CN114957268B

CN114957268B - Compound, organic electroluminescent device and electronic device

Info

Publication number: CN114957268B
Application number: CN202110301323.4A
Authority: CN
Inventors: 马天天; 郑奕奕; 南朋
Original assignee: Shaanxi Lighte Optoelectronics Material Co Ltd
Current assignee: Shaanxi Lighte Optoelectronics Material Co Ltd
Priority date: 2021-03-22
Filing date: 2021-03-22
Publication date: 2023-06-09
Anticipated expiration: 2041-03-22
Also published as: CN114957268A; WO2022199256A1

Abstract

The chemical structure of the organic compound comprises a large condensed structure, the structure improves hole mobility, and the organic compound also comprises a proper electron infusion group, has a high first triplet state energy level as a whole, has proper HOMO energy level distribution and can be used as a luminescent main material in an organic luminescent material. The compound can improve the efficiency of the device and prolong the service life of the organic electroluminescent device when used in the electroluminescent device.

Description

Compound, organic electroluminescent device and electronic device

Technical Field

The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a compound, an organic electroluminescent device using the same and an electronic device.

Background

Organic electroluminescent devices, such as Organic Light Emitting Diodes (OLEDs), typically include oppositely disposed cathodes and anodes, and a functional layer disposed between the cathodes and anodes. The functional layer is composed of a plurality of organic or inorganic film layers, and generally includes an organic light emitting layer, a hole transport layer between the organic light emitting layer and the anode, and an electron transport layer between the organic light emitting layer and the cathode. When voltage is applied to the cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the electroluminescent layer under the action of the electric field, holes at the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the electroluminescent layer emits light outwards.

Materials that can be used to produce light-emitting layers in organic electroluminescent devices are disclosed in the prior art. However, the current organic electroluminescent materials still have the problems of short luminescent life and low luminescent efficiency. Accordingly, there is a need to continue to develop new materials to further improve the lifetime and efficiency performance of organic electroluminescent devices.

Disclosure of Invention

The invention aims to provide an organic electroluminescent material with excellent performance, which can be used as a light-emitting layer in an organic electroluminescent device.

In order to achieve the above object, the present invention provides a compound selected from the following structures 1-1 or 1-2:

wherein R is ₁ 、R ₂ And R is ₃ Each independently selected from hydrogen, deuterium, cyano, halogen groups, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, and halogenated alkyl groups having 1 to 10 carbon atoms;

L ₁ 、L ₂ and L are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

Ar ₁ 、Ar ₂ each independently selected from hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms;

Het is selected from 6-18 membered electron-deficient nitrogen-containing heteroarylene;

R ₅ 、R ₆ 、R ₇ 、R ₈ each independently selected from the group consisting of hydrogen, deuterium, cyano, halogen, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 30 carbon atoms, alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triarylsilyl having 18 to 20 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 15 carbon atoms, arylthio having 6 to 15 carbon atoms, phosphino having 6 to 15 carbon atoms;

n ₅ selected from 0, 1, 2 or 3;

n ₆ 、n ₇ 、n ₈ each independently selected from 0, 1, 2, 3 or 4;

L ₁ 、L ₂ 、L、Ar ₁ 、Ar ₂ in (a) and (b)The substituents are the same or different and are each independently selected from deuterium, cyano, halogen, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triarylsilyl having 18 to 20 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 15 carbon atoms, arylthio having 6 to 15 carbon atoms, phosphino having 6 to 15 carbon atoms; optionally, two adjacent substituents are linked to each other to form a saturated or unsaturated 5-to 13-membered aliphatic ring or a 5-to 13-membered aromatic ring.

According to a second aspect of the present application, there is provided an organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the compound.

Further, in the organic electroluminescent device, the functional layer comprises a light emitting layer body and a dopant, and the light emitting layer body comprises the compound.

According to a third aspect of the present application, there is provided an electronic device comprising an organic electroluminescent device of the present application.

The core structure of the compound is that on the basis of indolocarbazole, carbazole and 2, 2-biphenyl are condensed into 7-membered ring, so that a large condensed structure is formed; the structure has great conjugation and rigidity, improves hole mobility, has high first triplet energy level, contains proper electron infusion groups, has proper energy level distribution of the whole molecule, can be used as a luminescent main body material in an organic luminescent material, and improves the efficiency performance of the organic luminescent material. The large plane conjugated structure of the molecule improves the thermal stability of the material, the fusing mode of indole and carbazole in the compound mother nucleus is limited to be that indole is fused at the 1, 2-or 2-3-position of carbazole ring, and two nitrogen atoms must be in the same direction, so that the fusing mode ensures that the mother nucleus has proper space structure and larger dipole moment, the polarity of the molecule is increased, and the compound has higher carrier mobility after the mother nucleus is matched with proper electron transport groups; on the other hand, the steric hindrance between groups connected to nitrogen atoms is larger, which is favorable for molecules to exhibit better stereoscopic properties and better film forming property, and the luminescent layer is used in an OLED device, so that the luminous efficiency and the service life of the device can be improved.

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

Drawings

The accompanying drawings are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate the application and, together with the description, do not limit the application. 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 view of an electronic device according to an embodiment of the present application.

The main device reference numerals in the drawings are as follows:

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

Detailed Description

The following detailed description of specific embodiments of the present application refers to the accompanying drawings. It should be understood that the detailed description is presented herein for purposes of illustration and explanation only and is not intended to limit the present application.

In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings denote the same or similar structures, and thus detailed descriptions thereof will be omitted.

In the present application,

and->

All refer to the same meaning as the position of attachment to other substituents or binding sites.

In the present application, the carbon atom position on the carbazole ring in the carbazole ring-condensed biphenyl mother nucleus is expressed according to the label in the following structural formula:

in the present application, L ₁ 、L ₂ 、L、R ₁ 、R ₂ 、R ₃ 、R ₅ 、R ₆ 、R ₇ 、R ₈ 、Ar ₁ And Ar is a group ₂ In (c), the number of carbon atoms of the substituted aryl or heteroaryl refers to the total number of carbon atoms of the aryl or heteroaryl and the substituents thereon, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and substituents being 18. For example, 2, 4-diphenyl-1, 3, 5-triazinyl is a substituted heteroaryl group having 15 carbon atoms.

The descriptions used in this application, "each … … is independently" and "… … is each independently" and "… … is independently selected from" being interchangeable, and should be understood in a broad sense to mean that the specific options expressed between the same symbols in different groups do not affect each other, or that the specific options expressed between the same symbols in the same groups do not affect each other. For example: at the position of

Wherein each q is independently 0, 1, 2 or 3, and each R "is independently selected from the group consisting of hydrogen, fluorine, chlorine" and has the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents Q substituents R 'on each benzene ring of biphenyl, and the number Q of R' substituents on two benzene rings The R's may be the same or different, and the options of each R' are not affected.

In this application, "optional" or "optionally" means that the subsequently described event or circumstance may but need not occur, and that the description includes instances where the event or circumstance occurs or does not. For example, "a heterocyclic group optionally substituted with an alkyl group" means that an alkyl group may be, but is not necessarily, present, and the description includes situations where the heterocyclic group is substituted with an alkyl group and situations where the heterocyclic group is not substituted with an alkyl group.

In the present application, the term "substituted or unsubstituted" means that there is no substituent or is substituted with one or more substituents. Such substituents include, but are not limited to, deuterium, halogen groups (F, cl, br), cyano, alkyl, haloalkyl, aryl, heteroaryl, aryloxy, arylthio, cycloalkyl, heterocyclyl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio.

In this application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 12 carbon atoms, in this application, a numerical range such as "1 to 12" refers to each integer in the given range; for example, "1 to 12 carbon atoms" refers to an alkyl group that may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms. In some embodiments, the alkyl group contains 1 to 4 carbon atoms. The alkyl group may be optionally substituted with one or more substituents described herein. Examples of alkyl groups include, but are not limited to, methyl (Me, -CH ₃ ) Ethyl (Et, -CH) ₂ CH ₃ ) N-propyl (n-Pr, -CH) ₂ CH ₂ CH ₃ ) Isopropyl (i-Pr, -CH (CH) ₃ ) ₂ ) N-butyl (n-Bu, -CH) ₂ CH ₂ CH ₂ CH ₃ ) Isobutyl (i-Bu, -CH) ₂ CH(CH ₃ ) ₂ ) Sec-butyl (s-Bu, -CH (CH) ₃ )CH ₂ CH ₃ ) Tert-butyl (t-Bu, -C (CH) ₃ ) ₃ ) Etc. This isIn addition, alkyl groups may be substituted or unsubstituted.

In the present application, trialkylsilyl refers to

Wherein R is ^G1 、R ^G2 、R ^G3 Specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, propyldimethylsilyl group;

in the present application, triarylsilyl refers to

Wherein R is ^G4 、R ^G5 、R ^G6 Specific examples of the aryl group, the triarylsilyl group, and the like, each independently, include, but are not limited to, triphenylsilyl group, and the like.

In the present application, a halogen group as a substituent includes fluorine, chlorine, bromine or iodine.

In this application, "alkoxy" means an alkyl group attached to the remainder of the molecule through an oxygen atom, wherein the alkyl group has the meaning as described herein. Unless otherwise specified, the alkoxy groups contain 1 to 10 carbon atoms. In one embodiment, the alkoxy group contains 1 to 6 carbon atoms; in another embodiment, the alkoxy group contains 1 to 4 carbon atoms. Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, 1-propoxy, 2-propoxy, 1-butoxy, 2-methyl-l-propoxy, 2-butoxy, 2-methyl-2-propoxy, and the like.

In this application, "haloalkyl" or "haloalkoxy" means an alkyl or alkoxy group substituted with one or more halogen atoms, wherein the alkyl and alkoxy groups have the meaning as described herein, examples of which include, but are not limited to, trifluoromethyl, trifluoromethoxy, and the like.

Cycloalkyl in this application refers to a radical obtained by removing a hydrogen atom from a monocyclic or polycyclic saturated cyclic hydrocarbon, and the "cycloalkyl" may have one or more points of attachment to the remainder of the molecule. In some embodiments, cycloalkyl is a ring system containing 3 to 12 ring carbon atoms; in other embodiments, cycloalkyl is a ring system containing 5 to 10 ring carbon atoms; in other embodiments, cycloalkyl is a ring system containing 5 to 7 ring carbon atoms; in other embodiments, cycloalkyl groups are ring systems containing 3 to 6 ring carbon atoms. The cycloalkyl groups may independently be unsubstituted or substituted with one or more substituents described herein. As non-limiting examples thereof, cycloalkyl groups are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.

In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered aryl groups herein. Where fused ring aryl refers to two or more rings in a ring system where two carbon atoms are common to two adjoining rings, wherein at least one of the rings is aromatic, e.g., the other rings may be cycloalkyl, cycloalkenyl, aryl. For example, in the present application, biphenyl, terphenyl, and the like are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, tetrabiphenyl, pentabiphenyl, benzo [9,10 ] ]Phenanthryl, pyrenyl, benzofluoranthenyl,

A base, etc. In the present specification, the number of carbon atoms of the aryl group may be selected from 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 25 or 30. In some embodiments, the aryl group is an aryl group having from 6 to 30 carbon atoms, in other embodiments, the aryl group is an aryl group having from 6 to 15 carbon atoms, in other embodiments, the aryl group is an aryl group having from 6 to 25 carbon atoms, in other embodiments, the aryl group is an aryl group having from 6 to 20 carbon atomsA base.

In the present application, a substituted aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as a deuterium atom, a halogen group, a cyano (-CN), an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, a haloalkyl group, an aryloxy group, an arylthio group, an aryl group, a heterocyclic group, or the like. It is understood that the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and its substituents being 18.

In the present application, fluorenyl as aryl may be substituted, and two substituents may be combined with each other to form a spiro structure, specific examples include, but are not limited to, the following structures:

Aryl groups as substituents in the present application are, for example, but not limited to, phenyl, biphenyl, naphthyl, phenanthryl, anthracyl, fluorenyl, dimethylfluorenyl, terphenyl.

In the present application, arylene is a 2-valent or multivalent group, and the above description of aryl may be applied in addition thereto.

In this application heteroaryl means a mono-or polycyclic ring system containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms independently selected from O, N, P, si, se, B and S in the ring, and wherein at least one ring system is aromatic. Each ring system in heteroaryl groups contains a ring of 5 to 7 ring atoms and has one or more attachment points to the remainder of the molecule. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Fused ring heteroaryl refers to two or more rings in a ring system where two atoms are common to two adjoining rings, wherein at least one of the rings is aromatic, e.g., the other rings may be cycloalkyl, aryl.

Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, isothiazolyl, oxadiazolyl, triazolyl, oxazolyl, furazayl, pyridyl, bipyridyl, phenanthridinyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridyl), N-alkyl carbazolyl (e.g., N-methyl carbazolyl), and the like, without limitation. Wherein thienyl, furyl, phenanthroline and the like are heteroaryl groups of a single aromatic ring system type, and N-arylcarbazolyl and N-heteroarylcarbazolyl are heteroaryl groups of a polycyclic ring system type which are conjugated and connected through carbon-carbon bonds.

In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. It is understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl. For example, a substituted heteroaryl group having 14 carbon atoms refers to a heteroaryl group and a substituent having 14 total carbon atoms.

In this application, the number of carbon atoms of the heteroaryl group may be 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, the heteroaryl is a heteroaryl having 3 to 12 carbon atoms, in other embodiments the heteroaryl is a heteroaryl having 5 to 18 carbon atoms, in other embodiments the heteroaryl is a heteroaryl having 5 to 12 carbon atoms.

Heteroaryl groups as substituents in the present application are, for example, but not limited to, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, dibenzothienyl, dibenzofuranyl, carbazolyl, quinazolinyl, quinoxalinyl, pyrazinyl, pyridazinyl, and the like.

In this application, the heteroarylene group may be a divalent group or a polyvalent group, and the above description of the heteroaryl group may be applied thereto.

In the present application, "hetero" means that at least 1 heteroatom such as B, N, O, S, se, si or P is included in one functional group and the remaining atoms are carbon and hydrogen when no specific definition is provided otherwise. Unsubstituted alkyl groups may be "saturated alkyl groups" without any double or triple bonds.

In this application, a ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6 membered aryl. The 6-13 membered aromatic ring means benzene ring, indene ring, naphthalene ring, etc.

In the present application, electron-deficient nitrogen-containing heteroarylene means that it comprises at least one sp ² Heteroaryl groups with nitrogen atoms hybridized, wherein the lone pair electrons in the nitrogen atoms in the heteroaryl groups do not participate in conjugation, so that the overall electron density is lower. "6-18 membered electron-deficient nitrogen-containing heteroarylene" is a heteroaryl ring containing an sp2 hybridized nitrogen atom formed from 6-18 atoms. Such as, but not limited to, pyridinyl, pyrimidinyl, triazinyl, pyridazinyl, pyrazinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, quinolinyl, quinazolinyl, quinoxalinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, benzimidazolyl, benzothiazolyl, phenanthrolinyl, and the like.

The term "non-aligned connection" as used herein refers to a single bond extending from a ring system

Or->

Which means that one end of the bond can be attached to any position in the ring system through which the bond extends, anotherOne end is attached to the remainder of the compound molecule. For example, the naphthyl group represented by formula (X) is linked to the other positions of the molecule via two non-positional linkages extending through the bicyclic ring, as shown in formula (X) below, and the meaning of the linkage includes any of the possible linkages shown in formulas (X-1) to (X-10).

For example, the phenanthryl group represented by the following formula (X ') is linked to the other position of the molecule through an unoriented linkage extending from the middle of one benzene ring, and the meaning represented by the formula (X ' -1) to (X ' -4) includes any possible linkage as shown in the formulas (X ' -1) to (X ' -4).

An delocalized substituent in this application refers to a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, the substituent R represented by the following formula (Y) is linked to the quinoline ring through an unoositioned linkage, and the meaning represented by this linkage includes any one of the possible linkages represented by the formulae (Y-1) to (Y-7).

The present application provides a compound selected from the following structures 1-1 or 1-2:

R ₁ 、R ₂ and R is ₃ Each independently selected from hydrogen, deuterium, cyano, halogen groups, aryl groups having 6 to 20 carbon atoms, and carbon atomsHeteroaryl groups of 3 to 20, alkyl groups of 1 to 10 carbon atoms, deuterated alkyl groups of 1 to 10 carbon atoms and halogenated alkyl groups of 1 to 10 carbon atoms;

n ₅ Selected from 0, 1, 2 or 3; n is n ₅ When the number is greater than 1, each R ₅ The same or different;

n ₆ 、n ₇ 、n ₈ each independently selected from 0, 1, 2, 3 or 4; n is n ₆ When the number is greater than 1, each R ₆ The same or different;

n ₇ when the number is greater than 1, each R ₇ The same or different; n is n ₈ When the number is greater than 1, each R ₈ The same or different;

L ₁ 、L ₂ 、L、Ar ₁ 、Ar ₂ the substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms, and C atomsAlkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triarylsilyl group having 18 to 20 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, aryloxy group having 6 to 15 carbon atoms, arylthio group having 6 to 15 carbon atoms, and phosphinoxy group having 6 to 15 carbon atoms; optionally, two adjacent substituents are linked to each other to form a saturated or unsaturated 5-to 13-membered aliphatic ring or a 5-to 13-membered aromatic ring.

In the present application, "two adjacent substituents are connected to each other to form a saturated or unsaturated 5-to 13-membered aliphatic ring or 5-to 13-membered aromatic ring" means that two substituents may or may not form a ring, that is, a scenario in which two substituents are connected to each other to form a saturated or unsaturated 5-to 13-membered aliphatic ring or 5-to 13-membered aromatic ring, or a scenario in which two substituents exist independently of each other is included. Wherein "adjacent substituents" include both two substituents attached to the same atom and two substituents attached to adjacent atoms.

In some embodiments of the present application, L ₁ 、L ₂ 、L、Ar ₁ 、Ar ₂ The substituents of (a) are the same or different and are each independently selected from deuterium, cyano, fluoro, phenyl, naphthyl, biphenyl, phenanthryl, fluorenyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, tridentate methyl, trimethylsilyl, triphenylsilyl, cyclopentyl, cyclohexenyl, methoxy, ethoxy, isopropoxy, diphenylphosphinoxy; optionally, two adjacent substituents are linked to each other to form a spiro fluorene ring

In some embodiments of the present application, the R ₁ 、R ₂ And R is ₃ Are each independently hydrogen, deuterium, cyano.

In some implementations of the present applicationIn an embodiment, het is selected from electron-deficient heteroaryl groups (also known as electron-deficient heteroaryl groups) which are nitrogen-containing, sp on Het ² The hybrid nitrogen atom can reduce the electron cloud density of the conjugated system of the heteroaryl group as a whole rather than improve the electron cloud density of the conjugated system of the heteroaryl group, the lone pair electrons on the heteroatom do not participate in the conjugated system, and the heteroatom reduces the electron cloud density of the conjugated system due to stronger electronegativity. For example, electron-deficient heteroaryl groups may include, but are not limited to, triazinyl, pyrimidinyl, quinolinyl, quinoxalinyl, quinazolinyl, isoquinolinyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, benzoquinazolinyl, phenanthroimidazolyl, benzofuranopyrimidinyl, benzothiophenopyrimidinyl, and the like. In this way, the Het group may form an electron transporting core group of the compound, so that the compound can effectively realize electron transport, and can effectively balance the transport rate of electrons and holes in the organic light emitting layer. In this way, the compound may be used as a host material of a bipolar organic light-emitting layer to simultaneously transport electrons and holes, or may be used as a host material of an electron-type organic light-emitting layer to be combined with a host material of a hole-type organic light-emitting layer.

In some more specific embodiments of the present application, the Het group is selected from triazinylene, pyrimidinylene, quinolinylene, quinoxalinylene, quinazolinylene, isoquinolylene, benzimidazolylene, benzothiazolylene, benzoxazolylene, phenanthroline, benzoquinazolinylene, phenanthreneimidazolylene, benzofuranopyrimidino, benzothiophenopyrimidino, or the following groups:

in some embodiments of the present application, the L ₁ 、L ₂ And L is each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 4 to 18 carbon atoms.

In some embodiments of the present application, the L ₁ 、L ₂ Each L is independently selected from one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted dibenzofuran subunit, a substituted or unsubstituted dibenzothiophene subunit, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolene group, a substituted or unsubstituted carbazole group, or a subunit group formed by single bond connection of two or three of the above subunits.

Optionally, the L ₁ 、L ₂ The substituents in L are the same or different from each other and are each independently selected from the group consisting of deuterium, fluorine, chlorine, bromine, cyano, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, deuteroalkyl having 1 to 4 carbon atoms, trialkylsilyl having 3 to 9 carbon atoms, cycloalkyl having 5 to 7 carbon atoms, aryl having 6 to 15 carbon atoms and heteroaryl having 5 to 12 carbon atoms.

In some embodiments of the present application, the L ₁ 、L ₂ L are each independently selected from single bond, substituted or unsubstituted group W ₁ Wherein the unsubstituted radical W ₁ Selected from the group consisting of:

wherein the radical W ₁ The substituents on each are independently selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, tridentate methyl, trimethylsilyl, phenyl, naphthyl, and when substituted W ₁ When the number of substituents is plural, any two substituents may be the same or different.

In some more specific embodiments of the present application, the L ₁ 、L ₂ Each independently selected from the group consisting of a single bond or:

in some more specific embodiments of the present application, the L is independently selected from the group consisting of a single bond or:

In some embodiments of the present application, ar ₁ 、Ar ₂ Each independently selected from hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms.

In some embodiments of the present application, ar ₁ And Ar is a group ₂ Each independently selected from the group consisting of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylenyl, and substituted or unsubstituted spirobifluorenyl.

Alternatively, ar ₁ And Ar is a group ₂ The substituents in (a) are each independently selected from deuterium, fluorine, chlorine, cyano, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, and C6 to 15 carbon atoms Aryl, heteroaryl with 5-12 carbon atoms, alkylthio with 1-4 carbon atoms, halogenated alkyl with 1-4 carbon atoms, deuterated alkyl with 1-4 carbon atoms and trialkyl silicon with 3-9 carbon atoms, wherein any two substituents are the same or different.

In some embodiments of the present application, ar ₁ And Ar is a group ₂ Each independently selected from hydrogen, substituted or unsubstituted groups W ₂ Wherein W is unsubstituted ₂ Selected from the group consisting of:

group W ₂ The substituents on each are independently selected from: fluoro, deuterium, cyano, trifluoromethyl, tridentate methyl, trimethylsilyl, methyl, ethyl, isopropyl, t-butyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, tridentate methyl, cyclopentyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl; and when W is ₂ When the number of substituents is plural, any two substituents may be the same or different.

In some more specific embodiments of the present application, ar ₁ And Ar is a group ₂ Each independently selected from the group consisting of hydrogen or:

Ar ₁ 、Ar ₂ The group is not limited to the above.

In some embodiments of the present application, R ₅ 、R ₆ 、R ₇ 、R ₈ Each independently selected from hydrogen, deuterium, cyano, fluoro, trifluoromethyl, tridentate methyl, trimethylsilyl, methyl, ethyl, isopropyl, t-butyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, cyclopentaneA cyclohexenyl group, a phenyl group, a biphenyl group, a naphthyl group, a 9, 9-dimethylfluorenyl group, a pyridyl group, a quinolyl group, and an isoquinolyl group.

In some embodiments of the present application, formula 1-1 or formula 1-2

Selected from the following groups:

optionally, the compound is selected from the group consisting of:

the application also provides an organic electroluminescent device, which comprises an anode and a cathode which are oppositely arranged, and an organic light-emitting layer arranged between the anode and the cathode; the organic light emitting layer contains the above-described compound to improve voltage characteristics, efficiency characteristics, and lifetime characteristics of the organic electroluminescent device.

The compounds of the present application may be used as one of a single-component host material or a two-component hybrid host material.

For example, as shown in fig. 1, the organic electroluminescent device may include an anode 100, a hole transport layer 321, an organic light emitting layer 330, an electron transport layer 340, and a cathode 200, which are sequentially stacked. The compound provided by the application can be applied to the organic light-emitting layer 330 of the organic electroluminescent device to improve the service life of the organic electroluminescent device, improve the light-emitting efficiency of the organic electroluminescent device or reduce the driving voltage of the organic electroluminescent device.

Alternatively, the anode 100 includes an anode material, which is optionally a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include, but are not limited to: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide such as ZnO, al or SnO ₂ Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline. Optionally including a material comprising indium tin oxide (indium tin oxide,an Indium Tin Oxide) (ITO) as the transparent electrode of the anode.

Alternatively, the hole transport layer 321 may include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited herein.

Alternatively, the organic light emitting layer 330 may include 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 recombined at the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.

In one embodiment of the present application, the host material may consist of the compounds of the present application. The compound can simultaneously transmit electrons and holes and balance the transmission efficiency of the holes and the electrons, so that the electrons and the holes can be efficiently compounded in the organic light-emitting layer, and the light-emitting efficiency of the organic electroluminescent device is improved.

In another embodiment of the present application, the host material may be a composite material, for example, may include the compound of the present application and an electron-type organic light emitting layer host material. The compound can effectively transport holes, so that the hole transport efficiency is balanced with the electron transport efficiency of the organic light-emitting layer, and further electrons and holes can be efficiently compounded in the organic light-emitting layer, and the light-emitting efficiency of the organic electroluminescent device is improved. For example, the host material may include a compound of the present application and p-GH.

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 are not particularly limited herein. In one embodiment of the present application, the guest material of the organic light emitting layer 330 may be Ir (piq) ₂ (acac), and the like. In another embodiment of the present application, the guest material of the organic light emitting layer 330 may be Ir (ppy) ₃ Etc.

Alternatively, the electron transport layer 340 may be a single layer structure or a multi-layer structure, which may include one or more electron transport materials, which may be selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials.

Alternatively, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. 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; or a multi-layer material such as LiF/Al, liq/Al, liO ₂ Al, liF/Ca, liF/Al and BaF ₂ and/Ca. A metal electrode comprising aluminum is optionally included as a cathode. In one embodiment of the present application, the material of the cathode 200 may be magnesium silver alloy.

Optionally, 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 a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. For example, hole injection layer 310 may be composed of F4-TCNQ.

Optionally, as shown in fig. 1, an electron blocking layer 322 may be further disposed between the hole transport layer 321 and the organic light emitting layer 330 to block the electron transport to the hole transport layer 321 side, to increase the recombination rate of electrons and holes in the organic light emitting layer 330 and to protect the hole transport layer 321 from the impact of electrons. The material of the electron blocking layer 322 may be a carbazole multimer, a carbazole-linked triarylamine compound, or other viable structures.

Optionally, as shown in fig. 1, an electron injection layer 350 may also be provided 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, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. For example, the electron injection layer 350 may include LiQ.

The present application also provides an electronic device 400, as shown in fig. 2, where the electronic device 400 includes any one of the organic electroluminescent devices described in the above-mentioned embodiments of the organic electroluminescent device. The electronic device 400 may be a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc. Since the electronic device 400 has any one of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device, the same advantageous effects are achieved, and the description thereof is omitted herein.

Synthesis example:

in the synthesis examples described below, all temperatures are in degrees celsius unless otherwise indicated. Some reagents were purchased from commercial suppliers such as Aldrich Chemical Company, arco Chemical Company and Alfa ChemicalCompany, and some 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 conventional reagents are purchased from Shandong chemical plant, guangdong chemical reagent plant, guangzhou chemical reagent plant, tianjin good chemical company, tianjin Fuchen chemical reagent plant, wuhan Xinhua Yuan technology development Limited, qingdao Teng chemical reagent Limited, qingdao ocean chemical plant and the like. The reactions in each synthesis example are typically carried out under nitrogen or argon positive pressure, or a dry tube is placed over anhydrous solvent (unless otherwise stated); in the reaction, the reaction flask was capped with a suitable rubber stopper and the substrate was injected into the flask via syringe. The individual glassware used was dried.

In purification, the chromatographic column is a silica gel column, and silica gel (100-200 mesh) is purchased from Qingdao ocean chemical plant.

In each synthesis example, the measurement conditions for low resolution Mass Spectrometry (MS) data were: agilent 6120 four-stage HPLC-M (column type: zorbax SB-C18, 2.1X130 mm,3.5 μm, 6min, flow rate 0.6mL/min. Mobile phase: 5% -95% (acetonitrile with 0.1% formic acid) in water with 0.1% formic acid) was detected by electrospray ionization (ESI) at 210nm/254nm with UV.

Nuclear magnetic resonance hydrogen spectrum: bruker 400MHz nuclear magnetic instrument, under room temperature condition, CDCl ₃ TMS (0 ppm) was used as a reference standard for solvents (in ppm). When multiple peaks occur, the following abbreviations will be used: s (single, singlet), d (doublet ), t (triplet), m (multiplet ).

The target compound was detected by UV at 210nm/254nm using Agilent 1260pre-HPLC or Calesep pump 250pre-HPLC (column model: NOVASEP50/80mm DAC).

The synthesis of the compounds of the present application was performed using the following procedure:

preparation example

1. Synthesis of intermediate a-1

Indolo [2,3-A ] carbazole (50.0 g,195.3 mmol), 2-bromo-2 '-chloro-1, 1' -biphenyl (52.2 g,196.3 mmol), tris [ dibenzylideneacetone ] dipalladium (1.8 g,1.9 mmol), tri-tert-butylphosphine (3.9 mL,1 mol/L), sodium tert-butoxide (41.2 g,429.2 mmol), xylene (500 mL) were added to the flask, the temperature was raised to 140℃and the reaction was allowed to proceed for 4h, the reaction was completed, cooled to room temperature, extracted with dichloromethane and water, the organic phase anhydrous magnesium sulfate was taken to remove water, and the organic phase was concentrated to give an off-black crude product; purification by silica gel column chromatography using methylene chloride/n-heptane mixed solvent as a mobile phase afforded intermediate a-1 (64.8 g; yield: 75%) as a solid product.

Intermediate a-2 of Table 1 was synthesized using a similar method to that used for synthesizing intermediate a-1, using reactant A shown in Table 1 in place of indolo [2,3-A ] carbazole.

Table 1: synthesis of intermediate a-2 to intermediate a-4

2. Synthesis of intermediate b-1

Adding intermediate a-1 (64 g,144.7 mmol), palladium acetate (0.32 g,1.44 mmol), tricyclohexylphosphine fluoroborate (1.1 g,2.9 mmol), cesium carbonate (141 g,434.3 mmol) and o-dichlorobenzene (640 mL) into a reactor, carrying out reflux reaction for 5h, extracting distilled water and toluene after the reaction is finished, drying an organic phase by anhydrous magnesium sulfate, and concentrating the organic phase until the organic phase is not discharged to obtain a gray black crude product; purification by silica gel column chromatography using methylene chloride/n-heptane mixed solvent as a mobile phase afforded intermediate b-1 (47.0 g; yield: 80%) as a solid product.

Intermediate B-2 of Table 2 was synthesized using a similar method to that for intermediate B-1, using reactant B shown in Table 2 in place of intermediate B-1.

Table 2: synthesis of intermediate b-2 to intermediate b-4

3. Synthesis of intermediate c-1

2, 4-dichloro-6-phenyl-1, 3, 5-triazine (20 g,88.5 mmol), quinoline-3-boric acid (15.6 g,90.2 mmol) sodium carbonate (20.6 g,194.6 mmol), tetrabutylammonium bromide TBAB (5.7 g,17.7 mmol), toluene (160 mL), tetrahydrofuran THF (40 mL) and water (40 mL) are added into the flask, under the protection of nitrogen, catalyst tetra (triphenylphosphine) palladium (1.02 g,0.88 mmol) is added, the mixture is stirred fully and slowly heated to 65 ℃, the constant temperature reaction is carried out for 8h, the reaction is completed, the temperature is naturally reduced to room temperature, dichloromethane and water are used for extraction, and the organic phase is dehydrated and concentrated until the organic phase cannot be discharged, and crude products are obtained; purification by silica gel column chromatography using methylene chloride/n-heptane mixed solvent as a mobile phase afforded intermediate product c-1 (19.7 g; yield: 70%).

Using a method similar to that for the synthesis of intermediate C-2, intermediate C-2 of Table 3 was synthesized using reactant C shown in Table 3 in place of quinoline-3-boronic acid.

Table 3: synthesis of intermediate c-2

4. Synthesis of preparation example 1

Adding intermediate a-2 (10 g,24.6 mmol), 2, 4-diphenyl-6-chloro-1, 3, 5-triazine (6.6 g,24.6 mmol) into a flask, cooling to 0 ℃ to-10 ℃, adding sodium hydride (0.65 g,27.1 mmol), carrying out heat preservation reaction for 2h, naturally heating to room temperature, extracting by using dichloromethane and water, and concentrating an organic phase until water is not removed to obtain a crude product; purification by silica gel column chromatography using methylene chloride/n-heptane mixed solvent as a mobile phase afforded compound 1 (11.0 g; yield: 70%) as a solid product.

Using a method similar to that for the synthesis of Compound 1, preparation 2 to preparation 27 of Table 4 were synthesized using reactant D shown in Table 4 in place of intermediate a-2 and reactant E in place of 2, 4-diphenyl-6-chloro-1, 3, 5-triazine.

Table 4: synthesis of preparation examples 2 to 27

5. Synthesis of intermediate d-1

Intermediate b-2 (20 g,49.2 mmol), 1, 4-dibromonaphthalene (13.4 g,46.7 mmol), tris [ dibenzylideneacetone ] dipalladium (0.45 g,0.49 mmol), tri-tert-butylphosphorus (0.98 ml,1 mol/L), sodium tert-butoxide (10.4 g,108.2 mmol) were added to the flask, the temperature was raised to 140 ℃, the reaction was completed, the reaction was cooled to room temperature, dichloromethane and water were used for extraction, the organic phase anhydrous magnesium sulfate was taken for water removal, and the organic phase was concentrated until no grey black crude product was obtained; purification by silica gel column chromatography using methylene chloride/n-heptane mixed solvent as a mobile phase afforded intermediate d-1 (21.6 g; yield: 72%) as a solid product.

Intermediate d-2 to intermediate d-4 of Table 5 were synthesized using a similar method to that for synthesizing intermediate d-1, using reactant F shown in Table 5 in place of intermediate b-1, and reactant G shown in Table 5 in place of 1, 4-dibromonaphthalene.

Table 5: synthesis of intermediates d-2 to d-4

6. Synthesis of intermediate e-1

Adding an intermediate d-1 (20 g,32.7 mmol) and tetrahydrofuran (200 mL) into a flask, cooling to-78 ℃ under the protection of nitrogen, dropwise adding a tetrahydrofuran (2.5M) solution (15.7 mL,39.2 mmol) of n-butyllithium under the stirring condition, keeping the temperature and stirring for 1 hour after the dropwise adding, keeping the temperature and stirring for-78 ℃ to dropwise adding a tetrahydrofuran (15 mL) solution in which trimethyl borate (3.7 g,35.9 mmol) is dissolved, keeping the temperature and stirring for 1 hour after the dropwise adding, heating to room temperature and stirring for 24 hours, adding a water (23 mL) solution of hydrochloric acid (12M) (4.9 mL,58.8 mmol) into the reaction solution, stirring for 1 hour, separating the liquid, washing the organic phase to be neutral by using water, adding anhydrous magnesium sulfate, drying under reduced pressure, removing the solvent to obtain a crude product, and purifying the crude product by silica gel column chromatography by using a dichloromethane/n-heptane system to obtain a white solid product intermediate e-1 (11.3 g, 60%).

Using a method similar to that for synthesizing intermediate e-1, intermediates e-2 to e-4 were synthesized using reactant H shown in Table 6 in place of intermediate e-1:

Table 6: synthesis of intermediate e-2 to intermediate e-4

7. Synthesis of preparation 38

Intermediate e-1 (10 g;17.3 mmol), 2-phenyl-4- (4-fluorophenyl) -6-chloro-1, 3, 5-triazine (4.7 g;16.5 mmol), tetrakis (triphenylphosphine) palladium (0.19 g;0.16 mmol), potassium carbonate (5.0 g;36.3 mmol), tetrabutylammonium bromide (1.1 g;3.3 mmol) were added to the flask and a mixed solvent of toluene (80 mL), ethanol (40 mL) and water (20 mL) was added under nitrogen protection, and the temperature was raised to 80℃and maintained at stirring for 8 hours; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying by using anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by silica gel column chromatography using n-heptane as the mobile phase afforded product 305 as a white solid (10 g; yield 80%).

Using a method similar to Synthesis preparation 35, using the compound shown in Table 7 as reactant I in place of intermediate e-1 and the compound shown in reactant J in place of 2-phenyl-4- (4-fluorophenyl) -6-chloro-1, 3, 5-triazine, preparation 37 through 38:

table 7: synthesis of preparation 39 to preparation 41

Mass spectrometry analysis was performed on the above synthesized products, resulting in the data shown in table 8 below:

table 8: mass spectral data of partial compounds

Preparation example 1	Compound 1	m/z＝638.2[M+H] ⁺	PREPARATION EXAMPLE 22	Compound 69	m/z＝611.2[M+H] ⁺
						Preparation example 2	Compound 2	m/z＝714.3[M+H] ⁺	Preparation example 23	Compound 312	m/z＝727.2[M+H] ⁺
Preparation example 3	Compound 8	m/z＝728.2[M+H] ⁺	PREPARATION EXAMPLE 24	Compound 313	m/z＝715.2[M+H] ⁺
						Preparation example 4	Compound 14	m/z＝744.2[M+H] ⁺	Preparation example 25	Compound 309	m/z＝611.2[M+H] ⁺
Preparation example 5	Compound 49	m/z＝790.3[M+H] ⁺	PREPARATION EXAMPLE 26	Compound 219	m/z＝689.2[M+H] ⁺
						Preparation example 6	Compound 22	m/z＝764.3[M+H] ⁺	Preparation example 27	Compound 79	m/z＝585.2[M+H] ⁺
Preparation example 7	Compound 98	m/z＝688.2[M+H] ⁺	PREPARATION EXAMPLE 28	Compound 315	m/z＝661.23[M+H] ⁺
						Preparation example 8	Compound 101	m/z＝714.3[M+H] ⁺	Preparation example 29	Compound 71	m/z＝651.2[M+H] ⁺
Preparation example 9	Compound 103	m/z＝728.2[M+H] ⁺	Preparation example 30	Compound 316	m/z＝687.2[M+H] ⁺
						Preparation example 10	Compound 109	m/z＝744.2[M+H] ⁺	Preparation example 31	Compound 74	m/z＝661.2[M+H] ⁺
PREPARATION EXAMPLE 11	Compound 111	m/z＝754.3[M+H] ⁺	PREPARATION EXAMPLE 32	Compound 317	m/z＝663.2[M+H] ⁺
						Preparation example 12	Compound 186	m/z＝714.3[M+H] ⁺	PREPARATION EXAMPLE 33	Compound 318	m/z＝711.2[M+H] ⁺
Preparation example 13	Compound 190	m/z＝728.2[M+H] ⁺	PREPARATION EXAMPLE 34	Compound 314	m/z＝820.2[M+H] ⁺
						PREPARATION EXAMPLE 14	Compound 191	m/z＝744.2[M+H] ⁺	Preparation example 35	Compound 319	m/z＝656.2[M+H] ⁺
Preparation example 15	Compound 202	m/z＝738.3[M+H] ⁺	Preparation example 36	Compound 322	m/z＝661.2[M+H] ⁺
						PREPARATION EXAMPLE 16	Compound 209	m/z＝818.3[M+H] ⁺	Preparation example 37	Compound 323	m/z＝651.2[M+H] ⁺
Preparation example 17	Compound 228	m/z＝661.2[M+H] ⁺	Preparation example 38	Compound 305	m/z＝782.2[M+H] ⁺
						PREPARATION EXAMPLE 18	Compound 237	m/z＝666.3[M+H] ⁺	Preparation example 39	Compound 311	m/z＝820.2[M+H] ⁺
Preparation example 19	Compound 246	m/z＝744.2[M+H] ⁺	Preparation example 40	Compound 320	m/z＝727.2[M+H] ⁺
						Preparation example 20	Compound 256	m/z＝790.3[M+H] ⁺	PREPARATION EXAMPLE 41	Compound 321	m/z＝839.3[M+H] ⁺
Preparation example 21	Compound 245	m/z＝728.2[M+H] ⁺	PREPARATION EXAMPLE 42	Compound 324	m/z＝714.3[M+H] ⁺

The nuclear magnetic data were supplemented as follows:

preparative example 1 (compound 1): ¹ HNMR(CD ₂ Cl ₂ ,400MHz):8.78(d,1H),8.53-8.51(m,4H),8.39(d,1H),8.15-8.01(m,6H),7.88-7.81(m,2H),7.66(t,1H),7.59-7.54(m,6H),7.51-7.45(m,2H),7.41-7.31(m,2H),7.26(d,1H),6.99(d,1H).

preparation 12 (compound 186): ¹ HNMR(CD ₂ Cl ₂ ,400MHz):9.3(s,1H),8.70(s,1H),8.52(d,2H),8.29(t,2H),8.11(d,2H),7.98-7.88(m,4H),7.79-7.74(m,3H),7.70-7.56(m,7H),7.46-7.32(m,8H),6.89(d,1H).

preparation 9 (compound 103): ¹ HNMR(CD ₂ Cl ₂ ,400MHz):8.53-8.49(m,4H),8.40-8.38(m,1H),8.27(t,3H),8.08-8.06(m,2H),7.94(d,3H),7.88(d,1H),7.79-7.73(m,2H),7.68-7.64(m,1H),7.58-7.56(m,3H),7.52-7.45(m,3H),7.40-7.31(m,4H),7.27-7.25(d,1H),6.99(d,1H).

preparation 20 (compound 256): ¹ HNMR(CD ₂ Cl ₂ ,400MHz):8.72(s,2H),8.57(s,1H),8.52(d,2H),8.46(s,1H),8.21(d,1H),8.15-8.09(m,2H),7.98-7.83(m,5H),7.76(d,1H),7.72(d,2H),7.66-7.56(m,7H),7.54-7.47(m,5H),7.45-7.31(m,5H),6.89(d,1H).

preparation and performance evaluation of organic electroluminescent devices

Example 1: green organic electroluminescent device

The anode was prepared by the following procedure: the ITO thickness is equal to

Is cut into a size of 40mm by 0.7mm, and is prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern by using a photolithography process, and ultraviolet ozone and O ₂ :N ₂ The plasma was surface treated to increase the work function of the anode (experimental substrate) and to descum.

Vacuum evaporating F4-TCNQ on experimental substrate (anode) to obtain a thickness of

Is deposited with NPB to form a Hole Injection Layer (HIL) having a thickness of +.>

Is provided.

Vacuum evaporating PAPB on the first hole transport layer to obtain a film with a thickness of

Is provided.

On the second hole transport layer, compound 1: P-GH: ir (ppy) ₃ And (6): 4: co-evaporation is carried out at a ratio of 5% (evaporation rate) to form a film with a thickness of

Green organic light emitting layer (EML).

Mixing ET-06 and BimiBphen in a weight ratio of 1:1 and evaporating to form

A thick Electron Transport Layer (ETL) on which Yb is vapor deposited to form a thickness +.>

Electron Injection Layer (EIL) of (a), then magnesium (Mg) and silver (Ag) are mixed at 1:11, and vacuum evaporating on the electron injection layer to form a film having a thickness +.>

Is provided. />

Vapor deposition thickness on the cathode is

And forming an organic capping layer (CPL), thereby completing the manufacture of the organic light emitting device.

Example 2-example 41

An organic electroluminescent device was fabricated by the same method as in example 1, except that the compound shown in table 10 below was substituted for the compound 1 at the time of forming the light-emitting layer.

Comparative example 1

An organic electroluminescent device was fabricated by the same method as in example 1, except that the compound a shown in table 9 below was substituted for the compound 1 at the time of forming the light emitting layer.

Comparative example 2

An organic electroluminescent device was fabricated by the same method as in example 1, except that the compound B shown in table 9 below was substituted for the compound 1 at the time of forming the light-emitting layer.

Comparative example 3

An organic electroluminescent device was fabricated by the same method as in example 1, except that the compound C shown in table 9 below was substituted for the compound 1 at the time of forming the light-emitting layer.

Comparative example 4

An organic electroluminescent device was fabricated by the same method as in example 1, except that the compound D shown in table 9 below was substituted for the compound 1 at the time of forming the light-emitting layer.

Comparative example 5

An organic electroluminescent device was fabricated by the same method as in example 1, except that compound E shown in table 9 below was substituted for compound 1 at the time of forming the light-emitting layer.

Comparative example 6

An organic electroluminescent device was fabricated by the same method as in example 1, except that compound F shown in table 9 below was substituted for compound 1 at the time of forming the light-emitting layer.

Comparative example 7

An organic electroluminescent device was fabricated by the same method as in example 1, except that compound G shown in table 9 below was substituted for compound 1 at the time of forming the light-emitting layer.

In examples 1 to 39 and comparative examples 1 to 7, the structural formulas of the respective materials used are shown in table 9 below.

Table 9: materials used in device embodiments

For the organic electroluminescent device prepared as above, the temperature was 20mA/cm ² The device performance was analyzed under the conditions and the results are shown in table 10 below:

table 10: device embodiment test results

From the results of the above table 10, it is understood that examples 1 to 42, which are compounds of light-emitting host materials, have a drive voltage reduced by about 0.1V, a current efficiency (Cd/a) improved by at least 16.7%, and a life time improved by at least 20% as compared with comparative examples 1 to 7, using the compounds of the present invention as a host material of the light-emitting layer.

The experimental result of the device proves that the fusing mode of indole and carbazole in the compound parent nucleus is limited to the mode that indole is fused at the 1,2 or 2-3 positions of carbazole ring, and two nitrogen atoms must be in the same direction, so that the fusing mode enables the parent nucleus to have proper space structure and larger dipole moment, the molecular polarity is increased, the hole mobility is better, and the compound overall has higher carrier mobility after the parent nucleus is matched with proper electron transport groups. Further, the steric hindrance between the groups connected to the two nitrogen atoms is larger when the 1,2 positions of the carbazole ring are condensed, which is favorable for molecules to exhibit better stereoscopic properties, has better film forming property, and can improve the service life of the device when used in the luminescent layer of the OLED device. The proper space distance between two nitrogen atoms when the 2,3 positions of the carbazole ring are condensed enables the carrier mobility of the compound to be optimal, so that the device has higher efficiency.

The foregoing describes in detail the optional embodiments of the present application with reference to the accompanying drawings, but the present application is not limited to the specific details of the foregoing embodiments, and various simple modifications may be made to the technical solutions of the present application within the scope of the technical concept of the present application, and all the simple modifications belong to the protection scope of the present application.

In addition, the specific features described in the foregoing embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described in detail. Moreover, any combination of the various embodiments of the present application may be made without departing from the spirit of the present application, which should also be considered as disclosed herein.

Claims

1. A compound, wherein the compound is selected from the following structures 1-1 or 1-2:

R ₁ 、R ₂ and R is ₃ Each independently selected from hydrogen, deuterium, or cyano;

L ₁ 、L ₂ each L is independently selected from one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuran subunit, a substituted or unsubstituted dibenzothiophene subunit, and a substituted or unsubstituted carbazole group;

the L is ₁ 、L ₂ The substituents in L are the same or different and are each independently selected from deuterium, fluorine, cyano or alkyl or phenyl with 1-4 carbon atoms;

Ar ₁ And Ar is a group ₂ Each independently selected from the group consisting of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl;

Ar ₁ and Ar is a group ₂ Each substituent of (a) is independently selected from deuterium, fluorine, chlorine, cyano, alkyl with 1-4 carbon atoms, deuterated alkyl with 1-4 carbon atoms and phenyl, and any two substituents are the same or different;

the Het group is selected from triazinylene, quinoxalinylene, quinazolinylene, phenanthroline or from the group consisting of:

R ₅ 、R ₆ 、R ₇ 、R ₈ each independently selected from hydrogen, deuterium, cyano, fluoro, trifluoromethyl, tridentate methyl, ethyl, isopropyl or t-butyl;

n ₅ selected from 0, 1, 2 or 3;

n ₆ 、n ₇ 、n ₈ Each independently selected from 0, 1, 2, 3 or 4.

2. The compound of claim 1, wherein said R ₁ 、R ₂ And R is ₃ Each independently is hydrogen or deuterium.

3. The compound of claim 1, wherein L ₁ 、L ₂ L are each independently selected from single bond, substituted or unsubstituted group W ₁ Wherein W is unsubstituted ₁ Selected from the group consisting of:

wherein the radical W ₁ The substituents on each are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl or phenyl, and when substituted W ₁ When the number of substituents is plural, any two substituents may be the same or different.

4. The compound of claim 1, wherein Ar ₁ And Ar is a group ₂ Each independently selected from hydrogen, substituted or unsubstituted groups W ₂ Wherein W is unsubstituted ₂ Selected from the group consisting of:

group W ₂ The substituents on each are independently selected from: fluorine, deuterium, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl; and when W is ₂ When the number of substituents is plural, any two substituents may be the same or different.

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

6. An organic electroluminescent device, wherein the organic electroluminescent device comprises an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode;

the functional layer comprises the compound according to any one of claims 1 to 5.

7. The organic electroluminescent device according to claim 6, wherein the functional layer comprises a hole injection layer, a hole transport layer, an organic electroluminescent layer containing the compound according to any one of claims 1 to 5, an electron transport layer, and an electron injection layer.

8. An electronic device, wherein the electronic device comprises the organic electroluminescent device of claim 6 or 7.