CN115322162A - Organic compound, organic electroluminescent device, and electronic device - Google Patents
Organic compound, organic electroluminescent device, and electronic device Download PDFInfo
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- CN115322162A CN115322162A CN202211000585.8A CN202211000585A CN115322162A CN 115322162 A CN115322162 A CN 115322162A CN 202211000585 A CN202211000585 A CN 202211000585A CN 115322162 A CN115322162 A CN 115322162A
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Abstract
The application belongs to the field of organic light-emitting materials, and particularly relates to an organic compound, an organic electroluminescent device and an electronic device. The structure of the organic compound is shown in formula I, and the nitrogen-containing compound is used in an organic electroluminescent device and can improve the performance of the device.
Description
Technical Field
The application belongs to the technical field of organic light-emitting materials, and particularly provides an organic compound, an organic electroluminescent device comprising the organic compound and an electronic device comprising the organic compound.
Background
With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is more and more extensive. In recent years, organic electroluminescent devices (OLEDs) have gradually entered the field of vision as a new generation of display technology. Such electronic components generally include a cathode and an anode that are oppositely disposed, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the light emitting layer under the action of the electric field, electrons on the anode side also move to the light emitting layer, the electrons and the light emitting layer are combined to form excitons in the light emitting layer, the excitons are in an excited state and release energy outwards, and the process of releasing energy from the excited state to a ground state releases energy emits light outwards.
At present, the organic electroluminescent device still has the problem of poor performance, and especially how to improve the service life of the device under the condition of ensuring that the device has lower driving voltage and higher luminous efficiency, still needs to be solved urgently.
Disclosure of Invention
In view of the above problems of the prior art, it is an object of the present application to provide an organic compound, and an organic electroluminescent device and an electronic device including the same. The organic compound is used in an organic electroluminescent device, and can improve the performance of the device.
In order to achieve the above object, a first aspect of the present application provides an organic compound having a structure represented by formula I:
in the formula I, R 1 And R 2 Identical or different and are each independently selected from hydrogen or methyl; n is selected from 1 or 2;
x is selected from C (R) 5 R 6 ) O or S; r 5 And R 6 The same or different, and each is independently selected from alkyl with 1-10 carbon atoms and aryl with 6-20 carbon atoms, optionally, R 5 And R 6 Are connected with each other to form a saturated or unsaturated 5-15 membered ring;
R 0 represents hydrogen or
R represents hydrogen or
L、L 1 、L 2 、L a The same or different, and each is 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 5 to 25 carbon atoms;
Ar 1 、Ar 2 、Ar a the same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
L、L 1 、L 2 、L a 、Ar 1 、Ar 2 and Ar a Substituent of (1) and R 3 And R 4 The same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl group with 1-10 carbon atoms, halogenated alkyl group with 1-10 carbon atoms, deuterated alkyl group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, triphenylsilyl group, aryl group with 6-18 carbon atoms, heteroaryl group with 3-15 carbon atoms and cycloalkyl group with 3-10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3-to 15-membered ring;
n 3 represents R 3 When n is 0, 1 or 2 3 When is 2, each R 3 The same or different; n is 4 Represents R 4 When n is 0, 1,2 or 3 2 When greater than 1, each R 4 The same or different;
het represents a nitrogen-containing heteroarylene group having 2 to 15 carbon atoms.
A second aspect of the present application provides an organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises an organic compound according to the first aspect of the present application.
A third aspect of the present application provides an electronic device comprising an organic electroluminescent device as described in the second aspect of the present application.
The organic compound of the present application can significantly enhance the electron transport property of the organic compound of the present application. When the compound is used as a main material, the carrier balance in a light-emitting layer can be improved, the carrier recombination region can be widened, the exciton generation and utilization efficiency can be improved, the light-emitting efficiency of a device can be improved, and the service life of the device can be prolonged.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Description of the reference numerals
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 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; 400. an electronic device.
Detailed Description
The following detailed description of embodiments of the invention refers to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the preferred embodiment of the invention, are given by way of illustration and explanation only, not limitation.
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application.
In the application, the description mode of ' each 8230 ' \8230; ' and ' 8230 '; ' 823030 '; ' and ' 8230 '; ' are independently selected from ' interchangeable ' and should be broadly understood, which can mean that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. For example,') "
Wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents biphenyl having Q substituents R "on each benzene ring, the number Q of R" substituents on two benzene rings may be the same or different, each R "may be the same or different, and the choice of each R" isWithout mutual influence.
In this application, the terms "optional" and "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, "optionally, any two adjacent substituents form a ring" means that any two substituents may form a ring but need not form a ring, which includes: a scenario where two adjacent substituents form a ring and a scenario where two adjacent substituents do not form a ring.
In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having a substituent Rc. Wherein Rc, which is the substituent, may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, an alkyl group, a haloalkyl group, a cycloalkyl group, a trialkylsilyl group, or the like. In the present application, a "substituted" functional group may be substituted with 1 or 2 or more of the above Rc; when two substituents Rc are attached to the same atom, these two substituents Rc may be independently present or attached to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent two substituents Rc may exist independently or may form a ring fused with the functional group to which they are attached.
In the present application, "any two adjacent substituents form a saturated or unsaturated ring having 3 to 15 carbon atoms", the saturated ring formed may be, for example, cyclopentane
Cyclohexane
The unsaturated ring formed may be, for example, a benzene ring, a naphthalene ring or a fluorene ring
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group means all the number of carbon atoms. For example, if L 1 Is a substituted arylene group having 12 carbon atoms, all of the carbon atoms of the arylene group and the substituents thereon are 12. For another example: ar (Ar) 1 Is composed of
The number of carbon atoms is 10; l is
The number of carbon atoms is 12.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bonds in a conjugated manner, a monocyclic aryl group and a fused ring aryl group joined by carbon-carbon bonds in a conjugated manner, or two or more fused ring aryl groups joined by carbon-carbon bonds in a conjugated manner. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain heteroatoms such as B, N, O, S, P, se, si and the like. In this specification, both biphenyl and fluorenyl groups are referred to as aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl a benzofluoranthenyl group,
And the like.
In the present application, a substituted aryl group may be one in which one or two or more hydrogen atoms are substituted with a group such as deuterium, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, a haloalkyl group, an alkyl group, a cycloalkyl group, or the like. It is understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group having a carbon number of 18, refers to a total number of carbon atoms in the aryl group and its substituents of 18. In addition, in the present application, the fluorenyl group may be substituted, and when having two substituents, the two substituents may be combined with each other to form a spiro structure. Specific examples of substituted fluorenyl groups include, but are not limited to,
in this application, reference to arylene is to divalent or trivalent or higher valent groups formed by further loss of one hydrogen atom from an aryl group.
In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6 to 30. Specifically, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6,7,8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30.
In the present application, heteroaryl refers to a monovalent aromatic ring or derivatives thereof containing 1,2, 3,4, 5 or more heteroatoms in the ring, which may be one or more of B, O, N, P, si, se and S. 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 thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without being limited thereto. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and the N-phenylcarbazolyl is heteroaryl of a polycyclic system type which is connected by carbon-carbon bond conjugation. In this application, reference to heteroarylene is to a divalent or higher radical formed by a heteroaryl group further lacking one or more hydrogen atoms.
In the present application, nitrogen-containing heteroaryl refers to heteroaryl groups including an N atom in the ring.
In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more than two hydrogen atoms are substituted with groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.
In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group may be 3 to 30. For example, the number of carbon atoms of the substituted or unsubstituted heteroaryl group may be 5,6,7,8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, and the like.
In this application, an delocalized linkage refers to a single bond extending from a ring system
It means that one end of the linkage may be attached to any position in the ring system through which the linkage runs, and the other end to the rest of the compound molecule. For example, as shown in formula (f), naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positioned bonds penetrating through the bicyclic ring, and the meanings represented by the naphthyl include any possible connection modes as shown in formulas (f-1) to (f-10):
as another example, as shown in the following formula (X '), the dibenzofuranyl group represented by formula (X') is attached to another position of the molecule via an delocalized bond extending from the middle of the phenyl ring on one side, which has the meaning shown in any of the possible attachment means as shown in formulas (X '-1) to (X' -4).
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, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is bonded to the quinoline ring via an delocalized bond, which means any possible bonding as shown in the formulae (Y-1) to (Y-7):
in the present application, the number of carbon atoms of the alkyl group may be 1 to 10, and specifically may be 1,2, 3,4, 5,6,7,8, 9 or 10, and the alkyl group may include a straight chain alkyl group and a branched chain alkyl group. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl, and the like.
In the present application, the halogen group may include fluorine, iodine, bromine, chlorine.
In the present application, the aryl group as a substituent may have 6 to 18 carbon atoms, and specific examples thereof include, but are not limited to, 6, 10, 12, 13, 14, 15, 16, 18, etc., and specific examples thereof include, but are not limited to, phenyl, naphthyl, biphenyl, phenanthryl, anthracenyl, fluorenyl, etc.
In the present application, the carbon number of the heteroaryl group as the substituent may be 3 to 15, and specific examples thereof include, for example, 5,8, 9,10, 12, 13, 14, 15, etc., and specific examples thereof include, but are not limited to, pyridyl, quinolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, etc.
In the present application, the number of carbon atoms of the trialkylsilyl group as the substituent may be 3 to 12, for example, 3, 6,7,8, 9, etc., and specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl group, ethyldimethylsilyl group, triethylsilyl group, etc.
In the present application, the number of carbon atoms of the cycloalkyl group as a substituent may be 3 to 10, for example, 5,6, 8 or 10, and specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, and the like.
In the present application, the number of carbon atoms of the haloalkyl group as a substituent may be 1 to 10. For example, the haloalkyl group may be a fluoroalkyl group having 1 to 4 carbon atoms or a fluoroalkyl group having 1 to 5 carbon atoms. Specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.
In the present application, the carbon number of the deuterated alkyl group as the substituent may be 1 to 10. For example, the deuterated alkyl group can be a deuterated alkyl group having 1 to 4 carbon atoms or a deuterated alkyl group having 1 to 5 carbon atoms. Specific examples of deuterated alkyls include, but are not limited to, trideuteromethyl.
In a first aspect, the present application provides an organic compound having a structure according to formula I:
in the formula I, R 1 And R 2 The same or different and are each independently selected from hydrogen or methyl; n is selected from 1 or 2;
x is selected from C (R) 5 R 6 ) O or S; r is 5 And R 6 Are the same or different, andeach independently selected from alkyl of 1-10 carbon atoms, aryl of 6-20 carbon atoms, and optionally R 5 And R 6 Are connected with each other to form a saturated or unsaturated 5-15 membered ring;
R 0 represents hydrogen or
R represents hydrogen or
L、L 1 、L 2 、L a The same or different, and each is 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 5 to 25 carbon atoms;
Ar 1 、Ar 2 、Ar a the same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
L、L 1 、L 2 、L a 、Ar 1 、Ar 2 and Ar a Substituent of (1) and R 3 And R 4 The same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl group with 1-10 carbon atoms, halogenated alkyl group with 1-10 carbon atoms, deuterated alkyl group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, triphenylsilyl group, aryl group with 6-18 carbon atoms, heteroaryl group with 3-15 carbon atoms and cycloalkyl group with 3-10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3-to 15-membered ring;
n 3 represents R 3 When n is 0, 1 or 2 3 When is 2, each R 3 The same or different; n is 4 Represents R 4 When n is 0, 1,2 or 3 2 When greater than 1, each R 4 The same or different;
het represents a nitrogen-containing heteroarylene group having 2 to 15 carbon atoms.
In the present application, when n is 1, the structure of formula I is specifically as follows:
when n is 2, the structure of formula I is specifically as follows:
In a preferred embodiment, R 1 And R 2 Are all hydrogen. That is, the structure of formula I is shown as formula A or formula B:
preferably, the organic compound has a structure shown in formula B, and X is O or S, so that the service life of the organic electroluminescent device can be further prolonged.
In this application, the nitrogen-containing heteroarylene group represented by Het is an electron-deficient heteroaryl group. Alternatively, the nitrogen-containing heteroarylene is a 6-to 14-membered nitrogen-containing heteroarylene. In one embodiment, the nitrogen-containing heteroarylene group includes at least two N atoms, for example, two N atoms or three N atoms.
Alternatively, het is selected from the group consisting of triazinylene, pyrimidylene, quinolylene, quinoxalylene, isoquinolylene, quinazolinylene, and the following groups:
each of the triazinylene, pyrimidylene, quinolylene, quinoxalylene, isoquinolylene and quinazolinylene has three connecting bonds respectively, and the three connecting bonds are connected to L and L respectively 1 And R 0 . Examples of such applications areSaid triazinylene group has the structure
Three connecting keys in the structure
Are respectively connected to L and L 1 And R 0 。
Alternatively,
selected from the group consisting of:
In some embodiments, the structure of the organic compound is selected from the group consisting of:
in the application, when R is H, R 4 R may be substituted or unsubstituted. For example, when the organic compound has a structure as shown in formulas 1-6 (R is H), and n is 3 Is 0,R 4 Is deuterium, n 4 When 3, in formulas 1 to 6
Is composed of
Alternatively, R 3 And R 4 The same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, fluoroalkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, aryl having 6 to 12 carbon atoms, and heteroaryl having 5 to 12 carbon atoms. R 3 And R 4 Specific examples of (d) include, but are not limited to, deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, or naphthyl.
Alternatively, R 5 And R 6 Identical or different and are each independently selected from alkyl groups having 1 to 4 carbon atoms (for example, methyl) or phenyl, optionally R 5 And R 6 Are linked to each other to form a cyclopentane, cyclohexane or fluorene ring.
Alternatively, L 1 、L 2 And L a The same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 15 carbon atoms. For example, L 1 、L 2 And L a May each be independently selected from a single bond, a substituted or unsubstituted arylene group having 6,7,8, 9,10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 7,8, 9,10, 11, 12, 13, 14 or 15 carbon atoms.
Alternatively, L 1 、L 2 And L a The same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene groupSubstituted or unsubstituted carbazolyl groups.
Further optionally, L 1 、L 2 And L a The same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group.
Alternatively, L 1 、L 2 And L a Wherein the substituents are independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms and an aryl group having 6 to 12 carbon atoms.
Alternatively, L 1 、L 2 And L a Each substituent in (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl or naphthyl.
In a specific embodiment, L 1 、L 2 And L a The same or different, and each is independently selected from the group consisting of a single bond and:
alternatively, ar 1 、Ar 2 And Ar a The same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 25 carbon atoms. For example, ar 1 、Ar 2 And Ar a May each be independently selected from: a substituted or unsubstituted aryl group having 6,7,8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 5,6,7,8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.
Alternatively, ar 1 、Ar 2 And Ar a Are the same or different and are each independently selected from substituted or unsubstitutedA phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzoxazolyl group.
Alternatively, ar 1 、Ar 2 And Ar a Wherein the substituents are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, fluoroalkyl having 1 to 5 carbon atoms, deuterated alkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, aryl having 6 to 12 carbon atoms and heteroaryl having 5 to 12 carbon atoms; ar (Ar) 1 、Ar 2 And Ar a Optionally, any two adjacent substituents form a 5-to 15-membered saturated or unsaturated ring.
Alternatively, ar 1 、Ar 2 And Ar a Each substituent in (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl; ar (Ar) 1 、Ar 2 And Ar a Optionally, any two adjacent substituents form a benzene, naphthalene, cyclopentane, cyclohexane or fluorene ring.
In one embodiment, ar 1 And Ar 2 Identical or different and are each independently selected from substituted or unsubstituted groups Z, wherein the unsubstituted groups Z are selected from the group consisting of:
the substituted group Z has one or more substituents each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl or naphthyl; when the number of the substituents is more than 1, the substituents may be the same or different.
Alternatively, ar 1 And Ar 2 Each independently selected from the group consisting of:
alternatively, ar 1 And Ar 2 Each independently selected from the group consisting of:
in one embodiment of the method of the present invention,
the same or different, and each is independently selected from the group consisting of:
in one embodiment, ar a Selected from a substituted or unsubstituted group V, wherein the unsubstituted group V is selected from the group consisting of:
the substituted group V has one or more substituents each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, trifluoromethyl, trideuteromethyl, trimethylsilyl or phenyl; when the number of the substituents is more than 1, the substituents may be the same or different.
Alternatively, the first and second liquid crystal display panels may be,
selected from the group consisting of:
alternatively, the first and second liquid crystal display panels may be,
selected from the group consisting of:
in one embodiment of the method of the present invention,
selected from the group consisting of:
optionally, the organic compound is selected from the group consisting of:
the synthesis method of the organic compound provided herein is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the organic compound of the present invention in combination with the preparation method provided in the synthesis examples section. In other words, the synthetic examples section of the present invention illustratively provides methods for the preparation of organic compounds, and the starting materials employed may be obtained commercially or by methods well known in the art. All of the organic compounds provided herein are available to those skilled in the art from these exemplary preparative methods, and all specific preparative methods for preparing the organic compounds will not be described in detail herein, and should not be construed as limiting the application to which the skilled artisan is entitled.
A second aspect of the present application provides an organic electroluminescent device comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode, wherein the functional layer may contain the organic compound of the first aspect of the present application.
The organic compound provided by the application can be used for forming at least one organic film layer in the functional layer so as to improve the characteristics of the organic electroluminescent device such as service life and the like.
Optionally, the functional layer comprises an organic light emitting layer comprising an organic compound as provided herein.
Alternatively, the organic electroluminescent device may be a green device, a red device, or a blue device.
Preferably, the organic electroluminescent device is a red organic electroluminescent device or a green organic electroluminescent device.
According to one embodiment, the organic electroluminescent device includes an anode 100, a hole transport layer 320, an organic light emitting layer 330 as an energy conversion layer, 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 organic light-emitting layer 330 of the organic electroluminescent device to effectively improve the performance of the organic electroluminescent device.
Alternatively, the organic light emitting layer 330 includes a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form excitons, the excitons transfer 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 may comprise an organic compound of the present application.
The guest material of the organic light emitting layer 330 may be selected with reference to the related art, and may be selected from, for example, iridium (III) organometallic complex, platinum (II) organometallic complex, and ruthenium (II) complex. Specifically, the guest material may be selected from at least one of the following compounds:
in a specific embodiment, the guest material is D-6, i.e., ir (piq) 2 (dpm). In another specific embodiment, the guest material is D-7, ir (3 mppy) 3 。
Optionally, the anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. such as ZnO: al orSnO 2 Sb; 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.
In the present application, the material of the hole transport layer 320 may be selected from phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, benzidine type triarylamine, styrene amine type triarylamine, diamine type triarylamine, or other types of materials, and may be selected by those skilled in the art with reference to the prior art. For example, the material of the hole transport layer is selected from the group consisting of:
in the present application, the hole transport layer 320 may have a one-layer or two-layer structure. Alternatively, as shown in fig. 1, the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322 which are stacked, wherein the first hole transport layer 321 is closer to the anode 100 than the second hole transport layer 322. In a specific embodiment, the first hole transport layer 321 is comprised of HT-5 (i.e., α -NPD) and the second hole transport layer 322 is comprised of HT-6.
In the present application, 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 materials may generally include a metal complex and/or a nitrogen-containing heterocyclic derivative, wherein the metal complex material may be selected from LiQ, alq, and the like 3 、Bepq 2 Etc.; the nitrogen-containing heterocyclic derivative may be an aromatic ring having a nitrogen-containing six-or five-membered ring skeleton, a fused aromatic ring compound having a nitrogen-containing six-or five-membered ring skeleton, or the like, and specific examples include, but are not limited to, 1, 10-phenanthroline compounds such as BCP, bphen, NBphen, DBimiBphen, bimiBphen, or the like, or compounds having the structure shown below. In one specific embodiment, the electron transport layer 340 comprises LiQ andET-1。
optionally, the cathode 200 comprises a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. 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, liO 2 Al, liF/Ca, liF/Al and BaF 2 and/Ca, but is not limited thereto. Preferably, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 is 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. For example, the hole injection layer 310 is selected from the group consisting of:
in a specific embodiment, the material of the hole injection layer 310 is HAT-CN.
Optionally, as shown in fig. 1, an electron injection layer 350 is 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. For example, the material of the electron injection layer 350 may be selected from LiF, naCl, csF, li 2 O、BaO、LiQ、NaCl、CsF、Cs 2 CO 3 One or more of Na, li, ca, al and Yb. In a specific embodiment, the material of the electron injection layer 350 may include LiQ or Yb.
In a third aspect, the present application provides an electronic device comprising the above organic electroluminescent device.
As shown in fig. 2, the electronic device is an electronic device 400, and the electronic device 400 may be a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.
The invention is further illustrated by the following examples, but is not to be construed as being limited thereto. No mention is made of the starting products from which the compounds of the synthetic process are commercially available.
1. Synthesis of Sub-aX
The synthesis of each Sub-aX is illustrated by the example of Sub-a1.
Under nitrogen atmosphere, 3-bromo-5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-ol (14.1lg, 50mmol), 4-chloro-2-fluorobenzeneboronic acid (9.59g, 55mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh) were added to a 500mL three-necked flask in this order 3 ) 4 0.58g,0.5 mmol), anhydrous potassium carbonate (13.82g, 100mmol), toluene (140 mL), anhydrous ethanol (35 mL) and deionized water (35 mL), stirring and heating were started, and the temperature was raised to reflux for 16h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. Silica gel column chromatography of the crude product using n-heptane as the mobile phase gave Sub-a1 as a white solid (7.16 g, 43% yield).
The other Sub-aX listed in Table 1 was synthesized with reference to the synthesis method of Sub-a1, except that 3-bromo-5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalene-2-ol was replaced with reactant A and 4-chloro-2-fluorobenzeneboronic acid was replaced with reactant B.
TABLE 1
2. Synthesis of Sub-bX
The synthesis of each Sub-bX is described by taking Sub-b1 as an example.
Under nitrogen atmosphere, sub-a1 (16.64g, 50mmol), cesium carbonate (32.58g, 100mmol) and dimethyl sulfoxide (DMSO, 160 mL) were added to a 250mL three-necked flask, stirred and heated, and allowed to warm to 80 ℃ for 4h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. Silica gel column chromatography of the crude product using n-heptane as a mobile phase gave Sub-b1 (13.92 g, 89% yield) as a white solid.
Other Sub-bX listed in Table 2 were synthesized with reference to the synthesis method of Sub-b1, except that the Sub-a1 was replaced with the reactant C.
TABLE 2
3. Synthesis of Sub-cX
The synthesis of each Sub-cX is illustrated by the example of Sub-c 1.
Under the nitrogen atmosphere, adding Sub-a9 (15g, 43.6 mmol) into a 10L three-neck bottle, starting to heat to be molten, then adding sublimed sulfur (25.8g, 100.5mmol), wherein the system is yellow, continuously heating to 115-120 ℃, then adding aluminum trichloride (0.35g, 2.6 mmol) in batches, gradually changing the system to be black in the process of adding the aluminum trichloride, discharging a large amount of hydrogen sulfide gas, keeping the temperature for 4h after the aluminum trichloride is added, starting to slowly heat to 200-210 ℃, pouring the reaction liquid into a 250mL single-neck bottle while the reaction liquid is hot after 4h reaction, carrying out reduced pressure distillation, ensuring the vacuum degree of an oil pump to be about 40Pa, collecting fractions between 120 and 130 ℃, obtaining 8.2g of white crystals, dissolving the solids by absolute ethyl alcohol, crystallizing at-20 ℃, and repeating twice, thus obtaining Sub-c1 (7.3 g, yield 45%).
Other Sub-cX listed in Table 3 were synthesized with reference to the synthesis of Sub-c1 except that the Sub-a9 was replaced with the reactant D.
TABLE 3
4. Synthesis of Sub-d1
Sub-a11 (20.78g, 55mmol) was dissolved in 50mL of THF in a 250mL three-necked flask, cooled to-78 deg.C, then n-BuLi (22mL, 2.5M, 55mmol) was added dropwise, after 4h of reaction, benzophenone (10g, 55mmol) was added, after 30min of incubation, warmed to room temperature for 30min of reaction, quenched with methanol, and the solvent was removed under reduced pressure. Glacial acetic acid (100 mL) and hydrochloric acid (25 mL) were then added, the mixture was refluxed for 24h, then cooled to room temperature, the reaction mixture was washed with water to neutrality, the precipitate was filtered, and the precipitate was dried to give Sub-d1 (15.87 g, yield 62.3%).
5. Synthesis of Sub-e 1:
in a 250mL three-necked flask, 2, 5-dichloro-2, 5-dimethylhexane (10g, 54.6mmol) was dissolved in 50mL of Dichloroethane (DCE), and the reaction solution was cooled to 0 ℃ to add AlCl 3 (7.3 g,54.6 mmol), 2-bromo-9, 9-dimethyl-9H-fluorene (14.9 g,54.6 mmol) of DCE (50 mL), and after 30min of reaction, the temperature of the reaction solution was raised to 80 ℃ for 12h. Then, the mixture was cooled to room temperature, and ice (100 g) and concentrated hydrochloric acid (20 mL) were added thereto and the mixture was stirred for 20min. The reaction solution was extracted three times with dichloromethane, dried over anhydrous magnesium sulfate, passed through a silica gel column to give a crude product, which was finally recrystallized using dichloromethane/methanol to give Sub-e1 (16.5 g, yield 78.6%).
6. Synthesis of Sub-fX
The synthesis of each Sub-fX is illustrated by the example of Sub-f 1.
Under nitrogen atmosphere, sub-b1 (15.64g, 50mmol), pinacol diboron (15.24g, 60mmol), potassium acetate (10.8g, 110mmol) and 1, 4-dioxane (160 mL) were added in sequence to a 500mL three-necked flask, stirring was started and heating was continued, and when the temperature of the system was raised to 40 ℃, tris (dibenzylideneacetone) dipalladium (Pd) was rapidly added 2 (dba) 3 0.46g,0.5 mmol) and 2-dicyclohexylphosphine-2 ',4',6' triisopropylbiphenyl (XPhos, 0.48g, 1mmol), and was further heated to reflux and stirred for reaction overnight. After the system is cooled to room temperature, adding 200mL of water into the system, stirring for 30min, carrying out vacuum filtration, washing a filter cake to be neutral by using deionized water, and then leaching by using 100mL of absolute ethyl alcohol to obtain a gray solid; the crude product was slurried with n-heptane once, washed with 200mL of toluene, passed through a silica gel column to remove the catalyst and concentrated to give Sub-f1 as a white solid (15.36 g, 76% yield).
Other Sub-fX listed in Table 4 were synthesized with reference to the synthesis of Sub-f1, except that the reactant E was used in place of Sub-b1.
TABLE 4
7. Synthesis of Sub-gX
The synthesis of each Sub-gX is illustrated by the example of Sub-g 1.
2, 4-dichloro-6-phenyl-1, 3, 5-triazine (16.95g, 75mmol), dibenzothiophene-1-boronic acid (11.40g, 50mmol), tetrakis (triphenylphosphine) palladium (0.58g, 0.5mmol), tetrabutylammonium bromide (1.61g, 5mmol), anhydrous potassium carbonate (13.82g, 100mmol), toluene (170 mL) and deionized water (45 mL) were added sequentially to a 500mL three-necked flask under a nitrogen atmosphere, stirred and heated to 65-70 ℃ for reaction for 16h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was recrystallized from toluene to give Sub-g1 as a white solid (12.15 g, 65% yield).
Other Sub-gX listed in Table 5 were synthesized with reference to the synthesis of Sub-G1, except that reactant F was used instead of 2, 4-dichloro-6-phenyl-1, 3, 5-triazine and reactant G was used instead of dibenzothiophene-1 boronic acid.
TABLE 5
8. Synthesis of Sub-hX
The synthesis of each Sub-hX is illustrated by the example of Sub-h 1:
under a nitrogen atmosphere, 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (13.38g, 50mmol), dibenzothiophene-1-boronic acid (11.35g, 55mmol), tetrakis (triphenylphosphine) palladium (0.58g, 0.5mmol), tetrabutylammonium bromide (1.61g, 5 mmol), anhydrous potassium carbonate (13.82g, 100mmol), toluene (140 mL), tetrahydrofuran (35 mL) and deionized water (35 mL) were added in this order to a 500mL three-necked flask, stirred and heated, and the temperature was raised to reflux for 16h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was recrystallized from toluene to give Sub-h1 as a white solid (16.15 g, yield 82%).
Other Sub-hX listed in Table 6 were synthesized by reference to the synthesis method of Sub-H1, except that reactant H was used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and reactant J was used instead of dibenzothiophene-1-boronic acid.
TABLE 6
9. Synthesis of Sub-jX
The synthesis of each Sub-hX is illustrated by the example of Sub-j 1:
under a nitrogen atmosphere, 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (13.38g, 50mmol), sub-f12 (24.13g, 55mmol), tetrakis (triphenylphosphine) palladium 0.58g, 0.5mmol), tetrabutylammonium bromide (1.61g, 5mmol), anhydrous potassium carbonate (13.82g, 100mmol), toluene (240 mL), anhydrous ethanol (60 mL) and deionized water (60 mL) were added in this order to a 500mL three-necked flask, stirred and heated, and the temperature was raised to reflux for 16h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was recrystallized from toluene to give Sub-j1 as a white solid (20.95 g, 77% yield).
Other Sub-jX listed in Table 7 were synthesized by reference to the synthesis of Sub-j1 except that reactant K was used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and reactant L was used instead of Sub-f12.
TABLE 7
10. Synthesis of Sub-kX
The synthesis of each Sub-kX is illustrated by the example of Sub-k 1:
under nitrogen atmosphere, sub-b8 (21.55g, 55mmol), 9H-carbazole (8.36g, 50mmol) and Pd were sequentially added into a 500mL three-necked flask 2 (dba) 3 (0.916g, 1mmol), XPhos (0.95g, 2mmol), sodium tert-butoxide (9.61g, 100mmol) and xylene (220 mL), heating to reflux, stirring and reacting overnight; after the system is cooled to room temperature, pouring the reaction solution into 500mL of deionized water, fully stirring for 30min, carrying out suction filtration, leaching the filter cake to be neutral by using the deionized water, and leaching by using anhydrous ethanol (200 mL) to remove water; the filter cake was recrystallized from toluene to give Sub-k1 as a gray solid (16.73 g, 70% yield).
Other Sub-kX listed in Table 8 were synthesized with reference to the synthesis of Sub-k1, except that the reactant M was used in place of Sub-b8 and the reactant N was used in place of 9H-carbazole.
TABLE 8
11. Synthesis of Sub-mX
The synthesis of each Sub-mX is illustrated by the example of Sub-m 1:
under nitrogen atmosphere, a 500mL three-necked flask was charged with Sub-j3 (23.95g, 50mmol), pinacol diboron (15.24g, 60mmol), potassium acetate (10.8g, 110mmol) and 1, 4-dioxane (240 mL) in this order, stirred and heated, and Pd was added after the temperature of the system had risen to 40 ℃ 2 (dba) 3 (0.46g, 0.5mmol) and XPhos (0.48g, 1mmol), and the reaction mixture was stirred overnight while the temperature was increased to reflux. After the system is cooled to room temperature, adding 500mL of water into the system, fully stirring for 30min, carrying out vacuum filtration, washing a filter cake to be neutral by using deionized water, and then leaching by using 100mL of absolute ethyl alcohol to obtain a gray solid; the crude product was slurried once with n-heptane, then washed with 200mL of toluene and passed through a silica gel column to remove the catalyst and concentrated to give Sub-m1 as a white solid (19.11 g, 67% yield).
Other Sub-mX listed in Table 9 were synthesized with reference to the synthesis method of Sub-m1, except that the reactant O was used instead of Sub-j3.
TABLE 9
Synthesis example 1
Synthesis of Compound 1:
under a nitrogen atmosphere, sub-f4 (22.24g, 55mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (13.38g, 50mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh) were added to a 500mL three-necked flask in this order 3 ) 4 0.58g,0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61g,5 mmol), anhydrous potassium carbonate (13.82g, 100mmol), toluene (220 mL), tetrahydrofuran (55 mL) and deionized water (55 mL), stirring and heating were started, and the temperature was raised to reflux for 16h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was recrystallized from toluene to give compound 1 as a white solid (21.15 g, 83% yield), ms spectrum: m/z =510.3[ m ] +H] + 。
Synthesis examples 2 to 71
The compounds listed in Table 10 were synthesized with reference to the synthesis method of Compound 1, except that Sub-f4 was replaced with reactant P and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine was replaced with reactant Q, and the main raw materials used, the corresponding synthesized compounds, and the results of the yield and mass spectrum characterization thereof are shown in Table 10.
Watch 10
Synthesis example 72
Synthesis of compound 676:
under a nitrogen atmosphere, sub-j7 (32.21g, 50mmol), 9H-carbazole (9.20g, 55mmol) and tris (dibenzylideneacetone) dipalladium (Pd) were added in this order to a 500mL three-necked flask 2 (dba) 3 0.916g, 1mmol), XPhos (0.95g, 2mmol), sodium tert-butoxide (9.61g, 100mmol) and xylene (220 mL), heating to reflux, stirring and reacting overnight; after the system is cooled to room temperature, pouring the reaction solution into 500mL of deionized water, fully stirring for 30min, carrying out suction filtration, leaching the filter cake to be neutral by using the deionized water, and leaching by using anhydrous ethanol (200 mL) to remove water; after the filter cake was recrystallized from toluene, a white solid was finally obtained, i.e. compound 676 (24.0 g, yield 62%); mass spectrum: m/z =775.3[ m ] +H] + 。
Synthesis examples 73 to 75
The compounds listed in Table 11 were synthesized by referring to the synthesis method of the compound 676, except that the reactant R was used instead of Sub-j7 and the reactant S was used instead of Sub-j7, and the main raw materials used, the corresponding synthesized compounds, and the yield and mass spectrum characterization results thereof are shown in Table 11.
TABLE 11
The nuclear magnetic data for some of the compounds are shown in table 12:
TABLE 12
Example 1: red organic electroluminescent device
The anode pretreatment is carried out by the following processes: in the thickness sequence of
The ITO/Ag/ITO substrate is subjected to surface treatment by ultraviolet ozone and O2: N2 plasma to increase the work function of an anode, and the surface of the ITO substrate is cleaned by an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.
HAT-CN was vacuum-deposited on an experimental substrate (anode) to a thickness of
And then vacuum evaporating α -NPD on the hole injection layer to form a layer having a thickness of
The first hole transport layer of (1).
Vacuum evaporating compound HT-6 on the first hole transport layer to a thickness of
The second hole transport layer of (1).
Next, on the second hole transporting layer, RH — P: compound 6 ir (piq) 2 (dpm) was formed at 49%: the film thickness ratio of 49% to 2% is subjected to co-evaporation to form a film with a thickness of
The red organic light emitting layer.
On the organic light-emitting layer, compounds ET-1 and LiQ were mixed at a weight ratio of 1
A thick Electron Transport Layer (ETL) formed by depositing Yb on the electron transport layer
Then magnesium (Mg) and silver (Ag) were mixed at an evaporation rate of 1On the electron injection layer, is formed to a thickness of
The cathode of (1).
The thickness of the vacuum deposition on the cathode is set to
Thereby completing the fabrication of the red organic electroluminescent device.
Examples 2 to 60
Organic electroluminescent devices were produced in the same manner as in example 1, except that compounds (collectively referred to as "compound X") in table 13 below were each substituted for compound 6 in example 1 in the production of the organic light-emitting layer.
Comparative examples 1 to 5
An organic electroluminescent device was produced in the same manner as in example 1, except that compound a, compound B, compound C, compound D and compound E were each used instead of compound 1 in example 1 in the production of the organic light-emitting layer.
In the above examples and comparative examples, the main material structures used were as follows:
performance test was performed on the red organic electroluminescent devices prepared in examples 1 to 60 and comparative examples 1 to 5, specifically at 10mA/cm 2 The IVL performance of the device is tested under the condition of (1), and the service life of the T95 device is 20mA/cm 2 The test was carried out under the conditions shown in Table 13.
Watch 13
Example 61: preparation of green light organic electroluminescent device
The anode pretreatment is carried out by the following processes: in the thickness sequence of
The ITO/Ag/ITO substrate is subjected to surface treatment by ultraviolet ozone and O2: N2 plasma to increase the work function of an anode, and the surface of the ITO substrate is cleaned by an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.
HAT-CN was vacuum-deposited on the test substrate (anode) to a thickness of
And then vacuum evaporating α -NPD on the hole injection layer to form a layer having a thickness of
The first hole transport layer of (1).
Vacuum evaporating a compound HT-6 on the first hole transport layer to a thickness of
The second hole transport layer of (1).
On the second hole transport layer, compound 1: GH-P: ir (3 mppy) 3 At a rate of 45%:45%: co-evaporation is carried out at a film thickness ratio of 10% to form a film having a thickness of
The green organic light emitting layer of (1).
In organic hairOn the optical layer, compounds ET-1 and LiQ were mixed at a weight ratio of 1
A thick Electron Transport Layer (ETL) formed by depositing Yb on the electron transport layer
And then magnesium (Mg) and silver (Ag) were mixed at an evaporation rate of 1
The cathode of (1).
The thickness of the vacuum deposition on the cathode is set to
Thereby completing the fabrication of the green organic electroluminescent device.
Examples 62 to 75
Organic electroluminescent devices were produced in the same manner as in example 61, except that in the production of the light-emitting layer, compounds in table 14 below (collectively referred to as "compound X") were used instead of compound 1 in example 61.
Comparative examples 6 to 7
An organic electroluminescent device was produced in the same manner as in example 61, except that compound F and compound G were used instead of compound 1 in example 61, respectively, in producing a light-emitting layer.
The green organic electroluminescent devices prepared in examples 61 to 75 and comparative examples 6 to 7 were tested for their performance, in particular in 10 mA-cm 2 The IVL performance of the device is tested under the condition of (1), and the service life of the T95 device is 20mA/cm 2 The test was carried out under the conditions shown in Table 14.
TABLE 14
Referring to table 13 and table 14 above, when the organic compound of the present application is used as a host material of an organic electroluminescent device, the efficiency is improved by at least 13.6% and the lifetime is improved by at least 16% when the organic compound is used as a red light host material; when the material is used as a green light host material, the efficiency is improved by at least 15.6 percent, and the service life is improved by at least 17.1 percent. The preferred embodiments of the present invention have been described in detail with reference to the accompanying drawings, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protection scope of the present invention.
Claims (15)
1. An organic compound, characterized in that the structure of the organic compound is shown in formula I:
in the formula I, R 1 And R 2 The same or different and are each independently selected from hydrogen or methyl; n is selected from 1 or 2;
x is selected from C (R) 5 R 6 ) O or S; r is 5 And R 6 The same or different, and each is independently selected from alkyl with 1-10 carbon atoms and aryl with 6-20 carbon atoms, optionally, R 5 And R 6 Are connected with each other to form a saturated or unsaturated 5-15 membered ring;
R 0 represents hydrogen or
R represents hydrogen or
L、L 1 、L 2 、L a The same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 25 carbon atoms;
Ar 1 、Ar 2 、Ar a the same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
L、L 1 、L 2 、L a 、Ar 1 、Ar 2 and Ar a Substituent of (1) and R 3 And R 4 The same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl group with 1-10 carbon atoms, halogenated alkyl group with 1-10 carbon atoms, deuterated alkyl group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, triphenylsilyl group, aryl group with 6-18 carbon atoms, heteroaryl group with 3-15 carbon atoms and cycloalkyl group with 3-10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3-to 15-membered ring;
n 3 represents R 3 When n is 0, 1 or 2 3 When is 2, each R 3 The same or different; n is 4 Represents R 4 When n is 0, 1,2 or 3 2 When greater than 1, each R 4 The same or different;
het represents a nitrogen-containing heteroarylene group having 2 to 15 carbon atoms.
2. An organic compound according to claim 1, wherein Het is selected from the group consisting of triazinylene, pyrimidylene, quinolylene, quinoxalylene, isoquinolylene, quinazolinylene and:
3. the organic compound according to claim 1,
selected from the group consisting of:
4. the organic compound of claim 1, wherein the structure of the organic compound is selected from the group consisting of:
5. the organic compound of claim 1, wherein R 5 And R 6 The same or different, and each is independently selected from alkyl or phenyl with 1-4 carbon atoms, optionally, R 5 And R 6 Are linked to each other to form a cyclopentane, cyclohexane or fluorene ring.
6. The organic compound according to claim 1, wherein L and L are 1 、L 2 And L a The same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 15 carbon atoms;
preferably, L 1 、L 2 And L a Wherein the substituents are each independently selected fromDeuterium, fluorine, a cyano group, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, and an aryl group having 6 to 12 carbon atoms.
7. The organic compound according to claim 1, wherein L, L 1 、L 2 And L a The same or different, and each is independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolyl group;
preferably, L 1 、L 2 And L a Each substituent in (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl or naphthyl.
8. The organic compound according to claim 1, wherein Ar is Ar 1 、Ar 2 And Ar a The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-25 carbon atoms, and substituted or unsubstituted heteroaryl with 5-25 carbon atoms;
Ar 1 、Ar 2 and Ar a Wherein the substituents are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a fluoroalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 5 to 12 carbon atoms; ar (Ar) 1 、Ar 2 And Ar a Optionally, any two adjacent substituents form a 5-to 15-membered saturated or unsaturated ring.
9. The organic compound of claim 1, which isIn (Ar) 1 、Ar 2 And Ar a The same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxazolyl;
Ar 1 、Ar 2 and Ar a Each substituent in (a) is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl, or carbazolyl; ar (Ar) 1 、Ar 2 And Ar a Optionally, any two adjacent substituents form a benzene, naphthalene, cyclopentane, cyclohexane or fluorene ring.
10. The organic compound according to claim 1, wherein Ar is Ar 1 And Ar 2 Identical or different and each independently selected from substituted or unsubstituted groups Z selected from the group consisting of:
the substituted group Z has one or more substituents each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl or naphthyl; when the number of the substituents is more than 1, the substituents may be the same or different.
11. Organic compound according to claim 1A compound of formula (I), wherein Ar a Selected from the group consisting of substituted or unsubstituted groups V selected from the group consisting of:
the substituted group V has one or more substituents, each substituent is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, trifluoromethyl, trideuteromethyl, trimethylsilyl or phenyl; when the number of the substituents is more than 1, the substituents may be the same or different.
12. The organic compound according to claim 1,
the same or different, and each is independently selected from the group consisting of:
alternatively,
selected from the group consisting of:
13. the organic compound of claim 1, wherein the organic compound is selected from the group consisting of:
14. the organic electroluminescent device is characterized by comprising an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; the functional layer comprises an organic compound according to any one of claims 1 to 13;
preferably, the functional layer includes an organic light emitting layer containing the organic compound.
15. An electronic device comprising the organic electroluminescent device of claim 14.
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| KR20220109864A (en) * | 2021-01-29 | 2022-08-05 | 주식회사 엘지화학 | Compound, and organic light emitting device comprising same |
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| KR20220109864A (en) * | 2021-01-29 | 2022-08-05 | 주식회사 엘지화학 | Compound, and organic light emitting device comprising same |
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