CN114075185B - Nitrogen-containing compound, and electronic element and electronic device comprising same - Google Patents

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

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CN114075185B
CN114075185B CN202110120037.8A CN202110120037A CN114075185B CN 114075185 B CN114075185 B CN 114075185B CN 202110120037 A CN202110120037 A CN 202110120037A CN 114075185 B CN114075185 B CN 114075185B
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nitrogen
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CN114075185A (en
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杨敏
韩超
南朋
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Abstract

The application belongs to the technical field of organic materials, and provides a nitrogen-containing compound, an electronic element and an electronic device containing the nitrogen-containing compound, wherein the structure of the nitrogen-containing compound is shown as a chemical formula 1:

Description

Nitrogen-containing compound, and electronic element and electronic device comprising same
Technical Field
The application relates to the technical field of organic electroluminescence, in particular to a nitrogen-containing compound, an electronic element containing the same and an electronic device containing the same.
Background
With the acceleration of globalization, the technological knowledge is fully exchanged, and the pace of technological progress is further accelerated. Under such a large environment, the organic flat display field is rapidly advancing, and organic light emitting diodes, also called organic electroluminescence, are rapidly developed and industrialized at a beginning scale. The OLED material is mainly applied to the display field and the illumination field, wherein the display field is mainly concentrated in the display field and the illumination field of televisions, computers, mobile phones and the like, and the display field is mainly concentrated on the display screens of the televisions, the computers, the mobile phones and the like. The OLED material has the advantages of low working voltage, high reaction speed, flexible folding, high luminous brightness, high efficiency and the like, so that the OLED material is sought after by the industry. Therefore, the light source is known as dream technology of future light sources and display technologies of human beings.
Under the action of an external electric field, the radiative transitions of the singlet excitons and the triplet excitons to the ground state generate fluorescence and phosphorescence, respectively. OLED materials are classified into fluorescent materials and phosphorescent materials according to the principle of luminescence. Due to the spin orbit coupling effect of heavy metals, the phosphorescent material can simultaneously utilize 25% of singlet excitons and 75% of triplet excitons, so that the luminous efficiency is remarkably improved. However, phosphorescent materials suffer from two major problems of concentration quenching and triplet-order-quenching, and are unable to achieve college luminescence. In the development of this industrialized hot trend, how to improve the device efficiency and extend the lifetime is a critical issue.
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 present application is directed to overcoming the shortcomings of the prior art and providing a nitrogen-containing compound, an electronic device and an electronic component comprising the same, which can improve the 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 consisting of structures shown in chemical formula 1 and chemical formula 2:
wherein, the connection point of chemical formula 1 and chemical formula 2 is represented, and any two adjacent connection points in chemical formula 2 are connected with chemical formula 1;
x is selected from O or S;
y is selected from substituted or unsubstituted aryl with 6-18 carbon atoms;
X 1 、X 2 and X3 Identical or different, each independently selected from N or CH, and X 1 、X 2 and X3 At least one of which is N;
R 1 、R 2 and R3 Are identical or different from each other and are each independently selected from deuterium, halogen, cyano, alkyl having 1 to 5 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, and carbon atomsA heterocycloalkyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms;
R 1 、R 2 、R 3 by R i Representing n 1 ～n 3 With n i Representing n i R represents i I is a variable, 1, 2 and 3 are represented, and when i is 1 and 3, n is i Selected from 0, 1, 2, 3 or 4; when i is 2, ni is selected from 0, 1 or 2; and when n i When the number is greater than 1, any two n i The same or different;
L、L 1 and L2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar2 The same or different and are respectively and independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
the substituent group in the Y is selected from deuterium, halogen group, cyano, aryl with 6-12 carbon atoms and alkyl with 1-5 carbon atoms;
said L, L 1 and L2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms and alkoxy having 1 to 10 carbon atoms;
the Ar is as follows 1 and Ar2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms and alkoxy having 1 to 10 carbon atoms.
The nitrogen-containing compound provided by the application comprises an azacyclic structure (pyridine, pyrimidine or triazine) and a structure in which phenanthrene and aryl substituted nitrogen-containing five-membered rings (thiazole and oxazole) are fused. When the structure is combined as a main material of the organic light-emitting layer in a specific mode, the target compound has higher electron mobility, is favorable for balancing electrons and holes in the organic light-emitting layer, widens the composite region of the electrons and the holes in the light-emitting layer, improves the light-emitting efficiency of electroluminescence, reduces the driving voltage of the organic electroluminescence and prolongs the service life of the device. The nitrogen-containing compound is more suitable as an electronic host material in a hybrid host of an organic electroluminescent device, and is particularly suitable as an electronic host material for a red light device. When the nitrogen-containing compound is used for a luminescent layer material of an organic electroluminescent device, the electron transmission performance of the device is effectively improved, 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 electronic 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 electronic element 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, the structural formula of which consists of structures shown in chemical formula 1 and chemical formula 2:
wherein, the connection point of chemical formula 1 and chemical formula 2 is represented, and any two adjacent connection points in chemical formula 2 are represented by the following chemical formula1 is connected with R 1 、R 2 Or R is 3 Must include at least one of formula 1;
x is selected from O or S;
y is selected from substituted or unsubstituted aryl with 6-18 carbon atoms;
X 1 、X 2 and X3 Identical or different, each independently selected from N or CH, and X 1 、X 2 and X3 At least one of which is N;
R 1 、R 2 and R3 Are identical to or different from each other and are each independently selected from deuterium, halogen, cyano, alkyl having 1 to 5 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 3 to 30 carbon atoms;
R 1 、R 2 、R 3 by R i Representing n 1 ～n 3 With n i Representing n i R represents i I is a variable, 1, 2 and 3 are represented, and when i is 1 and 3, n is i Selected from 0, 1, 2, 3 or 4; when i is 2, ni is selected from 0, 1 or 2; and when n i When the number is greater than 1, any two n i The same or different;
L、L 1 and L2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar2 The same or different and are respectively and independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
the substituent group in the Y is selected from deuterium, halogen group, cyano, aryl with 6-12 carbon atoms and alkyl with 1-5 carbon atoms;
said L, L 1 and L2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen, cyano, heteroaryl with 3-20 carbon atoms, aryl with 6-20 carbon atoms, trialkylsilyl with 3-12 carbon atoms and alkyl with 1-10 carbon atoms A group, 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;
the Ar is as follows 1 and Ar2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms and alkoxy having 1 to 10 carbon atoms.
Optionally, the nitrogen-containing compound has a structure represented by any one of formula 1-1, formula 1-2, formula 1-3, formula 1-4, formula 1-5, formula 1-6, formula 1-7, formula 1-8, formula 2-1, formula 2-2, formula 2-3, formula 2-4, formula 2-5, formula 2-6, formula 2-7, formula 2-8, formula 3-1, formula 3-2, formula 3-3, formula 3-4, formula 3-5, formula 3-6, formula 3-7, formula 3-8, formula 4-1, formula 4-2, formula 4-3, formula 4-4, formula 4-5, formula 4-6, formula 4-7, formula 4-8, formula 5-1, formula 5-2, formula 5-3, formula 5-4, formula 5-5, formula 5-6, formula 5-7, and formula 5-8:
in the present application, the description modes "each independently selected from" and "each independently selected from" are interchangeable, and are to be understood in a broad sense, and may refer to both that in different groups, the same The specific options expressed between symbols do not affect each other, or it may mean that the specific options expressed between the same symbols do not affect each other in the same group. 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, halogen, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms optionally substituted with deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, or alkoxy 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 number of carbon atoms of the substituted or unsubstituted functional group meansAll carbon numbers. 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 isThe number of carbon atoms is 7; l is->The number of carbon atoms is 12.
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 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 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 to 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 small, ordinary rings having 3 to 10 carbon atoms. Furthermore, cycloalkyl groups may be substituted or unsubstituted. For example, a cyclohexyl group. Heterocycloalkyl means that one or more carbon atoms in the cycloalkyl group are replaced by heteroatoms such as B, N, O, S, P, si or Se.
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 polycyclic aryl, in other words, aryl may be monocyclic aryl, fused ring aryl, two or more monocyclic aryl groups linked by carbon-carbon bond conjugation, monocyclic aryl and fused ring aryl groups linked by carbon-carbon bond conjugation, two or more fused ring aryl groups linked by carbon-carbon bond conjugation. 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 the number of carbon atoms in the aryl group may be from 6 to 20, in some embodiments the number of carbon atoms in the aryl group may be from 6 to 18, and in other embodiments the number of carbon atoms in the aryl group may be from 6 to 12. 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, heterocycloalkyl 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 or a derivative thereof containing at least one heteroatom in the ring, and the heteroatom 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-phenylcarbazolyl (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. "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 20, 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, a heterocycloalkyl 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, 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 the following formula (f), the naphthyl group represented by the formula (f) is linked to other positions of the molecule through two non-positional linkages penetrating through the bicyclic ring, and the meaning of the linkage includes any one of the possible linkages shown in the formulas (f-1) to (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 formulas (X '-1) to (X' -4).
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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, the Y is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl;
optionally, the substituent in Y is selected from phenyl, naphthyl.
In one embodiment of the application, said Y is selected from the group consisting of:
in one embodiment of the application, the L, L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 12 carbon atoms.
Optionally, the L, L 1 、L 2 The substituent of (C) is selected from deuterium, halogen group, cyano, phenyl, alkyl with 1-5 carbon atoms.
Specifically, the L, L 1 、L 2 Specific examples of substituents in (a) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
Optionally, the L, L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene groupPhenyl.
Further alternatively, the L 1 ，L 2 Each independently selected from a single bond or a phenylene group.
In another embodiment of the application, the L is selected from a single bond or a group consisting of:
in one embodiment of the application, the Ar 1 and Ar2 Each independently selected from a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.
Optionally, the Ar 1 、Ar 2 The substituents in (a) are independently selected from deuterium, halogen group, cyano group, aryl group with 6-12 carbon atoms and alkyl group with 1-5 carbon atoms.
Specifically, the Ar 1 and Ar2 Specific examples of substituents in (a) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
Further alternatively, the Ar 1 and Ar2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted N-phenylcarbazolyl.
In another embodiment of the present application, the Ar 1 and Ar2 Each independently selected from the group consisting of substituted or unsubstituted W, unsubstituted W being selected from the group consisting of:
wherein, the chemical bond is represented; the substituted W has one or more substituents thereon, each of which is independently selected from the group consisting of: deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl; when the number of substituents of W is greater than 1, each substituent is the same or different.
Alternatively, ar 1 and Ar2 Each independently selected from the group consisting of:
the present application also provides an electronic component 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, there is provided an organic electroluminescent device having a device structure 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 320, an organic electroluminescent layer 330, a hole blocking layer 340, an electron transport layer 350, and an electron injection layer 360; the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322; the hole injection layer 310, the hole transport layer 320, the organic electroluminescent layer 330, the hole blocking layer 340, the electron transport layer 350, and the electron injection layer 360 may be sequentially formed on the anode 100, and the organic electroluminescent layer 330 may contain an organic compound according to the first aspect of the present application, preferably at least one of the compounds 1 to 376.
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; metallic oxygen Compounds 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 320 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, the hole transport layer 320 may include a first hole transport layer 321 and a second hole transport layer 322; the first hole transport layer 321 is adjacent to the second hole transport layer 322 and is closer to the anode than the second hole transport layer 322. For example, in one embodiment of the present application, the first hole transport layer 321 is composed of compound HT-01 and the second hole transport layer 322 is composed of compound 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 host material of the organic electroluminescent layer 330 is a nitrogen-containing compound provided by the present application. The nitrogen-containing compound provided by the application comprises an azacyclic structure (pyridine, pyrimidine or triazine) and a structure in which phenanthrene and aryl substituted nitrogen-containing five-membered rings (thiazole and oxazole) are fused. When the structures are combined with each other to be used as a main material of the organic light-emitting layer, the hole mobility of the light-emitting layer is improved due to the large electron cloud density, so that the balance between electrons and holes in the organic light-emitting layer is facilitated, the light-emitting efficiency of electroluminescence is improved, and the driving pressure of organic electroluminescence is reduced. Because the fused structure of the phenanthrene and the nitrogen-containing five-membered ring has larger space volume, the whole molecular structure has better three-dimensional configuration by adopting the connecting mode, so that the molecular structure has better rigidity, the energy level of the material T1 is improved while the mobility is higher, and the crystallinity is lower. The nitrogen-containing compound is more suitable as an electronic host material in a hybrid host of an organic electroluminescent device, and is particularly suitable as an electronic host material for a red light device. When the nitrogen-containing compound is used for a luminescent layer material of an organic electroluminescent device, the electron transmission performance of the device is effectively improved, and the luminescent efficiency and the service life of the device are improved.
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 guest material of the organic light emitting layer 330 may be Ir (piq) 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 BTB 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, the hole injection layer 310 may be composed of m-MTDATA.
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 electronic element.
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.
(1) Synthesis of intermediate C-1
A three-necked flask equipped with a mechanical stirrer, a thermometer and a bulb condenser was purged with nitrogen (0.100L/min) for 15 minutes, and then a mixed solvent of reactant A-1 (5.0 g,18.2 mmol), reactant B-1 (3.37 g,18.2 mmol), tetrakis (triphenylphosphine) palladium (1.05 g,0.91 mmol), potassium carbonate (7.56 g,54.7 mmol), tetrabutylammonium bromide (0.25 g,0.91 mmol), toluene (40 mL), ethanol (20 mL) and deionized water (10 mL) was added. Stirring is started, the temperature is raised to 75-85 ℃ for reaction for 12 hours, and after the reaction is finished, the mixture is cooled to room temperature. Toluene (100 mL) was added for extraction, the organic phases were combined, the organic phases were dried over anhydrous magnesium sulfate, and after filtration, the filtrate was distilled off under reduced pressure to remove the solvent; purification of the crude product by column chromatography on silica gel using n-heptane as eluent was followed by recrystallization from a dichloromethane/ethyl acetate system (1:5) to give intermediate C-1 (4.56 g, 75% yield).
Referring to the synthesis of intermediate C-1, intermediate C-X shown in Table 1 below was synthesized, wherein X was 1-14, and reactant A-1, reactant A-2, reactant A-3, reactant A-4, reactant A-5, reactant A-6 and reactant A-7 were used in place of reactant A-1, reactant B-1 and reactant B-2 were used in place of reactant B-1, and intermediate C-X was prepared as shown in Table 1 below:
TABLE 1
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(2) Synthesis of intermediate D-1
A three-port bottle with mechanical stirring, a thermometer and a constant pressure dropping funnel is filled with nitrogen (0.100L/min) for 15min for replacement, methoxymethyl triphenyl phosphorus chloride (5.9 g,17.2 mmol) and tetrahydrofuran (50 mL) are sequentially added, the system temperature is reduced to-10 to-15 ℃, potassium tert-butoxide (2.18 g,19.5 mmol) is added into the bottle in batches, the system temperature is controlled to-10 to-5 ℃, after 2h of heat preservation, intermediate C-1 (5.0 g,15.0 mmol) is weighed, dissolved by 15 times tetrahydrofuran and then added into the system by using the constant pressure dropping funnel, about 1h of dropping is completed, the system temperature is controlled to be about-5 ℃, the reaction is further kept for 2h, and the temperature is increased to room temperature after the reaction is finished. Toluene (100 mL) was added for extraction, the organic phases were combined, the organic phases were dried over anhydrous magnesium sulfate, and after filtration, the filtrate was distilled off under reduced pressure to remove the solvent; the crude product was purified by silica gel column chromatography using toluene as a eluent to give intermediate D-1 (3.79 g, yield 70%).
Referring to the synthesis method of intermediate D-1, intermediate D-X shown in Table 2 below was synthesized, wherein X was 1-14, and intermediate C-X was used in place of intermediate C-1, and the resulting intermediate D-X was shown in Table 2 below:
TABLE 2
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(3) Synthesis of intermediate E-1
Nitrogen (0.100L/min) is introduced into a three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser for 15min replacement, and intermediate D-1 (5.0 g,13.8 mmol), eton reagent (0.99 g,4.14 mmol) and chlorobenzene (50 mL) are sequentially and respectively added, the temperature is raised, the reflux stirring reaction is carried out for 1h, and after the reaction is finished, the reaction is cooled to room temperature. Dichloromethane (100 mL) is added into the system, water (100 mL) and sodium bicarbonate (5.0 g) are added after stirring, the mixture is fully stirred, the mixture is kept stand for liquid separation, an organic phase is washed to be neutral by water, dichloromethane (100 mL) is used for extraction, the organic phases are combined, anhydrous magnesium sulfate is added into the organic phase for drying, and the filtrate is distilled under reduced pressure to remove the solvent after filtration; the crude product was purified by silica gel column chromatography using toluene as a eluent to give intermediate E-1 (2.96 g, yield 35%).
Referring to the synthesis method of intermediate E-1, intermediate E-X shown in Table 3 below was synthesized, wherein X was 1-27, and intermediate D-X was used in place of intermediate D-1, and the resulting intermediate E-X was shown in Table 3 below:
TABLE 3 Table 3
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(4) Synthesis of intermediate F-1
A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was charged with nitrogen (0.100L/min) for 15min for replacement, intermediate E-1 (5.0 g,15.2 mmol), pinacol biborate (3.9 g,15.2 mmol), tris (dibenzylideneacetone) dipalladium (0.14 g,0.15 mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.14 g,0.30 mmol), potassium acetate (4.5 g,45.5 mmol) and 1, 4-dioxane (50 mL) were added, the temperature was raised to 105-115℃and the mixture was stirred under reflux for 5h, followed by cooling to room temperature after the reaction was completed. Extracting the reaction solution with dichloromethane and water, drying the organic phase with anhydrous magnesium sulfate, filtering, passing through a short silica gel column, and distilling the filtrate under reduced pressure to remove the solvent; purification of the crude product by silica gel column chromatography using methylene chloride/n-heptane yielded intermediate F-1 (5.0 g, 78% yield).
Referring to the synthesis method of intermediate F-1, intermediate F-X shown in Table 4 below was synthesized, wherein X was 1-25, and intermediate E-X was used in place of intermediate E-1, and the resulting intermediate F-X was shown in Table 4 below:
TABLE 4 Table 4
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(5) Synthesis of intermediate G-1
A three-necked flask equipped with a mechanical stirrer, a thermometer and a bulb-shaped condenser was purged with nitrogen (0.100L/min) for 15 minutes, and then a mixed solvent of intermediate F-1 (5.0 g,11.9 mmol), reactant SM-1 (2.4 g,11.9 mmol), tetrakis (triphenylphosphine) palladium (0.68 g,0.6 mmol), potassium carbonate (4.9 g,35.6 mmol), tetrabutylammonium bromide (0.16 g,0.59 mmol), toluene (40 mL), ethanol (20 mL) and deionized water (10 mL) was added. Stirring is started, the temperature is raised to 75-85 ℃ for reaction for 12 hours, and after the reaction is finished, the mixture is cooled to room temperature. Toluene (100 mL) was added for extraction, the organic phases were combined, the organic phases were dried over anhydrous magnesium sulfate, and after filtration, the filtrate was distilled off under reduced pressure to remove the solvent; purification by silica gel column chromatography using n-heptane as the mobile phase and recrystallization using a dichloromethane/ethyl acetate system afforded intermediate G-1 (3.8G, 78% yield).
Referring to the synthesis method of intermediate G-1, intermediate G-X shown in Table 5 below was synthesized, wherein X was 1-4, intermediate F-2 and intermediate F-6 were used in place of intermediate F-1, and reactant SM-2, reactant SM-3 and reactant SM-4 were used in place of reactant SM-1, and intermediate G-X was prepared as shown in Table 5 below:
TABLE 5
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(5) Synthesis of Compound 100
A three-necked flask equipped with a mechanical stirrer, a thermometer and a bulb-shaped condenser was purged with nitrogen (0.100L/min) for 15 minutes, and then a mixed solvent of intermediate F-1 (5.0 g,11.9 mmol), reaction H-1 (3.18 g,11.9 mmol), tetrakis (triphenylphosphine) palladium (0.68 g,0.59 mmol), potassium carbonate (4.92 g,35.6 mmol), tetrabutylammonium bromide (0.16 g,0.59 mmol), toluene (40 mL), ethanol (20 mL) and deionized water (10 mL) was added. Stirring is started, the temperature is raised to 75-85 ℃ for reaction for 12 hours, and after the reaction is finished, the mixture is cooled to room temperature. Toluene (100 mL) was added for extraction, the organic phases were combined, the organic phases were dried over anhydrous magnesium sulfate, and after filtration, the filtrate was distilled off under reduced pressure to remove the solvent; silica gel column chromatography using n-heptane as the mobile phase crude product followed by recrystallization from a dichloromethane/ethyl acetate system afforded compound 100 (4.81 g, 77% yield), mass spectrum: m/z=527.2 [ m+h ] + 。
Referring to the synthesis method of compound 100, compound X shown in Table 6 below was synthesized using intermediate F-X or intermediate G-X instead of intermediate F-1 and reactant H-X instead of reactant H-1, and compound X was prepared as shown in Table 6 below:
TABLE 6
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The nuclear magnetic data of a part of the compounds are shown in Table 7 below
TABLE 7
Preparation and performance evaluation of organic electroluminescent devices
Example 1
Red organic electroluminescent device
Will be of the thickness ofThe anode 100ITO substrate of (1) was cut into a size of 40mm (length) ×40mm (width) ×0.7mm (thickness), and a photolithography process was used to prepare an experimental substrate having a pattern of a cathode 200, an anode 100 and an insulating layer, using ultraviolet ozone and O 2 :N 2 The plasma is surface-treated to increase the work function of the anode 100 (experimental substrate), and the surface of the ITO substrate is cleaned with an organic solvent to remove scum and oil stains on the surface of the ITO substrate.
Vacuum evaporating compound m-MTDATA (4, 4' -tris (N-3-methylphenyl-N-phenylamino) triphenylamine) (structural formula shown below) on experimental substrate to form a film having a thickness ofA hole injection layer 310 (HIL); and vacuum evaporating the compound HT-01 over the hole injection layer 310 (HIL) to form a thickness +.>Is a first hole transport layer 321 (HTL 1). Vacuum vapor-depositing a layer HT-02 on the first hole transport layer 321 (HTL 1) to a thickness of +. >And a second hole transport layer 322 (HTL 2).
On the second hole transport layer 322 (HTL 2), compound 100 is reacted with Ir (piq) 2 (acac) at 95%: co-evaporation is carried out at a doping ratio of 5% to form a film with a thickness ofRed light emitting layer 330 (EML).
Mixing BTB and LiQ in a weight ratio of 1:1, and evaporating to formA thick electron transport layer 350 (ETL), and Yb is then deposited on the electron transport layer 350 (ETL) to a thickness of +.>Electron injection layer 360 (EIL).
Vacuum evaporating magnesium (Mg) and silver (Ag) on the electron injection layer at a film thickness ratio of 1:9 to obtain a film with a thickness ofIs provided.
In addition, a layer with a thickness ofAnd forming a capping layer (CPL), thereby completing the manufacture of the organic light emitting device.
Examples 2 to 34
A red organic electroluminescent device was fabricated in the same manner as in example 1, except that the compound shown in table 6 was used instead of the compound 100 when forming the light emitting layer (EML).
Comparative example 1
A red organic electroluminescent device was fabricated by the same method as in example 1 using compound a instead of compound 100.
Comparative example 2
A red organic electroluminescent device was fabricated by the same method as in example 1 using compound B instead of compound 100.
Wherein m-MTDATA, HT-01, HT-02, ir (piq) 2 (acac), BTB, liQ, CP-01, compound A, compound B, the structural formulas of which are shown in Table 8 below:
TABLE 8
For the organic electroluminescent device prepared as above, the temperature was 20mA/cm 2 The performance of the equipment was analyzed under the conditions, and the results are shown in Table 9.
TABLE 9 Performance test results of Red organic electroluminescent devices
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From the results of table 9, it is understood that the organic electroluminescent devices prepared in examples 1 to 34 have improved properties compared to the comparative examples in the OLED device using the compound as the organic electroluminescent layer. Wherein the driving voltage was reduced by at least 0.25V, the luminous efficiency was improved by at least 10.38%, and the lifetime was improved by at least 13.79% as compared with comparative example 1 and comparative example 2, which are compounds of the light emitting layer. From the above data, it is clear that the nitrogen-containing compound of the present application is used as an organic electroluminescent layer of an electronic device having significantly improved light-emitting efficiency (Cd/a), external Quantum Efficiency (EQE) and lifetime (T95). Therefore, the nitrogen-containing compound can be used in an organic electroluminescent layer to prepare an organic electroluminescent device with high luminous efficiency and long service life.
The compound of the application has improved voltage, efficiency and life compared with the compound B of the comparative example. Although the difference is that the fused position of the oxazole and the phenanthrene is different, compared with the compound B of the comparative example, the fused mode of the compound has higher electron mobility, is favorable for balancing electrons and holes in an organic light-emitting layer, widens the composite area of the electrons and the holes in the light-emitting layer, improves the light-emitting efficiency of electroluminescence, reduces the driving voltage of the organic electroluminescence and prolongs the service life of a device.
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 (8)

1. A nitrogen-containing compound, characterized in that the structural formula of the nitrogen-containing compound is composed of structures represented by chemical formula 1 and chemical formula 2:
wherein, the connection point of chemical formula 1 and chemical formula 2 is represented, and any two adjacent connection points in chemical formula 2 are connected with chemical formula 1;
x is selected from O or S;
y is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted terphenyl;
The substituent in the Y is selected from phenyl and naphthyl;
X 1 、X 2 and X3 Identical or different, each independently selected from N or CH, and X 1 、X 2 and X3 At least one of which is N;
R 1 、R 2 and R3 Are identical to or different from each other and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms;
R 1 、R 2 、R 3 by R i Representing n 1 ～n 3 With n i Representing n i R represents i I is a variable, 1, 2 and 3 are represented, and when i is 1 and 3, n is i Selected from 0; when i is 2, ni is selected from 0;
L、L 1 and L2 Each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene;
said L, L 1 、L 2 The substituent of (a) is selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl and phenyl;
Ar 1 and Ar2 The same or different and are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted N-phenylcarbazolyl;
The Ar is as follows 1 and Ar2 The substituent of (C) is selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl,Tert-butyl, phenyl;
and the nitrogen-containing compound is not:
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2. the nitrogen-containing compound according to claim 1, wherein Ar 1 and Ar2 Each independently selected from the group consisting of substituted or unsubstituted W, unsubstituted W being selected from the group consisting of:
wherein ,represents a chemical bond; the substituted W has one or more substituents thereon, each of which is independently selected from the group consisting of: deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl; when the number of substituents of W is greater than 1, each substituent is the same or different.
3. The nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
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4. an electronic component 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 3.
5. The electronic component according to claim 4, wherein the functional layer includes a light-emitting layer including the nitrogen-containing compound.
6. The electronic component of claim 4, wherein the electronic component is an organic electroluminescent device.
7. The electronic component of claim 6, wherein the organic electroluminescent device is a red organic electroluminescent device.
8. An electronic device comprising the electronic component of any one of claims 4-7.
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