阅读说明：本技术 有机化合物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 马天天 边春阳 刘云 于 2021-09-01 设计创作，主要内容包括：本申请涉及一种有机化合物及使用其的电子元件和电子装置,本申请化合物在吲哚咔唑母核化合物中固定连接4-菲基,化合物达到高的第一三重态能级；可以保障载流子的传输与复合并将激子能量高效传递至客体材料。化合物用于器件的发光层主体材料时使器件具有优异的发光效率；另一方面,本化合物具有较好的激子耐受度,可以提高器件的使用寿命。(The present application relates to an organic compound, and an electronic element and an electronic device using the same, wherein the compound is fixedly connected with a 4-phenanthryl group in an indole carbazole parent nucleus compound, and the compound reaches a high first triplet state energy level; can ensure the transmission and recombination of carriers and efficiently transfer exciton energy to guest materials. When the compound is used for a main material of a light-emitting layer of a device, the device has excellent light-emitting efficiency; on the other hand, the compound has better exciton tolerance and can prolong the service life of the device.)

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

wherein Ar is₁Selected from substituted or unsubstituted C6-30Substituted aryl, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;

Ar₂and Ar₃The two groups are the same or different, one of the two groups has a structure shown in a formula 2, and the other group is selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

L、L₁、L₂and L₃Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

R₁、R₂、R₃and R₄The same or different, and are respectively and independently selected from deuterium, cyano, halogen group, alkyl with 1-10 carbon atoms, aryl with 6-12 carbon atoms, naphthenic base with 3-10 carbon atoms and trialkylsilyl with 3-12 carbon atoms;

n₁represents R₁Number of (2), n₁Selected from 0, 1,2, 3 or 4; when n is₁Greater than 1, any two R₁The same or different; optionally, any two adjacent R₁Are linked to each other to form a 5-15 membered saturated or unsaturated ring;

n₂represents R₂Number of (2), n₂Selected from 0, 1 or 2; when n is₂Greater than 1, any two R₂The same or different; optionally, any two adjacent R₂Are linked to each other to form a 5-15 membered saturated or unsaturated ring;

n₃represents R₃Number of (2), n₃Selected from 0, 1,2, 3 or 4; when n is₃Greater than 1, any two R₃The same or different; optionally, any two adjacent R₃Are linked to each other to form a 5-15 membered saturated or unsaturated ring;

n₄represents R₄Number of (2), n₄Selected from 0, 1,2, 3,4, 5, 6, 7, 8 or 9; when n is₄Greater than 1, any two R₄The same or different;

L、L₁、L₂、L₃、Ar₁、Ar₂and Ar₃Wherein the substituents are the same or different and are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group with 3-20 carbon atoms, an aryl group with 6-20 carbon atoms, a trialkylsilyl group with 3-12 carbon atoms, a triarylsilyl group with 18-24 carbon atoms, an alkyl group with 1-10 carbon atoms, a haloalkyl group with 1-10 carbon atoms, a cycloalkyl group with 3-10 carbon atoms, a heterocycloalkyl group with 2-10 carbon atoms, an alkoxy group with 1-10 carbon atoms, an alkylthio group with 1-10 carbon atoms, an aryloxy group with 6-18 carbon atoms, an arylthio group with 6-18 carbon atoms and a phosphinyloxy group with 6-18 carbon atoms;

optionally, in Ar₁、Ar₂And Ar₃In (b), two substituents attached to the same atom form a 5-15 membered saturated or unsaturated ring.

2. The organic compound of claim 1, wherein the organic compound has a structure represented by formula 1-1 or 1-2:

3. the organic compound of claim 1, wherein said L₁、L₂And L₃The two or more groups are respectively and independently selected from one 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 dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyridinylene group, or a new subunit group formed by connecting two or three of the subunits through a single bond;

optionally, said L₁、L₂And L₃Wherein the substituents are the same or different and are independently selected from deuterium, fluorine, cyano, C1-4 alkylAnd a C1-4 haloalkyl group or a phenyl group.

4. The organic compound according to claim 1, wherein L is selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or substituted naphthylene group, a substituted or unsubstituted biphenylene group;

optionally, the substituent in L is selected from deuterium, fluorine, cyano, phenyl, alkyl with 1-5 carbon atoms or phenyl.

5. The organic compound of claim 1, wherein the Ar is₂And Ar₃One of the two groups has a structure shown in formula 2, and the other group is selected from substituted or unsubstituted aryl with 6-25 carbon atoms and substituted or unsubstituted heteroaryl with 5-20 carbon atoms;

optionally, the Ar is₂And Ar₃Wherein the substituents are the same or different and are independently selected from deuterium, fluorine, cyano, alkyl having 1-4 carbon atoms, haloalkyl having 1-4 carbon atoms, aryl having 6-15 carbon atoms, heteroaryl having 5-12 carbon atoms, and trialkylsilyl having 3-7 carbon atoms; optionally, in Ar₂And Ar₃Wherein two substituents attached to the same atom form a cyclopentane, cyclohexane or fluorene ring.

6. The organic compound of claim 1, wherein the Ar is₂And Ar₃The two groups are the same or different, one of the two groups has a structure shown in a formula 2, and the other group is selected from a substituted or unsubstituted group V, and the unsubstituted group V is selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group V carries one or more substituents each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, carbazolyl, dibenzothienyl or dibenzofuranyl; when the substituted group V includes a plurality of substituents thereon, the substituents may be the same or different.

7. The organic compound of claim 1, wherein the Ar is₁Selected from the group consisting of substituted or unsubstituted groups 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 thereon, each of which is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, carbazolyl, dibenzothienyl or dibenzofuranyl; when the substituted group W carries multiple substituents, the substituents may be the same or different.

8. The organic compound of claim 1, wherein R is₄Each independently selected from deuterium, fluoro, cyano, trimethylsilyl, methyl, ethyl, n-propyl, isopropyl or tert-butyl.

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

10. 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 comprises an organic compound according to any one of claims 1 to 9;

optionally, the electronic element is an organic electroluminescent device;

optionally, the functional layer comprises an organic light emitting layer comprising the organic compound.

11. An electronic device comprising the electronic component according to claim 10.

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

Organic electroluminescent materials (OLEDs), as a new generation display technology, have the advantages of being ultra-thin, self-luminescent, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption, and the like, and have been widely used in the industries of flat panel display, flexible display, solid state lighting, vehicle-mounted display, and the like.

The organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. The organic material layer is generally formed in a multi-layered structure composed of different materials to improve the luminance, efficiency and lifetime of the organic electroluminescent device, and may be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the organic light emitting device structure, when a voltage is applied between two electrodes, holes and electrons are injected from an anode and a cathode into an organic material layer, respectively, excitons are formed when the injected holes and electrons meet, and light is emitted when the excitons return to a ground state. The most important problems of the conventional organic electroluminescent device are lifetime and efficiency, and as the display has been increased in area, the driving voltage has been increased, the luminous efficiency and the power efficiency have been increased, and a certain service life has been ensured, so that organic materials have to solve the efficiency or lifetime problems, and it has been required to continuously develop new materials for organic electroluminescent devices having high efficiency and long lifetime, which are suitable for mass production.

Disclosure of Invention

An object of the present application is to provide an organic compound capable of improving the light emission efficiency and the service life of an electronic element, and an electronic element and an electronic device using the same.

In order to achieve the above object, a first aspect of the present application provides an organic compound having a structure represented by the following formula 1:

wherein Ar is₁Selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

Ar₂and Ar₃The two are the same or different, one of the two has a structure shown in formula 2, and the other is selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted aryl with 3-30 carbon atomsUnsubstituted heteroaryl;

L、L₁、L₂and L₃Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

R₁、R₂、R₃and R₄The same or different, and are respectively and independently selected from deuterium, cyano, halogen group, alkyl with 1-10 carbon atoms, aryl with 6-12 carbon atoms, naphthenic base with 3-10 carbon atoms and trialkylsilyl with 3-12 carbon atoms;

n₁represents R₁Number of (2), n₁Selected from 0, 1,2, 3 or 4; when n is₁Greater than 1, any two R₁The same or different; optionally, any two adjacent R₁Are linked to each other to form a 5-15 membered saturated or unsaturated ring;

n₂represents R₂Number of (2), n₂Selected from 0, 1 or 2; when n is₂Greater than 1, two R₂The same or different; optionally, any two adjacent R₂Are linked to each other to form a 5-15 membered saturated or unsaturated ring;

n₃represents R₃Number of (2), n₃Selected from 0, 1,2, 3 or 4; when n is₃Greater than 1, any two R₃The same or different; optionally, any two adjacent R₃Are linked to each other to form a 5-15 membered saturated or unsaturated ring;

n₄represents R₄Number of (2), n₄Selected from 0, 1,2, 3,4, 5, 6, 7, 8 or 9; when n is₄Greater than 1, any two R₄The same or different;

L、L₁、L₂、L₃、Ar₁、Ar₂and Ar₃Wherein the substituents are the same or different and are independently selected from deuterium, a halogen group, cyano, a heteroaryl group having 3-20 carbon atoms, an aryl group having 6-20 carbon atoms, a trialkylsilyl group having 3-12 carbon atoms, a triarylsilyl group having 18-24 carbon atoms, an alkyl group having 1-10 carbon atoms, or a substituted or unsubstituted alkyl group having 1-10 carbon atomsHaloalkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, aryloxy with 6-18 carbon atoms, arylthio with 6-18 carbon atoms and phosphinyl with 6-18 carbon atoms;

optionally, in Ar₁、Ar₂And Ar₃In (b), two substituents attached to the same atom form a 5-15 membered saturated or unsaturated ring.

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 according to the first aspect of the present application;

optionally, the electronic element is an organic electroluminescent device;

optionally, the functional layer comprises an organic light emitting layer comprising the organic compound.

A third aspect of the present application provides an electronic device comprising the electronic component according to the second aspect of the present application.

The compound is fixedly connected with 4-phenanthryl in an indole carbazole mother nucleus compoundThe phenanthryl of the connecting position and the adjacent group have the most proper steric hindrance, and the compound has a higher first triplet energy level; can ensure the transmission and recombination of carriers and efficiently transfer exciton energy to guest materials. When the compound is used for a main material of a light-emitting layer of a device, the device has excellent light-emitting efficiency; on the other hand, the compound has better exciton tolerance and can improve the service life of the device.

Additional features and advantages of the present application will be described in detail in the detailed description which follows.

Drawings

The accompanying drawings are included to provide a further understanding of the disclosure, and are incorporated in and constitute a part of this specification, illustrate embodiments of the disclosure and together with the description serve to explain the disclosure without limiting the disclosure. In the 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 diagram of an electronic device according to an embodiment of the present application.

Description of the reference numerals

100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic light emitting layer; 340. a hole blocking layer; 350. an electron transport layer; 360. an electron injection layer; 400. an electronic device.

Detailed Description

The following detailed description of embodiments of the present application will be made with reference to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present application, are given by way of illustration and explanation only, and are not intended to limit the present application.

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

wherein Ar is₁Selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

Ar₂and Ar₃The two groups are the same or different, one of the two groups has a structure shown in a formula 2, and the other group is selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

L、L₁、L₂and L₃Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

R₁、R₂、R₃and R₄The same or different, and each independentlySelected from deuterium, cyano, halogen group, alkyl group having 1-10 carbon atoms, aryl group having 6-12 carbon atoms, cycloalkyl group having 3-10 carbon atoms, trialkylsilyl group having 3-12 carbon atoms;

n₁represents R₁Number of (2), n₁Selected from 0, 1,2, 3 or 4; when n is₁Greater than 1, any two R₁The same or different; optionally, any two adjacent R₁Are linked to each other to form a 5-15 membered saturated or unsaturated ring;

n₂represents R₂Number of (2), n₂Selected from 0, 1 or 2; when n is₂Greater than 1, any two R₂The same or different; optionally, any two adjacent R₂Are linked to each other to form a 5-15 membered saturated or unsaturated ring;

n₃represents R₃Number of (2), n₃Selected from 0, 1,2, 3 or 4; when n is₃Greater than 1, any two R₃The same or different; optionally, any two adjacent R₃Are linked to each other to form a 5-15 membered saturated or unsaturated ring;

n₄represents R₄Number of (2), n₄Selected from 0, 1,2, 3,4, 5, 6, 7, 8 or 9; when n is₄Greater than 1, any two R₄The same or different;

L、L₁、L₂、L₃、Ar₁、Ar₂and Ar₃Wherein the substituents are the same or different and are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group with 3-20 carbon atoms, an aryl group with 6-20 carbon atoms, a trialkylsilyl group with 3-12 carbon atoms, a triarylsilyl group with 18-24 carbon atoms, an alkyl group with 1-10 carbon atoms, a haloalkyl group with 1-10 carbon atoms, a cycloalkyl group with 3-10 carbon atoms, a heterocycloalkyl group with 2-10 carbon atoms, an alkoxy group with 1-10 carbon atoms, an alkylthio group with 1-10 carbon atoms, an aryloxy group with 6-18 carbon atoms, an arylthio group with 6-18 carbon atoms and a phosphinyloxy group with 6-18 carbon atoms;

optionally, in Ar₁、Ar₂And Ar₃In, connectTwo substituents on the same atom form a 5-15 membered saturated or unsaturated ring.

Specifically, the organic compound has a structure represented by formula 1-1 or 1-2:

in this application L, L₁、L₂、L₃、Ar₁、Ar₂And Ar₃The number of carbon atoms of (b) means all the number of carbon atoms. For example, if L₁Selected from the group consisting of arylene groups substituted with 10 carbon atoms, the sum of all carbon atoms of the arylene group and the substituents thereon is 10. For example, if Ar₁Is 9, 9-dimethylfluorenyl, then Ar₁Is a substituted fluorenyl group having 15 carbon atoms, Ar₁The number of ring-forming carbon atoms of (2) is 13.

The terms "optional" or "optionally" mean that the subsequently described event or circumstance may occur, but not necessarily, and that the description includes instances where the event occurs or does not occur. For example, "optionally, at Ar₁、Ar₂And Ar₃In the above description, the two substituents bonded to the same atom form a ring "means that any two substituents bonded to the same atom may be bonded to each other to form a spiro ring or may be present independently of each other. This scheme includes a scenario in which two substituents that are linked to a common atom are linked to each other to form a ring, and also includes a scenario in which two substituents are present independently of each other.

The descriptions used in this application that "… … independently" and "… … independently" and "… … independently selected from" are interchangeable and should be understood in a broad sense to mean that the particular items expressed between the same symbols do not interfere with each other in different groups or that the particular items expressed between the same symbols do not interfere with each other in the same groups.

For example: in thatWherein each q is independently 0, 1,2 or 3, and each R "is independently selected from the group consisting of hydrogen, 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, when a specific definition is not otherwise provided, "hetero" means that at least 1 hetero atom of B, N, O, S, Se, Si, or P, etc. is included in one functional group and the remaining atoms are carbon and hydrogen.

In the present application, the term "substituted or unsubstituted" means that the functional group described later in the term may have a substituent or not, and the number of substituents may be 1 or 2 or more. For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent or an unsubstituted aryl group. "substituted" means that it may be substituted with a substituent selected from the group consisting of: deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, 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 phosphinyloxy group having 6 to 18 carbon atoms, and the like; when the number of the substituents is more than 1, the respective substituents may be the same or different.

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 1,2, 3,4, 5, 6, 7, 8, 9,10 carbon atoms. In some casesIn embodiments, the alkyl group contains 1 to 4 carbon atoms; in still other embodiments, the alkyl group contains 1 to 3 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl (Me, -CH)₃) Ethyl group (Et, -CH)₂CH₃) N-propyl (n-Pr, -CH)₂CH₂CH₃) Isopropyl group (i-Pr, -CH (CH)₃)₂) N-butyl (n-Bu, -CH)₂CH₂CH₂CH₃) Isobutyl (i-Bu, -CH)₂CH(CH₃)₂) Sec-butyl (s-Bu, -CH (CH)₃)CH₂CH₃) Tert-butyl (t-Bu, -C (CH)₃)₃) And the like.

In this application, cycloalkyl refers to cyclic saturated hydrocarbons, including monocyclic and polycyclic structures. Cycloalkyl groups may have 3-10 carbon atoms, for example, "3 to 10 carbon atoms" refers to cycloalkyl groups that may contain 3,4, 5, 6, 7, 8, 9,10 carbon atoms. In some embodiments, cycloalkyl is 5 to 10 membered cycloalkyl, in other embodiments 5 to 8 membered cycloalkyl, examples of which may be, but are not limited to: five-membered cycloalkyl, i.e., cyclopentyl, six-membered cycloalkyl, i.e., cyclohexyl, 10-membered polycycloalkyl, e.g., adamantyl, and the like.

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 hetero atom such as B, N, O, S, Se, Si or P. Examples of the aryl group may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, perylenyl, benzofluoranthenyl, pyrenyl, perylene,A group, 9 dimethylfluorenyl group, 9 diphenylfluorenyl group, spirobifluorenyl group, indenyl group, etc., without being limited thereto.

In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be selected from 6, 10, 12, 13, 14, 15, 16, 18, 20, 25 or 30. Of course, the number of carbon atoms may be other numbers, and is not listed here. In some embodiments, a substituted or unsubstituted aryl group is an aryl group having from 6 to 30 carbon atoms, in other embodiments a substituted or unsubstituted aryl group is an aryl group having from 6 to 25 carbon atoms, in other embodiments a substituted or unsubstituted aryl group is an aryl group having from 6 to 18 carbon atoms, and in other embodiments a substituted or unsubstituted aryl group is an aryl group having from 6 to 15 carbon atoms; in other embodiments, the substituted or unsubstituted aryl group is an aryl group having 6 to 12 carbon atoms.

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, F, Cl, I, -CN, hydroxyl, branched alkyl, linear alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio, aryl, heteroaryl, trialkylsilyl, or other group. It is understood that the number of carbon atoms of the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, an 18-substituted aryl group having 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituent on the aryl group is 18.

In the present application, the fluorenyl group may be substituted, and the substituent may be one or more than two, wherein two substituents may be combined with each other to form a spiro structure, and specific examples of the substituted fluorenyl group include, but are not limited to, the following structures:

in the present application, heteroaryl refers to a monovalent aromatic ring containing 1,2, 3,4, 5, or 6 heteroatoms in the ring, which may be at least one of B, O, N, P, Si, Se, and S, or derivatives 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, any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring, and any one of the aromatic ring systems contains the heteroatom. Exemplary heteroaryl groups 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, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, or the like, without being limited thereto.

In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group is selected from 3,4, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30. In some embodiments, a substituted or unsubstituted heteroaryl group is a heteroaryl group having 5 to 25 carbon atoms, in other embodiments a substituted or unsubstituted heteroaryl group is a heteroaryl group having 5 to 18 carbon atoms, and in other embodiments a substituted or unsubstituted heteroaryl group is a heteroaryl group having 5 to 12 carbon atoms.

In this application, substituted heteroaryl refers to heteroaryl wherein one or more hydrogen atoms are replaced by a group thereof, e.g., at least one hydrogen atom is replaced by a deuterium atom, F, Cl, Br, -CN, alkyl, haloalkyl, cycloalkyl, aryl, heteroaryl, aryloxy, arylthio, silyl, phosphinoxy or other group.

In this application, the explanation for aryl applies to arylene and the explanation for heteroaryl applies equally to heteroarylene.

In this application, "aryloxy" means that the aryl group is attached to the rest of the molecule through an oxygen atom, wherein the aryl group has the meaning as described herein. In the present specification, "arylthio" means that an aryl group is attached to the rest of the molecule through a sulfur atom, wherein the aryl group has the meaning as described in the present invention.

In the present invention, the ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl. The 6-to 10-membered aromatic ring may include a benzene ring, an indene ring, a naphthalene ring and the like.

The "ring" in the present application includes saturated rings as well as unsaturated rings; saturated rings, i.e., cycloalkyl, heterocycloalkyl; unsaturated rings, i.e., cycloalkenyl, heterocycloalkenyl, aryl, and heteroaryl.

In this application "any two adjacent R_xThe term "linked to each other to form a saturated or unsaturated ring linked to each other to form a 5-to 15-membered ring" means that two adjacent substituents are linked to each other to form a ring structure having 5 to 15 atoms; such as but not limited to: cyclopentane, cyclohexane, benzene rings, fluorene rings, and the like. Where "any two adjacent" refers to two substituents attached to the same atom, or two substituents attached to two adjacent atoms, respectively.

In the present application, trialkylsilyl meansWherein R is^G1、R^G2、R^G3Each independently an alkyl group, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, propyldimethylsilyl.

An delocalized bond in the present application refers to a single bond extending from a ring systemIt means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule. For example, the following formula (f) representsNaphthyl is attached to the rest of the molecule through two non-positional bonds through the bicyclic ring, and the meaning of the bond includes any of the possible attachments as shown by formulas (f-1) to (f-10).

As another example, as shown in the following formula (X '), the carbazolyl group represented by the formula (X') is bonded to another position of the molecule through an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the carbazolyl group represented by the formula (X '-1) to (X' -5) includes any possible bonding manner shown in the formulas (X '-1) to (X' -5).

An delocalized substituent, as used herein, refers to a substituent attached by a single bond extending from the center of the ring system, meaning that the substituent may be attached at any possible position in the ring system. For example, in the following formula (Y), the substituent R group represented by the formula (Y) is bonded to the quinoline ring via an delocalized bond, and the meaning thereof includes any of the possible bonding modes shown by the formulas (Y-1) to (Y-7).

In the present application, the number of carbon atoms of the haloalkyl group having 1 to 10 carbon atoms may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9,10, including but not limited to trifluoromethyl and the like.

In the present application, the alkoxy group having 1 to 10 carbon atoms may be a chain, cyclic or branched alkoxy group. The number of carbon atoms can be, for example, 1,2, 3,4, 5, 6, 7, 8, 9,10, including but not limited to methoxy, isopropoxy, and the like.

In the present application, the trialkylsilyl group having 3 to 12 carbon atoms. The number of carbon atoms may be, for example, 3,4, 5, 6, 7, 8, 9,10, 11, 12, including but not limited to trimethylsilyl and the like.

In the present application, the halogen group may be selected from fluorine, chlorine, bromine, iodine.

In the present application, the substituted or unsubstituted aryl group having 6 to 30 carbon atoms may be selected from the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, anthracenyl, phenanthrenyl, perylenyl, pyrenyl, and the like.

In the present application, the substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms may be selected from the following substituted or unsubstituted groups: dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, quinolyl, isoquinolyl, 9, 10-dihydroacridine, 10H-phenothiazine, 10H-phenoxazine, N-phenylcarbazolyl, and the like.

In the present application, the substituents in the substituted or unsubstituted aryl group having 6 to 30 carbon atoms and the substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms may each be independently selected from deuterium, fluorine, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group, trimethylsilyl group, trifluoromethyl group, phenyl group, naphthyl group, biphenyl group, pyridyl group, dibenzofuranyl group, dibenzothiophenyl group or carbazolyl group.

In some embodiments of the present application, L₁、L₂And L₃The same or different, and are respectively and independently selected from one 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 dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyridinylene group, or a new subunit group formed by connecting two or three of the subunits through a single bond.

Alternatively, L₁、L₂And L₃Wherein the substituents are the same or different and are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms or phenyl.

In some embodiments of the present application, L₁、L₂、L₃A single bond or a group consisting of:

in some embodiments of the present application, L₃Selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or substituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted pyridinylene group.

In some embodiments of the present application, L₃The substituents in (2) are each independently selected from deuterium, a halogen group, a cyano group, a phenyl group, an alkyl group having 1 to 4 carbon atoms, and a phenyl group.

In some embodiments of the present application, L in formula 1-1₃And L in the formula 1-2₂The same or different, and are each independently selected from the group consisting of a single bond or the following groups:

in some embodiments of the present application, L is selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group.

Optionally, the substituent in L is selected from deuterium, fluorine, cyano, phenyl, alkyl with 1-5 carbon atoms or phenyl.

In some embodiments of the present application, L is the same or different and each is independently selected from the group consisting of a single bond or the following groups:

in bookIn some embodiments of the application, said Ar₂And Ar₃One of the two groups has a structure shown in formula 2, and the other group is selected from substituted or unsubstituted aryl with 6-25 carbon atoms and substituted or unsubstituted heteroaryl with 5-20 carbon atoms.

Optionally, the Ar is₂And Ar₃Wherein the substituents are the same or different and are independently selected from deuterium, fluorine, cyano, alkyl having 1-4 carbon atoms, haloalkyl having 1-4 carbon atoms, aryl having 6-15 carbon atoms, heteroaryl having 5-12 carbon atoms, and trialkylsilyl having 3-7 carbon atoms; optionally, in Ar₂And Ar₃Wherein two substituents attached to the same atom form a cyclopentane, cyclohexane or fluorene ring.

In some embodiments of the present application, the Ar is₂And Ar₃The two groups are the same or different, one of the two groups has a structure shown in a formula 2, and the other group is selected from a substituted or unsubstituted group V, and the unsubstituted group V is selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group V carries one or more substituents each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, carbazolyl, dibenzothienyl or dibenzofuranyl; when the substituted group V has a plurality of substituents thereon, the substituents may be the same or different.

In some embodiments of the present application, Ar₂And Ar₃Are identical to each otherOr not identical, one of the two has a structure shown in formula 2, and the other is selected from the group consisting of,

optionally, the Ar is₁Wherein the substituents are the same or different and are independently selected from deuterium, fluorine, cyano, alkyl having 1-4 carbon atoms, haloalkyl having 1-4 carbon atoms, aryl having 6-15 carbon atoms, heteroaryl having 5-12 carbon atoms, and trialkylsilyl having 3-7 carbon atoms; optionally, in Ar₁Wherein two substituents attached to the same atom form a cyclopentane, cyclohexane or fluorene ring.

In some embodiments of the present application, the Ar is₁Selected from the group consisting of substituted or unsubstituted groups 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 thereon, each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, carbazolyl, dibenzothienyl or dibenzofuranyl; when the substituted group W carries multiple substituents, the substituents may be the same or different.

In some embodiments of the present application, Ar₁Selected from the group consisting of:

in some embodiments of the present application, n₁、n₂And n₃Are all 0.

In some embodiments of the present application, each R is₄Identical or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or trimethylsilyl.

In some embodiments of the present application, the organic compound is selected from the group consisting of:

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 according to the first aspect of the present application.

In the present application, the electronic element includes an organic electroluminescent device or a photoelectric conversion device.

According to one embodiment, the electronic component is an organic electroluminescent device. As shown in fig. 1, the organic electroluminescent device may include an anode 100 and a cathode 200 oppositely disposed, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 contains an organic compound as provided in the first aspect of the present application.

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

In one embodiment of the present application, the functional layer 300 includes an organic light emitting layer 330 including the organic compound.

In one embodiment, 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 as an energy conversion layer, an electron transport layer 350, and a cathode 200, which are sequentially stacked.

In one embodiment, the anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. The anode material specifically includes: 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 such as ZnO: al and SnO₂: sb; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxygen)Yl) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Also, it is preferable to include a transparent electrode including Indium Tin Oxide (ITO) as an anode.

In one embodiment, the first hole transport layer 321 may include one or more hole transport materials, and the first hole transport layer material may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not specifically limited herein. For example, the first hole transport layer 321 may be composed of a compound NPB.

In one embodiment, the second hole transport layer 322 may include one or more hole transport materials, and the second hole transport layer material may be selected from carbazole polymers or other types of compounds, which are not particularly limited in this application. In one embodiment, the second hole transport layer 322 is comprised of the compound TAPC.

In the present application, the electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport materials further include one or more electron transport materials selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which are not particularly limited in this application. In one embodiment, the electron transport layer 350 may be composed of BPhen and LiQ together.

In one embodiment, the organic light emitting layer 330 may be composed of a single light emitting material, or may be composed of a host material and a guest material. Preferably, the organic light emitting layer 330 is composed of a host material and a guest 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, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

The host material of the organic light emitting layer 330 may be the organic compound of the present application, or may be composed of the organic compound of the present application and other light emitting host materials, such as metal chelate compounds, bisstyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials, which are not limited in this application. In one embodiment, the host material of the organic light emitting layer 330 is composed of both the organic compound of the present application and GHp 1. When the compound is used as a main material of a light-emitting layer of a device, the device has excellent light-emitting efficiency; on the other hand, the compound has better exciton tolerance and can improve the service life of the device.

The guest 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, the guest material of the organic light emitting layer 330 is Ir (ppy)₃。

Optionally, the cathode 200 comprises a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specifically, specific examples of the cathode material include, but are not limited to: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; multilayer materials such as LiF/Al, Liq/Al, LiO₂Al, LiF/Ca, LiF/Al and BaF₂But not limited thereto,/Ca. Preferably, a metal electrode comprising silver and magnesium is included as a cathode.

In the present application, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the first 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. In one embodiment of the present application, the hole injection layer 310 may be composed of m-MTDATA.

In one embodiment, as shown in fig. 1, an electron injection layer 360 may be further disposed between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. Specifically, the electron injection layer 360 may include ytterbium (Yb).

In a specific embodiment, a hole blocking layer 340 may be further disposed between the organic light emitting layer 330 and the electron transport layer 350. A third aspect of the present application provides an electronic device comprising the electronic component provided in the second aspect of the present application.

In one embodiment, as shown in FIG. 2, the present application provides an electronic device 400. The electronic device 400 includes the organic electroluminescent device in the above embodiment. The electronic device 400 may be a display device, a lighting device, an optical communication device, or other types of electronic devices, and may include, but is not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.

The present application is further illustrated by the following examples, which are not intended to be limiting in any way.

The synthesis method of the organic compound provided herein is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the organic compound of the present invention in combination with the preparation methods provided in the preparation examples section. All organic compounds provided herein are available to those skilled in the art from these exemplary preparative methods, and all specific preparative methods for preparing the organic compounds will not be described in detail herein, and those skilled in the art should not be construed as limiting the present application.

In the synthesis examples described below, all temperatures are in degrees celsius unless otherwise stated. Some of the reagents were purchased from commercial suppliers such as Aldrich Chemical Company, and some of the intermediates that could not be purchased directly were prepared by simple reactions from commercially available starting materials and were used without further purification unless otherwise stated. The rest of conventional reagents are purchased from Nanjing Congralin chemical industry and industry Co., Ltd, Qingdao Tenglong chemical reagent Co., Ltd, Qingdao ocean chemical plant, etc.

In purification, the column was silica gel column, silica gel (80-120 mesh) was purchased from Qingdao oceanic plant.

In each synthesis example, the conditions for measuring low resolution Mass Spectrometry (MS) data were: agilent 6120 four-stage rod HPLC-M (column model: Zorbax SB-C18, 2.1X 30mm,3.5 μ M, 6min, flow rate 0.6 mL/min. mobile phase: ratio of 5% -95% (acetonitrile containing 0.1% formic acid) in (water containing 0.1% formic acid)), using electrospray ionization (ESI), at 210nm/254nm, with UV detection.

Hydrogen nuclear magnetic resonance spectroscopy: bruker 400MHz NMR instrument in CDCl at room temperature₃Or CD₂Cl₂TMS (0ppm) was used as a reference standard for the solvent (in ppm).

When describing the concentration, M means mol/L.

Preparation of intermediates

Sub 1-I-A1(50.0g, 194.45mmol), m-chlorobenzoic acid (25.34g, 162.04mmol), tetrakis (triphenylphosphine) palladium (1.87g, 1.62mmol), potassium carbonate (55.9g, 405.11mmol), tetrabutylammonium bromide (0.52g, 1.62mmol), toluene (400mL), ethanol (200mL) and deionized water (100mL) were added to a three-necked flask, warmed to 76 ℃ under nitrogen, heated to reflux and stirred for 8 h. After the reaction is finished, cooling the solution to room temperature, adding toluene and water to extract the reaction solution, combining organic phases, drying an organic layer by anhydrous magnesium sulfate, filtering and concentrating; the crude product was purified by silica gel column chromatography (dichloromethane/n-heptane) to give sub 1-II-A1(33.7g, 72% yield) as a solid intermediate.

Sub 1-II-A1(30.0g, 103.89mmol), indolo [2,3-A]Carbazole (29.3g, 114.31mmol), Pd₂(dba)₃Adding (0.95g, 1.03mmol), X-phos (0.99g, 2.07mmol) and sodium tert-butoxide (19.9g, 207.8mmol) into a three-neck flask, adding xylene (300mL) solvent, heating to 140 ℃ under the protection of nitrogen, keeping the temperature and stirring for 5 hours;cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; recrystallization from dichloromethane/ethanol gave the product sub A-1 as a white solid (41.2g, 78% yield).

Synthesizing intermediates sub A-2 to sub A-11 shown in the following table 1 by referring to the intermediate sub A-1, except that in the sub A-2 to sub A-10, the raw material 1 is used to replace m-chlorobenzene boric acid to react with sub 1-I-A1, and then reacts with indolo [2,3-A ] carbazole; in sub A-11, sub 1-I-A1 is directly reacted with indolo [2,3-A ] carbazole.

TABLE 1

PREPARATION EXAMPLE 1 preparation of Compound 67

Adding the intermediates sub A-1(20.0g, 39.3mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (12.6g, 47.2mmol) and DMF (200mL) into a three-neck flask, cooling to 0 ℃ under the protection of nitrogen, adding NaH (1.0g, 41.3mmol) to change the system from white to yellow, naturally heating to room temperature to complete solid precipitation reaction, adding water into the obtained reaction solution system, filtering to obtain a solid product, leaching with a small amount of ethanol, and recrystallizing the crude product with toluene to obtain a compound 313(19.7g, 68% yield). Mass spectrum: 740.28[ M + H ] M/z]⁺。

The compounds shown in table 2 below were synthesized in a similar manner to preparation example 1, except that intermediates sub a-2 to sub a-9 were used instead of sub a-1, and that raw material 3 was used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine.

TABLE 2

Preparation of intermediates

Mixing indolo [2,3-A ]]Carbazole (50.0g, 195.1mmol), bromobenzene (27.5g, 175.5mmol), Pd₂(dba)₃(3.5g,3.9mmol), tri-tert-butylphosphine (1.6g,7.8mmol), sodium tert-butoxide (41.2g,429.2mmol) and xylene (500mL) were added to a three-necked flask, and the mixture was heated to 140 ℃ under nitrogen protection, refluxed and stirred for 10 hours. After the reaction is finished, cooling the solution to room temperature, adding toluene and water to extract the reaction solution, combining organic phases, drying an organic layer by anhydrous magnesium sulfate, filtering and concentrating; the crude product was purified by silica gel column chromatography (dichloromethane/n-heptane) to give sub A-17(42.5g, 73% yield) as a solid.

The intermediates shown in table 3 below were synthesized in a similar manner to intermediate sub a-17, except that starting material 6 was used instead of bromobenzene.

TABLE 3

Preparation of intermediates

Sub 1-I-A1(55.0g, 213.9mmol), pinacol diboron (65.18g, 256.68mmol), Pd were added to the reaction flask₂(dba)₃(1.95g, 2.13mmol), x-phos (1.7g, 4.27mmol) and KOAc (52.48g, 534.74mmol) were added to the mixture, and 1, 4-dioxane (520mL) was added thereto, followed by refluxing at 100 ℃ for 14 hours. When the reaction was complete, extraction was performed using toluene and water. Using MgSO₄The organic layer was dried and concentrated, and the resultant compound was slurried with ethanol 2 times to obtain intermediate sub 1-I-B1(55.9g, yield 86%).

Sub 1-I-B1(45.5g, 147.9mmol), 2, 4-dichloro-6-phenyl-1, 3, 5-triazine (40.1g, 177.5mmol), palladium tetratriphenylphosphine (1.7g,1.47mmol), potassium carbonate (51.1g,369.8mmol), tetrabutylammonium bromide (0.24g,0.74mmol), tetrahydrofuran (320mL) and deionized water (80mL) were charged into a three-necked flask, warmed to 65 ℃ under nitrogen, heated to reflux and stirred for 10 h. After the reaction, the solution was cooled to room temperature, toluene and water were added to extract the reaction solution, and the organic phases were combined and anhydrous MgSO₄Drying the organic layer, filtering and concentrating; the crude product was purified by silica gel column chromatography (dichloromethane/n-heptane) to give sub B-1(33.7g, yield 62%) as a solid intermediate.

Intermediates sub B-X shown in table 4 below were synthesized in a similar manner to sub B-1 except that starting material 8 was used instead of 2, 4-dichloro-6-phenyl-1, 3, 5-triazine.

TABLE 4

Preparation example 17: preparation of Compound 221

Adding intermediates sub B-1(27.7g, 75.3mmol), sub A-17(20.0g, 60.2mmol) and DMF (200mL) into a three-neck flask, cooling to 0 ℃ under the protection of nitrogen, adding NaH (1.5g, 63.17mmol) to change the system from white to yellow, naturally heating to room temperature to finish the solid precipitation reaction, adding water into the obtained reaction solution system, filtering to obtain a solid product, leaching with a small amount of ethanol, and recrystallizing the crude product with toluene to obtain the compound 221(33.7g, yield 82%). Mass spectrum: 664.24[ M + H ] M/z]⁺。

The compounds in table 5 were prepared in the same manner as in preparation example 17, except that the following sub a-X was used instead of preparing sub a-17, and sub B-X was used instead of sub B-1.

TABLE 5

The partial compound nuclear magnetic data are shown in table 6 below:

TABLE 6

Example 1: green organic electroluminescent device

An anode is formed of Indium Tin Oxide (ITO) on a substrate having a reflective layer formed thereon and has a thickness ofCutting into size of 40mm × 40mm × 0.7mm, performing photolithography to prepare experimental substrate with cathode, anode and insulating layer patterns, and treating with ultraviolet ozone and 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 impurities and oil stains on the surface of the ITO substrate.

The experimental substrate (anode) was vacuum evaporated with m-MTDATA (4,4' -tris (N-3-methylphenyl-N-phenylamino) triphenylamine) to a thickness ofAnd NPB is vapor-deposited on the hole injection layer to form a thickness ofThe first hole transport layer of (1).

Vacuum evaporating TAPC on the first hole transport layer to form a layer with a thickness ofThe second hole transport layer of (1).

On the second hole transport layer, a compound 313: GHp 1: ir (ppy)₃In 45%: 45%: co-evaporation is carried out at a film thickness ratio of 10% to form a film having a thickness ofGreen organic light emitting layer (EML).

BPhen and LiQ (8-hydroxyquinoline-lithium) are mixed in a weight ratio of 1:1 and evaporated to formA thick Electron Transport Layer (ETL) formed by depositing Yb on the electron transport layerAnd then magnesium (Mg) and silver (Ag) are mixed in a ratio of 1: 9 is vacuum-evaporated on the electron injection layer to a thickness ofThe cathode of (1).

The thickness of the vapor deposition on the cathode is set toForming an organic capping layer (CPL), thereby completing the fabrication of the organic light emitting device.

Examples 2 to 26

An organic electroluminescent device was produced in the same manner as in example 1, except that the compounds shown in table 8 were used in the formation of the green organic light-emitting layer, respectively.

Comparative examples 1 to 4

An organic electroluminescent device was fabricated in the same manner as in example 1, except that compound a, compound B, compound C and compound D were used, respectively, in forming the green organic light-emitting layer.

Examples 1-26 and comparative examples 1-4 use the following main material structures as shown in table 7:

TABLE 7

At 20mA/cm²Performance analysis was performed on the organic electroluminescent devices prepared in examples 1 to 26 and comparative examples 1 to 4 under the conditions shown in table 8:

TABLE 8

As can be seen from the data in table 8, examples 1-26, using the compounds of the present application as green organic light emitting layer hybrid host materials, exhibited two different device improvement directions compared to comparative examples 1-4.

Compared with comparative examples 1-4, the compounds used in examples 1-26 mainly improve the luminous efficiency and the lifetime of the device, reduce the driving voltage by at least 0.13V, improve the current efficiency (luminous efficiency) by at least 12.6%, and improve the lifetime by at least 17.4%.

Therefore, when the organic compound is used for preparing a green organic electroluminescent device, the service life of the organic electroluminescent device can be effectively prolonged and the luminous efficiency can be improved under the condition of ensuring that the device has lower driving voltage.

The compound is fixedly connected with 4-phenanthryl in an indole carbazole mother nucleus compound, the steric hindrance of the phenanthryl at the connecting position and the adjacent group is most suitable, and the compound has a higher first triplet state energy level; can ensure the transmission and recombination of carriers and efficiently transfer exciton energy to guest materials. The 4-phenanthryl is connected to triazine, so that the energy transmission efficiency can be improved, and the luminous efficiency of the device can be further remarkably improved; the 4-phenanthryl is connected to the indolocarbazole mother nucleus, so that the film forming property and the exciton tolerance of the compound can be improved, and the T95 service life of the device can be further prolonged.

The preferred embodiments of the present application have been described in detail with reference to the accompanying drawings, however, the present application is not limited to the details of the above embodiments, and various simple modifications can be made to the technical solution of the present application within the technical idea of the present application, and these simple modifications are all within the protection scope of the present application. It should be noted that, in the foregoing embodiments, various features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described in the present application.