阅读说明：本技术 一种有机化合物以及使用其的电子元件和电子装置 (Organic compound, and electronic element and electronic device using same ) 是由 李应文 张鹤鸣 于 2021-09-09 设计创作，主要内容包括：本申请属于有机材料领域,涉及一种有机化合物以及使用其的电子元件和电子装置,所述有机化合物具有化学式1所示的结构,所述有机化合物应用于有机电致发光器件中,可显著改善器件的性能。(The application belongs to the field of organic materials, and relates to an organic compound, an electronic element and an electronic device using the organic compound, wherein the organic compound has a structure shown in a chemical formula 1, and the organic compound is applied to an organic electroluminescent device, so that the performance of the device can be obviously improved.)

1. An organic compound having a structure represented by chemical formula 1:

wherein ring B is selected from adamantane, norborneol and cyclohexane;

L₁and L₃The substituents on the phenylene and the naphthylene are respectively and independently selected from deuterium, a halogen group, a cyano group, an alkyl group with 1-5 carbon atoms and a halogenated alkyl group with 1-5 carbon atoms;

ar is selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 5-30 carbon atoms;

L₂selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms;

ar and L₂Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 5 to 20 carbon atoms;

R₁and R₂The same or different, and each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 3 to 12 carbon atoms;

n₁is R₁The number of (2); n is₁Selected from 0, 1,2, 3 or 4, when n is₁When greater than 1, any two R₁The same or different;

n₂is R₂The number of (2); n is₂Selected from 0, 1,2 or 3, when n is₂When greater than 1, any two R₂The same or different.

2. The organic compound of claim 1, wherein L₁And L₃Each independently selected from a substituted or unsubstituted group W selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group W has one or more substituents, each of which is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl.

3. The organic compound of claim 1, wherein L₁And L₃Each independently selected from the group consisting of:

4. the organic compound of claim 1, wherein L₂Selected from a single bond, an arylene group substituted or unsubstituted with 6 to 20 carbon atoms, and a heteroarylene group having 5 to 20 carbon atoms;

alternatively, L₂Wherein the substituents are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, and aryl having 6 to 12 carbon atoms.

5. The organic compound of claim 1, wherein L₂Selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted dibenzothiophenylene group;

preferably, L₂The substituents in (1) are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl.

6. The organic compound according to claim 1, wherein Ar is selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms;

optionally, the substituent in Ar is selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms, cycloalkyl with 5-10 carbon atoms, aryl with 6-12 carbon atoms and heteroaryl with 5-12 carbon atoms.

7. The organic compound of claim 1, wherein Ar is selected from a substituted or unsubstituted group T selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group T has one or two or more substituents each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, adamantyl, phenyl, naphthyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl.

8. The organic compound of claim 1, wherein Ar is selected from the group consisting of:

9. the organic compound of claim 1, wherein R₁And R₂Each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl.

10. The organic compound of claim 1, wherein the organic compound is selected from the group consisting of:

11. 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; wherein the functional layer comprises the organic compound according to any one of claims 1 to 10.

12. The electronic element according to claim 11, wherein the functional layer comprises a hole transport layer containing the organic compound;

optionally, the electronic element is an organic electroluminescent device or a photoelectric conversion device;

further optionally, the electronic component is an organic electroluminescent device, and the hole transport layer comprises a first hole transport layer and a second hole transport layer, the first hole transport layer being closer to the anode than the second hole transport layer, wherein the second hole transport layer comprises the organic compound.

13. An electronic device comprising the electronic component of claim 11 or 12.

Technical Field

The present invention relates to the field of organic electroluminescence technology, and in particular, to an organic compound, and an electronic element 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.

In the conventional organic electroluminescent device, the lifetime and efficiency are the most important problems, and as the area of the display is increased, the driving voltage is also increased, and the luminous efficiency and lifetime are also required to be increased. The current research on the improvement of the performance of the organic electroluminescent device includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the organic electroluminescent device, a 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.

Disclosure of Invention

An object of the present disclosure is to provide an organic compound which can improve the performance of a device, and an electronic element and an electronic device using the same.

A first aspect of the present application provides an organic compound having a structure represented by chemical formula 1:

wherein ring B is selected from adamantane, norborneol and cyclohexane;

L₁and L₃The substituents on the phenylene and the naphthylene are respectively and independently selected from deuterium, a halogen group, a cyano group, an alkyl group with 1-5 carbon atoms and a halogenated alkyl group with 1-5 carbon atoms;

ar is selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 5-30 carbon atoms;

L₂selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms;

ar and L₂Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 5 to 20 carbon atoms;

R₁and R₂The same or different, and each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 3 to 12 carbon atoms;

n₁is R₁The number of (2); n is₁Selected from 0, 1,2, 3 or 4, when n is₁When greater than 1, any two R₁The same or different;

n₂is R₂The number of (2); n is₂Selected from 0, 1,2 or 3, when n is₂When greater than 1, any two R₂The same or different. .

The compound combines cycloalkane spirofluorene with arylamine and triphenylsilicon base, and the arylamine and cycloalkane spirofluorene are connected together by phenylene or naphthylene, so that on one hand, the conjugation degree of cycloalkane spirofluorene is large, and the hole transport capability, namely the hole mobility, can be effectively improved, and the triphenylsilicon base and the phenylene or naphthylene before N of triarylamine enable the material to have a deeper HOMO energy level, improve the matching between a hole transport layer and a light-emitting layer, and effectively improve the efficiency of a device; on the other hand, phenylene and naphthylene between arylamine and cycloparaffin spirofluorene can effectively regulate the stacking degree of molecules, regulate and control the molecular configuration, make the material have more stable amorphous state, improve film-forming property and prolong the service life of devices.

According to a second aspect of the present application, there is provided an electronic component comprising an anode, a cathode, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the organic compound described above.

According to a third aspect of the present application, there is provided an electronic device including the above electronic component.

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 disclosure.

Drawings

The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and together with the description serve to explain the principles of the application and not to limit the application.

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 diagram of a first electronic device according to an embodiment of the present application.

Fig. 3 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.

Fig. 4 is a schematic structural diagram of a second electronic device according to an embodiment of the present application.

Description of the reference numerals

100. Anode 200, cathode 300, functional layer 310, hole injection layer

320. Hole transport layer 321, first hole transport layer 322, second hole transport layer 330, organic light emitting layer

340. Electron transport layer 350, electron injection layer 360, photoelectric conversion layer 400, first electronic device

500. 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 disclosure.

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 present application provides an organic compound having a structure represented by chemical formula 1:

wherein ring B is selected from adamantane, norborneol and cyclohexane;

L₁and L₃The substituents on the phenylene and the naphthylene are respectively and independently selected from deuterium, a halogen group, a cyano group, an alkyl group with 1-5 carbon atoms and a halogenated alkyl group with 1-5 carbon atoms;

ar is selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 5-30 carbon atoms;

L₂selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms;

ar and L₂Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 5 to 20 carbon atoms;

R₁and R₂The same or different, and each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 3 to 12 carbon atoms;

n₁is R₁The number of (2); n is₁Selected from 0, 1,2, 3 or 4, when n is₁When greater than 1, any two R₁The same or different;

n₂is R₂The number of (2); n is₂Selected from 0, 1,2 or 3, when n is₂When greater than 1, any two R₂The same or different.

In the present application, ring B may be selected from:

in the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The substituent Rc may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, an alkyl group, a haloalkyl group, a cycloalkyl group, or the like.

In the present application, the description that "… … is independently" and "… … is independently" and "… … is independently selected from" is used interchangeably and should 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 the present application, the number of carbon atoms of the substituted or unsubstituted functional group means all the number of carbon atoms. For example, if L₁Is a substituted arylene group having 12 carbon atoms, thenAll carbon atoms of the aryl group and the substituents thereon are 12.

In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bond conjugation, monocyclic aryl and fused ring aryl groups joined by carbon-carbon bond conjugation, two or more fused ring aryl groups joined by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. Among them, the fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain a hetero atom such as B, N, O, S, P, Se or Si. For example, biphenyl, terphenyl, and the like are aryl groups in this application. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl,and the like. In this application, reference to arylene is to a divalent group formed by an aryl group further deprived of a hydrogen atom.

In the present application, a substituted aryl group may be one in which one or two or more hydrogen atoms are substituted with a group such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophenyl-substituted phenyl, pyridyl-substituted phenyl, and the like. It is understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, a substituted aryl group having a carbon number of 18 refers to the total number of carbon atoms of the aryl group and the substituent being 18.

In the present application, heteroaryl means a monovalent aromatic ring containing at least one heteroatom, which may be at least one of B, O, N, P, Si, Se and S, in the ring or a derivative thereof. 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, heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without being limited thereto. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and the N-phenylcarbazolyl and the N-pyridylcarbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. In this application, a heteroarylene group refers to a divalent group formed by a heteroaryl group further lacking one hydrogen atom.

In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, phenyl-substituted pyridyl, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.

In the present application, the aryl group as a substituent may have 6 to 20 carbon atoms, for example, 6, 7, 8, 9,10, or,11. 12, 13, 14, 15, 16, 17, 18, 19, 20, specific examples of the aryl group as the substituent include, but are not limited to, phenyl, biphenyl, naphthyl, fluorenyl, anthracenyl, fluorenyl, or the like,And (4) a base.

In the present application, the number of carbon atoms of the heteroaryl group as the substituent may be 5 to 20, for example, the number of carbon atoms may be 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, and specific examples of the heteroaryl group as the substituent include, but are not limited to, pyridyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl, isoquinolyl.

In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9,10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl, and the like.

In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, iodine.

Specific examples of haloalkyl groups in the present application include, but are not limited to, trifluoromethyl.

In the present application, the number of carbon atoms of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3,4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.

In one embodiment of the present application, L₁And L₃Each independently selected from a substituted or unsubstituted group W selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group W has one or more substituents, each of which is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl.

Alternatively, L₁And L₃Each independently selected from the group consisting of:

further optionally, L₁And L₃Each independently selected from the group consisting of:

in one embodiment of the present application, L₂Selected from a single bond, an arylene group having 6 to 20 carbon atoms which may be substituted or unsubstituted, and a heteroarylene group having 5 to 20 carbon atoms. For example, L₂Selected from single bond, substituted or unsubstituted arylene with 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19 and 20 carbon atoms, and heteroarylene with 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19 and 20 carbon atoms.

Alternatively, L₂Wherein the substituents are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, and aryl having 6 to 12 carbon atoms.

Alternatively, L₂Selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 12 carbon atoms.

Alternatively, L₂Wherein the substituents are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, and phenyl.

Alternatively, L₂Selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted dibenzothiophenylene group.

Alternatively, L₂The substituents in (1) are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl.

Alternatively, L₂Selected from the group consisting of substituted or unsubstituted groups V selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group V has one or more substituents, each of which is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl.

Alternatively, L₂Selected from a single bond or the group consisting of:

further optionally, L₂Selected from a single bond or the group consisting of:

in one embodiment of the present application, Ar is selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 20 carbon atoms and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms. For example, Ar is selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18 carbon atoms.

Optionally, the substituent in Ar is selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms, cycloalkyl with 5-10 carbon atoms, aryl with 6-12 carbon atoms and heteroaryl with 5-12 carbon atoms.

Alternatively, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.

Alternatively, the substituents in Ar are selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, adamantyl, phenyl, naphthyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl.

Alternatively, Ar is selected from a substituted or unsubstituted group T selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group T has one or two or more substituents each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, adamantyl, phenyl, naphthyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl.

Alternatively, Ar is selected from the group consisting of:

further alternatively, Ar is selected from the group consisting of:

in one embodiment of the present application, R₁And R₂Each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl.

Optionally, the organic compound is selected from the group formed by:

a second aspect of the present application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises an organic compound of the present application.

Alternatively, the electronic element may be an organic electroluminescent device or a photoelectric conversion device.

Optionally, the functional layer comprises a hole transport layer comprising an organic compound of the present application.

Further optionally, the electronic component is an organic electroluminescent device, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the first hole transport layer is closer to the anode than the second hole transport layer, wherein the second hole transport layer comprises an organic compound of the present application.

In one embodiment, as shown in fig. 1, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330, an electron transport layer 340, and a cathode 200, which are stacked. The first hole transport layer 321 and the second hole transport layer 322 constitute a hole transport layer 320.

Optionally, the anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO₂Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.

Alternatively, the first hole transport layer 321 includes one or more hole transport materials, and the hole transport materials may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not specifically limited in this application. For example, the first hole transporting layer 321 may be composed of a compound NPB, and the second hole transporting layer 322 may contain a compound of the present application.

Alternatively, the organic light emitting layer 330 may be composed of a single light emitting layer material, and may also include a host material and a dopant material. Alternatively, the organic light emitting layer 330 is composed of a host material and a dopant material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfer energy to the dopant material, thereby enabling the dopant material to emit light.

The host material of the organic light emitting 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 light emitting layer 330 may be RH-1.

The doping material of the organic light emitting 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 doping material of the organic light emitting layer 330 may be Ir (dmpq)₂acac。

The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, TPBi, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. In one embodiment of the present application, the electron transport layer material may be comprised of ET-1 and LiQ.

In the present application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection of a material into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and leadOr an alloy thereof; or a multilayer material such as LiF/Al, Liq/Al, LiO₂Al, LiF/Ca, LiF/Al and BaF₂and/Ca. Preferably, a metal electrode comprising magnesium and silver is included as a cathode.

Alternatively, as shown in fig. 1, a hole injection layer 310 may be disposed between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. For example, the hole injection layer 310 may be HAT-CN.

Optionally, as shown in fig. 1, an electron injection layer 350 may be disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. For example, the electron injection layer 350 may include Yb.

Alternatively, the organic electroluminescent device may be a red device, a blue device, or a green device.

According to another embodiment, the electronic component may be a photoelectric conversion device. As shown in fig. 3, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises an organic compound as provided herein.

According to a specific embodiment, as shown in fig. 3, the photoelectric conversion device may include an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are sequentially stacked.

Optionally, the hole transport layer comprises an organic compound of the present application.

Alternatively, the photoelectric conversion device may be a solar cell, and particularly may be an organic thin film solar cell. For example, in one embodiment of the present application, a solar cell may include an anode, a hole transport layer, an organic light emitting layer, an electron transport layer, and a cathode, which are sequentially stacked, wherein the hole transport layer includes the organic compound of the present application.

A third aspect of the present application provides an electronic device comprising the electronic component provided in the second aspect of the present application.

According to one embodiment, as shown in fig. 2, the electronic device is a first electronic device 400 including the organic electroluminescent device described above. The first electronic device 400 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.

In another embodiment, as shown in fig. 4, the electronic device is a second electronic device 500 including the above-described photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation apparatus, a light detector, a fingerprint recognition apparatus, a light module, a CCD camera, or other types of electronic devices.

The following will specifically explain the method for synthesizing the organic compound of the present application by referring to the synthesis examples, but the present disclosure is not limited thereto.

Compounds of synthetic methods not mentioned in this application are all commercially available starting products.

Synthetic examples

1. Synthesis of intermediate IM a-1

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring thermometer and a spherical condenser for replacement for 15min, adding p-chlorobenzeneboronic acid (11.61g, 75mmol), o-bromoiodobenzene (20.00g, 70.6mmol), 120mL of toluene, 40mL of ethanol, 40mL of water, potassium carbonate (19.54g, 141.3mmol) and tetrabutylammonium bromide (2.28g, 7.07mmol), stirring and heating to 60 ℃, quickly adding tetrakis (triphenylphosphine) palladium (0.41g, 0.35mmol), continuously heating to 60-65 ℃ after the addition is finished, carrying out reflux reaction for 12h, and cooling to room temperature after the reaction is finished. Extracting and separating an organic phase by using toluene, drying the organic phase by using anhydrous magnesium sulfate, filtering, and then distilling and concentrating the filtrate under reduced pressure; recrystallization from n-heptane gave IM a-1(12.29g, 65% yield).

The method referred to IM a-1 synthesizes IM a-x listed in Table 1, except that raw material 1 was used instead of p-chlorobenzeneboronic acid, wherein the main raw materials used, the intermediates synthesized and their yields are shown in Table 1.

TABLE 1

2. Synthesis of intermediate IM b-1

Introducing nitrogen (0.100L/min) into a three-mouth bottle provided with a mechanical stirring, thermometer and constant-pressure dropping funnel for replacement for 15min, adding IM a-1(12.29g, 45.94mmol) and 98mL of tetrahydrofuran, stirring for 10min until the IM a-1 is dissolved, cooling to-85 ℃ to-90 ℃, dropwise adding a 2.5M n-butyllithium solution (18.4mL) in a heat preservation manner, preserving heat for 1h after dropwise adding is finished, sampling and detecting, after the reaction of lithium salt is finished, dropwise adding a THF (62mL) solution of 2-adamantanone (6.90g, 45.94mol), keeping the temperature at-85 ℃ to-90 ℃ in the dropwise adding process, preserving heat for 1h after dropwise adding is finished, heating to room temperature, adding water for quenching, and stopping the reaction. After completion of the reaction, extraction was carried out, washing with water was carried out to neutrality, and the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure to obtain IM b-1 as an oil (10.90g, yield 70%).

The process referred to IM b-1 synthesizes IM b-y listed in Table 2, except that IM a-x was used instead of IM a-1, wherein the main starting materials used, the intermediates synthesized and their yields are shown in Table 2.

TABLE 2

IM b-y shown in Table 3 was synthesized by referring to the above-mentioned methods of IM a-1 and IM b-1, except that starting material 2 was used in place of p-chlorobenzeneboronic acid and starting material 3 was used in place of 2-adamantanone, wherein the main starting materials used, the intermediates synthesized and the yields thereof are shown in Table 3.

TABLE 3

3. Synthesis of intermediate IM1-1

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring, thermometer and constant-pressure dropping funnel for replacement for 15min, adding IM b-1(10.90g, 32.16mmol) and 87.2mL of dichloromethane, preserving the temperature at 20-25 ℃, dropping 0.32g of concentrated sulfuric acid, and naturally heating to room temperature at 20-30 ℃ after dropping for reaction for 5 h. After the reaction is finished, adding water for quenching, extracting, combining organic phases, drying by using anhydrous magnesium sulfate, filtering, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using an ethanol/ethyl acetate system to give IM1-1 (8.77g, 85% yield).

IM 1-x shown in Table 4 was synthesized by the method referred to IM1-1, except that IM b-y was used in place of IM b-1, wherein the main starting materials used, the intermediates synthesized and the yields thereof were as shown in Table 4.

TABLE 4

4. Synthesis of intermediate IM 1-1-1

Introducing nitrogen (0.100L/min) into a three-neck flask equipped with mechanical stirring, thermometer and spherical condenser for 15min, adding IM1-1 (10.00g, 31.2mmol), pinacol ester of diboronic acid (11.87g, 47mmol), 100mL of 1, 4-dioxane and 6.12g of potassium acetate, stirring and heating to 60 deg.C, rapidly adding 0.30g of x-PHOS and 0.29g of Pd₂(dba)₃And after the addition is finished, continuously heating to 90-95 ℃ for reflux reaction for 4 hours, and cooling to room temperature after the reaction is finished. Extracting and separating an organic phase by using toluene, drying the organic phase by using anhydrous magnesium sulfate, filtering, and then distilling and concentrating the filtrate under reduced pressure; recrystallization from n-heptane gave IM 1-1-1(11.18g, 87% yield).

The IM 1-1-x listed in Table 5 was synthesized by referring to the method for IM 1-1-1, except that IM 1-x was used instead of intermediate IM1-1, wherein the main raw materials used, the intermediates synthesized and the yields thereof were as shown in Table 5.

TABLE 5

5. Synthesis of intermediate IM A

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring thermometer and a spherical condenser for replacement for 15min, adding IM 1-1-1(11.18g, 27.1mmol), 4-chloro-1-iodobenzene (6.79g, 28.48mmol), 67mL of toluene, 23mL of ethanol, 23mL of water, potassium carbonate (7.49g, 54.2mmol) and tetrabutylammonium bromide (0.87g, 2.7mmol), stirring and heating to 60 ℃, rapidly adding tetrakis (triphenylphosphine) palladium (0.16g, 0.14mmol), continuously heating to 60-65 ℃ after the addition, refluxing for 5h, and cooling to room temperature after the reaction is finished. Extracting and separating an organic phase by using toluene, drying the organic phase by using anhydrous magnesium sulfate, filtering, and then distilling and concentrating the filtrate under reduced pressure; recrystallization from 5 volumes of ethyl acetate gave IM A (8.61g, 80% yield).

IM X listed in Table 6 below was synthesized by reference to the procedure for IM A, except that IM 1-1-X was used in place of IM 1-1-1 and starting material 4 was used in place of 4-chloro-1-iodobenzene, wherein the main starting materials used, the intermediates synthesized, and the yields thereof are shown in Table 6.

TABLE 6

6. Synthesis of intermediate IM 2-1

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring device, a thermometer and a spherical condenser for replacement for 15min, adding IMA (12.37g, 31.2mmol), 4-aminobiphenyl (5.27g, 31.2mmol), 80mL of toluene and sodium tert-butoxide (5.99g, 62.3mmol), stirring, heating to 60-70 ℃, and slowly adding 0.15g of x-phos and 0.14g of Pd₂(dba)₃And after the addition is finished, continuously heating to 100-105 ℃ for reflux reaction for 1h, and cooling to room temperature after the reaction is finished. The organic phase was separated by extraction with toluene, dried over anhydrous magnesium sulfate, filtered, the solvent removed under reduced pressure and the crude product recrystallized from toluene to give IM 2-1(14.85g, 90% yield).

IM 2-X shown in Table 7 was synthesized by a method referred to IM 2-1, except that IM X was used in place of IM A and that raw material 5 was used in place of 4-aminobiphenyl, wherein the main raw materials used, the intermediates synthesized, and the yields thereof were as shown in Table 7.

TABLE 7

7. Synthesis of intermediate IM 3-1

Introducing nitrogen (0.100L/min) into a three-mouth bottle provided with a mechanical stirring, thermometer and constant-pressure dropping funnel for replacement for 15min, adding 1, 4-dibromonaphthalene (10.00g, 35mmol) and 60mL of tetrahydrofuran, stirring for 10min until reactants are dissolved, cooling to-85 to-90 ℃, keeping the temperature, dropping 12.14mL of 2.5M n-butyllithium solution, keeping the temperature for 1h after dropping, sampling and detecting, dropping THF (20mL) solution of triphenylchlorosilane (9.21g, 31.2mmol) after the reaction of lithium salt is finished, keeping the temperature at-85 to-90 ℃ in the dropping process, heating to room temperature for reaction for 2h after dropping is finished, adding water for quenching, and stopping the reaction. After the reaction, extraction, water washing to neutrality, merging organic phases, drying with anhydrous magnesium sulfate, filtering, removing the solvent under reduced pressure, pulping with n-heptane for solidification, filtering and drying to obtain IM 3-1(11.66g, yield 80%).

8. Synthesis of Compound 2

Introducing nitrogen (0.100L/min) into a three-neck flask equipped with a mechanical stirrer, a thermometer and a spherical condenser for replacement for 15min, adding IM 2-1(14.85g, 28mmol), 4-bromotetraphenylsilane (11.65g, 28mmol), 102mL of toluene and sodium tert-butoxide (5.39g, 56mmol), stirring, heating to 70-80 deg.C, slowly adding 0.12g of s-phos and 0.13g of Pd₂(dba)₃And after the addition is finished, continuously heating to 100-105 ℃ for reflux reaction for 1h, and cooling to room temperature after the reaction is finished. The organic phase was separated by extraction with toluene, dried over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and the crude product was subjected to column chromatography and recrystallization using a toluene-n-heptane system to give compound 2(19.38g, yield 80%) with mass spectrum (M/z) of 864.40[ M + H%]⁺。

The compounds listed in Table 8 were synthesized by referring to the method of Compound 2, except that IM 2-x was used in place of IM 2-1 and that raw material 6 was used in place of 4-bromotetraphenylsilane, wherein the main raw materials used, the synthesized compounds and their yields, mass spectra were as shown in Table 8.

TABLE 8

Part of the compound NMR data are shown in Table 9 below

TABLE 9

Preparation and performance evaluation of organic electroluminescent device

Example 1

Red organic electroluminescent device

Will have a thickness ofThe anode ITO substrate of (1) was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), prepared into an experimental substrate having an anode and an insulating layer pattern by a photolithography process, and subjected to ultraviolet ozone and O₂∶N₂Plasma is used for surface treatment to increase the work function of an anode (experimental substrate), and an organic solvent is used for cleaning the surface of the ITO substrate to remove scum and oil stains on the surface of the ITO substrate.

A compound HAT-CN (structural formula shown below) was vacuum-evaporated on an experimental substrate to a thickness ofA Hole Injection Layer (HIL); and vacuum evaporating NPB compound on the hole injection layer to form a layer with a thickness ofA first hole transport layer (HTL 1).

Compound 2 was vacuum-deposited on the first hole transport layer (HTL1) to a thickness ofAnd a second hole transport layer (HTL 2).

On the second hole transport layer (HTL2), RH-1: Ir (dmpq)₂The acac is evaporated together with the ratio of 95 percent to 5 percent to form the film with the thickness ofRed emitting layer (EML).

Mixing compound ET-1 (structural formula shown below) and LiQ (structural formula shown below) at a weight ratio of 1: 1, and forming by vacuum evaporation processA thick Electron Transport Layer (ETL). Subsequently, Yb was vapor-deposited on the electron transport layer to form a film having a thickness ofElectron Injection Layer (EIL).

Mixing magnesium (Mg) and silver (Ag) at a ratio of 1: 9, vacuum-evaporating on the Electron Injection Layer (EIL) to obtain a mixture with a thickness ofThe cathode of (1).

Further, a layer having a thickness ofCP-1 (structural formula is shown below), a capping layer (CPL) is formed, thereby completing the fabrication of the organic light emitting device.

Wherein, HAT-CN, NPB, RH-1, Ir (dmpq)₂The structural formulas of acac, ET-1, LiQ, CP-1, compound A and compound B are as follows:

examples 2 to 18

A red organic electroluminescent device was fabricated in the same manner as in example 1, except that the compound shown in table 10 was used instead of the compound 2 in the second hole transport layer (HTL 2).

Comparative examples 1 to 2

A second hole transport layer (HTL2) was formed using compound a and compound B instead of compound 2, and a red organic electroluminescent device was fabricated in the same manner as in example 1.

Wherein IVL (Current, Voltage, luminance) data is at 10mA/cm²The test result at the current density, T95 life was 20mA/cm²Test results at current density.

Table 10: performance test results of red organic electroluminescent device

From the results of table 10, it is understood that the light-emitting efficiency (Cd/a) of the organic electroluminescent devices of examples 1 to 18, which are compounds of the light-emitting layer, is improved by at least 11.1% and the lifetime is improved by at least 13.0% as compared with those of comparative examples 1 to 2, which are devices corresponding to known compounds. Therefore, the compound has the characteristics of improving the luminous efficiency and prolonging the service life. From the above data, it can be seen that the organic compound of the present application as the second hole transport layer of the organic electroluminescent device significantly improves the luminous efficiency (Cd/a) and the lifetime (T95) of the organic electroluminescent device. Therefore, the organic compound of the present application can be used in the second hole transport layer to prepare an organic electroluminescent device with high luminous efficiency and long service life. When L1 is naphthalene, the lifetime performance of the organic electroluminescent device is relatively better.

It is to be understood that the present application is capable of other embodiments and of being practiced and carried out in various ways. The foregoing variations and modifications are within the scope of the present application. It will 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 a number of alternative aspects of the present application.