydrofuran, slowly dropwise adding the system, and stirring at the temperature of 60 ℃ for 1H to prepare a Grignard reagent; 2, 4-dichloro-6-phenyl-1, 3, 5-triazine (15.9 g;70.0 mmol) and tetrahydrofuran (160 ml) are added into a round-bottomed flask, uniformly stirred under the protection of nitrogen, a newly prepared Grignard reagent is added into the system dropwise at the temperature of 0 ℃ and stirred for reaction for 2 hours after the dropwise addition; concentrating most tetrahydrofuran after the reaction is finished, separating the reaction solution by using water and dichloroethane, drying an organic phase by using anhydrous magnesium sulfate, and removing a solvent under reduced pressure to obtain a crude product; purification of the crude product by silica gel column chromatography using dichloromethane/n-heptane as eluent afforded compound intermediate i1 (16.3 g, 85%)
Synthesis of Compound A-1-1:
intermediate a1 (5.0 g;9.5 mmol), intermediate i1 (3.8 g;13.3 mmol) and N, N-Dimethylformamide (DMF) (50 mL) were added to a round bottom flask, the temperature of the system was reduced to 0℃under nitrogen, and then sodium hydride (298 mg,12.35 mmol) was added to continue the reaction at room temperature for 12h; washing the reaction solution with water, separating the reaction solution, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification of the crude product by silica gel column chromatography using dichloromethane/n-heptane as eluent followed by recrystallization purification using a toluene/n-heptane solvent system yielded intermediate i21 (5.74 g, 46%)
Referring to the synthesis of compound A1, using reactant J instead of intermediate A1 and reactant K instead of intermediate i1 in the following table, the intermediate compounds shown in the following table were synthesized:
TABLE 7
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Mass spectrum data for some compounds are shown in table 8 below:
TABLE 8
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The nuclear magnetic data of a part of the compounds are shown in Table 9 below
TABLE 9
Preparation and performance evaluation of organic electroluminescent devices
Example 1
Green organic electroluminescent device
An anode is formed of Indium Tin Oxide (ITO) on a substrate with a reflective layer formed thereon, and has a thickness ofCutting into dimensions of 40mm x 0.7mm, preparing an experimental substrate with a cathode, an anode and an insulating layer pattern by adopting a photoetching procedure, and cleaning the surface of the ITO substrate by adopting an organic solvent to remove impurities on the surface of the ITO substrate; or by ultraviolet ozone and O 2 :N 2 Plasma surface treatment to increase the work function of the anode.
PtPC is vacuum evaporated on the anode of the substrate by PVD to form a film of thicknessIs deposited on the hole injection layer>HT-01 of (A) forms a hole transport layer.
Vapor deposition on hole transport layerHT-02 of (A) forms a hole assist layer.
On the hole-assist layer, compound a-1-1: GH-P: ir (3 mppy) 3 45%:45%: co-evaporation was performed at a rate of 10% to form a film having a thickness ofAn organic electroluminescent layer (green light-emitting layer).
Evaporating BCP and LiQ in a ratio of 1:1 to formA thick electron transport layer, toYb is evaporated on the electron transport layer to form a thickness +.>Magnesium and silver at 1:9 vapor deposition ratio is co-evaporated on the electron injection layer to form a thickness of +.>Is provided.
In addition, the thickness of the vapor deposited on the cathode isAn organic capping layer (CPL) is formed, thereby realizing the preparation of an organic light emitting device.
Examples 2 to 28:
in forming the green light-emitting layer, an organic electroluminescent device was fabricated by the same method as in example 1, except that the compound a-1-1 in example 1 was replaced with the compound shown in table 11.
Comparative example 1:
referring to table 11, an organic electroluminescent device was prepared in the same manner as in device example 1, except that compound a-1-1 was replaced with compound a in example 1.
Comparative example 2:
referring to table 11, an organic electroluminescent device was fabricated in the same manner as in device example 1, except that compound B was used instead of compound a-1-1 in example 1.
The material structures used in device examples 1-28 and comparative examples 1 and 2 are shown in table 10 below:
table 10
For the organic electroluminescent device prepared as above, the temperature was 20mA/cm 2 The IVL performance of the device was analyzed under the conditions of T95 lifetime at 15mA/cm 2 The results are shown in Table 11 below:
TABLE 11
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As can be seen from the data shown in table 11 above, when the compound of the present application was used as an organic electroluminescent device, the current efficiency was improved by at least 12.0%, the external quantum efficiency was improved by at least 12.5%, and the lifetime T95 was improved by at least 11.5% as compared with the comparative example.
Compared with comparative example 1, the compound has obviously higher luminous efficiency and longer service life under the condition of close driving voltage. The reason for this is probably that the indolo [2,3-a ] carbazole core group used in the present application gives the molecule a distorted structure compared to the compound a, thereby increasing the energy level of the material T1. The organic electroluminescent devices prepared in examples 1 to 28 also have improved current efficiency and lifetime compared to comparative example 2. The reason for this is probably that the benzimidazole groups introduced in the present application enhance the electron mobility of the material compared to the compound B.
Red organic electroluminescent device
Example 29
The ITO thickness is equal toIs cut into a size of 40mm by 0.7mm, and a test substrate having a cathode, an anode and an insulating layer pattern is prepared by using a photolithography process, and ultraviolet ozone and O are used 2 :N 2 The plasma is surface treated to remove surface particles and to increase the work function of the anode.
PtPC is vacuum evaporated on a substrate by PVD method to form a film with a thickness ofAnd is in the airEvaporating HT-01 on the hole injection layer to form a layer with a thickness of +.>Is provided.
Vapor deposition thickness on hole transport layerHT-02, a hole assist layer formed.
On the hole-assist layer, compound RH-P: compounds A-1-26: ir (dmpq) 2 acac at 49%:49%: co-evaporation is carried out at a ratio of 2% (evaporation rate) to formAn organic electroluminescent layer (red light-emitting layer).
Mixing and evaporating BCP and LiQ in a weight ratio of 1:1 to formA thick electron transport layer, yb is evaporated on the electron transport layer to form +.>Then magnesium and silver are mixed with 1:10, vacuum vapor deposition on the electron injection layer to form +>Is provided.
Vapor deposition on the cathodeAnd forming an organic coating layer (CPL) on the CP-01 with the thickness to finish the manufacture of the organic light-emitting device.
Examples 30 to 35:
in forming the red light-emitting layer, the compounds a-1 to 26 in example 1 were replaced with the compounds shown in table 13, and an organic electroluminescent device was produced by the same method as in example 29.
Comparative example 3:
referring to Table 13, an organic electroluminescent device was prepared in the same manner as in example 29, except that compound C was used instead of compounds A-1 to 26 in example 1.
Comparative example 4:
referring to Table 13, an organic electroluminescent device was prepared in the same manner as in example 29, except that compound D was used instead of compounds A-1 to 26 in example 1.
In examples 30 to 35 and comparative examples 3 to 4, the structural formulas of the respective materials used are shown in Table 12 below:
table 12
For the organic electroluminescent device prepared as above, the temperature was 20mA/cm 2 The IVL performance of the device was analyzed under the conditions of T95 lifetime at 15mA/cm 2 The results are shown in Table 13 below:
TABLE 13
As can be seen from the data shown in Table 13 above, when the compound of the present application was used as an organic electroluminescent device, the voltage was reduced by at least 0.26V, the current efficiency was improved by at least 13.4%, the external quantum efficiency was improved by at least 13.3%, and the lifetime was improved by at least 14% as compared with comparative examples 3 to 4. The compound of the application is used as an organic electroluminescent device, and the performance is improved compared with the comparative example, and the reason is probably that the benzimidazole group introduced in the application improves the mobility of electrons of the material.
It should be understood that the application is not limited in its application to the details of construction and the arrangement of components set forth in the specification. The application is capable of other embodiments and of being practiced and carried out in various ways. The foregoing variations and modifications are intended to fall within the scope of the present application. It should be understood that the application disclosed and defined in this specification extends to all alternative combinations of two or more of the individual features mentioned or evident from the text and/or drawings. All of these different combinations constitute various alternative aspects of the present application. The embodiments described in this specification illustrate the best mode known for carrying out the application and will enable those skilled in the art to make and use the application.

Claims (9)

1. The nitrogen-containing compound is characterized by having a structural general formula shown in formula 1:
wherein ,a represents a bond, a is selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted fluorenyl group;
B is selected from structures shown in formulas 1-1, 1-2 or 1-3;
the substituents in A are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, and cyclohexenyl;
X 1 、X 2 、X 3 are all N;
each R, R 1 、R 2 、R 3 、R 4 、R 5 Or R is 6 Each independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl;
n 1 represents a substituent R 1 Number n of (n) 1 Selected from 1, 2, 3 or 4, when n 1 When the number is greater than 1, any two R 1 Identical or different, optionally, any two adjacent R 1 Forming benzene ring;
n 2 represents a substituent R 2 Number n of (n) 2 Selected from 1 or 2, when n 2 When the number is greater than 1, any two R 2 Identical or different, optionally, any two adjacent R 2 Forming benzene ring;
n 3 represents a substituent R 3 Number n of (n) 3 Selected from 1, 2, 3 or 4, when n 3 When the number is greater than 1, any two R 3 Identical or different, any two adjacent R' s 3 Forming benzene ring;
n 4 represents a substituent R 4 Number n of (n) 4 Selected from 1, 2 or 3, when n 4 When the number is greater than 1, any two R 4 The same or different;
n 5 represents a substituent R 5 Number n of (n) 5 Selected from 1, 2, 3 or 4, when n 5 When the number is greater than 1, any two R 5 The same or different;
n 6 represents a substituent R 6 Number n of (n) 6 Selected from 1, 2, 3 or 4, when n 6 When the number is greater than 1, any two R 6 The same or different;
L、L 1 、L 2 、L 3 each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group;
L、L 1 、L 2 、L 3 wherein each substituent is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl;
Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 respectively are provided withIndependently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted carbazolyl;
Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 the substituents in (a) are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexenyl, phenyl.
2. The nitrogen-containing compound according to claim 1, wherein the L, L 1 、L 2 、L 3 Each independently selected from a single bond, a substituted or unsubstituted group V; wherein the unsubstituted group V is selected from the group consisting of:
wherein ,represents a chemical bond; the substituted group V has one or more substituents thereon, each of which is independently selected from deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl; when the number of substituents of V is greater than 1, the substituents may be the same or different.
3. The nitrogen-containing compound according to claim 1, wherein Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Each independently selected from the group consisting of substituted or unsubstituted groups W; wherein the unsubstituted group W is selected from the group consisting of:
wherein ,represents a chemical bond; the substituted group W has one or more substituents thereon, each of which is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, cyclohexenyl, phenyl; when the number of substituents of W is greater than 1, each substituent is the same or different.
4. The nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
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5. an organic electroluminescent device comprising an anode, a cathode, and at least one functional layer between the anode and the cathode, the functional layer comprising the nitrogen-containing compound according to any one of claims 1 to 4.
6. The organic electroluminescent device of claim 5, wherein the functional layer comprises an organic electroluminescent layer comprising the nitrogen-containing compound.
7. The organic electroluminescent device of claim 5, wherein the organic electroluminescent device is a green organic electroluminescent device.
8. The organic electroluminescent device of claim 5, wherein the organic electroluminescent device is a red organic electroluminescent device.
9. An electronic device comprising an organic electroluminescent device as claimed in any one of claims 5 to 8.
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CN110950846A (en) * 2020-01-02 2020-04-03 西安瑞联新材料股份有限公司 Benzimidazole bipyrimidine derivative and application thereof

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