CN113121572A - Heterocyclic compound, organic electroluminescent device, and electronic apparatus - Google Patents

Heterocyclic compound, organic electroluminescent device, and electronic apparatus Download PDF

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CN113121572A
CN113121572A CN202011519965.3A CN202011519965A CN113121572A CN 113121572 A CN113121572 A CN 113121572A CN 202011519965 A CN202011519965 A CN 202011519965A CN 113121572 A CN113121572 A CN 113121572A
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heterocyclic compound
independently selected
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CN113121572B (en
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王金平
薛震
陈志伟
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Abstract

The application provides a heterocyclic compound shown as a formula 1, an organic electroluminescent device and electronic equipment, and belongs to the technical field of organic electroluminescence. The heterocyclic compound can improve the performance of an organic electroluminescent device.
Figure DDA0002849180130000011

Description

Heterocyclic compound, organic electroluminescent device, and electronic apparatus
Technical Field
The application relates to the technical field of organic electroluminescence, in particular to a heterocyclic compound, an organic electroluminescent device and electronic equipment.
Background
Organic electroluminescent devices, such as Organic Light Emitting Diodes (OLEDs), typically include a cathode and an anode disposed opposite each other, and a functional layer disposed between the cathode and the anode. The functional layer is composed of a plurality of organic or inorganic film layers and generally comprises an organic light-emitting layer, a hole transport layer positioned between the organic light-emitting layer and an anode, and an electron transport layer positioned between the organic light-emitting layer and a cathode. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the electroluminescent layer under the action of the electric field, holes on the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the electroluminescent layer emits light outwards.
The prior art has already filed for materials that can be used to produce the light-emitting layer in organic electroluminescent devices. However, there is still a need to develop new materials to further improve the performance of the organic electroluminescent device.
The above information of the background section application is only for enhancement of understanding of the background of the present application and therefore it may contain information that does not constitute prior art known to a person of ordinary skill in the art.
Disclosure of Invention
An object of the present application is to provide a heterocyclic compound, an organic electroluminescent device, and an electronic apparatus to improve the performance of the organic electroluminescent device.
In order to achieve the purpose of the invention, the following technical scheme is adopted in the application:
according to a first aspect of the present application, there is provided a heterocyclic compound having a structure represented by formula 1-1:
Figure BDA0002849180110000011
wherein X is selected from C (R)1R2)、N(R3) O, S or Si (R)1R2)；R1To R3Each independently selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 12 carbon atoms;
Ar1to Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-18 carbon atoms, substituted or unsubstituted heteroaryl with 6-15 carbon atoms; ar (Ar)1To Ar2Wherein the substituents in (A) are each independently selected from the group consisting of fluorine, deuterium, a cyano group, a phenyl group, an alkyl group having 1 to 4 carbon atoms, a cyclopentyl group and a cyclohexyl group.
According to a second aspect of the present application, there is provided a heterocyclic compound having a structure represented by formula 1:
Figure BDA0002849180110000021
x is selected from C (R)1R2)、N(R3) O, S or Si (R)1R2)；
R1To R3Each independently selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 12 carbon atoms; wherein R is1And R2May also be linked to form a ring together with the atoms to which they are commonly attached;
a1、a2each independently selected from 1,2, 3;
Z1and Z2Each independently selected from hydrogen, deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 4 carbon atoms; any two Z1Same or different, any two Z2The same or different;
ar is selected from substituted or unsubstituted aryl with 12-60 carbon atoms and substituted or unsubstituted heteroaryl with 12-30 carbon atoms;
when Ar has a substituent, the substituent in Ar is selected from: deuterium, halogen group, cyano group, Si (R)4)3Alkyl, cycloalkyl, alkoxy, alkylthio, aryloxy, arylthio, wherein R4Selected from alkyl or phenyl, and any two R4The same or different.
According to a third aspect of the present application, there is provided an organic electroluminescent device 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 the heterocyclic compound described above.
According to a fourth aspect of the present application, there is provided an electronic device comprising the above-described organic electroluminescent device.
The utility model provides a formula 1 heterocyclic compound molecular structure wholly becomes planar structure, is favorable to the electron transfer, improves electron transmission rate, and luminous efficacy is high, and the molecule contains a plurality of donor atom nitrogens and the structure can form big conjugation formation simultaneously, and electron cloud density is big, and is efficient. In a preferred embodiment, the heterocyclic compound has a structure shown in formula 1-1, in the structure, pyrido [2,3-b ] indole in the heterocyclic compound is combined with triazine group which is also electron-deficient, so that electron injection and transport capability of the material can be effectively improved, balance degree of hole and electron injection is enhanced, and the heterocyclic compound is particularly suitable to be used as a light-emitting layer main body material, and luminous efficiency and service life of a device are improved.
Drawings
The above and other features and advantages of the present application will become more apparent by describing in detail exemplary embodiments thereof with reference to the attached drawings.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
The reference numerals of the main elements in the figures are explained as follows:
100. an anode; 200. a cathode; 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
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals denote the same or similar structures in the drawings, and thus detailed descriptions thereof will be omitted.
The application provides a heterocyclic compound, the structure of which is shown as formula 1:
Figure BDA0002849180110000031
x is selected from C (R)1R2)、N(R3) O, S or Si (R)1R2)；
R1To R3Each independently selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 12 carbon atoms; wherein R is1And R2May also be linked to form a ring together with the atoms to which they are commonly attached;
a1、a2each independently selected from 1,2, 3;
Z1and Z2Each independently selected from hydrogen, deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 4 carbon atoms; any two Z1Same or different, any two Z2The same or different;
ar is selected from substituted or unsubstituted aryl with 12-60 carbon atoms and substituted or unsubstituted heteroaryl with 12-30 carbon atoms; when Ar has a substituent, the substituents in Ar are each independently selected from: deuterium, halogen group, cyano group, Si (R)4)3Alkyl, cycloalkyl, alkoxy, alkylthio, aryloxy, arylthio, wherein R4Selected from alkyl or phenyl, and any two R4The same or different.
In the present application, the number of carbon atoms of Ar means all the number of carbon atoms. For example, if Ar is selected from substituted aryl groups having 10 carbon atoms, then all carbon atoms of the aryl group and substituents thereon are 10. For another example, if Ar is 9, 9-dimethylfluorenyl, Ar is substituted fluorenyl having 15 carbon atoms, the substituents in Ar are two methyl groups, and the number of ring-forming carbon atoms of Ar is 13.
In the present application, "R1And R2The atoms that may also be linked to form a ring together with the atoms to which they are commonly attached "include both: r1And R2The case where they are linked to form a ring together with the atom to which they are commonly linked; and R1And R2They are present independently of each other, and they are not connected to each other, and do not form a ring.
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, Si, Se, or P, etc. is included in one functional group and the remaining atoms are carbon and hydrogen. An unsubstituted alkyl group can be a "saturated alkyl group" without any double or triple bonds.
In the present application, aryl refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group can be a monocyclic aryl group or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group (i.e., a fused aryl group), two or more monocyclic aryl groups joined by carbon-carbon bond conjugation, a monocyclic aryl group and a fused ring aryl group joined by carbon-carbon bond conjugation, two or more fused ring aryl groups joined by carbon-carbon bond conjugation. That is, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as an aryl group in the present application. Wherein the aryl group does not contain a heteroatom such as B, N, O, S or P. For example, biphenyl, terphenyl, and the like are aryl groups in this application. Examples of the aryl group may include phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl, phenanthrenyl, pyrenyl,
Figure BDA0002849180110000032
and the like, without limitation.Among them, naphthyl, fluorenyl, anthryl, phenanthryl and the like belong to condensed ring aryl groups, and monocyclic aryl groups connected by a carbon-carbon single bond such as phenyl, biphenyl, terphenyl and the like do not belong to condensed ring aryl groups.
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 deuterium atoms, F, Cl, I, CN, branched alkyl, linear alkyl, cycloalkyl, alkoxy, alkylthio, or other groups. 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, a 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. For example, the 9, 9-dimethylfluorenyl group is a fluorenyl group substituted with a methyl group having 15 carbon atoms.
In the present application, the heteroaryl group may be a heteroaryl group including at least one of B, O, N, P, Se, Si and S as a heteroatom. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzosilyl, dibenzofuryl, phenyl-substituted dibenzofuryl, Dibenzofuranyl-substituted phenyl, 4, 6-diaryl-1, 3, 5-triazin-2-yl, and the like, without being limited thereto. Wherein, thienyl, furyl, phenanthroline and the like are heteroaryl of a single aromatic ring system, and N-phenylcarbazolyl, N-heteroaryl carbazolyl, phenyl-substituted dibenzofuryl and the like are heteroaryl of a plurality of aromatic ring systems connected by carbon-carbon bond conjugation.
In the present application, the descriptions "… … is independently" and "… … is independently" and "… … is independently selected from" are interchangeable, and should be understood in a broad sense, which means that the specific items expressed between the same symbols do not affect each other in different groups, or that the specific items expressed between the same symbols do not affect each other in the same groups.
For example: in "
Figure BDA0002849180110000041
Wherein 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.
An delocalized bond in the present application refers to a single bond extending from a ring system
Figure BDA0002849180110000042
It 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, as shown in the following formula (f), naphthyl represented by the formula (f) is connected with other positions of the molecule through two non-positioned connecting bonds penetrating through a double ring, and the meaning of the naphthyl represented by the formula (f-1) comprises any possible connecting mode shown in the formula (f-10).
Figure BDA0002849180110000051
As another example, in the following formula (X '), the phenanthryl group represented by formula (X') is bonded to the rest of the molecule via an delocalized bond extending from the middle of the phenyl ring on one side, and the meaning of the phenanthryl group includes any of the possible bonding modes shown in formulas (X '-1) to (X' -4).
Figure BDA0002849180110000052
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).
Figure BDA0002849180110000053
In the present application, the alkyl group may have 1 to 10 carbon atoms as a substituent, and specifically, a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms may be included. The number of carbon atoms may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9, 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl, and the like.
In the present application, the number of carbon atoms of the alkoxy group as the substituent may be 1 to 10, for example, 1,2, 3,4, 5, 6, 7, 8, 9,10, and specific examples of the alkoxy group include, but are not limited to, methoxy group, ethoxy group, n-propoxy group, and the like.
In the present application, as the substituent, the number of carbon atoms of the alkylthio group may be 1 to 10, and for example, may be 1,2, 3,4, 5, 6, 7, 8, 9,10, and specific examples of the alkylthio group include, but are not limited to, methylthio, ethylthio, n-propylthio and the like.
In the present application, the number of carbon atoms of the cycloalkyl group as a substituent may be 3 to 10, and specific examples thereof include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, and the like.
In the present application, aryl as a substituent
In the present application, the halogen group may include fluorine, bromine, chlorine, iodine, and the like.
In this application, optionally, the substituents in Ar are each independently selected from: deuterium, fluorine, chlorine, cyano, Si (R)4)3An alkyl group having 1 to 3 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, an alkylthio group having 1 to 3 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, an arylthio group having 6 to 12 carbon atoms, wherein R is4Selected from alkyl or phenyl with 1-3 carbon atoms, and any two R4The same or different. Wherein, Si (R)4)3Specific examples of (a) include, but are not limited to, triphenylsilyl, trimethylsilyl, dimethylphenylsilyl, and the like.
Alternatively, specific examples of substituents in Ar include, but are not limited to, deuterium, fluoro, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, trimethylsilyl, and the like.
In this application, R1And R2Specific examples of each include, but are not limited to, methyl, ethyl, n-propyl. R3Specific examples of (b) include methyl, naphthyl, biphenyl.
Alternatively,
Figure BDA0002849180110000061
selected from the group consisting of:
Figure BDA0002849180110000062
alternatively,
Figure BDA0002849180110000063
is an unsubstituted group Q, wherein the unsubstituted group Q is selected from the group consisting of:
Figure BDA0002849180110000064
wherein represents an unsubstituted group Q and
Figure BDA0002849180110000071
is bonded to Ar is an unsubstituted group Q.
In some embodiments, Ar is selected from the group represented by the following formula:
Figure BDA0002849180110000072
wherein M is1Selected from a single bond or
Figure BDA0002849180110000073
G1～G5Each independently selected from N or C (F)1) And G is1～G5At least one is selected from N; when G is1～G5Two or more of C (F)1) When, two arbitrary F1The same or different;
G6～G13each independently selected from N or C (F)2) And G is6～G13At least one is selected from N; when G is6～G13Two or more of C (F)2) When, two arbitrary F2The same or different;
G14～G23each independently selected from N or C (F)3) And G is14～G23At least one is selected from N; when G is14～G23Two or more of them are selected fromC(F3) When, two arbitrary F3The same or different;
G24～G33each independently selected from N or C (F)4) And G is24～G33At least one is selected from N; when G is24～G33Two or more of C (F)4) When, two arbitrary F4The same or different;
H11～H19、H21、F1～F4each independently selected from: deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 18 carbon atoms, arylthio having 6 to 18 carbon atoms; h11～H20、H22Any one of the above groups can be independently selected from aryl with 6-18 carbon atoms; f1～F4Any one of the above groups can be independently selected from hydrogen and aryl with 6-18 carbon atoms;
hkis a substituent HkK is any integer of 11-19 and 21; wherein, when k is 17, hkSelected from 0, 1,2 or 3; when k is selected from 12, 15, 16, 18 or 21, hkSelected from 0, 1,2, 3 or 4; when k is 14, hkSelected from 0, 1,2, 3,4 or 5; when k is 13, hkSelected from 0, 1,2, 3,4, 5 or 6; when k is selected from 10 or 19, hkSelected from 0, 1,2, 3,4, 5, 6 or 7; when k is 11, hkSelected from 0, 1,2, 3,4, 5, 6, 7, 8 or 9; when h is generatedkWhen greater than 1, any two HkThe same or different;
K1is selected from N (H)28)、C(H23H24)、Si(H23H24) (ii) a Wherein H28、H23、H24Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, or the above H23And H24Atoms that are linked to each other to be commonly bound to them form a ring;
K2selected from single bond, C (H)26H27)、Si(H26H27) (ii) a Wherein H25、H26、H27Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, or the above H26And H27The atoms that are linked to each other to be commonly linked to them form a ring.
Alternatively, Ar is selected from the group consisting of:
Figure BDA0002849180110000081
wherein Ar is1And Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-18 carbon atoms, substituted or unsubstituted heteroaryl with 6-15 carbon atoms; ar (Ar)3Selected from substituted or unsubstituted aryl groups having 6 to 15 carbon atoms; ar (Ar)1To Ar3Wherein the substituents in (A) are each independently selected from the group consisting of fluorine, deuterium, a cyano group, an alkyl group having 1 to 4 carbon atoms, a phenyl group, a cyclopentyl group and a cyclohexyl group.
Alternatively, Ar1To Ar2The same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted pyridyl.
Alternatively, Ar3Selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted biphenyl. Further optionally, Ar3Selected from phenyl, naphthyl or biphenyl.
Alternatively, Ar1To Ar2The same or different, and each is independently selected from substituted or unsubstituted groups W, wherein the unsubstituted groups W are selected from the group consisting ofGroup (c):
Figure BDA0002849180110000082
wherein, the substituted group W has one or more than two substituents, and the substituents are respectively and independently selected from deuterium, fluorine, cyano, methyl, tertiary butyl, phenyl, cyclopentyl and cyclohexyl.
Further optionally, Ar1To Ar2Each independently selected from the group consisting of:
Figure BDA0002849180110000091
optionally, Ar is selected from the group consisting of:
Figure BDA0002849180110000092
in a preferred embodiment, the heterocyclic compound has the structure shown in formula 1-1:
Figure BDA0002849180110000093
wherein, X and Ar1、Ar2As defined above. In this embodiment, the pyrido [2,3-b ] in the heterocyclic compound]The indole is combined with the triazine group with the same electron deficiency, so that the electron injection and transmission capability of the material can be effectively improved, the balance degree of hole injection and electron injection is enhanced, and the indole is particularly suitable for being used as a main material of a light-emitting layer, the light-emitting efficiency of a device is improved, and the service life of the device is prolonged.
Alternatively, the heterocyclic compound has the structure shown below:
Figure BDA0002849180110000101
in another embodiment, Ar is selected from substituted or unsubstituted fused aryl groups having 13 to 40 ring carbon atoms. The number of ring-forming carbon atoms means the number of carbon atoms constituting the fused aromatic ring structure, and for example, the number of ring-forming carbon atoms of an anthracenyl group is 14, the number of ring-forming carbon atoms of a fluorenyl group is 13, the number of ring-forming carbon atoms of a spirobifluorenyl group is 25, the number of ring-forming carbon atoms of 9, 9-diphenylfluorene is 13, and the total number of carbon atoms of 9, 9-diphenylfluorene is 25.
Alternatively, the substituents in Ar are each independently selected from fluoro, deuterium, cyano, alkyl having 1 to 4 carbon atoms (e.g., methyl, t-butyl), phenyl, cyclopentyl, cyclohexyl.
Optionally, the total number of carbon atoms of Ar may be 15 to 40.
Optionally, the fused aryl group is selected from anthracenyl, phenanthrenyl, pyrenyl, triphenylenyl, fluorenyl, spirobifluorenyl.
Alternatively, Ar is selected from the group consisting of:
Figure BDA0002849180110000102
to Ar3As defined above.
Alternatively, the heterocyclic compound is selected from the group consisting of:
Figure BDA0002849180110000103
Figure BDA0002849180110000111
Figure BDA0002849180110000121
Figure BDA0002849180110000131
Figure BDA0002849180110000141
Figure BDA0002849180110000151
Figure BDA0002849180110000161
Figure BDA0002849180110000171
Figure BDA0002849180110000181
Figure BDA0002849180110000191
Figure BDA0002849180110000201
Figure BDA0002849180110000211
Figure BDA0002849180110000221
Figure BDA0002849180110000231
Figure BDA0002849180110000241
Figure BDA0002849180110000251
Figure BDA0002849180110000261
Figure BDA0002849180110000271
Figure BDA0002849180110000281
the method for synthesizing the heterocyclic compound provided herein is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the heterocyclic compound of the present invention in combination with the preparation methods of the examples. In other words, the examples section herein illustratively provides methods for the preparation of heterocyclic compounds, and the starting materials employed can be obtained commercially or by methods well known in the art. All heterocyclic compounds provided by the present invention can be obtained by the person skilled in the art according to the preparation methods of these illustrative examples, and all specific preparation methods for preparing the heterocyclic compounds will not be described in detail herein, and the person skilled in the art should not be understood as limiting the present application.
The present application also provides an organic electroluminescent device. As shown in fig. 1, the organic electroluminescent device includes an anode 100 and a cathode 200 oppositely disposed, and a functional layer disposed between the anode 100 and the cathode 200; the functional layer comprises a heterocyclic compound provided herein. The heterocyclic compound provided by the application can be used for forming at least one organic thin layer in the functional layer so as to improve the service life characteristic and the efficiency characteristic of the organic electroluminescence device. The organic electroluminescent device may be a blue device or a green device.
Alternatively, the functional layer includes an organic light emitting layer 330, and the organic light emitting layer 330 contains the heterocyclic compound of the present application.
According to one embodiment, 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 heterocyclic compound provided by the application can be applied to the organic light-emitting layer 330 of the organic electroluminescent device so as to prolong the service life of the organic electroluminescent device and improve the light-emitting efficiency of the organic electroluminescent device.
Optionally, the anode 100 comprises an anode material, which is preferably 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 metals and oxides, e.g. ZnO: Al or SnO2Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole and polyaniline. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Alternatively, the hole transport layer 321 may include one or more hole transport materials, and the hole transport material may be selected from carbazole multimer, carbazole-linked triarylamine-based compound, or other types of compounds, which are not specifically 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 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 composed of the heterocyclic compound of the present application. 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.
Alternatively, the electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, 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 comprise a cathode material, which is a material with 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 multilayer material such as LiF/Al, Liq/Al, LiO2Al, LiF/Ca, LiF/Al and BaF2and/Ca. Preferably, a metal electrode comprising aluminum is included as a cathode. In one embodiment of the present application, the material of the cathode 200 may be a 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 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.
Alternatively, 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 electrons from being transported to the hole transport layer 321 side, to improve a recombination rate of the electrons and the holes in the organic light emitting layer 330, and to protect the hole transport layer 321 from the impact of the electrons. The material of the electron blocking layer 322 may be carbazole multimer, carbazole-linked triarylamine-based compound, or other feasible structures.
Optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material.
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 organic electroluminescent device embodiments. 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. 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 advantages are obtained, and details are not repeated herein.
The present invention will be described in further detail below with reference to examples. However, the following examples are merely illustrative of the present invention and are not intended to limit the present invention.
Synthesis example 1: synthesis of Compound 6:
Figure BDA0002849180110000301
(1) introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirrer, a thermometer and a condenser tube for replacement for 15min, and sequentially adding raw material 6d (50mmol), raw material 6c (37.5mmol), potassium carbonate (100mmol), 18-crown-6-ether (6mmol), 1, 10-phenanthroline (6mmol), cuprous iodide (12mmol) and xylene (125 mL). Starting stirring, heating to 130-135 ℃, reacting for 7h, adding 125mL of toluene and 125mL of water into the reaction solution under stirring, separating the solution, and extracting the aqueous phase with 125mL of toluene for 1 time. The combined organic phases were washed 2 times with water, dried over 5g of anhydrous sodium sulfate, filtered, concentrated (50-60 ℃ C., -0.09-0.08 MPa) until no droplets flowed out, stirred with 30mL of ethanol, and filtered to give intermediate 6-1(24mmol, yield 64%).
Figure BDA0002849180110000302
(2) Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring, thermometer and constant-pressure dropping funnel for replacement for 15min, adding an intermediate 6-1(24mmol), tetrahydrofuran 60mL, starting stirring, cooling to-80-90 ℃ by liquid nitrogen, dropping n-hexane solution (28mmol) of 2mol/L n-butyllithium, preserving heat for 1h after dropping, dropping tributyl borate (32mmol), adding 150mL water, 30.00mL petroleum ether and 2.4mL concentrated hydrochloric acid into the reaction solution after preserving heat for 1h, fully stirring, separating, washing an organic phase for 4 times, filtering an obtained crude product, pulping for 0.5h by using 24.0mL toluene, filtering, leaching by using toluene, and obtaining an intermediate 6-2(15mmol, yield 63%).
Figure BDA0002849180110000303
(3) Introducing nitrogen (0.100L/min) into a three-mouth reaction bottle provided with a mechanical stirrer, a thermometer and a condenser for replacement for 15min, adding raw material 6e (15mmol), intermediate 6-2(15mmol), potassium carbonate (30mmol), palladium (0.15mmol), 35mL of toluene and 15mL of water, starting stirring, heating to 65-70 ℃, carrying out heat preservation reaction for 4h, adding 35mL of water into the reaction solution under stirring, standing for liquid separation, extracting the aqueous phase with 35mL of toluene for 1 time, carrying out liquid separation, combining organic phases, and washing with 35mL of water for 2 times. Adding 5g of anhydrous sodium sulfate into the organic phase, drying, filtering, concentrating the organic phase (-0.08-0.09 MPa, 55-65 ℃) until the organic phase is not discharged, adding 15mL of petroleum ether under stirring, and filtering to obtain a compound 6(7.49g, yield 83%) with M/z being 602.3[ M + H ]]+。
Synthesis examples 2 to 7
The compounds listed in Table 1 were synthesized according to the method for Compound 6, except that the starting materials Id and Ie were used instead of the starting materials 6d and 6e, respectively, the main raw materials used, the structure of the synthesized compound, the total yield of the compound in the whole process, and the results of mass spectrometry were as shown in Table 1.
TABLE 1
Figure BDA0002849180110000311
Figure BDA0002849180110000321
Synthesis of intermediate I
1. Synthesis of intermediate 1
Figure BDA0002849180110000322
(1) Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirrer, a thermometer and a condenser for replacement for 15min, and sequentially adding 1-1(8.4g, 50mmol) of raw materials, 1-2(16.8g, 55mmol) of raw materials, 13.8g, 100mmol of potassium carbonate, 18-crown-6-ether (1.3g, 5mmol), 1, 10-phenanthroline (1.0g, 5mmol), cuprous iodide (1.9g, 10mmol) and 130mL of xylene. Starting stirring, heating to 130-135 ℃ and reacting for 10 h. 130mL of toluene and 130mL of water were added to the reaction mixture under stirring, the mixture was separated, and the aqueous phase was extracted 1 time with 130mL of toluene. The combined organic phases were washed 2 times with water, dried over 5g anhydrous sodium sulfate, filtered, concentrated (50-60 ℃ C., -0.09-0.08 MPa) until no droplets were drained, stirred with 25mL ethanol, and filtered to give intermediates 1-3(15.8g, 80% yield).
Figure BDA0002849180110000323
(2) Introducing nitrogen (0.100L/min) into a three-neck flask equipped with mechanical stirring and thermometer for 15min, sequentially adding intermediate 1-3(15.8g, 40mmol) and pinacol diboron (12.2g, 48mmol), potassium acetate (7.9g, 80mmol) and 80mL of 1, 4-dioxane are stirred, the temperature is raised to 60-65 ℃, bis (tricyclohexylphosphine) palladium dichloride (0.30g, 0.4mmol) is added, the temperature is raised to 85-90 ℃ continuously and is kept for 5h, 60mL of water is added, 100mL of dichloromethane is used for extraction, the water phase is extracted by 30mL of dichloromethane, the organic phase is washed by water for 2 times, the organic phase is dried by 2g of anhydrous sodium sulfate, the filtration is carried out, the organic phase is concentrated (40-45 ℃, minus 0.06-minus 0.05MPa) until no liquid flows out, 20mL of cyclohexane is added, and the filtration is carried out, so that an intermediate 1(15.1g, the yield is 77.5%) is obtained.
2. Intermediates shown in table 2 were synthesized with reference to the synthesis method of intermediate 1, except that starting material I-2 was used instead of starting material 1-2, and starting material I-2, intermediate structures and overall yields are shown in table 3.
TABLE 2
Figure BDA0002849180110000324
Figure BDA0002849180110000331
Synthesis example 8: synthesis of Compound 95
Figure BDA0002849180110000332
Introducing nitrogen (0.100L/min) into a three-mouth reaction bottle provided with a mechanical stirring device, a thermometer and a condensing tube for replacement for 15min, adding intermediate 1(9.7g, 20mmol), raw material 95a (7.2g, 21mmol), potassium carbonate (5.5g, 40mmol), tetrakis (triphenylphosphine) palladium (0.23g, 0.2mmol), 50mL of toluene and 20mL of water, starting stirring, heating to 65-70 ℃, keeping the temperature for reaction for 4h, adding 50mL of water into the reaction solution under stirring, standing for liquid separation, extracting the aqueous phase with 50mL of toluene for 1 time, liquid separation, combining organic phases, and washing with 50mL of water for 2 times. Adding 5g of anhydrous sodium sulfate into the organic phase, drying, filtering, concentrating the organic phase (-0.08-0.09 MPa, 55-65 ℃) until the organic phase is not discharged, adding 20mL of ethanol while stirring, and filtering to obtain a compound 95(12.0g, yield 90.0%), wherein M/z is 668.3[ M + H ] (-)]+. The nuclear magnetization of compound 95 is shown by,1H-NMR(CDCl3,400MHz)δppm：8.71-8.68(m,2H)，8.45-8.41(m,3H)，8.21-8.17(m,2H)，8.06-8.02(m,3H)，7.93(s,1H)，7.81-7.77(m,3H)，7.70(s,1H)，7.62-7.56(m,6H)，7.50-7.48(m,1H)，7.43-7.40(m,1H)，7.30-7.26(dd,2H)，7.19-7.15(m,2H)，2.54(s,6H)。
synthesis examples 9 to 30
The compounds listed in table 4 were synthesized by referring to the method of synthesis example 8, except that intermediate I was used instead of intermediate 1, starting material Ia was used instead of starting material 95, and the main starting materials used and the compound yields and mass spectrometry results are shown in table 4.
TABLE 4
Figure BDA0002849180110000341
Figure BDA0002849180110000351
Figure BDA0002849180110000361
Figure BDA0002849180110000371
Wherein, the nuclear magnetization of compound 229,1H-NMR(CDCl3,400MHz)δppm：9.12(s,1H)，9.07(s,1H)，8.59-8.56(m,2H)，8.53-8.50(m,2H)，8.45-8.43(d,1H)，8.27-8.24(m,2H)，8.18-8.15(m,3H)，8.11-8.06(m,5H)，7.69-7.65(m,4H)，7.62-7.59(m,2H)，7.38-7.34(m,2H)，7.25-7.21(m,2H)。
synthesis of intermediate II
Figure BDA0002849180110000381
Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring thermometer and a constant-pressure dropping funnel for replacement for 15min, adding 6-bromo-2-chloro-9, 9-dimethyl-9H-fluorene (15.3g, 50mmol) and tetrahydrofuran (100 mL), starting stirring, cooling liquid nitrogen to-80 ℃ to-90 ℃, dropping a n-hexane solution (60mmol) of 2mol/L n-butyllithium, keeping the temperature for 1H after dropping, dropping tributyl borate (15.0g, 65.2mmol), adding 200mL of water, 40mL of petroleum ether and 3mL of concentrated hydrochloric acid into a reaction solution after keeping the temperature for 1H, fully stirring, separating, washing an organic phase for 4 times, filtering the obtained crude product, pulping for 0.5H by using 50.0mL of toluene, and filtering to obtain an intermediate II (9.7g, yield 71%).
Synthesis example 32: synthesis of Compound 168
Figure BDA0002849180110000382
(1) Introducing nitrogen (0.100L/min) into a three-mouth reaction bottle provided with a mechanical stirring device, a thermometer and a condensing tube for replacement for 15min, adding intermediate II (8.2g, 30mmol), raw material 168c (11.5g, 30mmol), potassium carbonate (8.3g, 60mmol), tetrakis (triphenylphosphine) palladium (0.35g, 0.3mmol), toluene 60mL and water 20mL, starting stirring, heating to 65-70 ℃, keeping the temperature for reaction for 5h, adding 50mL of water into the reaction solution under stirring, standing for liquid separation, extracting the aqueous phase with 50mL of toluene for 1 time, liquid separation, combining organic phases, and washing with 50mL of water for 2 times. The organic phase was dried over 5g of anhydrous sodium sulfate, filtered, concentrated (-0.08-0.09 MPa, 55-65 ℃ C.) to completion, and 20mL of cyclohexane was added with stirring and filtered to obtain intermediate 168d (13.8g, yield 80.0%).
Figure BDA0002849180110000383
(2) Introducing nitrogen (0.100L/min) into a three-neck flask equipped with mechanical stirring, thermometer and condenser for 15min, sequentially adding intermediate 168d (11.5g, 20mmol) and 9H-pyrido [2,3-B ]]Indole (3.7g, 22mmol), potassium carbonate (5.5g, 40mmol), 18-crown-6-ether (0.5g, 2mmol), 1, 10-phenanthroline (0.4g, 2mmol), cuprous iodide (0.8g, 4mmol) and 60mL of xylene, starting stirring, and heating to 130-135 ℃ for reaction for 15 h. To the reaction mixture were added 80mL of toluene and 80mL of water with stirring, followed by liquid separation and extraction of the aqueous phase with 50mL of toluene 1 time. The combined organic phases were washed 2 times with water, dried over 5g anhydrous sodium sulfate, filtered, concentrated (50-60 ℃, -0.09 to-0.08 MPa) until no droplets were drained, 15mL ethanol was added with stirring, and filtered to obtain compound 168(8.5g, yield 60%) with M/z ═ 708.3[ M + H ], (yield 60%)]+。
Synthesis examples 33 to 34
Compounds 178 and 171 were each synthesized by referring to the method of Synthesis example 32 except that the raw material 168c was replaced with the raw material Ic, and the raw material Ic, the total yield of the compounds and the results of mass spectrometry are shown in Table 5.
TABLE 5
Figure BDA0002849180110000391
Fabrication of organic electroluminescent devices
Example 1
A method of manufacturing an organic light emitting device, comprising the steps of:
(1) firstly, distilled water and methanol are sequentially used for ultrasonic cleaning
Figure BDA0002849180110000393
Drying a glass bottom plate of an Indium Tin Oxide (ITO) electrode;
(2) cleaning the anode base plate for 5 minutes by using oxygen plasma, and then loading the cleaned anode base plate into vacuum deposition equipment;
(3) the compound 2T-NATA (CAS: 185690-41-9) was vacuum deposited on the ITO electrode
Figure BDA0002849180110000394
A hole injection layer of a certain thickness, and vacuum depositing NPB (CAS: 123847-85-8) on the hole injection layer
Figure BDA0002849180110000395
A hole transport layer of thickness, TQTPA (CAS: 1142945-07-0) vapor deposited on the hole transport layer to form
Figure BDA0002849180110000396
A thick electron blocking layer. Then, the compound 6 as a luminescent host material and the dopant BNP3FL (CAS: 669016-17-5) as a guest material are co-deposited on the electron blocking layer according to the film thickness ratio of 100:3 to form the electron blocking layer
Figure BDA0002849180110000397
A light emitting layer of thickness;
(4) vacuum deposition of TPBi on the light-emitting layer
Figure BDA0002849180110000398
A hole blocking layer of thickness;
(5) mixing DBimiBphen and LiQ were mixed at a weight ratio of 1:1, and vacuum deposited on the hole-blocking layer to form
Figure BDA0002849180110000399
Electron transport layer of thickness. Then depositing LiQ on the electron transport layer to form
Figure BDA00028491801100003910
An electron injection layer with a thickness, mixing magnesium (Mg) and silver (Ag) at a vapor deposition rate of 1: 9, and vacuum-evaporating on the electron injection layer to form
Figure BDA00028491801100003911
A cathode of thickness.
Finally, CP-1 is evaporated on the cathode to form a film with a thickness of
Figure BDA00028491801100003912
Thereby completing the fabrication of the organic light emitting device. Wherein the structures of TPBi, DBimiBphen, LiQ and CP-1 are as follows:
Figure BDA0002849180110000392
examples 2 to 9
Organic electroluminescent devices were fabricated in the same manner as in example 1, except that in examples 2 to 9, compounds shown in table 3 were used as host materials instead of compound 6, respectively, to produce organic electroluminescent devices.
Comparative examples 1 to 4
In comparative examples 1 to 4, organic electroluminescent devices were fabricated in the same manner as in example 1, except that DMFL-CBP, compound a, compound B, and compound C were used as host materials for the light-emitting layer, respectively, instead of compound 6. Wherein the structural formulas of the DMFL-CBP, the compound A, the compound B and the compound C are respectively as follows:
Figure BDA0002849180110000401
for the organic electroluminescent device prepared as above, the current density was 15mA/cm2The life of the T95 device was tested under the condition that the data voltage, efficiency and color coordinate are 10mA/cm at constant current density2The following tests were carried out and the results are shown in Table 6.
TABLE 6
Figure BDA0002849180110000402
As can be seen from table 6, the current efficiencies of the organic electroluminescent devices prepared in examples 1 to 9 were improved by at least 3.4% as compared with those of the organic electroluminescent devices of comparative examples 1 to 4, and by at least 5.5% as compared with the external quantum efficiency of comparative examples. The T95 lifetimes of examples 1-9 were at least 5.6% greater than the T95 lifetimes of comparative examples 1-4. In addition, the devices of examples 1-9 also had lower driving voltages.
Example 10
The thickness of ITO is set as
Figure BDA0002849180110000403
The ITO substrate (manufactured by Corning) of (1) was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O2:N2The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
Vacuum evaporation of m-MTDATA on an experimental substrate (anode) to a thickness of
Figure BDA0002849180110000413
And NPB is vapor-deposited on the hole injection layer to form a layer having a thickness of
Figure BDA0002849180110000414
The hole transport layer of (1).
Evaporating EB-1 on the hole transport layer to form a layer with a thickness of
Figure BDA0002849180110000415
The electron blocking layer of (1).
Vapor-plating compound 95 as a host on the hole-blocking layer while doping Ir (ppy)3As the guest, the film is formed by vapor deposition at a film thickness ratio of 100:3 to a thickness of
Figure BDA0002849180110000416
The light emitting layer of (1).
ET-1 and LiQ are mixed according to the weight ratio of 1:1 and evaporated to form
Figure BDA0002849180110000417
A thick electron transport layer, LiQ is evaporated on the electron transport layer to form a layer with a thickness of
Figure BDA0002849180110000418
And 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 of
Figure BDA0002849180110000419
The cathode of (1).
The thickness of the vapor deposition on the cathode is set to
Figure BDA00028491801100004110
Forming an organic capping layer (CPL), thereby completing the fabrication of the organic light emitting device. The main material structure adopted for preparing the device is as follows:
Figure BDA0002849180110000411
examples 11 to 34
Organic electroluminescent devices were produced in the same manner as in example 10, except that the compounds shown in table 7 were used for each of the light-emitting hosts in forming the light-emitting layer.
Comparative examples 5 to 6
In comparative examples 5 to 6, organic electroluminescent devices were fabricated in the same manner as in example 10, except that compound D and compound E, the structural formulae of which are shown below, were used instead of compound 95, respectively:
Figure BDA0002849180110000412
Figure BDA0002849180110000421
for the organic electroluminescent device prepared as above, the current density was 15mA/cm2The life of the T95 device was tested under the condition that the driving voltage, efficiency and color coordinate were 10mA/cm at constant current density2The following tests were carried out and the results are shown in Table 7.
TABLE 7
Figure BDA0002849180110000422
As can be seen from the results shown in table 7, the current efficiencies of the organic electroluminescent devices prepared in examples 10 to 34 were improved by at least 15.7% as compared with those of comparative examples 5 to 6, the external quantum efficiencies were improved by at least 12.7%, and the T95 lifetimes of the organic electroluminescent devices of examples 10 to 34 were improved by at least 21.3% as compared with those of comparative examples 5 to 6.
It can be seen that the organic electroluminescent devices prepared in examples 1 to 34 have higher luminous efficiency and higher external quantum efficiency, and the lifetime characteristics of the devices are also significantly improved, while having lower driving voltage, compared to the devices of the comparative examples.
Therefore, the heterocyclic compound can be applied to an organic electroluminescent device, especially can be used as a main material of an organic light-emitting layer, and can effectively improve the light-emitting efficiency and the external quantum efficiency of the organic electroluminescent device; meanwhile, the service life of the organic electroluminescent device is improved, and the comprehensive performance of the device is improved.
It should be understood that this application is not intended to limit the application to the details of construction and the arrangement of components set forth in the specification. The application is capable of other embodiments and of being practiced and carried out in various ways. The foregoing variations and modifications are within the scope of the present application. It should be understood that the present application and the defined applications of this specification extend to all alternative combinations of two or more of the individual features mentioned or evident from the text and/or drawings. All of these different combinations constitute a number of alternative aspects of the present application. The embodiments described in this specification illustrate the best mode known for carrying out the application and will enable those skilled in the art to make and use the application.

Claims (17)

1. A heterocyclic compound, wherein the heterocyclic compound has a structure represented by formula 1-1:
Figure FDA0002849180100000011
wherein X is selected from C (R)1R2)、N(R3) O, S or Si (R)1R2)；R1To R3Each independently selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 12 carbon atoms;
Ar1to Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-18 carbon atoms, substituted or unsubstituted heteroaryl with 6-15 carbon atoms; ar (Ar)1To Ar2Wherein the substituents in (A) are each independently selected from the group consisting of fluorine, deuterium, a cyano group, a phenyl group, an alkyl group having 1 to 4 carbon atoms, a cyclopentyl group and a cyclohexyl group.
2. The heterocyclic compound according to claim 1, characterized in that,
Figure FDA0002849180100000012
selected from the group consisting of:
Figure FDA0002849180100000013
3. the heterocyclic compound according to claim 1, characterized in that Ar is Ar1To Ar2Identical or different and each independently selected from substituted or unsubstituted groups W, wherein the unsubstituted groups W are selected from the group consisting of:
Figure FDA0002849180100000014
wherein, the substituted group W has one or more than two substituents, and the substituents are respectively and independently selected from deuterium, fluorine, cyano, methyl, tertiary butyl, phenyl, cyclopentyl and cyclohexyl.
4. The heterocyclic compound according to claim 1, characterized in that Ar is Ar1To Ar2Each independently selected from the group consisting of:
Figure FDA0002849180100000021
5. the heterocyclic compound according to claim 1, characterized in that Ar is Ar1To Ar2The total number of carbon atoms of (a) is 12 to 30.
6. A heterocyclic compound, wherein the heterocyclic compound has a structure represented by formula 1:
Figure FDA0002849180100000022
x is selected from C (R)1R2)、N(R3) O, S or Si (R)1R2)；
R1To R3Each independently selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 12 carbon atoms; wherein R is1And R2May be linked to form a ring together with the atoms to which they are commonly attached;
a1、a2each independently selected from 1,2, 3;
Z1and Z2Each independently selected from hydrogen, deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 4 carbon atoms; any two Z1Same or different, any two Z2The same or different;
ar is selected from substituted or unsubstituted aryl with 12-60 carbon atoms and substituted or unsubstituted heteroaryl with 12-30 carbon atoms; when Ar has a substituent, the substituents in Ar are each independently selected from: deuterium, halogen group, cyano group, Si (R)4)3Alkyl, cycloalkyl, alkoxy, alkylthio, aryloxy, arylthio, wherein R4Selected from alkyl or phenyl, and any two R4The same or different.
7. The heterocyclic compound according to claim 6, characterized in that the substituents for Ar are each independently selected from: deuterium, fluorine, chlorine, cyano, Si (R)4)3An alkyl group having 1 to 3 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, an alkylthio group having 1 to 3 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, an arylthio group having 6 to 12 carbon atoms, wherein R is4Selected from alkyl or phenyl with 1-3 carbon atoms, and any two R4The same or different.
8. The heterocyclic compound according to claim 6, wherein Ar is selected from a substituted or unsubstituted fused aryl group having 13 to 40 ring-forming carbon atoms; preferably, the fused aryl group is selected from the group consisting of anthracenyl, phenanthrenyl, pyrenyl, triphenylenyl, fluorenyl, spirobifluorenyl.
9. The heterocyclic compound according to claim 6, characterized in that Ar is selected from the group represented by the following chemical formula:
Figure FDA0002849180100000031
wherein M is1Selected from a single bond or
Figure FDA0002849180100000032
G1～G5Each independently selected from N or C (F)1) And G is1～G5At least one is selected from N; when G is1～G5Two or more of C (F)1) When, two arbitrary F1The same or different;
G6～G13each independently selected from N or C (F)2) And G is6～G13At least one is selected from N; when G is6～G13Two or more of C (F)2) When, two arbitrary F2The same or different;
G14～G23each independently selected from N or C (F)3) And G is14～G23At least one is selected from N; when G is14～G23Two or more of C (F)3) When, two arbitrary F3The same or different;
G24～G33each independently selected from N or C (F)4) And G is24～G33At least one is selected from N; when G is24～G33Two or more of C (F)4) When, two arbitrary F4The same or different;
H11～H19、H21、F1～F4each independently selected from: deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atomsAn aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms; h11～H20、H22Any one of the above groups can be independently selected from aryl with 6-18 carbon atoms; f1～F4Any one of the above groups can be independently selected from hydrogen and aryl with 6-18 carbon atoms;
hkis a substituent HkK is any integer of 11-19 and 21; wherein, when k is 17, hkSelected from 0, 1,2 or 3; when k is selected from 12, 15, 16, 18 or 21, hkSelected from 0, 1,2, 3 or 4; when k is 14, hkSelected from 0, 1,2, 3,4 or 5; when k is 13, hkSelected from 0, 1,2, 3,4, 5 or 6; when k is selected from 10 or 19, hkSelected from 0, 1,2, 3,4, 5, 6 or 7; when k is 11, hkSelected from 0, 1,2, 3,4, 5, 6, 7, 8 or 9; when h is generatedkWhen greater than 1, any two HkThe same or different;
K1is selected from N (H)28)、C(H23H24)、Si(H23H24) (ii) a Wherein H28、H23、H24Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, or the above H23And H24Atoms that are linked to each other to be commonly bound to them form a ring;
K2selected from single bond, C (H)26H27)、Si(H26H27) (ii) a Wherein H25、H26、H27Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, or the above H26And H27The atoms that are linked to each other to be commonly linked to them form a ring.
10. The heterocyclic compound according to claim 6, characterized in that Ar is selected from the group consisting of:
Figure FDA0002849180100000041
wherein Ar is1And Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-18 carbon atoms, substituted or unsubstituted heteroaryl with 6-15 carbon atoms; ar (Ar)3Selected from substituted or unsubstituted aryl groups having 6 to 15 carbon atoms; ar (Ar)1To Ar3Wherein the substituents are independently selected from fluorine, deuterium, cyano, alkyl having 1 to 4 carbon atoms, phenyl, cyclopentyl, and cyclohexyl;
preferably, Ar3Selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted biphenyl.
11. The heterocyclic compound according to claim 6, characterized in that Ar is selected from the group consisting of:
Figure FDA0002849180100000042
12. the heterocyclic compound according to claim 6, characterized in that,
Figure FDA0002849180100000043
selected from the group consisting of:
Figure FDA0002849180100000051
13. the heterocyclic compound according to claim 6,
Figure FDA0002849180100000052
is unsubstitutedWherein the unsubstituted group Q is selected from the group consisting of:
Figure FDA0002849180100000053
wherein represents an unsubstituted group Q and
Figure FDA0002849180100000054
is bonded to Ar is an unsubstituted group Q.
14. The heterocyclic compound according to any one of claims 1 to 13, which is selected from the group consisting of:
Figure FDA0002849180100000055
Figure FDA0002849180100000061
Figure FDA0002849180100000071
Figure FDA0002849180100000081
Figure FDA0002849180100000091
Figure FDA0002849180100000101
Figure FDA0002849180100000111
Figure FDA0002849180100000121
Figure FDA0002849180100000131
Figure FDA0002849180100000141
Figure FDA0002849180100000151
Figure FDA0002849180100000161
Figure FDA0002849180100000171
Figure FDA0002849180100000181
Figure FDA0002849180100000191
Figure FDA0002849180100000201
Figure FDA0002849180100000211
Figure FDA0002849180100000221
Figure FDA0002849180100000231
15. an organic electroluminescent device, comprising an anode and a cathode which are oppositely arranged, and a functional layer which is arranged between the anode and the cathode;
the functional layer comprises the heterocyclic compound according to any one of claims 1 to 14.
16. The organic electroluminescent device according to claim 15, wherein the functional layer comprises an organic light-emitting layer containing the heterocyclic compound;
preferably, the host material of the organic light emitting layer is the heterocyclic compound.
17. An electronic device comprising an electromechanical electroluminescent device according to claim 15 or 16.
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