Nitrogen-containing compound, electronic component, and electronic device
阅读说明：本技术 含氮化合物、电子元件和电子装置 (Nitrogen-containing compound, electronic component, and electronic device ) 是由 杨敏 南朋 李林刚 马天天 于 2020-05-20 设计创作，主要内容包括：本申请提供了一种含氮化合物、电子元件和电子装置,属于有机材料技术领域。所述含氮化合物的结构如化学式1所示,A为化学式2所示的基团；所述含氮化合物能够改善电子元件的性能。<Image he="414" wi="700" file="DDA0002501072710000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(The application provides a nitrogen-containing compound, an electronic element and an electronic device, and belongs to the technical field of organic materials. The structure of the nitrogen-containing compound is shown in chemical formula 1, A is a group shown in chemical formula 2; the nitrogen-containing compound can improve the performance of an electronic component.)
1. A nitrogen-containing compound, wherein the structure of the nitrogen-containing compound is shown in chemical formula 1:
wherein the content of the first and second substances,
a is a group represented by chemical formula 2;
x is C (R)3R4)，R3And R4Each independently selected from hydrogen and alkyl with 1-10 carbon atoms;
R1and R2The same or different, and are independently selected from hydrogen, alkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms, and heteroaryl with 3-20 carbon atoms;
n1selected from 1,2, 3 or 4, when n is1When not less than 2, any two R1The same or different;
n2selected from 1,2, 3 or 4, when n is2When not less than 2, any two R2The same or different;
n3is selected from 0, 1 or 2 when n3When not less than 2, any two R3Identical or different, any two R4The same or different;
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar1selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
Ar2is a group represented by chemical formula 3;
the L and Ar1The substituents are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, and an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, and a phosphonooxy group having 6 to 18 carbon atoms.
2. The nitrogen-containing compound according to claim 1, characterized in that: the nitrogen-containing compound is selected from the group consisting of the following chemical formulas:
3. the nitrogen-containing compound according to claim 1 or 2, characterized in that: r1And R2The same or different, and are independently selected from hydrogen, alkyl with 1-6 carbon atoms, and aryl with 6-12 carbon atoms;
preferably, R1And R2The same or different, and each is independently selected from hydrogen, methyl, ethyl, propyl, tert-butyl, phenyl, biphenyl, naphthyl;
preferably, R1And R2Are respectively selected from isopropyl.
4. The nitrogen-containing compound according to claim 1 or 2, characterized in that: l is selected from a single bond and substituted or unsubstituted arylene with 6-18 carbon atoms.
5. The nitrogen-containing compound according to claim 1 or 2, characterized in that: l is selected from a single bond or a group represented by the formula j-1 to the formula j-6:
wherein M is2Selected from a single bond or
E1～E10Each independently selected from: deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a carbon atom1-10 halogenated alkyl groups, 2-6 alkenyl groups, 2-6 alkynyl groups, 3-10 cycloalkyl groups, 2-10 heterocycloalkyl groups, 5-10 cycloalkenyl groups, 4-10 heterocycloalkenyl groups, 1-10 alkoxy groups, 1-10 alkylthio groups, 1-10 aryloxy groups, 6-18 arylthio groups, 6-18 phosphoxy groups, 3-18 heteroaryl groups, and 6-18 aryl groups;
eris a substituent ErR is any integer of 1-10; when r is selected from 1,2, 3,4, 5, 6, erSelected from 0, 1,2, 3 or 4; when r is 7, erSelected from 0, 1,2, 3,4, 5 or 6; when r is 10, erSelected from 0, 1,2, 3 or 4; when r is selected from 8 or 9, erSelected from 0, 1,2, 3,4, 5, 6, 7 or 8; when e isrWhen greater than 1, any two of ErThe same or different.
6. The nitrogen-containing compound according to claim 1 or 2, characterized in that: l is selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted fluorenylene.
7. The nitrogen-containing compound according to claim 1 or 2, characterized in that: l is selected from a single bond or a group consisting of:
8. the nitrogen-containing compound according to claim 1 or 2, characterized in that: l is selected from a single bond or
9. The nitrogen-containing compound according to claim 1 or 2, characterized in that: ar (Ar)1Is selected from substituted or unsubstituted aryl with 6-20 carbon atoms.
10. The nitrogen-containing compound according to claim 1 or 2, characterized in that: ar (Ar)1Selected from the group consisting of groups represented by the following formulae i-1 to i-4:
wherein H1～H9Each independently selected from: deuterium, a halogen group, a heteroaryl group having 3 to 18 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, and a phosphonoxy group having 6 to 18 carbon atoms;
H7to H9The aryl can also be independently selected from aryl with 6-12 carbon atoms;
hkis a substituent HkK is any integer of 1-9; wherein, when k is selected from 5, hkSelected from 0, 1,2 or 3; when k is selected from 2, 7, 8, hkSelected from 0, 1,2, 3 or 4; when k is selected from 1, 3,4, 6, 9, hkSelected from 0, 1,2, 3,4 or 5;
when h is generatedkWhen greater than 1, any two HkThe same or different.
11. The nitrogen-containing compound according to claim 1 or 2, characterized in that: ar (Ar)1Selected from the group consisting of:
12. the nitrogen-containing compound according to claim 1 or 2, characterized in that: ar (Ar)1Selected from the group consisting of:
13. the nitrogen-containing compound according to claim 1 or 2, characterized in that: the nitrogen-containing compound is selected from the group consisting of:
wherein when n is3＝At 0, the structural formula of chemical formula 1 isWhen n is3When 1, the structural formula of formula 1 is
"-" represents R1Attached to the 1,2, 3,4 position of formula 1, "-" indicates R2Attached to the 5, 6, 7, 8 position of formula 1;
R-A, R-B, R-C, R-D, R-E, R-F represents R with different structures1Or R2And each corresponds to the group shown below;
L-A, L-B, L-C, L-D, L-E, L-F, L-G, L-H, L-I represents L with different structures and respectively corresponds to groups shown in the specification
＊＊ denotes an
I-A, I-B, I-C, I-D, I-E, I-F, I-G, I-H, I-I, I-J, I-K, I-L, I-M represents Ar with different structures1And each corresponds to the group shown below
14. The nitrogen-containing compound according to claim 1 or 2, characterized in that: the nitrogen-containing compound is selected from the group consisting of:
15. an electronic component, characterized in that: the cathode comprises an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; wherein the functional layer comprises the nitrogen-containing compound of any one of claims 1 to 14.
16. The electronic component of claim 15, wherein: the functional layer includes a hole-adjusting layer including the nitrogen-containing compound.
17. The electronic component according to claim 15 or 16, wherein: the electronic element is an organic electroluminescent device or a photoelectric conversion device;
preferably, the organic electroluminescent device is a red organic electroluminescent device or a green organic electroluminescent device.
18. The electronic component according to claim 15, wherein the functional layer comprises a hole transport layer comprising the nitrogen-containing compound;
preferably, the electronic element is a blue organic electroluminescent device.
19. An electronic device, characterized in that it comprises an electronic component according to any one of claims 15-18.
Technical Field
The present disclosure relates to the field of organic materials, and more particularly to a nitrogen-containing compound, an electronic device using the same, and an electronic device using the same.
Background
With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is more and more extensive. Such electronic components generally include a cathode and an anode that are oppositely disposed, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
For example, when the electronic element is an organic electroluminescent device, it generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the electroluminescent layer under the action of the electric field, holes on the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the electroluminescent layer emits light outwards.
Organic hole transport materials reported so far are generally small in molecular weight, such as CN109574925A, CN103108859A, KR1020190041938A and WO2018164265a 1. The glass transition temperature of the materials is low, and the materials are easy to crystallize due to repeated charge and discharge in the use process of the materials, so that the uniformity of the thin film is damaged, and the service life of the materials is influenced. Therefore, the stable and efficient organic hole transport material is developed, so that the driving voltage is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the organic hole transport material has important practical application value.
The above information disclosed in this background section is only for enhancement of understanding of the background of the application and therefore it may contain information that does not constitute prior art that is known to a person of ordinary skill in the art.
Disclosure of Invention
An object of the present application is to provide a nitrogen-containing compound, an electronic component, and an electronic device, in order to improve the performance of the electronic component and the electronic device.
In order to achieve the purpose of the invention, the following technical scheme is adopted in the application:
according to a first aspect of the present application, there is provided a nitrogen-containing compound having a structure represented by chemical formula 1:
wherein the content of the first and second substances,represents a chemical bond;
a is a group represented by chemical formula 2;
x is C (R)3R4)，R3And R4Each independently selected from hydrogen and alkyl with 1-10 carbon atoms;
R1and R2The same or different, and are independently selected from hydrogen, alkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms, and heteroaryl with 3-20 carbon atoms;
n1selected from 1,2, 3 or 4, when n is1When not less than 2, any two R1The same or different;
n2selected from 1,2, 3 or 4, when n is2When not less than 2, any two R2The same or different;
n3is selected from 0, 1 or 2 when n3When not less than 2, any two R3Identical or different, any two R4The same or different;
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar1selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
Ar2is a group represented by chemical formula 3;
the L and Ar1The substituents are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, and an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, and a phosphonooxy group having 6 to 18 carbon atoms.
The nitrogen-containing compound is a spiro compound, and aromatic amine groups with strong electron donating capability are introduced into a spiro system with a large conjugated structure and good luminescence performance, wherein the spiro system has a rigid plane structure and high luminescence quantum efficiency, and can improve the advantages of thermal stability, film stability, carrier migration stability, good intersolubility and the like of materials; and one substituent of the arylamine is required to be an adamantine fluorene group, the adamantine fluorene group has proper molecular weight and steric hindrance effect, the glass transition temperature of the material can be effectively improved, and the adamantyl group screwed on the fluorene group has large spatial volume and strong rigidity.
The nitrogen-containing compound provided by the application can reduce the interaction force between large plane conjugated structures, reduce pi-pi stacking between molecules, and adjust the stacking degree between molecules, so that the nitrogen-containing compound is not easy to crystallize or aggregate during film formation, and can have a more stable amorphous state, and the material has the advantages of low voltage, high efficiency and long service life in a device.
According to a second aspect of the present application, there is provided an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the above-mentioned nitrogen-containing compound. According to one embodiment of the present application, the electronic component is an organic electroluminescent device. According to another embodiment of the present application, the electronic component is a solar cell.
According to a third aspect of the present application, there is provided an electronic device including the above electronic component.
Drawings
The above and other features and advantages of the present application will become more apparent by describing in detail exemplary embodiments thereof with reference to the attached drawings.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.
Fig. 3 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Fig. 4 is a schematic structural diagram of an electronic device according to another embodiment of the present application.
The reference numerals of the main elements in the figures are explained as follows:
100. an anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 321. a hole transport layer; 322. a hole-adjusting layer; 330. an organic electroluminescent layer; 340. a hole blocking layer; 350. an electron transport layer; 360. an electron injection layer; 370. a photoelectric conversion layer; 400. a first electronic device; 500. a second electronic device.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, 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 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 denote the same or similar structures in the drawings, 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 subject matter of the present application can be practiced without one or more of the specific details, or with other methods, components, materials, and so forth. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring major technical ideas of the application.
The application provides a nitrogen-containing compound, wherein the structure of the nitrogen-containing compound is shown in chemical formula 1:
wherein the content of the first and second substances,represents a chemical bond;
a is a group represented by chemical formula 2;
x is C (R)3R4)，R3And R4Each independently selected from hydrogen and alkyl with 1-10 carbon atoms;
R1and R2The same or different, and are independently selected from hydrogen, alkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms, and heteroaryl with 3-20 carbon atoms;
n1is selected from1,2, 3 or 4, when n is1When not less than 2, any two R1The same or different;
n2selected from 1,2, 3 or 4, when n is2When not less than 2, any two R2The same or different;
n3is selected from 0, 1 or 2 when n3When not less than 2, any two R3Identical or different, any two R4The same or different;
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar1selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
Ar2is a group represented by chemical formula 3;
the L and Ar1The substituents are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, and an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, and a phosphonooxy group having 6 to 18 carbon atoms.
In the present application, in chemical formula 1
In the present application, since adamantane is a three-dimensional structure, in the structure diagram of the compound, since drawing angles are different, planar shapes are different, and the cyclic structures formed on 9, 9-dimethylfluorene are all adamantane, and the connecting positions are also the same. For example:
all have the same structure.
The nitrogen-containing compound is a spiro compound, and aromatic amine groups with strong electron donating capability are introduced into a spiro system with a large conjugated structure and good luminescence performance, wherein the spiro system has a rigid plane structure and high luminescence quantum efficiency, and can improve the advantages of thermal stability, film stability, carrier migration stability, good intersolubility and the like of materials; and one substituent of the arylamine is required to be an adamantine fluorene group, the adamantine fluorene group has proper molecular weight and steric hindrance effect, the glass transition temperature of the material can be effectively improved, and the adamantyl group screwed on the fluorene group has large spatial volume and strong rigidity.
The nitrogen-containing compound provided by the application can reduce the interaction force between large plane conjugated structures, reduce pi-pi stacking between molecules, and adjust the stacking degree between molecules, so that the nitrogen-containing compound is not easy to crystallize or aggregate during film formation, and can have a more stable amorphous state, and the material has the advantages of low voltage, high efficiency and long service life in a device.
In the present application, the description is taken of the phrase "each … … is independently" and "… …The terms "and" … … "are used interchangeably and are to be understood broadly to mean that the particular items expressed between the same symbols in different groups do not affect each other, or that the particular items 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, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the 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 with each other.
In this application L, Ar1、R1To R4The number of carbon atoms of (b) means all the number of carbon atoms. For example, if L is selected from substituted arylene having 12 carbon atoms, then all of the carbon atoms of the arylene and the substituents thereon are 12. For example: ar (Ar)1Is composed ofThe number of carbon atoms is 7; l is
In the present application, when a specific definition is not otherwise provided, "hetero" means that at least 1 hetero atom of B, N, O, S or P or the like is included in one functional group and the remaining atoms are carbon and hydrogen. An unsubstituted alkyl group can be a "saturated alkyl group" without any double or triple bonds.
In the present application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 10 carbon atoms, and numerical ranges such as "1 to 10" refer herein 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. The alkyl group may also be a lower alkyl group having 1 to 6 carbon atoms. Further, the alkyl group may be substituted or unsubstituted.
Alternatively, the alkyl group is selected from alkyl groups having 1 to 6 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl.
In the present application, aryl refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group 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 monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl group and a fused ring aryl group connected by carbon-carbon bond conjugation, two or more fused ring aryl groups connected by carbon-carbon bond conjugation. That is, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as an aryl group in the present application. Wherein the aryl group does not contain a heteroatom such as B, N, O, S or P. For example, in the present application, phenyl, biphenyl, terphenyl, and the like are aryl groups. Examples of the aryl group may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl, phenanthrenyl, pyrenyl,
In this application, substituted aryl refers to an aryl group in which one or more hydrogen atoms are replaced with another group. For example, at least one hydrogen atom is substituted with a deuterium atom, a halogen group, a cyano group, a hydroxyl group, a branched alkyl group, a linear alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a phosphonooxy group, or other groups. It is understood that a substituted aryl group having 18 carbon atoms refers to an aryl group and the total number of carbon atoms in the substituents on the aryl group being 18. For example, 2, 3-dimethyl-6-phenylnaphthalene has a carbon number of 18, 9, 9-diphenylfluorenyl and spirobifluorenyl of 25. Among them, biphenyl can be interpreted as an aryl group or a substituted phenyl group.
In the present application, the heteroaryl group may be a heteroaryl group including at least one of B, O, N, P, Si and S as a heteroatom. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Illustratively, the heteroaryl group may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzosilyl, dibenzofuryl substituted phenyl, and the like, and is not limited thereto. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system, and N-aryl carbazolyl, N-heteroaryl carbazolyl and the like are heteroaryl of a plurality of aromatic ring systems connected by carbon-carbon bond conjugation.
In this application, substituted heteroaryl refers to heteroaryl wherein one or more hydrogen atoms are replaced by a group thereof, for example at least one hydrogen atom is replaced by a deuterium atom, a halogen group, a cyano group, an alkyl group, a haloalkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a silyl group, an arylsilyl group, a phosphonooxy group or other groups.
In this application, the explanation for aryl applies to arylene and the explanation for heteroaryl applies equally to heteroarylene.
In the present application, the halogen group may be fluorine, chlorine, bromine, iodine.
Due to the characteristics of the nitrogen-containing compound, the nitrogen-containing compound can be used for preparing organic electroluminescent devices and photoelectric conversion devices, and is particularly suitable for preparing hole transport layers or hole adjustment layers (also called hole auxiliary layers, second hole transport layers and the like) of the organic electroluminescent devices and the photoelectric conversion devices, so that the efficiency and the service life of the organic electroluminescent devices and the photoelectric conversion devices are improved, the working voltage of the organic electroluminescent devices is reduced, the open-circuit voltage of the photoelectric conversion devices is improved, and the mass production stability of the photoelectric conversion devices and the organic electroluminescent devices is improved.
According to one embodiment, the nitrogen-containing compound is selected from the group consisting of the following formulas:
alternatively, R1And R2The same or different, and are independently selected from hydrogen, alkyl with 1-6 carbon atoms, and aryl with 6-12 carbon atoms.
Alternatively, R1And R2The same or different, and are each independently selected from hydrogen, methyl, ethyl, propyl, tert-butyl, phenyl, biphenyl, naphthyl, isopropyl.
Alternatively, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms. Further alternatively, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms. More alternatively, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
Alternatively, L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted fluorenylene group.
Alternatively, the substituent of L is selected from deuterium, halogen, cyano, alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms. Specifically, the substituent of L is selected from, for example, deuterium, fluorine, cyano, methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl, biphenyl, cyclohexane, cyclopentyl, and adamantyl.
In some embodiments, L is selected from a single bond or a group of formula j-1 through formula j-6:
wherein M is2Selected from a single bond or
E1～E10Independently selected from: deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, a phosphonoxy group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms;
eris a substituent ErR is any integer of 1-10; when r is selected from 1,2, 3,4, 5, 6, erSelected from 0, 1,2, 3 or 4; when r is 7, erSelected from 0, 1,2, 3,4, 5 or 6; when r is 10, erSelected from 0, 1,2, 3 or 4; when r is selected from 8 or 9, erSelected from 0, 1,2, 3,4, 5, 6, 7 or 8; when e isrWhen greater than 1, any two of ErThe same or different.
Alternatively, L is selected from a single bond or the group consisting of:
preferably, L is selected from a single bond or
Optionally, L is
Alternatively, Ar1Is selected from substituted or unsubstituted aryl with 6-20 carbon atoms.
Alternatively, Ar1The substituent(s) is (are) deuterium, a halogen group, a cyano group, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, or an aryl group having 6 to 12 carbon atoms.
Alternatively, Ar1The substituent(s) is selected from deuterium, fluorine, cyano, methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl, biphenyl, cyclohexane, cyclopentyl, adamantyl, isopropyl.
In some embodiments, Ar1Selected from the group consisting of groups represented by the following formulae i-1 to i-4:
wherein H1～H9Each independently selected from: deuterium, a halogen group, a heteroaryl group having 3 to 18 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, and a phosphonoxy group having 6 to 18 carbon atoms;
H7to H9The aryl can also be independently selected from aryl with 6-12 carbon atoms;
hkis a substituent HkK is any integer of 1-9; wherein, when k is selected from 5, hkSelected from 0, 1,2 or 3; when k is selected from 2, 7, 8, hkSelected from 0, 1,2, 3 or 4; when k is selected from 1, 3,4, 6, 9, hkSelected from 0, 1,2, 3,4 or 5; when h is generatedkWhen greater than 1, any two HkThe same or different.
In a specific embodiment, Ar1Selected from the group consisting of:
alternatively, Ar1Selected from the group consisting of:
in one embodiment, Ar1Is composed of
Optionally, the nitrogen-containing compound is selected from the group formed by:
wherein when n is3＝At 0, the structural formula of chemical formula 1 isWhen n is3When 1, the structural formula of formula 1 is
"-" represents R1Attached to the 1,2, 3,4 position of formula 1, "-" indicates R2Attached to the 5, 6, 7, 8 position of formula 1;
R-A, R-B, R-C, R-D, R-E, R-F represents R with different structures1Or R2And each corresponds to the group shown below;
L-A, L-B, L-C, L-D, L-E, L-F, L-G, L-H, L-I represents L with different structures and respectively corresponds to groups shown in the specification
＊＊ denotes anConnection, ＊ denotes withIs/are as follows
I-A, I-B, I-C, I-D, I-E, I-F, I-G, I-H, I-I, I-J, I-K, I-L, I-M represents Ar with different structures1And each corresponds to the group shown below
Optionally, the nitrogen-containing compound is selected from the following compounds:
the application also provides an electronic element, which comprises an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; the functional layer comprises a nitrogen-containing compound of the present application. The electronic component can be used for realizing photoelectric conversion or electro-optical conversion.
The electronic element of the present application may be, for example, an organic electroluminescent device or a photoelectric conversion device.
According to one embodiment, the electronic component is an organic electroluminescent device. The organic electroluminescent device can be, for example, a red organic electroluminescent device, a green organic electroluminescent device, or a blue organic electroluminescent device.
As shown in fig. 1, the organic electroluminescent device includes an
Optionally, the
Optionally, the
In a specific embodiment, the hole-adjusting
In another embodiment, the
In a specific embodiment of the present application, the organic electroluminescent device may include an
Optionally, the
Alternatively, the
Alternatively, the hole-adjusting
Alternatively, the organic light emitting 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 light emitting layer 330 is composed of a host material and a guest material, and a hole injected into the organic light emitting layer 330 and an electron injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form an exciton, which transfers energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
The host material of the organic electroluminescent layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which is not particularly limited in the present application. In one embodiment of the present application, the host material of the organic electroluminescent layer 330 may be CBP or BH-01. 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 is not particularly limited in the present application. In one embodiment of the present application, the guest material of the organic electroluminescent layer 330 may be Ir (piq)2(acac)、Ir(ppy)3Or BD-01.
The
In the present application, the specific structures of EB-01, BH-01, BD-01, ET-06, and other compounds are shown in the following examples, and are not described herein again.
Optionally, the
Optionally, as shown in fig. 1, a
Optionally, as shown in fig. 1, an
Optionally, a
According to another embodiment, the electronic component is a photoelectric conversion device, which may include an
Optionally, the
Alternatively, as shown in fig. 2, the photoelectric conversion device may include an
Optionally, an
Optionally, a
Alternatively, the photoelectric conversion device may be a solar cell, and particularly may be an organic thin film solar cell. For example, as shown in fig. 2, in one embodiment of the present application, the solar cell includes an
The application also provides an electronic device which comprises the electronic element.
According to one embodiment, as shown in fig. 3, the electronic device provided by the present application is a first electronic device 400, and the first electronic device 400 includes the organic electroluminescent device. The electronic device may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like. Since the electronic device has the organic electroluminescent device, the electronic device has the same beneficial effects, and the details are not repeated.
According to another embodiment, as shown in fig. 4, the electronic device provided by the present application is a second
Hereinafter, the present application will be described in further detail with reference to examples. However, the following examples are merely illustrative of the present application and do not limit the present application.
Synthesis of compounds
Magnesium strips (67.5g,2812mmol) and diethyl ether (500mL) were placed in a dry round bottom flask under nitrogen and iodine (500mg) was added. Then, slowly dripping the solution of 2-bromo-3 '-chloro-1, 1' -biphenyl (240g,900mmol) dissolved in diethyl ether (1000mL) into the flask, heating to 35 ℃ after finishing dripping, and stirring for 3 hours; cooling the reaction solution to 0 ℃, slowly dropping an ether (1000mL) solution dissolved with adamantanone (112.5g, 745mmol), heating to 35 ℃ after dropping, and stirring for 6 hours; cooling the reaction solution to room temperature, adding 5% hydrochloric acid to the reaction solution until the pH value is less than 7, stirring the solution for 1 hour, adding diethyl ether (1000mL) to the solution for extraction, combining organic phases, drying the organic phases by using anhydrous magnesium sulfate, filtering the mixture, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using n-heptane as a mobile phase to obtain-Q-1 (210g, yield 84%) as a solid intermediate.
Adding intermediate-Q-1 (210g,619.5mmol), trifluoroacetic acid (211.5g,1855mmol) and dichloromethane (MC, 2500mL) into a round-bottom flask, and stirring for 2 hours under nitrogen; then, an aqueous sodium hydroxide solution was added to the reaction mixture until the pH became 8, followed by liquid separation, drying of the organic phase with anhydrous magnesium sulfate, filtration, and removal of the solvent under reduced pressure; the crude product was subjected to silica gel column chromatography using methylene chloride/n-heptane (1:2) to give intermediate-A (112.1g, yield 56%) as a white solid.
2-bromo-1-chloro-3-iodobenzene (CAS. NO.:1369793-66-7) (200g, 630.2mmol), phenylboronic acid (76.8g,630.2mmol), tetrakis (triphenylphosphine) palladium (36.4g,31.5mmol), potassium carbonate (260.9g,1890mmol), tetrabutylammonium chloride (8.72g,31.5mmol), 1.6L of toluene, 0.8L of ethanol, and 0.4L of deionized water were added to a three-necked flask, heated to 78 ℃ under nitrogen protection, and stirred for 6 hours; cooling the reaction liquid to room temperature, adding 500mL of toluene for extraction, combining organic phases, drying the organic phases with anhydrous magnesium sulfate, filtering to obtain filtrate, and concentrating the filtrate under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using n-heptane as the mobile phase, followed by recrystallization using a dichloromethane/n-heptane system (1:3) to give SM-A-1(134.9g, yield 80%).
Referring to the synthesis of intermediate-a, intermediate-X shown in table 1 was synthesized except that SM-a-G was used instead of 2' -bromo-3-chlorobiphenyl. X may be B, C and D, and G may be 1,2 and 3.
TABLE 1
A reaction flask was charged with intermediate-D (30g, 93.4mmol), pinacol diboron diboronate (23.7g, 93.4mmol), tris (dibenzylideneacetone) dipalladium (0.9g, 0.9mmol), 2-dicyclohexylphosphonium-2, 4, 6-triisopropylbiphenyl (0.8g, 1.8mmol), potassium acetate (18.3g, 186.9mmol) and 1, 4-dioxane (300mL), heated to 110 ℃ under nitrogen, and stirred under reflux for 5 h. After the reaction solution was cooled to room temperature, the reaction solution was extracted with dichloromethane and water, the organic layer was dried over anhydrous magnesium sulfate and filtered, and after filtration, the filtrate was passed through a short silica gel column, the solvent was removed under reduced pressure, and the crude product was purified by recrystallization using a dichloromethane/n-heptane (1:3) system to obtain compound D-M (27.3g, yield 71%).
In one embodiment, intermediate-X-M shown in Table 2 is synthesized with reference to the synthesis of intermediate-D-M, except that intermediate-X is used instead of intermediate-D for the preparation of intermediate-D-M, and the resulting intermediate-X-M is shown in Table 2 below.
TABLE 2
Adding intermediate-D-M (20g, 48.5mmol), p-bromoiodobenzene (13.7g,48.5mmol), tetrakis (triphenylphosphine) palladium (2.8g, 2.4mmol), potassium carbonate (13.4g, 96.9mmol), tetrabutylammonium bromide (0.3g,0.9mmol), toluene (160mL), ethanol (80mL) and deionized water (40mL) into a round-bottomed flask, heating to 80 ℃ under nitrogen protection, and stirring for 12 hours; cooling the reaction solution to room temperature, adding toluene (100mL) for extraction, combining organic phases, drying by using anhydrous magnesium sulfate, filtering, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using n-heptane as a mobile phase and then by recrystallization using a dichloromethane/ethyl acetate system (1:5) to obtain intermediate-S-1 (14.9g, yield 70%).
In one embodiment, intermediate-S-X shown in Table 3 is synthesized with reference to the synthesis of intermediate-S-1, except that compound SMS-X is used instead of p-bromoiodobenzene for the preparation of intermediate-S-1, intermediate-X-M is used instead of intermediate-D-M for the preparation of intermediate-S-1, and each compound SMS-X and intermediate-X-M combination produces the only corresponding intermediate-S-X, which is shown in Table 3 below
TABLE 3
A reaction flask was charged with intermediate-D (15g, 46.7mmol), SM-Z-1(4.35g, 46.7mmol), tris (dibenzylideneacetone) dipalladium (0.8g, 0.93mmol), 2-dicyclohexylphosphine-2, 4,6, -triisopropylbiphenyl (0.20, 0.5mmol), sodium tert-butoxide (6.7g, 70.1mmol) and toluene solvent (150mL), heated to 110 ℃ under nitrogen protection, and stirred under reflux for 3 h. After the reaction solution was cooled to room temperature, the reaction solution was extracted with dichloromethane and water, the organic layer was dried over anhydrous magnesium sulfate and filtered, after filtration, the filtrate was passed through a short silica gel column, the solvent was removed under reduced pressure, and the crude product was purified by recrystallization using a dichloromethane/n-heptane system (1:3) to give intermediate-Z-1 (12.4g, yield: 70%).
In one embodiment, intermediate-Z-X shown in Table 4 is synthesized with reference to the synthesis of intermediate-Z-1, except that compound SM-Z-X is used in place of SM-Z-1 for the preparation of intermediate-Z-1, intermediate-X is used in place of intermediate-D for the preparation of intermediate-Z-1, and each compound SM-Z-X and intermediate-X in combination produces intermediate-Z-X uniquely corresponding thereto, as shown in Table 4 below.
TABLE 4
Adding 3, 6-dibromofluorenone (100g,295.8mmol), 1-naphthalene phenylboronic acid (101.7g,591.7mmol), tetrakis (triphenylphosphine) palladium (34.2g,29.6mmol), potassium carbonate (244.9g,1775.1mmol), tetrabutylammonium chloride (8.2g,29.6mmol), toluene (800mL), ethanol (400mL) and deionized water (200mL) into a three-neck flask, heating to 78 ℃ under the protection of nitrogen, and stirring for 8 hours; cooling the reaction liquid to room temperature, adding toluene (500mL) for extraction, combining organic phases, drying the organic phases with anhydrous magnesium sulfate, filtering to obtain filtrate, and concentrating the filtrate under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using n-heptane as the mobile phase, followed by recrystallization from a dichloromethane/ethyl acetate (1:3) system to give intermediate-A-1 (102.3g, yield 80%).
In one embodiment, intermediate-A-X shown in Table 5 is synthesized with reference to the synthesis of intermediate-A-1, except that compound SM-A-X is used instead of 3, 6-dibromofluorenone for the preparation of intermediate-A-1, and SM-A-Y is used instead of 1-naphthylphenylboronic acid for the preparation of intermediate-A-1, and each of the compounds SM-A-X and SM-A-Y in combination can produce intermediate-A-X uniquely corresponding thereto, as shown in Table 5 below.
TABLE 5
In one embodiment, intermediate-B-X shown in Table 6 is synthesized with reference to the synthesis method of intermediate-A-1, except that compound SM-B-X is used instead of 3, 6-dibromofluorenone for preparing intermediate-A-1, and SM-B-Y is used instead of 1-naphthylphenylboronic acid for preparing intermediate-A-1, and each of the compounds SM-B-X and SM-B-Y can be combined to prepare intermediate-B-X uniquely corresponding thereto, and the prepared intermediate-B-X is shown in Table 6 below.
TABLE 6
In one embodiment, intermediate-C-X shown in Table 7 is synthesized with reference to the synthesis method of intermediate-A-1, except that compound SM-C-X is used instead of 3, 6-dibromofluorenone for preparing intermediate-A-1, and SM-C-Y is used instead of 1-naphthylphenylboronic acid for preparing intermediate-A-1, and each of the compounds SM-C-X and SM-C-Y can be combined to prepare intermediate-C-X uniquely corresponding thereto, and the prepared intermediate-C-X is shown in Table 7 below.
TABLE 7
The above compound (1346010-03-4) (100g,263.1mmol) was completely dissolved in tetrahydrofuran (1000mL), then n-BuLi (18.5g,289.4mmol) was slowly added dropwise thereto at a temperature of-78 deg.C, and the mixture was stirred for 1 hour while maintaining the temperature. At the same temperature, methyl iodide (56.0g,394.5mmol) was added dropwise thereto, and then the temperature was slowly raised to room temperature, and then, after mixing for 15 hours, the reaction was stopped with a saturated aqueous ammonium chloride solution. The organic layer collected by extraction reaction with ethyl acetate was dried by using anhydrous magnesium sulfate three times, and distilled under reduced pressure, and the product was purified by silica gel column chromatography, thereby obtaining intermediate-B-4 (39.5g, 60%).
In one embodiment, intermediate-M-X shown in Table 8 is synthesized with reference to the synthesis of intermediate-B-4, except that compound SM-M-X is used instead of compound (1346010-03-4) for intermediate-B-4 and SMY is used instead of methyl iodide for intermediate-B-4. And each compound SM-M-X and SMY can be combined to prepare an intermediate-M-X which is uniquely corresponding to the compound SM-M-X, and the prepared intermediate-M-X is shown in the following table 8.
TABLE 8
Adding SM-1(10.0g,37.4mmol) and tetrahydrofuran (100mL) into a three-mouth reaction bottle at one time under the protection of nitrogen, starting stirring, cooling the system to-78 ℃ after uniform stirring, starting dropwise adding n-butyl lithium (2.9g,44.9mmol) after the temperature is stabilized, preserving heat for 1h at-78 ℃ after dropwise adding is finished, then diluting an intermediate-A-1 (17.7g,41.1mmol)) with tetrahydrofuran (40mL), dropwise adding into the system, preserving heat for 1h at-78 ℃ after dropwise adding is finished, and then naturally heating to 25 ℃ and stirring for 12 h. After completion of the reaction, the reaction solution was poured into water (200mL), stirred for 10min, and then dichloromethane (200mL) was added to conduct extraction operation 2 times, the organic phases were combined, dried over anhydrous magnesium sulfate and passed through a silica gel funnel, and then the filtrate was concentrated to dryness to give intermediate-D-A-1 (13.9g, yield: 60%).
To a single-necked flask, intermediate-D-a-1 (10.0g,16.1mmol), trifluoroacetic acid (500mL) and stirring were added, followed by gradually raising the temperature to 80 ℃ and refluxing reaction for 11 hours, and after completion of the reaction, the reaction solution was poured into water (1: 20) stirred for 30min, filtered, rinsed with water (1:2), rinsed with ethanol (1:2) then crude product is obtained by dichloromethane: n-heptane ═ 1:2 to yield intermediate-E-A-1 (7.8g, yield 80%).
In one embodiment, intermediate-D-M-X shown in Table 9 and intermediate-E-M-X shown in Table 10 are synthesized with reference to the synthesis of intermediate-D-A-1, except that intermediate-M-X is used instead of intermediate-A-1 for preparing intermediate-D-A-1, and SM-X is used instead of SM-1 for preparing intermediate-D-A-1, and each compound intermediate-M-X and SM-X can be combined to prepare an intermediate-D-M-X and an intermediate-E-M-X which correspond to the compound intermediates, wherein the prepared intermediate-D-M-X and the intermediate-E-M-X are shown in the following tables 9 and 10.
TABLE 9
Watch 10
A100 mL reaction flask was charged with intermediate-E-A-9 (2.0g, 5.1mmol), intermediate-Z-13 (2.3g, 5.1mmol), tris (dibenzylideneacetone) dipalladium (0.04g, 0.05mmol), 2-dicyclohexylphosphine-2 ', 6' -dimethoxy-biphenyl (0.04g, 0.1mmol), sodium tert-butoxide (0.73g, 7.6mmol) and toluene solvent (20mL), heated to 110 ℃ under nitrogen, and stirred under reflux for 3 h. After the reaction solution was cooled to room temperature, the reaction solution was extracted with dichloromethane and water, the organic layer was dried over anhydrous magnesium sulfate and filtered, and after filtration, the filtrate was passed through a short silica gel column, the solvent was removed under reduced pressure, and the crude product was purified by recrystallization using a dichloromethane/n-heptane system to obtain compound a-1(2.9g, yield: 75%). The mass spectrum is as follows: m/z 768.4(M + H)+。
In one embodiment, compounds M-X shown in Table 11 are synthesized with reference to the synthesis of compound-A-1, except that intermediate-E-M-X is used in place of intermediate-E-A-9 for the preparation of compound-A-1, intermediate-Z-X is used in place of intermediate-Z-13 for the preparation of compound-A-1, and each compound intermediate-E-M-X and intermediate-Z-X in combination produces the compound M-X uniquely corresponding thereto, as shown in Table 11 below.
TABLE 11
The nuclear magnetic data of some of the compounds are shown in Table 12 below
TABLE 12
Preparation and evaluation of organic electroluminescent device
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