CN111004207A - Organic compound, electronic device, and electronic apparatus - Google Patents

Organic compound, electronic device, and electronic apparatus Download PDF

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CN111004207A
CN111004207A CN201911320582.0A CN201911320582A CN111004207A CN 111004207 A CN111004207 A CN 111004207A CN 201911320582 A CN201911320582 A CN 201911320582A CN 111004207 A CN111004207 A CN 111004207A
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carbon atoms
group
substituted
independently selected
unsubstituted
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李健
沙荀姗
喻超
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Priority to CN201911320582.0A priority Critical patent/CN111004207A/en
Priority to CN202010270448.0A priority patent/CN111303113B/en
Publication of CN111004207A publication Critical patent/CN111004207A/en
Priority to PCT/CN2020/122968 priority patent/WO2021120838A1/en
Priority to US17/623,844 priority patent/US11605784B2/en
Priority to KR1020217042824A priority patent/KR102397562B1/en
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Abstract

The present application relates to an organic compound, and an electronic device comprising the organic compound and an electronic apparatus comprising the electronic device. The main body of the organic compound is a condensed heteroaromatic ring group containing fluorene or silafluorene, a large plane structure is shown in a three-dimensional space, and an arylamine or heteroaromatic amine substituent group rich in electrons is introduced to the 9 th site of the fluorene or silafluorene group, so that the hole transport performance of the compound is excellent.

Description

Organic compound, electronic device, and electronic apparatus
Technical Field
The present application relates to the technical field of organic compounds, and in particular, to an organic compound, an electronic device, and an electronic apparatus.
Background
An Organic Light Emitting Device (OLED) is a self-luminous Light Emitting device. The principle of the method is that when an electric field is applied to the anode and the cathode, holes on the anode side and electrons on the cathode side move to the light emitting layer and are combined to form excitons on the light emitting layer, the excitons are in an excited state and release energy outwards, and the excitons emit light outwards in the process of changing the energy released from the excited state to the energy released from the ground state. Therefore, it is important to improve the recombination of electrons and holes in the OLED device.
In order to improve the luminance, efficiency and lifetime of organic electroluminescent devices, a multilayer structure is generally used in the devices. These multilayer structures include: a hole injection layer (hole injection layer), a hole transport layer (hole transport layer), an electron blocking layer (electron-blocking layer), a light emitting layer (emitting layer), and an electron transport layer (electron transport layer). These organic layers have the ability to increase the efficiency of carrier (hole and electron) injection between the interfaces of the layers, balancing carrier transport between the layers, and thus increasing the brightness and efficiency of the device.
However, the currently commercialized OLED device still has many problems such as high driving voltage, low light emitting efficiency, poor thermal stability, short lifetime, especially in the case of the blue OLED device, and thus, the development of the OLED device and related materials having low driving voltage, high light emitting efficiency, high thermal stability, and long lifetime has become a problem that has to be overcome in the current organic electroluminescence field.
Chinese patent No. CN201510472766.4, an organic compound and its use, and an organic electroluminescent device, discloses a compound capable of improving the luminous efficiency of an organic electroluminescent device, but there is still a need to continuously develop new compounds applied to organic electroluminescent devices to further improve the performance of electronic devices.
Disclosure of Invention
An object of the present invention is to provide an organic compound having excellent carrier transport properties, and to provide an organic electroluminescent electronic device comprising the organic compound, which has a lower driving voltage, a higher luminous efficiency and a longer service life, and an electronic apparatus comprising the electronic device.
According to one aspect of the present application, there is provided an organic compound having the structure of formula i:
Figure BDA0002327037290000011
wherein X is selected from C or Si;
Y1and Y2Identical or different, each independently selected from O or S;
R1and R2Each independently selected from hydrogen, deuterium or the following groups: a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a pharmaceutically acceptable carrier, a pharmaceutically,
Figure BDA0002327037290000021
And R is1And R2At least one of them is
Figure BDA0002327037290000022
Each Ar1And Ar2The same or different, each is independently selected from one of hydrogen, deuterium, a substituted or unsubstituted aralkyl group having 7 to 25 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms;
L1and L2The same or different, each is independently selected from one of single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 1-30 carbon atoms, and when R is1Is composed of
Figure BDA0002327037290000023
When L is1Not a single bond, when R2Is composed of
Figure BDA0002327037290000024
When L is2Is not a single bond;
ar is1，Ar2，L1，L2The substituents are the same or different and are independently selected from deuterium, a halogen group, cyano, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkylthio having 1 to 12 carbon atoms, haloalkyl having 1 to 12 carbon atoms, and tri-alkyl having 3 to 12 carbon atomsAlkylsilyl group, cycloalkyl group having 3 to 12 carbon atoms, aryloxy group having 6 to 18 carbon atoms, arylthio group having 6 to 18 carbon atoms, aryl group having 6 to 18 carbon atoms and aryl group having 3 to 18 carbon atoms.
According to another aspect of the present application, there is provided an electronic 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 organic compound described above.
According to a third aspect of the present application, there is provided an electronic apparatus comprising the above-described electronic device.
The main body of the organic compound is a condensed heteroaromatic ring group containing fluorene or silafluorene, the condensed heteroaromatic ring group shows a large plane structure in a three-dimensional space, and an arylamine or heteroaromatic amine substituent group rich in electrons is introduced to the 9 th site of the fluorene or silafluorene group, so that the hole transmission performance of the compound is excellent. The reason for this is that the hyperconjugated system formed by the main structure enhances the ability of the carrier to cross between different molecules. When the organic compound of the present application is used for a functional layer of an electronic device, the electronic device has characteristics of high luminous efficiency, low voltage, and long life.
The electronic device including the electronic device has the characteristics of high luminous efficiency, low voltage and long service life.
Drawings
Objects, technical solutions 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.
Fig. 3 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.
Fig. 4 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
The main device reference numbers in the figure are explained as follows:
100. an anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320. a hole transport layer; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 360. a photoelectric conversion layer; 400. an electronic device; 500. 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.
The terms "optional" or "optionally" mean 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" means that an alkyl may, but need not, be present, and the description includes the scenario where the heterocyclic group is substituted with an alkyl and the scenario where the heterocyclic group is not substituted with an alkyl. "optionally, R is attached to the same atomeAnd RfMay be linked to each other to form a saturated or unsaturated 5-to 10-membered aliphatic ring "means that R is attached to the same atomeAnd RfCan form a ring but does not have to form a ring, including ReAnd RfThe scenario of being interconnected to form a 5 to 10 membered aliphatic ring, saturated or unsaturated, also includes ReAnd RfScenarios that exist independently of each other.
In the context of the present application, it is,
Figure BDA0002327037290000031
refers to a position bonded to other substituents or bonding positions.
Description adopted in this applicationThe terms "… … independently" and "… … independently" and "… … independently selected from" are used interchangeably and are to be understood broadly to mean that the particular items expressed between the same symbols in different groups do not affect each other or that the particular items expressed between the same symbols in the same groups do not affect each other. For example, as "
Figure BDA0002327037290000032
Wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced with each other.
In the present application, the term "substituted or unsubstituted" means either no substituent or substituted with one or more substituents. Such substituents include, but are not limited to, deuterium (D), halogen groups (F, Cl, Br), cyano, alkyl, alkenyl, alkynyl, haloalkyl, aryl, heteroaryl, aryloxy, arylthio, silyl, alkylamino, arylamino, cycloalkyl, heterocyclyl, boranyl, phosphino.
"alicyclic ring" herein encompasses saturated cycloalkyl and partially unsaturated cycloalkyl groups, e.g., saturated cycloalkyl, cyclopentyl, cyclohexyl, adamantyl, and the like, partially unsaturated cycloalkyl, cyclobutene, and the like.
Herein, the "hetero" means that 1 to 3 hetero atoms selected from the group consisting of B, N, O, S, Se, Si and P are included in one functional group and the rest are carbon.
Wherein, in the present application, "alkyl" or "alkyl group" means a saturated, straight-chain or branched, monovalent hydrocarbon group containing 1 to 20 carbon atoms, wherein the alkyl group may be optionally substituted with one or more substituents described herein. Removing deviceUnless otherwise specified, the alkyl group contains 1 to 20 carbon atoms. In some embodiments, the alkyl group may contain 1 to 10 carbon atoms, in other embodiments, the alkyl group contains 1 to 6 carbon atoms; in still other embodiments, the alkyl group contains 1 to 4 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl (Me, -CH)3) Ethyl group (Et, -CH)2CH3) N-propyl (n-Pr, -CH)2CH2CH3) Isopropyl group (i-Pr, -CH (CH)3)2) N-butyl (n-Bu, -CH)2CH2CH2CH3) Isobutyl (i-Bu, -CH)2CH(CH3)2) Sec-butyl (s-Bu, -CH (CH)3)CH2CH3) Tert-butyl (t-Bu, -C (CH)3)3) And the like.
In the present application, the term "aryl" is used interchangeably with the term "aromatic ring" and refers to a single ring structure formed from a plurality of carbon atoms or a bicyclic or polycyclic ring system formed from a plurality of carbon atoms wherein at least one aromatic ring system is included and wherein each ring system may contain from 3 to 7 atoms, i.e., the aryl group may be a monocyclic aryl or polycyclic aryl group. In other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bond conjugation, monocyclic and fused ring aryl groups joined by carbon-carbon bond conjugation, two or more fused ring aryl groups joined by carbon-carbon bond conjugation. That is, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as an aryl group in the present application. For example, biphenyl, terphenyl, and the like are aryl groups in this application. An "aryl" group herein may contain from 6 to 30 carbon atoms, in some embodiments the number of carbon atoms in the aryl group may be from 6 to 25, in other embodiments the number of carbon atoms in the aryl group may be from 6 to 18, and in other embodiments the number of carbon atoms in the aryl group may be from 6 to 13. For example, the number of carbon atoms may be 6, 12, 13, 18, 20, 25 or 30, and of course, other numbers may be used, which are not listed here.
In the present application, the aryl group having 6 to 20 ring-forming carbon atoms means that the number of carbon atoms located on the aromatic ring in the aryl group is 6 to 20, and the number of carbon atoms in the substituent on the aryl group is not counted. The number of cyclic carbon atoms in the aryl group may be 6 to 20, 6 to 18, 6 to 14, or 6 to 10, but is not limited thereto.
Examples of the aryl group may include phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, fluoranthenyl, pyrenyl, benzofluoranthenyl,
Figure BDA0002327037290000041
Perylene, etc., without being limited thereto.
In this application, the ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl. The 6-to 10-membered aromatic ring means a benzene ring and a naphthalene ring.
As used herein, an "aryl" group may have one or more attachment points to the rest of the molecule. In this application, the explanation for aryl groups applies to arylene groups.
In this application, substituted aryl refers to an aryl group in which one or more hydrogen atoms are replaced by a group thereof, for example, at least one hydrogen atom is replaced by a deuterium atom, F, Cl, Br, CN, amino, alkyl, haloalkyl, cycloalkyl, aryloxy, arylthio, silyl, alkylamino, arylamino, boryl, phosphino, or other group.
It is understood that "substituted C6-C30 aryl," i.e., a substituted aryl group having 6 to 30 carbon atoms, refers to aryl groups and the total number of carbon atoms in the substituents on the aryl group being 6 to 30. The aryl group having 6 to 18 ring-forming carbon atoms means that the number of carbon atoms located on the aromatic ring in the aryl group is 6 to 18, and the number of carbon atoms in the substituent on the aryl group is not counted. The number of cyclic carbon atoms in the aryl group may be 6 to 30, 6 to 18, or 6 to 13, but is not limited thereto. Illustratively, the fluorenyl group is an aryl group having 13 ring-forming carbon atoms, and 9, 9-dimethylfluorenyl group is a substituted aryl group having 15 carbon atoms.
The term "heteroaryl" is monocyclic, bicyclic, and polycyclic ring systems wherein at least one ring system is aromatic and at least one aromatic ring system contains one or more heteroatoms selected from the group consisting of B, O, N, P, Si, Se, and S, wherein each ring system contains a ring of 5 to 7 atoms with one or more attachment points to the rest of the molecule. In the present application, the number of carbon atoms of the heteroaryl group may be 3 to 30, or 3 to 18, or 3 to 12. 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 may include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiadiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzosilyl, dibenzofuranyl, and the like. Wherein, thienyl, furyl, phenanthroline and the like are heteroaryl of a single aromatic ring system, and N-aryl carbazolyl, N-heteroaryl carbazolyl, phenyl-substituted dibenzofuryl, pyridine-substituted pyridyl and the like are heteroaryl of a plurality of aromatic ring systems connected by carbon-carbon bond conjugation.
In this application, substituted heteroaryl refers to heteroaryl groups in which one or more hydrogen atoms are replaced by a group thereof, for example at least one hydrogen atom is replaced by a deuterium atom, F, Cl, Br, CN, amino, alkyl, haloalkyl, cycloalkyl, aryloxy, arylthio, silyl, alkylamino, arylamino, boryl, phosphino, or other group.
It is understood that a "heteroaryl" group may have one, two, or more bonds to the rest of the molecule.
It is understood that "substituted heteroaryl of C3-C30," i.e., a substituted heteroaryl group of 3-30 carbon atoms, refers to heteroaryl and heteroaryl groups having a total number of 3-30 carbon atoms in the substituent group.
The heteroaryl group having a carbon number of 3 to 18 as a ring-forming carbon means that the number of carbon atoms located on the heteroaryl ring in the heteroaryl group is 3 to 18, and the number of carbon atoms in the substituent on the heteroaryl group is not counted. The number of carbon atoms on the heteroaryl group may be 3 to 18, 4 to 18, 3 to 12, 3 to 8, but is not limited thereto.
An delocalized bond in the present application refers to a single bond extending from a ring system
Figure BDA0002327037290000051
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 (X), naphthyl represented by the formula (X) is connected to 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 (X-1) to the formula (X-7) includes any possible connecting mode shown in the formula (X-1) to the formula (X-7).
Figure BDA0002327037290000052
For example, as shown in the following formula (X '), the phenanthryl group represented by the formula (X') is bonded to the rest of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the phenanthryl group includes any of the possible bonding modes as shown in the formulas (X '-1) to (X' -4).
Figure BDA0002327037290000053
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 BDA0002327037290000061
In this application, the explanation for aryl is applicable to arylene, and the explanation for heteroaryl is also applicable to heteroarylene.
The application provides an organic compound, the structure of which is shown in chemical formula I:
Figure BDA0002327037290000062
wherein X is selected from C or Si;
Y1and Y2Identical or different, each independently selected from O or S;
R1and R2Each independently selected from hydrogen, deuterium or the following groups: a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a pharmaceutically acceptable carrier, a pharmaceutically,
Figure BDA0002327037290000063
And R is1And R2At least one of them is
Figure BDA0002327037290000064
Each Ar1And Ar2The same or different, each is independently selected from one of hydrogen, deuterium, a substituted or unsubstituted aralkyl group having 7 to 25 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms;
L1and L2Identical or different, each independently selected from the group consisting of a single bond, substituted or unsubstitutedOne of arylene having 6 to 30 carbon atoms and substituted or unsubstituted heteroarylene having 1 to 30 carbon atoms, and when R is1Is composed of
Figure BDA0002327037290000071
When L is1Not a single bond, when R2Is composed of
Figure BDA0002327037290000072
When L is2Is not a single bond;
ar is1，Ar2，L1，L2The substituents on the above groups are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms and a heteroaryl group having 3 to 18 carbon atoms.
In some embodiments, the organic compound of formula i described herein is selected from the following compounds:
Figure BDA0002327037290000073
in some embodiments, L in the compounds of formula I described herein1And L2The same or different, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroarylene group having 4 to 18 carbon atoms.
In some embodiments, L in the compounds of formula I described herein1And L2The same or different, each independently selected from a single bond, or substituted as follows:
Figure BDA0002327037290000074
in the above-mentioned groups, the compounds of formula,x is selected from O, S, Se, C (R)3R4)、N(R5) And Si (R)3R4) The group of;
X1、X2、X3、X4、X5each independently selected from CR6And N, and X1～X5At least one of which is N;
each X6～X15Are each independently selected from CR6And N, when one group contains two or more R6When there are two arbitrary R6The same or different;
each Z1、Z2、R3、R4And R6Each independently selected from the group consisting of hydrogen, deuterium, fluorine, chlorine, bromine, cyano, alkyl having 1 to 6 carbon atoms, haloalkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, aryloxy having 6 to 18 carbon atoms, arylthio having 6 to 18 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 3 to 12 carbon atoms, silyl having 3 to 12 carbon atoms and cycloalkyl having 3 to 10 carbon atoms; or,
optionally, R attached to the same atom3And R4Are linked to each other to form a saturated or unsaturated 5-to 10-membered aliphatic ring; meaning, R in this application3And R4May be linked together with the atoms to which they are both attached to form an alicyclic ring, or R3And R4Each independently exists;
R5selected from the group consisting of hydrogen, alkyl having 1 to 6 carbon atoms, haloalkyl having 1 to 6 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 3 to 12 carbon atoms and cycloalkyl having 3 to 10 carbon atoms;
each n is1Independently selected from 0, 1,2, 3,4 or 5, each n2Independently selected from 0, 1,2, 3,4, 5, 6 or 7.
In some more specific embodiments, L in the compounds of formula I described herein1And L2The same or different, each independently selected from the group consisting of a single bond, substituted or unsubstituted:
Figure BDA0002327037290000091
wherein,
Figure BDA0002327037290000092
the above groups are used in the formula I
Figure BDA0002327037290000093
The position of the connecting key; the above groups are optionally substituted with 0, 1,2, 3,4 or 5 substituents selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, propoxy, cyclopentyl, cyclohexyl, trifluoromethyl, alkylsilyl groups of 3 to 9 carbon atoms. In the present application, however, L in the compounds of the formula I1And L2And is not limited to the above structure.
In some embodiments, each Ar in the compounds of formula I described herein is1、Ar2、R1And R2The same or different, and is selected from one of substituted or unsubstituted aryl with 6-25 carbon atoms and substituted or unsubstituted heteroaryl with 4-18 carbon atoms.
In some embodiments, each Ar in the compounds of formula I described herein is1、Ar2、R1And R2The same or different and each is independently selected from hydrogen, deuterium, substituted or unsubstituted:
Figure BDA0002327037290000101
each V1～V10And V12～V16Are each independently selected from CR8And N, and V1～V5At least one of which is N;
in the above groups, each V is independently selected from O, S, Se, N (R)7)、C(R9R10) And Si (R)9R10) The group of;
y and V11Each independently selected from O, S or N (R)7)；
Each Y is1～Y10Are each independently selected from CR8And N, when one group contains two or more R8When there are two arbitrary R8The same or different;
each R9、R10、R8Independently represent hydrogen, deuterium, fluorine, chlorine, bromine, cyano, alkyl with 1-6 carbon atoms, haloalkyl with 1-6 carbon atoms, aryl with 6-12 carbon atoms, heteroaryl with 3-12 carbon atoms, aryloxy with 6-18 carbon atoms, arylthio with 6-18 carbon atoms, silyl with 3-12 carbon atoms, alkylamino with 1-10 carbon atoms, arylamino with 6-18 carbon atoms and cycloalkyl with 3-10 carbon atoms;
R7selected from the group consisting of H, alkyl having 1 to 6 carbon atoms, haloalkyl having 1 to 6 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 3 to 12 carbon atoms and cycloalkyl having 3 to 10 carbon atoms; or,
optionally, two adjacent R8Can form an aromatic ring with 6-10 ring-forming atoms or a heteroaromatic ring with 5-12 ring-forming atoms together with the carbon atoms connected with the aromatic ring and the heteroaromatic ring; meaning two adjacent R in this application8May be linked to each other together with the atoms to which they are attached to form an aromatic or heteroaromatic ring, or each R may be8Independently exist;
optionally, R attached to the same atom9And R10May be linked to each other to form a saturated or unsaturated 5-to 10-membered aliphatic ring; meaning, R in this application9And R10May be bonded to each other with the atoms to which they are bonded to form an aliphatic ring, or may not form a ring, but R is9And R10Independently exist;
each of Ar mentioned above1And Ar2Optionally substituted by 0, 1,2, 3,4 or 5 substituents selected from deuterium, fluorine, chlorine, cyano, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 18 carbon atoms, and hetero having 3 to 18 carbon atomsAryl, alkoxy having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, and alkylsilyl having 3 to 9 carbon atoms.
In some embodiments, each Ar in the compounds of formula I described herein is1、Ar2、R1And R2The same or different and each is independently selected from hydrogen, deuterium, substituted or unsubstituted:
Figure BDA0002327037290000111
Figure BDA0002327037290000121
each of the foregoing groups is optionally substituted with 0, 1,2, 3,4, or 5 substituents selected from deuterium, fluorine, chlorine, cyano, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, alkylsilyl having 3 to 9 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 18 carbon atoms, and heteroaryl having 3 to 18 carbon atoms.
In some more specific embodiments, Ar in the compounds of formula I described herein1、Ar2The same or different and are each independently selected from hydrogen, deuterium, substituted or unsubstituted groups as follows:
Figure BDA0002327037290000122
Figure BDA0002327037290000131
the above groups are optionally substituted with 0, 1,2, 3,4 or 5 substituents selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, propoxy, cyclopentyl, cyclohexyl, trifluoromethyl, alkylsilyl groups of 3 to 9 carbon atoms.
In addition toIn some embodiments, in the present application, Ar in the compound of formula I1、Ar2And is not limited to the above groups.
Further, R in the compounds of formula I as described herein1And R2The same or different and each is independently selected from hydrogen, deuterium, substituted or unsubstituted:
Figure BDA0002327037290000141
the above groups are optionally substituted with 0, 1,2, 3,4 or 5 substituents selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, propoxy, cyclopentyl, cyclohexyl, trifluoromethyl, alkylsilyl groups of 3 to 9 carbon atoms.
In other embodiments, R in the compounds of formula I herein1、R2And is not limited to the above groups.
Further, the specific structure of the compound of formula i is selected from any one of the following, but not limited thereto:
Figure BDA0002327037290000142
Figure BDA0002327037290000151
Figure BDA0002327037290000161
Figure BDA0002327037290000171
Figure BDA0002327037290000181
Figure BDA0002327037290000191
Figure BDA0002327037290000201
Figure BDA0002327037290000211
Figure BDA0002327037290000221
Figure BDA0002327037290000231
Figure BDA0002327037290000241
Figure BDA0002327037290000251
Figure BDA0002327037290000261
the present application also provides an electronic device comprising an anode and a cathode disposed opposite one another, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound described above.
The organic compound provided herein may be used to form at least one organic film layer in a functional layer to improve voltage characteristics, efficiency characteristics, and lifetime characteristics of an electronic device. Optionally, an organic film layer containing the organic compounds of the present application is positioned between the anode and the energy conversion layer of the electronic device in order to improve the transport of electrons between the anode and the energy conversion layer. Further, the functional layer includes a hole transport layer including the organic compound described above.
For example, the electronic device may be 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 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises an organic compound as provided herein.
Alternatively, the organic compound provided herein may be used to form at least one organic thin layer in the functional layer 300 to improve the lifetime characteristics, efficiency characteristics, and reduce the driving voltage of the organic electroluminescent device; in some embodiments, the electrochemical stability and thermal stability of the organic electroluminescent device can also be improved, and the uniformity of the performance of the organic electroluminescent device in mass production can be improved.
Alternatively, the functional layer 300 includes a hole transport layer 320, the hole transport layer 320 including an organic compound provided herein. The hole transport layer 320 may be made of an organic compound provided herein, or may be made of an organic compound provided herein and other materials.
Optionally, the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322, and the first hole transport layer 321 is disposed on the surface of the second hole transport layer 322 close to the anode 100; the first hole transport layer 321 or the second hole transport layer 322 includes an organic compound provided herein. Here, one of the first hole transporting layer 321 and the second hole transporting layer 322 may contain an organic compound provided herein, or both the first hole transporting layer 321 and the second hole transporting layer 322 may contain an organic compound provided herein. It is to be understood that the first hole transport layer 321 or the second hole transport layer 322 may or may not contain other materials. It is understood that, in another embodiment of the present application, the second hole transport layer 322 may serve as an electron blocking layer of the organic electroluminescent device.
In one embodiment of the present application, as shown in fig. 1, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330, an electron transport layer 340, and a cathode 200, which are sequentially stacked. The organic compound provided by the application can be applied to the first hole transport layer 321 or the second hole transport layer 322 of the organic electroluminescent device, and can effectively improve the hole characteristics of the organic electroluminescent device. Here, the hole characteristics mean that holes formed in the anode 100 are easily injected into the organic light emitting layer 330 and are transported in the organic light emitting layer 330 according to conduction characteristics of HOMO level.
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 the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide, e.g. ZnO Al or SnO2Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, or may include a host material and a guest material. Optionally, the organic light emitting layer 330 is composed of a host material and a guest material, and a hole injected into the organic light emitting layer 330 and an electron injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form an exciton, and the exciton transfers energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.
The host material of the organic light emitting layer 330 may be a metal chelate octyl compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which are not particularly limited in the present application, in one embodiment of the present application, the host material of the organic light emitting layer 330 may be cbp, in another embodiment of the present application, the host material of the organic light emitting layer 330 may be α -ADN.
The guest material of the organic light emitting layer 330 may beA compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application. In one embodiment of the present application, the guest material of the organic light emitting layer 330 may be Ir (piq)2(acac). In another embodiment of the present application, the guest material of the organic light emitting layer 330 may be BD-1.
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, and the electron transport material may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which is not particularly limited in this application. For example, in one embodiment of the present application, the electron transport layer 340 may be composed of DBimiBphen and LiQ.
Alternatively, the cathode 200 comprises a cathode material that is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include: 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 BaF2But not limited thereto,/Ca. Preferably, a metal electrode comprising aluminum is included as a cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. In one embodiment of the present application, the hole injection layer 310 may be composed of m-MTDATA.
Optionally, the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322, and the first hole transport layer 321 is disposed on the surface of the second hole transport layer 322 close to the anode 100; the first hole transport layer 321 or the second hole transport layer 322 includes an organic compound provided herein. Here, one of the first hole transporting layer 321 and the second hole transporting layer 322 may contain an organic compound provided herein, or both the first hole transporting layer 321 and the second hole transporting layer 322 may contain an organic compound provided herein. It is to be understood that the first hole transport layer 321 or the second hole transport layer 322 may or may not contain other materials.
Optionally, the hole transport layer 320 may further include an inorganic doping material to improve the hole transport property of the hole transport layer 320.
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. In one embodiment of the present application, the electron injection layer 350 may include Yb.
As another example, the electronic device may be a photoelectric conversion device, as shown in fig. 3, which may include an anode 100 and a cathode 200 oppositely disposed, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises an organic compound as provided herein.
Alternatively, the organic compound provided herein may be used to form at least one organic thin layer in the functional layer 300 to improve the performance of the photoelectric conversion device, in particular, to improve the lifetime of the photoelectric conversion device, to improve the open circuit voltage of the photoelectric conversion device, or to improve the uniformity and stability of the performance of the photoelectric conversion device in mass production.
Alternatively, the functional layer 300 includes a hole transport layer 320, and the hole transport layer 320 includes the organic compound of the present application. The hole transport layer 320 may be made of an organic compound provided herein, or may be made of an organic compound provided herein and other materials. It is understood that the hole transport layer 320 may or may not contain other materials.
Optionally, the hole transport layer 320 may further include an inorganic doping material to improve the hole transport property of the hole transport layer 320.
In one embodiment of the present application, as shown in fig. 3, the photoelectric conversion device may include an anode 100, a hole transport layer 320, a photoelectric conversion layer 360 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Alternatively, the photoelectric conversion device may be a solar cell, and particularly may be an organic thin film solar cell. For example, in one embodiment of the present application, the solar cell includes an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are sequentially stacked, wherein the hole transport layer 320 includes the organic compound of the present application.
Embodiments of the present application further provide an electronic device including any one of the electronic devices described in the above electronic device embodiments. Since the electronic device has any one of the electronic devices described in the above electronic device embodiments, the electronic device has the same beneficial effects, and the details of the electronic device are not repeated herein.
For example, as shown in fig. 2, the present application provides an electronic device 400, and the electronic device 200 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.
By way of further example, as shown in fig. 4, the present application provides an electronic device 500, where the electronic device 500 includes any one of the organic electroluminescent devices described in the above-mentioned organic electroluminescent device embodiments. The electronic device 500 may be a solar power generation device, a light detector, a fingerprint recognition device, a light module, a CCD camera, or other types of electronic devices. Since the electronic device 500 has any one of the photoelectric conversion devices described in the above embodiments of the photoelectric conversion device, the same advantages are obtained, and details are not repeated herein.
The present application will be described in detail below with reference to examples, but the following description is intended to explain the present application, and not to limit the scope of the present application in any way.
Synthetic examples
Synthesis of Compound1
Figure BDA0002327037290000281
The method comprises the following steps: a mixture of 3.95g (15mmol) of 1-bromodibenzodioxin, 2.71g (15mmol) of 2- (methoxycarbonyl) phenylboronic acid, 4.14g (30mmol) of potassium carbonate, 0.1733g (0.15mmol) of tetrakis (triphenylphosphine) palladium and 0.0483g (0.15mmol) of tetrabutylammonium bromide was placed in a 100mL three-necked flask, a mixed solvent of 32mL/8mL of toluene/water was added to the flask, the air in the flask was replaced with nitrogen, the flask was heated to 80 ℃ with stirring for 10 hours, the reaction mixture was washed with water and dried with anhydrous magnesium sulfate, the organic phase was distilled under reduced pressure to remove toluene, the resulting oily solid was washed with ethanol once, and recrystallized from a mixed solvent of dichloromethane and n-heptane (1:5) to give compound 1-1(compound 1-1) (3.63g, yield 76%).
Figure BDA0002327037290000291
Step two: 3.2g (10mmol) of compound 1-1 and 30mL of tetrahydrofuran were put in a 100mL three-necked flask, 4.8g of methanesulfonic acid was slowly added with stirring, and after completion of the addition, the mixture was heated to 60 ℃ to react for 5 hours, 50mL of water was added to the reaction solution, the reaction solution was extracted with dichloromethane, the organic phase was dried over magnesium sulfate and then distilled under reduced pressure, and the obtained solid was boiled with n-heptane, whereby compound 1-2(compound 1-2) (2.2g, yield 77%) was obtained.
Figure BDA0002327037290000292
Step three: adding 1.15g (7.3mmol) of bromobenzene and 10mL of dried tetrahydrofuran into a 100mL three-neck flask, cooling to-30 ℃ under stirring, slowly dropwise adding 3.85mL (7.7mmol) of n-butyllithium n-hexane solution with the concentration of 2mol/L under the protection of nitrogen, preserving heat for 30min after dropwise adding, then slowly dropwise adding a mixed solution of 2.2g (7.7 mol) of compound 1-2 and 10mL of tetrahydrofuran, preserving heat for 30min after dropwise adding, continuing stirring for 2h after naturally rising to room temperature, dropwise adding water to quench the reaction, extracting the reaction solution with ethyl acetate, drying an organic phase with magnesium sulfate and then distilling under reduced pressure, recrystallizing the obtained solid with a mixed solution of dichloromethane and n-heptane (1:5), and obtaining the compound 1-3(compound 1-3) (2.1g, yield is 78%).
Figure BDA0002327037290000293
Step four: 2.1g (5.8mmol) of the compound 1-3, 20mL of toluene and 5mL of hydrobromic acid (47%) were put in a 100mL three-necked flask, stirred at room temperature for 24 hours under nitrogen, separated, the reaction solution was extracted with toluene, the organic phase was dried over magnesium sulfate and distilled under reduced pressure, and the resulting solid was recrystallized from dichloromethane and n-heptane (1:3) to obtain the compound 1-4(compound2-4) (2.07g, yield 84%).
Figure BDA0002327037290000301
Step five: under a nitrogen atmosphere, a mixture of 2.07g (4.8mmol) of compound1 to 4, 0.76g (4.8g mmol) of p-chlorobenzoic acid, 0.028g (0.024mmol) of tetrakis (triphenylphosphine) palladium, 0.008g (0.024mmol) of tetrabutylammonium bromide and 1.34g (9.7mmol) of potassium carbonate was put in a 100mL three-necked flask, a mixed solvent of 16mL/4mL of toluene/water was added to the flask, and the mixture was heated to 80 ℃ with stirring to react for 15 hours, the reaction solution was washed with water, then extracted with toluene, the organic phase was dried over magnesium sulfate, the solvent was removed by distillation under reduced pressure, and the resulting solid was washed with ethanol once and recrystallized from dichloromethane to give compound1 to 5(compound 1 to 5) (1.76g, yield 79%).
Figure BDA0002327037290000302
Step six: a mixture of 1.76g (3.8mmol) of compound 1-5, 0.65g (3.8mmol) of diphenylamine, 0.018g (0.019mmol) of tris (dibenzylideneacetone) dipalladium, 0.016g (0.038mmol) of 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl, and 0.55g (5.7mmol) of sodium tert-butoxide was charged in a 100mL three-necked flask under a nitrogen atmosphere, 20mL of toluene was added to the flask, and the mixture was heated under stirring to reflux for 5 hours, quenched with water, extracted with toluene, the organic phase was dried with magnesium sulfate, the solvent was removed by distillation under reduced pressure, and the resulting solid was separated by silica gel column chromatography using a mixed solvent of dichloromethane and n-heptane (1:4) to give compound 1(compound 1) (1.99g, yield 88%). The structure of the obtained compound was confirmed by LC-MS. LCMS M/z 592.2[ M + H ]]+
Synthesis of Compound2
Figure BDA0002327037290000303
The method comprises the following steps: 3.19g (10mmol) of the compound 1-1 was put into a 100mL three-necked flask, nitrogen gas was introduced to replace the air in the clean flask, 20mL of dried tetrahydrofuran was added, the reaction mixture was cooled to-40 ℃ with stirring, 10mL of a 2mol/L p-chlorophenyl magnesium bromide (n-hexane) Grignard reagent was slowly added dropwise while maintaining the temperature at-40 ℃ until the addition was completed, the reaction mixture was naturally warmed to room temperature and reacted for 2 hours, the reaction mixture was quenched with an aqueous ammonium chloride solution, the reaction mixture was extracted with ethyl acetate, the organic phase was dried over magnesium sulfate and then the solvent was distilled off under reduced pressure, and the obtained solid compound2-2 (compound2-2) was directly put into the next reaction (4.4g, purity 83%) without purification.
Figure BDA0002327037290000311
Step two: 3.13g of Compound2-2 (purity 83%) and 30mL of acetic acid were put in a 100mL three-necked flask, and 3mL of concentrated sulfuric acid was slowly added dropwise with stirring, and then heated to 80 ℃ to react for 8 hours, water was added to the reaction mixture and extracted with ethyl acetate, followed by liquid separation, drying of the organic phase over magnesium sulfate and distillation under reduced pressure, and the obtained solid was recrystallized from methylene chloride to give Compound2-3 (compound2-3) (1.63g, yield 65%).
Figure BDA0002327037290000312
Step three: a mixture of 1.63g (3.3mmol) of compound2-3, 1.12g (6.6mmol) of diphenylamine, 0.476g (4.96mmol) of sodium tert-butoxide, 0.0151g (0.016mmol) of tris (dibenzylideneacetone) dipalladium and 0.0136(0.033mmol) of 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl was placed in a 100mL three-necked flask, 20mL of toluene was added thereto, the flask was purged with nitrogen, the temperature was raised to 110 ℃ with stirring for 7 hours, the reaction solution was washed with water, separated, the organic phase was dried over magnesium sulfate and then distilled under reduced pressure, and the resulting solid was separated by silica gel column chromatography using dichloromethane and n-heptane (1:3) to give compound 2(compound2) (2.01g, yield 80%). The structure of the obtained compound was confirmed by LC-MS. LCMS M/z 759.3[ M + H ]]+
Synthesis of Compound 3
Figure BDA0002327037290000313
The method comprises the following steps: a mixture of 3g (10mmol) of 1-bromo-2-chlorodibenzodioxin, 1.58g (10mmol) of 2-chlorobenzeneboronic acid, 0.12g (0.1mmol) of tetrakis (triphenylphosphine) palladium, 0.033g (0.1mmol) of tetrabutylammonium bromide and 2.8g (20mmol) of potassium carbonate was placed in a 100mL three-necked flask, a mixed solvent of 20mL/5mL/5mL of toluene/ethanol/water was added to the flask, the temperature was raised to 80 ℃ under nitrogen protection and stirring for reaction for 12 hours, the reaction mixture was extracted with toluene, the organic phase was dried over magnesium sulfate and distilled under reduced pressure, the obtained solid was boiled with n-heptane, filtered and washed with a small amount of ethanol to obtain compound 3-1(compound 3-1) (2.6g, yield 78%).
Figure BDA0002327037290000321
Step two: under the protection of nitrogen, 2.54g (7.7mmol) of compound 3-1 is dissolved in 20mL of dried tetrahydrofuran, the temperature is reduced to-5 ℃ under stirring, 5mL (10mmol) of n-hexane solution (2M) of n-butyllithium is slowly added by a syringe, the temperature is preserved for 4 hours after dropwise adding, then the solution of 4-chlorophenyl-phenyldichlorosilane and 10mL of tetrahydrofuran is slowly dropwise added, the temperature is preserved for 1 hour after the dropwise adding, the solution is naturally raised to room temperature and stirred for reaction for 16 hours, after the reaction is finished, the reaction solution is poured into a dilute hydrochloric acid solution, a solid is separated out, filtered and a filter cake is dried, and the compound 3-2(compound 3-2) (2.87g, the purity is 77%) is directly put into the next reaction.
Figure BDA0002327037290000322
Step three: a mixture of 2.87g (purity 77%) of compound 3-2, 0.78g (4.6mmol) of diphenylamine, 0.042g (0.05mmol) of tris (dibenzylideneacetone) dipalladium, 0.038g (0.1mmol) of 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl, and 0.67g (6.9mmol) of sodium tert-butoxide was charged into a 100mL three-necked flask, the air in the flask was replaced with nitrogen gas, 30mL of toluene was added to the flask, the mixture was heated under stirring to reflux for 8 hours, water was added to the reaction mixture and stirred for 30min, the mixture was filtered, the filtrate was rinsed with ethanol and recrystallized from toluene to obtain compound 3(compound 3) (2.34g, yield 83%). The structure of the obtained compound was confirmed by LC-MS. LCMS M/z 608.2[ M + H ]]+
Synthesis of Compound4
Figure BDA0002327037290000323
The method comprises the following steps: a mixture of 2.7g (11mmol) of phenoxathiin-4-boronic acid, 2.38g (11mmol) of methyl 2-bromobenzoate, 3.06g (22mmol) of potassium carbonate, 0.1278g (0.1mmol) of tetrakis (triphenylphosphine) palladium and 0.0357g (0.1mmol) of tetrabutylammonium bromide was placed in a 100mL three-necked flask, a 20mL/10mL toluene/water mixed solvent was added to the flask, the air in the flask was replaced with nitrogen gas, the flask was heated to 80 ℃ with stirring to react for 6 hours, the reaction mixture was washed with water and dried over anhydrous magnesium sulfate, the organic phase was distilled under reduced pressure to remove toluene, and the resulting solid was recrystallized from ethyl acetate to give compound4-1 (compound4-1) (2.91g, 83%).
Figure BDA0002327037290000331
Step two: compound4 was synthesized in the same manner as in Steps two to five of the Synthesis of Compound1, except that Compound 1-1 in step two of the Synthesis of Compound1 was replaced with Compound4-1, to finally obtain 2.17g of Compound 4(compound4) in a yield of 63%. The structure of the obtained compound was confirmed by LC-MS. LCMS M/z 608.2[ M + H ]]+
Synthesis of Compound 5
Figure BDA0002327037290000332
Compound 5 was synthesized in the same manner as in the synthesis of Compound1 except that bromobenzene in step three of the synthesis of Compound1 was replaced with 2-bromodibenzothiophene, to give 1.96g of Compound 5(compound 5) in 71% yield. The structure of the obtained compound was confirmed by LC-MS. LCMS M/z 698.2[ M + H ]]+
Synthesis of Compound6
Figure BDA0002327037290000333
Compound6 was synthesized in the same manner as Compound1 except that bromobenzene in step three of the Synthesis of Compound1 was replaced with 4-bromobiphenyl and p-chlorobenzeneboronic acid in step five was replaced with 7-chlorodibenzofuran-3-boronic acid to give 2.33g of Compound 6(compound 6) in 58% yield. The structure of the obtained compound was confirmed by LC-MS. LCMS M/z 758.3[ M + H ]]+。
Synthesis of Compound 7
Figure BDA0002327037290000341
According toCompound 7 was synthesized in the same manner as in the synthesis of Compound 3 except that 4-chlorophenyl-phenyldichlorosilane was replaced with bis (4-chlorophenyl) -dichlorosilane in step two of the synthesis of Compound 3, to finally obtain 1.95g of Compound 7(compound 7) in a yield of 46%. The structure of the obtained compound was confirmed by LC-MS. LCMS M/z 775.3[ M + H ]]+。
Synthesis of Compound 17
Figure BDA0002327037290000342
The method comprises the following steps: a mixture of 3.22g (10mmol) of N- (4-bromophenyl) carbazole, 1.69g (10mmol) of 4-aminobiphenyl, 0.09g (0.1mmol) of tris (dibenzylideneacetone) dipalladium, 0.082g (0.2mmol) of 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl, and 1.44 g (15mmol) of sodium tert-butoxide was put in a 100mL three-necked flask, 30mL of toluene was added to the flask, and the mixture was heated under stirring to reflux for 2 hours, the reaction solution was quenched with water, extracted with toluene, the organic phase was dried over magnesium sulfate, filtered, the organic phase was subjected to silica gel column chromatography, the column solution was concentrated under reduced pressure, and the obtained solid was recrystallized from dichloroethane to obtain compound 17-1 (compound 17-1) (3.2g, yield 78%).
Figure BDA0002327037290000343
Step two: 3.2g (7.8mmol) of compound 17-1, 3.58g (7.8mmol) of compound 1-5, 0.07g (0.078mmol) of tris (dibenzylideneacetone) dipalladium, 0.06g (0.16mmol) of 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl, and 1.12g (11.7mmol) of sodium tert-butoxide were charged in a 100mL three-necked flask, nitrogen gas was introduced thereinto for protection, 30mL of toluene was added to the flask, the flask was heated with stirring to reflux for 17 hours, the organic phase was washed with water three times, the aqueous phase was extracted with toluene, the combined organic phases were concentrated to dryness, and recrystallization was carried out with a mixed solvent of dichloromethane and n-heptane (1:1) to obtain compound 17(compound 17) (3.63g, yield 56%). The structure of the resulting compound was confirmed by LC-MS. LCMS M/z 833.3[ M + H ]]+
Synthesis of Compound21
Figure BDA0002327037290000351
Compound21 was synthesized in the same manner as in the synthesis of Compound 17 except that N- (4-bromophenyl) carbazole in the first step of the synthesis of Compound 17 was replaced with 5-bromo-1, 10-phenanthroline to give 2.77g of Compound21 (compound21) in 66% yield. The structure of the obtained compound was confirmed by LC-MS. LCMS M/z 770.3[ M + H ]]+。
Synthesis of Compound41
Figure BDA0002327037290000352
The method comprises the following steps: under a nitrogen atmosphere, a mixture of 3.71g (15mmol) of 3-bromodibenzofuran, 3.14g (15mmol) of 3-amino 9,9 ' -dimethylfluorene, 0.14g (0.15mmol) of tris (dibenzylideneacetone) dipalladium, 0.12g (0.3mmol) of 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl, and 2.16g (22.5mmol) of sodium tert-butoxide was put in a 100mL three-necked flask, 30mL of toluene was added to the flask, the mixture was heated to reflux with stirring for 4 hours, after completion of the reaction, the organic phase was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to remove the solvent, and the obtained solid was recrystallized from a mixed solvent of dichloromethane and n-heptane (1:5) to obtain compound41-1 (compound41-1) (5g, yield 89%).
Figure BDA0002327037290000353
Step two: under a nitrogen atmosphere, a mixture of 4.28g (10mmol) of compound 1-4, 2.33g (10g mmol) of 4' -chloro-4-biphenylborate, 0.12g (0.1mmol) of tetrakis (triphenylphosphine) palladium, 0.03g (0.1mmol) of tetrabutylammonium bromide and 2.8g (20mmol) of potassium carbonate was charged in a 100mL three-necked flask, a 24mL/8mL/4mL mixed solvent of toluene/ethanol/water was added to the flask, the mixture was heated to 80 ℃ with stirring and reacted for 24 hours, the reaction solution was washed with water, then extracted with toluene, the organic phase was dried with magnesium sulfate, the solvent was removed by distillation under reduced pressure, and the obtained solid was recrystallized from ethyl acetate to give compound41-2 (compound41-2) (3.9g, yield 73%).
Figure BDA0002327037290000361
Step three: a mixture of 2.73g (7.3mmol) of compound41-1, 3.9g (7.3mmol) of compound41-2, 0.07g (0.07mmol) of tris (dibenzylideneacetone) dipalladium, 0.03g (0.07mmol) of 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl, and 1.4g (14.5mmol) of sodium tert-butoxide was added to a 100mL three-necked flask under a nitrogen atmosphere, 30mL of toluene was added to the flask, the mixture was heated to reflux with stirring for 16 hours, the reaction liquid was washed with water, the aqueous phase was extracted with toluene, the organic phase was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to remove the solvent, the resulting solid was dissolved with dichloromethane and n-heptane (1:4) and then purified by silica gel column chromatography to give compound41 (compound 41) (3.4g, yield 54%). The structure of the obtained compound was confirmed by LC-MS. LCMS M/z 874.3[ M + H ]]+。
Synthesis of Compound49
Figure BDA0002327037290000362
The method comprises the following steps: adding 5g (11.7mmol) of compound 1-4 and 40mL of dried tetrahydrofuran into a 100mL three-neck flask, cooling to-85 ℃ under stirring, dropwise adding 1g (15.2mmol) of n-butyllithium n-hexane solution with the concentration of 2mol/L in batches under the protection of nitrogen, preserving heat for 30min after dropwise adding, then slowly dropwise adding 1.8g (17.6mmol) of trimethyl borate, preserving heat for 60min after dropwise adding, naturally heating to room temperature, continuing stirring for 10 h, dropwise adding dilute hydrochloric acid to quench the reaction, extracting the reaction solution with ethyl acetate, drying an organic phase with magnesium sulfate, then distilling under reduced pressure, and recrystallizing the obtained solid with dichloromethane to obtain compound49-1 (compound49-1) (2.16g, the yield is 47%).
Figure BDA0002327037290000363
Step two: under a nitrogen atmosphere, a mixture of 2.16g (5.5mmol) of compound49-1, 1.88g (5.5mmol) of 3, 7-dibromodibenzothiophene, 0.06g (0.06mmol) of tetrakis (triphenylphosphine) palladium, 0.018g (0.06mmol) of tetrabutylammonium bromide and 1.52g (11mmol) of potassium carbonate was placed in a 100mL three-necked flask, 18mL/6mL of a toluene/water mixed solvent was added to the flask, and the mixture was heated to 80 ℃ with stirring to react for 12 hours, stopping the reaction, washing the reaction solution with water three times, drying the organic phase with magnesium sulfate, concentrating the organic phase under reduced pressure until no solvent remained, dissolving the obtained solid with n-heptane under heating, and separating and purifying by silica gel column chromatography to obtain compound 49-2 (compound 49-2) (2.48g, yield 74%).
Figure BDA0002327037290000371
Step three: compound49 was synthesized in the same manner as in step six of the synthesis of Compound1 to obtain Compound49 (compound 49) (1.99g, yield 70%). The structure of the obtained compound was confirmed by LC-MS. LCMS M/z 698.2[ M + H ]]+。
Synthesis of Compound61
Figure BDA0002327037290000372
The method comprises the following steps: under a nitrogen atmosphere, a mixture of 2.45g (15mmol) of 1-bromocyclohexane, 3.02g (15mmol) of p-bromobenzoic acid, 0.17g (0.15mmol) of tetrakis (triphenylphosphine) palladium, 0.05g (0.15mmol) of tetrabutylammonium bromide and 4.15g (30mmol) of potassium carbonate was placed in a 100mL three-necked flask, 20mL/5mL of a toluene/water mixed solvent was added to the flask, the mixture was heated to 80 ℃ with stirring to react for 4 hours, the reaction was stopped, the reaction mixture was extracted with ethyl acetate, the organic phase was dried over magnesium sulfate and concentrated under reduced pressure to remove the solvent, and the resulting solid was recrystallized from n-heptane to give compound61-1 (compound61-1) (3.13g, yield 87%).
Figure BDA0002327037290000373
Step two: compound61 was synthesized according to the same method as that for the synthesis of compound1, step three to step six, except thatCompound1 was prepared by substituting bromobenzene in step three of the synthesis of compound1 with compound61-1 and diphenylamine in step six of the synthesis of compound1 with bis (4-biphenylyl) amine to give compound61 (compound61) (3.54g, yield 33%). The structure of the resulting compound was confirmed by LC-MS. LCMS M/z 826.4[ M + H ]]+。
Synthesis of Compound87
Figure BDA0002327037290000381
The method comprises the following steps: adding 4g (20mmol) phenoxathiin and 40mL of dried tetrahydrofuran into a 100mL three-neck flask, cooling to-78 ℃ under stirring, dropwise adding 13mL (26mmol) of n-butyllithium n-hexane solution with the concentration of 2mol/L under the protection of nitrogen, preserving heat for 60min after dropwise adding, then slowly dropwise adding 5.64g (30mmol) of triisopropyl borate, preserving heat for 60min after dropwise adding, naturally heating to room temperature, continuing to stir for 12 h, dropwise adding dilute hydrochloric acid to quench the reaction, extracting the reaction solution with ethyl acetate, drying an organic phase with magnesium sulfate, distilling under reduced pressure, and boiling and washing the obtained solid with n-heptane to obtain a compound 87-1(compound 87-1) (3.7g, yield 76%).
Figure BDA0002327037290000382
Step two: a mixture of 3.7g (15.2mmol) of compound 87-1, 3.26g (15.2mmol) of methyl 2-bromobenzoate, 4.2g (30.3mmol) of potassium carbonate, 0.18g (0.15mmol) of tetrakis (triphenylphosphine) palladium and 0.05g (0.15mmol) of tetrabutylammonium bromide was placed in a 100mL three-necked flask, a 30mL/10mL/5mL mixed solvent of toluene/ethanol/water was added to the flask, the air in the flask was replaced with nitrogen, the temperature was raised to 80 ℃ with stirring for 8 hours, the reaction mixture was washed with water, dried with anhydrous magnesium sulfate, the organic phase was distilled under reduced pressure to remove toluene, and the resulting solid was recrystallized from a mixed solvent of dichloromethane and ethyl acetate (1:2) to give compound 87-2(compound 87-2) (4.1g, yield 81%).
Figure BDA0002327037290000383
Step three: compound 87-3 was synthesized in the same manner as in Steps two to five of the Synthesis of Compound1, except that Compound 1-1 in step two of the Synthesis of Compound1 was replaced with Compound 87-2 to finally obtain Compound 87-3(compound 87-3) (3.3g, yield 46%).
Figure BDA0002327037290000384
Step four: a mixture of 5g (29.5mmol) of 4-aminobiphenyl, 6.1g (29.5mmol) of 1-bromonaphthalene, 0.27g (0.3mmol) of tris (dibenzylideneacetone) dipalladium, 0.24g (0.6mmol) of 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl and 4.3 (44.3mmol) of sodium tert-butoxide was placed in a 100mL three-necked flask under a nitrogen atmosphere, 50mL of toluene was added to the flask, the mixture was heated to reflux with stirring for 2 hours, the reaction solution was washed with water, extracted with toluene, the organic phase was dried over magnesium sulfate, filtered, the organic phase was chromatographed through a silica gel column, the column solution was concentrated under reduced pressure, and the resulting solid was recrystallized from a mixed solvent of dichloromethane and n-heptane (1:1) to give compound87-4 (compound87-4) (7g, yield 80%).
Figure BDA0002327037290000391
Step five: a mixture of 3.3g (6.9mmol) of 87-3, 2.1g (6.9mmol) of 87-4, 0.06g (0.07mmol) of tris (dibenzylideneacetone) dipalladium, 0.06g (0.14mmol) of 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl, and 1g (10.4mmol) of sodium tert-butoxide was placed in a 100mL three-necked flask under a nitrogen atmosphere, 30mL of toluene was added to the flask, the reaction mixture was heated to reflux with stirring for 16 hours, the reaction mixture was quenched with water, washed with water and the aqueous phase was extracted with toluene, the organic phases were combined and dried over magnesium sulfate, the solvent was removed by distillation under reduced pressure, and recrystallization was carried out with toluene to obtain 87(compound87) (3.36g, 66% yield). The structure of the obtained compound was confirmed by LC-MS. LCMS M/z 734.2[ M + H ]]+。
Synthesis of Compound100
Figure BDA0002327037290000392
The method comprises the following steps: under the protection of nitrogen, adding 8.3g (25.2mmol) of diiodobenzene, 1.6g (50mmol) of sulfur powder, 10.4g (75mmol) of potassium carbonate, 0.36g (2.5mmol) of cuprous bromide and 2.5g (12.5mmol) of 1, 10-phenanthroline into a 100mL three-neck flask, adding 40mL of dimethyl sulfoxide into the flask, heating to 90 ℃ under stirring, reacting for 24 hours, cooling, quenching with a sodium thiosulfate solution, extracting the reaction solution with ethyl acetate for multiple times, drying an organic phase with magnesium sulfate, concentrating under reduced pressure, and purifying the obtained solid by a silica gel column chromatography separation method with dichloromethane and n-heptadecane (1: 10) to obtain a compound 100-1(3.7g, yield of 68%).
Figure BDA0002327037290000393
Step two: under the protection of nitrogen, adding 3.7g (17.1mmol) of compound 100-1 and dried 30mL tetrahydrofuran into a 100mL three-neck flask, cooling the system to-78 ℃, keeping the temperature, slowly dripping 11mL (22.2mmol) of n-butyllithium n-hexane solution with the concentration of 2mol/L, preserving the temperature for 60min after dripping, then slowly dripping 1.5g (9.4mmol) of bromine, preserving the temperature for 2h after dripping, continuing stirring for 24 h after rising to the room temperature, quenching the reaction by using a dilute sodium bicarbonate solution, extracting the reaction solution by using ethyl acetate, drying an organic phase by using magnesium sulfate, distilling under reduced pressure until no solvent remains, recrystallizing the obtained solid by using n-heptane to obtain compound 100-2, (2.8g, collecting 55%)
Figure BDA0002327037290000401
Step three: compound100 was synthesized in the same manner as Compound1 except that 1-bromodibenzodioxin in the first step of the synthesis of Compound1 was replaced with Compound 100-2 to finally obtain Compound100 (compound100) (2.13g, yield 36%). The structure of the obtained compound was confirmed by LC-MS. LCMS M/z 624.2[ M + H ]]+。
Synthesis of Compound 122
Figure BDA0002327037290000402
Compound 122 was synthesized according to the same method as that for the synthesis of Compound2, except that Compound 1-1 in step one for the synthesis of Compound2 was replaced with Compound4-1, to finally obtain Compound 122(compound 122) (3.26g, yield 33%). The structure of the obtained compound was confirmed by LC-MS. LCMS M/z 775.3[ M + H ]]+。
Preparation of organic electroluminescent device and performance evaluation thereof
Example 1:
organic electroluminescent device using compound1 as Hole Transport Layer (HTL) material
An organic electroluminescent device was prepared by the following procedure:
the thickness of ITO is set as
Figure BDA0002327037290000403
The ITO substrate (manufactured by Corning) of (1) was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), and then prepared into an experimental substrate (light-emitting pixel dot size of 3mm × 3mm) having an anode, a cathode overlapping region and an insulating layer using a photolithography process using ultraviolet ozone and O2:N2The plasma performs a surface treatment to increase the work function of the anode (test substrate) and remove dross.
HAT-CN (CAS number: 105598-27-4) was deposited on the anode as a Hole Injection Layer (HIL) at 10 nm.
Next, a Hole Transport Layer (HTL) was formed by evaporating a layer of the compound1 of the present invention at a thickness of 100 nm.
TCTA (CAS number: 139092-78-7) was vacuum-evaporated above the hole transport layer to form an Electron Blocking Layer (EBL) having a thickness of 15 nm.
An organic electroluminescent layer (EML) having a thickness of 22nm was formed by doping FIrN4(CAS number: 1219078-44-0) with 9, 10-bis (2-naphthyl) Anthracene (ADN) (CAS number: 122648-99-1) as a host and a dopant at a film thickness ratio of 30: 3. .
An organic film layer having a thickness of 30nm was vacuum-evaporated as an Electron Transport Layer (ETL) on the above light-emitting layer by using TPBI (CAS No.: 192198-85-9) and LiQ (CAS No.: 850918-68-2) at a ratio of 1: 1.
Evaporating a layer of Yb (CAS number: 850918-68-2) with the thickness of 1nm on the electron transport layer as an Electron Injection Layer (EIL);
then, evaporating magnesium (Mg) and silver (Ag) at a ratio of 1:9 to form a cathode with a thickness of 12 nm; finally, N4, N4 '-bis [4- [ bis (3-methylphenyl) amino ] phenyl ] -N4, N4' -dimethyl- [1,1 '-dimethyl ] -4, 4' -diurea (DNTPD) (CAS number: 199121-98-7) was deposited as a capping layer onto the cathode in a thickness of 70 nm.
The evaporated devices were encapsulated with uv curable resin in a nitrogen glove box (water, oxygen content is strictly controlled).
Examples 2 to 15
In the above-described device structure, organic electroluminescent devices were prepared in examples 2 to 15 in the same manner as in example 1, except that compound1 of the Hole Transport Layer (HTL) was replaced with compounds 2, 3,4, 5, 6, 7, 17, 21, 41, 49, 61, 87, 100, and 122.
Comparative example 1
In the above-mentioned device structure, an organic electroluminescent device was produced by the same production process as in example 1 except that compound1 of the Hole Transport Layer (HTL) was replaced with compound NPB (CAS No. 123847-85-8).
Comparative example 2
In the above-mentioned device structure, the same production process was used for producing an organic electroluminescent device as in example 1 except that compound1 of the Hole Transport Layer (HTL) was replaced with compound TCP (CAS No. 148044-07-9).
Comparative example 3
In the above-mentioned device structure, an organic electroluminescent device was produced by the same production process as in example 1 except that compound1 of the Hole Transport Layer (HTL) was replaced with compound TDATA (CAS No. 105389-36-4).
Comparative example 4
In the above-described device structure, the same production process as in example 1 was used to produce an organic electroluminescent device, except that instead of replacing compound1 of the Hole Transport Layer (HTL) with compound a, compound a was used.
Comparative example 5
In the above-described device structure, the same production process as in example 1 was used to produce an organic electroluminescent device, except that instead of replacing compound1 of the Hole Transport Layer (HTL) with compound B, compound B was used.
Comparative example 6
In the above-described device structure, the same production process as in example 1 was used to produce an organic electroluminescent device, except that instead of replacing compound1 of the Hole Transport Layer (HTL) with compound C.
Wherein HAT-CN, TCTA, ADN, FIRN4The structural formulas of TPBI, LiQ, DNTPD, NPB, TCP, TDATA, compound A, compound B and compound C are as follows:
Figure BDA0002327037290000411
Figure BDA0002327037290000421
the organic electroluminescent devices obtained in examples 1 to 15 and comparative examples 1 to 6 were measured for their performance, and the results are shown in Table 1.
TABLE 1 examination Properties of organic electroluminescent elements of examples and comparative examples
Figure BDA0002327037290000422
Figure BDA0002327037290000431
The driving voltage, current efficiency, color coordinates in the test performance in Table 1 were 10mA/cm at a constant current density2Test No. T95 device lifetime is at constant current density 15mA/cm2The test was performed.
As can be seen from the data in table 1, in the case of small CIE difference, the voltage of the organic electroluminescent devices of examples 1 to 15 is reduced by at least 0.22V, the luminous efficiency is improved by at least 11.1%, the lifetime is improved by at least 8.3%, and the improvement of the luminous efficiency of the device in the blue device is a significant improvement compared with comparative examples 1,2 and 3. Therefore, the organic electroluminescent devices of examples 1 to 15 generally have high efficiency, low voltage, and long life as compared with those of comparative examples 1 to 3. However, compared with the organic electroluminescent devices of comparative examples 4 to 6, the organic electroluminescent devices of examples 1 to 15 have substantially the same voltage and efficiency, and the service life is improved by at least 9.7%; therefore, the organic electroluminescent devices of examples 1 to 15 generally have a longer life than those of comparative examples 4 to 6.
Therefore, the compound provided by the invention is used for a hole transport layer of an organic electroluminescent device, so that the working voltage of the organic electroluminescent device can be remarkably reduced, the luminous efficiency of the organic electroluminescent device is improved, and the service life of the organic electroluminescent device is prolonged.
The reason for this is that the main body of the compound exemplified in the examples of the present invention is a fused heteroaromatic ring group containing fluorene or silafluorene, and exhibits a large planar structure in a steric space, and the hole transport performance of the compound is excellent by introducing an electron-rich arylamine or heteroaromatic amine substituent at the 9-position of the fluorene or silafluorene group.
In summary, the organic compound of the present application, using a specific structure, has certain advantages in a Hole Transport Layer (HTL) of an organic electroluminescent device compared to the conventional materials, has excellent carrier transport properties, and contributes to voltage reduction, efficiency improvement, and life extension of the organic electroluminescent device.
The above examples are only for illustrating the technical solutions of the present application, and are not limited thereto. Although the present application has been described in detail with reference to the foregoing embodiments, it should be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions in the embodiments of the present application.

Claims (15)

1. An organic compound having the structure shown in formula I:
Figure FDA0002327037280000011
wherein X is selected from C or Si;
Y1and Y2Identical or different, each independently selected from O or S;
R1and R2Each independently selected from hydrogen, deuterium or the following groups: a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a pharmaceutically acceptable carrier, a pharmaceutically,
Figure FDA0002327037280000012
And R is1And R2At least one of them is
Figure FDA0002327037280000013
Each Ar1And Ar2The same or different, each is independently selected from one of hydrogen, deuterium, a substituted or unsubstituted aralkyl group having 7 to 25 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms;
L1and L2The same or different, each is independently selected from one of single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 1-30 carbon atoms, and when R is1Is composed of
Figure FDA0002327037280000014
When L is1Not a single bond, when R2Is composed of
Figure FDA0002327037280000015
When L is2Is not a single bond;
ar is1、Ar2、L1、L2The substituents on the above groups are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms and an aryl group having 3 to 18 carbon atoms.
2. An organic compound according to claim 1, wherein the formula i is selected from the group consisting of:
Figure FDA0002327037280000021
3. the organic compound of claim 1, wherein L is1And L2The same or different, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroarylene group having 4 to 18 carbon atoms.
4. The organic compound of claim 1 or 2, wherein L is1And L2The same or different, each independently selected from a single bond, or any one of the following groups:
Figure FDA0002327037280000022
the above groupsIn the formula, X is selected from O, S, Se and C (R)3R4)、N(R5) And Si (R)3R4) The group of;
X1、X2、X3、X4、X5each independently selected from CR6And N, and X1～X5At least one of which is N;
each X6～X15Are each independently selected from CR6And N, when one group contains two or more R6When there are two arbitrary R6The same or different;
each Z1、Z2、R3、R4、R6Each independently selected from the group consisting of hydrogen, deuterium, fluorine, chlorine, bromine, cyano, alkyl having 1 to 6 carbon atoms, haloalkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, aryloxy having 6 to 18 carbon atoms, arylthio having 6 to 18 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 3 to 12 carbon atoms, silyl having 3 to 12 carbon atoms and cycloalkyl having 3 to 10 carbon atoms; or,
optionally, R attached to the same atom3And R4Are interconnected to form a saturated or unsaturated 5-to 10-membered aliphatic ring;
R5selected from the group consisting of H, alkyl having 1 to 6 carbon atoms, haloalkyl having 1 to 6 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 3 to 12 carbon atoms and cycloalkyl having 3 to 10 carbon atoms;
each n is1Independently selected from 0, 1,2, 3,4 or 5, each n2Independently selected from 0, 1,2, 3,4, 5, 6 or 7.
5. The organic compound of claim 1 or 2, wherein L is1And L2The same or different, each independently selected from the group consisting of a single bond, substituted or unsubstituted:
Figure FDA0002327037280000031
Figure FDA0002327037280000041
wherein,
Figure FDA0002327037280000042
the above groups are used in the formula I
Figure FDA0002327037280000043
The position of the connecting key;
the above groups are optionally substituted with 0, 1,2, 3,4 or 5 substituents selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, propoxy, cyclopentyl, cyclohexyl, trifluoromethyl, alkylsilyl groups of 3 to 9 carbon atoms.
6. The organic compound of claim 1 or 2, wherein each Ar is Ar1、Ar2、R1And R2The same or different, and are respectively and independently selected from substituted or unsubstituted aryl with 6-25 carbon atoms and substituted or unsubstituted heteroaryl with 4-18 carbon atoms.
7. An organic compound according to claim 1 or 2, wherein each Ar is Ar1、Ar2、R1And R2The same or different and each is independently selected from hydrogen, deuterium, substituted or unsubstituted:
Figure FDA0002327037280000044
each V1～V10And V12～V16Are each independently selected from CR8And N, and V1～V5At least one of which is N;
in the above groups, each V is independently selected from O, S, Se,N(R7)、C(R9R10) And Si (R)9R10) The group of;
y and V11Each independently selected from O, S or N (R)7)；
Each Y is1～Y10Are each independently selected from CR8And N, when one group contains two or more R8When there are two arbitrary R8The same or different;
each R9、R10、R8The aryl group is the same or different and is respectively and independently hydrogen, deuterium, fluorine, chlorine, bromine, cyano, alkyl with the carbon number of 1-6, halogenated alkyl with the carbon number of 1-6, aryl with the carbon number of 6-12, heteroaryl with the carbon number of 3-12, aryloxy with the carbon number of 6-18, arylthio with the carbon number of 6-18, silyl with the carbon number of 3-12, alkylamino with the carbon number of 1-10, arylamino with the carbon number of 6-18 and cycloalkyl with the carbon number of 3-10;
R7selected from the group consisting of hydrogen, alkyl having 1 to 6 carbon atoms, haloalkyl having 1 to 6 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 3 to 12 carbon atoms and cycloalkyl having 3 to 10 carbon atoms; or,
optionally, two adjacent R8Forming an aromatic ring with 6-10 ring-forming atoms or a heteroaromatic ring with 5-12 ring-forming atoms together with the carbon atoms connected with the aromatic ring and the heteroaromatic ring;
optionally, R attached to the same atom9And R10Are linked to each other to form a saturated or unsaturated 5-to 10-membered aliphatic ring;
each of Ar mentioned above1And Ar2Optionally substituted with 0, 1,2, 3,4 or 5 substituents selected from deuterium, fluorine, chlorine, cyano, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, aryl of 6 to 18 carbon atoms, heteroaryl of 3 to 18 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkylsilyl of 3 to 9 carbon atoms.
8. The organization according to claim 1 or 2A compound of formula (I), wherein each Ar is1、Ar2、R1And R2The same or different and each is independently selected from hydrogen, deuterium, substituted or unsubstituted:
Figure FDA0002327037280000051
Figure FDA0002327037280000061
each of the foregoing groups is optionally substituted with 0, 1,2, 3,4, or 5 substituents selected from deuterium, fluorine, chlorine, cyano, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, alkylsilyl having 3 to 9 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 13 carbon atoms, and heteroaryl having 3 to 12 carbon atoms.
9. The organic compound of claim 1 or 2, wherein Ar is Ar1、Ar2The same or different and each is independently selected from hydrogen, deuterium, substituted or unsubstituted:
Figure FDA0002327037280000062
Figure FDA0002327037280000071
the above groups are optionally substituted with 0, 1,2, 3,4 or 5 substituents selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, propoxy, cyclopentyl, cyclohexyl, trifluoromethyl, alkylsilyl groups of 3 to 9 carbon atoms.
10. The organic compound of claim 1 or 2, wherein R is1And R2The same or different and each is independently selected from hydrogen, deuterium, substituted or unsubstituted:
Figure FDA0002327037280000081
the above groups are optionally substituted with 0, 1,2, 3,4 or 5 substituents selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, propoxy, cyclopentyl, cyclohexyl, trifluoromethyl, alkylsilyl groups of 3 to 9 carbon atoms.
11. The organic compound of claim 1, wherein the specific structure of formula i is selected from any one of the following:
Figure FDA0002327037280000082
Figure FDA0002327037280000091
Figure FDA0002327037280000101
Figure FDA0002327037280000111
Figure FDA0002327037280000121
Figure FDA0002327037280000131
Figure FDA0002327037280000141
Figure FDA0002327037280000151
Figure FDA0002327037280000161
Figure FDA0002327037280000171
Figure FDA0002327037280000181
Figure FDA0002327037280000191
Figure FDA0002327037280000201
12. an electronic 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 an organic compound according to any one of claims 1 to 11.
13. The electronic device of claim 12, wherein said functional layer comprises a hole transport layer, said hole transport layer comprising said organic compound.
14. Electronic device according to claim 12 or 13, characterized in that it is an organic electroluminescent device or a solar cell.
15. An electronic device, characterized in that it comprises an electronic device according to any one of claims 12-14.
CN201911320582.0A 2019-12-19 2019-12-19 Organic compound, electronic device, and electronic apparatus Pending CN111004207A (en)

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CN111960953A (en) * 2020-08-26 2020-11-20 长春海谱润斯科技有限公司 Arylamine compound containing fluorene and organic electroluminescent device thereof
WO2021120838A1 (en) * 2019-12-19 2021-06-24 陕西莱特光电材料股份有限公司 Organic compound, electronic device, and electronic apparatus
CN114085202A (en) * 2020-08-24 2022-02-25 罗门哈斯电子材料韩国有限公司 Organic electroluminescent compounds and organic electroluminescent device comprising the same

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US11605784B2 (en) 2019-12-19 2023-03-14 Shaanxi Lighte Optoelectronics Material Co., Ltd. Organic compound, electronic element, and electronic device
CN114085202A (en) * 2020-08-24 2022-02-25 罗门哈斯电子材料韩国有限公司 Organic electroluminescent compounds and organic electroluminescent device comprising the same
CN111960953A (en) * 2020-08-26 2020-11-20 长春海谱润斯科技有限公司 Arylamine compound containing fluorene and organic electroluminescent device thereof
CN111960953B (en) * 2020-08-26 2021-10-15 长春海谱润斯科技股份有限公司 Arylamine compound containing fluorene and organic electroluminescent device thereof

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