CN117088870A - Compound, electron transport material, and electroluminescent device - Google Patents

Compound, electron transport material, and electroluminescent device Download PDF

Info

Publication number
CN117088870A
CN117088870A CN202311062671.6A CN202311062671A CN117088870A CN 117088870 A CN117088870 A CN 117088870A CN 202311062671 A CN202311062671 A CN 202311062671A CN 117088870 A CN117088870 A CN 117088870A
Authority
CN
China
Prior art keywords
group
groups
atom
atoms
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202311062671.6A
Other languages
Chinese (zh)
Inventor
孟献文
高荣荣
黎俊聪
陈磊
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BOE Technology Group Co Ltd
Chengdu BOE Optoelectronics Technology Co Ltd
Original Assignee
BOE Technology Group Co Ltd
Chengdu BOE Optoelectronics Technology Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BOE Technology Group Co Ltd, Chengdu BOE Optoelectronics Technology Co Ltd filed Critical BOE Technology Group Co Ltd
Priority to CN202311062671.6A priority Critical patent/CN117088870A/en
Publication of CN117088870A publication Critical patent/CN117088870A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
    • C07F9/65517—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
    • C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
    • C07F9/655354—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Abstract

The application relates to a compound, which has a molecular structure shown in a formula (I):wherein X is a group comprising a first atom and X is attached to the non-X portion of the compound through only one first atom; y is a direct bond or a group comprising a second atom and is attached to the non-Y part of the compound through only one second atom; a1 is an aromatic or heteroaromatic ring structure, or at least one H atom is bound by a radical R 3 Substituted aromatic or heteroaromatic ring structures; l is one of a direct bond, arylene, heteroarylene, or L is a group R having at least one H atom 4 One of a substituted arylene or heteroarylene group; g is an electron transporting group; r is R 1 、R 2 、R 3 、R 4 For substituents, m and n are each independently selected from the interval [0,4 ]]An integer of (a) is provided. The compound provided by the embodiment of the application has the advantages of weak crystallization, good film forming property and good thermal stability of a fused spiro structure.

Description

Compound, electron transport material, and electroluminescent device
Technical Field
The application relates to the technical field of display, in particular to a light emitting diode.
Background
Organic light-emitting diodes (OLED) and quantum dot light-emitting diodes (OLED) are new display technologies which are relatively similar in technology, and have the advantages of self-luminescence, wide viewing angle, low power consumption, full black display, full color and the like. The working principle is generally as follows: under the driving action of an electric field, holes are injected from the anode, the HOMO (highest occupied molecular orbital ) energy level of the functional layers such as the hole injection layer, the hole transport layer and the like is gradually transmitted to the light emitting layer, meanwhile, electrons are injected from the cathode, the LUMO energy level of the functional layers such as the electron injection layer, the electron transport layer and the like is gradually transmitted to the light emitting layer, and the holes and the electrons are recombined in the light emitting layer to generate excitons. When the exciton returns to the ground state from the excited state, energy is emitted in the form of light. Therefore, how to balance the injection and recombination of holes and electrons is an important research content for providing an OLED or QLED with excellent luminous efficiency.
When the OLED or QLED device is operated under the voltage application, joule heat can be generated, so that organic materials can be crystallized, and the service life and efficiency of the device are affected; the electron transport material is in a system of electron deficiency in molecular structure and has stronger electron withdrawing groups, so that the electron transport material has certain polarity, and is easier to crystallize relative to the hole transport material, so that the electron transport material has poor film forming capability and even can cause hole blocking of the material due to crystallization in the film forming process.
Disclosure of Invention
The embodiment of the application provides a compound, an electron transport material and an electroluminescent device, which are used for solving the technical problems of strong crystallinity and poor film forming property of the electron transport material.
In a first aspect, embodiments of the present application provide a compound having a molecular structure of formula (i):
wherein said X is a group comprising a first atom and said X is attached to a non-X moiety of said compound through only one of said first atoms;
the Y is a direct bond and is a direct bond,
or,
the Y is a group comprising a second atom, and the Y is attached to a non-Y moiety of the compound through only one of the second atoms;
A1 is an aromatic or heteroaromatic ring structure of 4 to 50 members, or 4 to 50 members, at least one H atom being bound by a radical R 3 Substituted aromatic or heteroaromatic ring structures;
l is one of a direct bond, an arylene group of 6 to 40 carbon atoms, a heteroarylene group of 3 to 40 carbon atoms, or L is a group R having at least one H atom 4 One of a substituted arylene group of 6 to 40 carbon atoms or a heteroarylene group of 3 to 40 carbon atoms;
g is an electron withdrawing group;
R 1 、R 2 、R 3 、R 4 is substituent, m is R 1 The number of groups, n is R 2 The number of groups, m and n are each independently selected from the interval [0,4 ]]An integer of (a) is provided.
In some embodiments of the application, R 1 、R 2 、R 3 、R 4 Each independently selected from one of the following groups or atoms:
-D，-F，-Cl，-Br，-I，-CHO，-CN，-C(＝O)Ar，-P(＝O)(Ar) 2 ，-S(＝O)Ar，-S(＝O) 2 Ar，-N(R) 2 ，-N(Ar) 2 ，-NO 2 ，-Si(R) 2 ，-B(OR) 2 ，-OSO 2 R；
an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, substituted or unsubstituted;
one of the-CH groups having 1 to 40C atoms, substituted or unsubstituted alkyl, alkoxy or thioalkyl groups 2 -a group or any at least two non-adjacent-CH 2 The radical is-CR=RC-, -C≡C-, -Si (R) 2 -、-Ge(R) 2 -、-Sn(R) 2 -、-C(＝O)-、-C(＝S)-、-C(＝Se)-、-P(＝O)(R)-、-S(＝O)-、-SO 2 -O-, -S-, or-C (=o) NR-, instead of the latter group;
5-60 membered, substituted or unsubstituted aryl or heteroaryl;
wherein the group R is-H, -D, -F, -Cl, -Br, -I, -CHO, -CN, an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, an aryl or heteroaryl group of 5 to 60 members.
In some embodiments of the application, R 1 、R 2 、R 3 、R 4 Each independently selected from one of the following groups or atoms:
an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, at least one H atom being substituted by a group R;
an alkyl group having 1 to 40C atoms, at least one H atom being substituted by a group R one-CH 2-group or any at least two non-adjacent-CH 2-groups of an alkoxy or thioalkyl group is substituted with-cr=rc-; C.ident.C-, -Si (R) 2 -、-Ge(R) 2 -、-Sn(R) 2 -、-C(＝O)-、-C(＝S)-、-C(＝Se)-、-P(＝O)(R)-、-S(＝O)-、-SO 2 -O-, -S-, or-C (=o) NR-, instead of the latter group;
aryl or heteroaryl groups having 5 to 60 members and at least one H atom substituted with a group R.
In some embodiments of the application, R is attached to adjacent carbon atoms 1 The groups are linked to each other; and/or the number of the groups of groups,
r being bound to adjacent carbon atoms 2 The groups are linked to each other.
In some embodiments of the application, the first atom is one of B, C, si, O, S; and/or the number of the groups of groups,
the second atom is one of C, si, O, S, N, se.
In some embodiments of the present application, X is one of-O-, -S-, -Se-;
and/or the number of the groups of groups,
y is a direct bond and is a direct bond, or-O-, -S-; -Se-, -B (R) 0 )-、-C(R 0 ) 2 -、-Si(R 0 ) 2 -、-C(＝O)-、-C(R 0 )＝C(R 0 )-、-SO 2 -any of the groups;
wherein R is 0 Is a substituent.
In some embodiments of the present application, G is one of G1, G2, G3, and G4, and the structural formulas of G1, G2, G3, and G4 are as follows:
wherein T is 1 ～T 8 Independently a C atom or an N atom, and T 1 ～T 8 At least one of which is an N atom;
T 9 ～T 11 independently C or N, and T 1 ～T 8 At least one of which is an N atom;
z is a group comprising a third atom, and the Z is attached to a non-Z part of the group G3 only through the third atom, the third atom being one of C, si, O, S, N;
Ar 1 、Ar 2 、Ar 3 、Ar 4 each independently selected from 5-23 membered, substituted or unsubstituted aryl or heteroaryl.
In some embodiments of the application, Z is-B (R 0 )-、-C(R 0 ) 2 -、-Si(R 0 ) 2 -、-C(＝O)-、-C＝N R 0 -、-C＝
C(R 0 ) 2 -、-O-、-S-、-S(＝O)-、-SO 2 -any of the groups; and/or the number of the groups of groups,
Ar 1 、Ar 2 、Ar 3 、Ar 4 each independently selected from 5-23 membered and having at least one H atom bound to a group R 0 A substituted aryl or heteroaryl group, and a substituted aryl or heteroaryl group,
wherein R is 0 Is a substituent.
In some embodiments of the application, R 0 Is one of the following groups or atoms:
-D，-F，-Cl，-Br，-I，-CN；
an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, substituted or unsubstituted;
one of the-CH groups having 1 to 40C atoms, substituted or unsubstituted alkyl, alkoxy or thioalkyl groups 2 -a group or any at least two non-adjacent-CH 2 The radical is-CR=RC-, -C≡C-, -Si (R) 2 -、-Ge(R) 2 -、-Sn(R) 2 -、-C(＝O)-、-C(＝S)-、-C(＝Se)-、-P(＝O)(R)-、-S(＝O)-、-SO 2 -O-, -S-, or-C (=o) NR-, instead of the latter group;
5-60 membered, substituted or unsubstituted aryl or heteroaryl;
wherein the group R is-H, -D, -F, -Cl, -Br, -I, -CHO, -CN, an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, an aryl or heteroaryl group of 5 to 60 members.
In some embodiments of the application, R 0 Is one of the following groups or atoms:
an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, at least one H atom being substituted by a group R;
one-CH 2-group or any at least two non-adjacent-CH groups of alkyl, alkoxy or thioalkyl groups having 1 to 40C atoms, at least one H atom being replaced by a radical R 2 The radical is-CR=RC-, -C≡C-, -Si (R) 2 -、-Ge(R) 2 -、-Sn(R) 2 -、-C(＝O)-、-C(＝S)-、-C(＝Se)-、-P(＝O)(R)-、-S(＝O)-、-SO 2 -O-, -S-, or-C (=o) NR-, instead of the latter group;
aryl or heteroaryl groups having 5 to 60 members and at least one H atom substituted with a group R.
In some embodiments of the application, the compound is one of the following having the molecular structure:
/>
in a second aspect, embodiments of the present application provide an electron transport material comprising a compound according to any of the embodiments of the first aspect.
In a third aspect, embodiments of the present application provide an electroluminescent device, including:
an anode;
a light emitting layer;
an electron transport layer, wherein the electron transport layer is made of the electron transport material according to any embodiment of the second aspect;
and a cathode.
Compared with the prior art, the technical scheme provided by the embodiment of the application has the following advantages:
the compound provided by the embodiment of the application has a fused and hybrid spiro structure, so that molecules of the compound have orthogonal space three-dimensional configuration, van der Waals force between molecules of the compound can be reduced, inhibition is formed on crystallization, and crystallinity of the compound can be reduced macroscopically; and the compound has a plurality of aromatic ring structures and has high rigidity, so that the compound has high glass transition temperature, and the film forming property and the thermal stability of the compound are improved macroscopically.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, illustrate embodiments consistent with the application and together with the description, serve to explain the principles of the application.
In order to more clearly illustrate the embodiments of the application or the technical solutions of the prior art, the drawings which are used in the description of the embodiments or the prior art will be briefly described, and it will be obvious to a person skilled in the art that other drawings can be obtained from these drawings without inventive effort.
Fig. 1 is a schematic structural diagram of a front-mounted device according to an embodiment of the present application;
fig. 2 is a schematic structural diagram of an inverted device according to an embodiment of the present application.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the embodiments of the present application more apparent, the technical solutions of the embodiments of the present application will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present application, and it is apparent that the described embodiments are some embodiments of the present application, but not all embodiments of the present application. All other embodiments, which can be made by those skilled in the art based on the embodiments of the application without making any inventive effort, are intended to be within the scope of the application.
Unless specifically stated otherwise, the terms used herein should be understood as meaning as commonly used in the art. Accordingly, unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. In case of conflict, the present specification will control.
Unless otherwise specifically indicated, the various raw materials, reagents, instruments, equipment and the like used in the present application are commercially available or may be prepared by existing methods.
The existing electron transport material has the technical problems of strong crystallinity and poor film forming property.
The technical scheme provided by the embodiment of the application aims to solve the technical problems, and the overall thought is as follows:
in a first aspect, embodiments of the present application provide a compound having a molecular structure of formula (i):
wherein said X is a group comprising a first atom and said X is attached to a non-X moiety of said compound through only one of said first atoms;
the Y is a direct bond and is a direct bond,
or,
the Y is a group comprising a second atom, and the Y is attached to a non-Y moiety of the compound through only one of the second atoms;
a1 is an aromatic or heteroaromatic ring structure of 4 to 50 members, or 4 to 50 members, at least one H atom being bound by a radical R 3 Substituted aromatic or heteroaromatic ring structures;
l is one of a direct bond, an arylene group of 6 to 40 carbon atoms, a heteroarylene group of 3 to 40 carbon atoms, or L is a group R having at least one H atom 4 One of a substituted arylene group of 6 to 40 carbon atoms or a heteroarylene group of 3 to 40 carbon atoms;
g is an electron withdrawing group;
R 1 、R 2 、R 3 、R 4 is substituent, m is R 1 The number of groups, n is R 2 The number of groups, m and n are each independently selected from the interval [0,4 ] ]An integer of (a) is provided.
As can be seen from formula (I), X is directly linked to two C atoms. Said X is attached to a non-X moiety of said compound through only one of said first atoms, which means: x is linked to the two carbon atoms through only one of the first atoms. As an example, X may be-NH-, -SiH 2 -、-CH 2 -an alike group. The first atom may in theory be any atom that can link two covalent bonds.
Similarly, Y is also directly linked to two C atoms. Said Y is attached to a non-Y moiety of said compound through only one of said second atoms, which means: y is linked to these two carbon atoms through only one of said second atoms. The second atom may in theory be any atom that can link two covalent bonds.
As can be seen from formula (I), R 1 Is linked to a benzene ring having 4 substitution positions. m is interval [0,4 ]]M is a number selected from 0, 1, 2, 3, and 4. The m is R 1 The number of groups, the numerical meaning of m, is to be understood as follows: connection R 1 In the 4 substitution positions on the benzene ring, m are R 1 The substitution takes up space. Specifically, when m=0, all of the 4 substituents of the benzene ring are bonded to a hydrogen atom, and R is not bonded to 1 The method comprises the steps of carrying out a first treatment on the surface of the When m=1, then any 1 of the 4 substitution positions of the benzene ring is substituted by R 1 The substitution occupies a place, and the rest 3 links are all hydrogen atoms; when m is 2 or 3, any m of the 4 substitution positions of the benzene ring is R 1 The substitution occupies a place, and the rest 4-m are all connected hydrogen atoms; when m is 4, the 4 substitution positions of the benzene ring are all R 1 The substitution takes up space.
The numerical meaning of n is understood in the same manner as that of m.
The compound disclosed by the application has a fused and hetero spiro structure, and molecules of the compound have an orthogonal space three-dimensional configuration. Specifically, the five-membered ring where X is located and R 1 The conjugated big pi bond is formed between the connected benzene rings, and it can be understood that the five-membered ring where X is positioned and R 1 The benzene rings attached being identical toOne plane forms a planar molecular structure. And A1 and R 2 The benzene ring being linked to the planar molecular structure by the same quaternary carbon, i.e. A1 and R 2 The benzene ring connected is not necessarily in the same plane as the planar molecular structure. The compounds have orthogonal spatial stereoconfigurations, as readily understood by the electronic configuration of the quaternary carbon. This is advantageous in reducing van der Waals forces between molecules of the compound, and in retarding formation of crystals, the crystallinity of the compound can be reduced macroscopically.
The compound has a plurality of aromatic ring structures and is high in rigidity, so that the compound has a high glass transition temperature, which is beneficial to macroscopically improving the film forming property and the thermal stability of the compound.
The compound provided by the application has a fused and hybrid spiro structure, so that molecules of the compound have orthogonal space three-dimensional configuration, van der Waals force among the molecules of the compound can be reduced, inhibition is formed on crystallization, and crystallinity of the compound can be reduced macroscopically; and the compound has a plurality of aromatic ring structures and has high rigidity, so that the compound has high glass transition temperature, and the film forming property and the thermal stability of the compound are improved macroscopically.
In some embodiments of the application, R 1 、R 2 、R 3 、R 4 Each independently selected from one of the following groups or atoms:
-D，-F，-Cl，-Br，-I，-CHO，-CN，-C(＝O)Ar，-P(＝O)(Ar) 2 ，-S(＝O)Ar，-S(＝O) 2 Ar，-N(R) 2 ，-N(Ar) 2 ，-NO 2 ，-Si(R) 2 ，-B(OR) 2 ，-OSO 2 R；
an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, substituted or unsubstituted;
one of the-CH groups having 1 to 40C atoms, substituted or unsubstituted alkyl, alkoxy or thioalkyl groups 2 -a group or any at least two non-adjacent-CH 2 The radical is-CR=RC-, -C≡C-, -Si (R) 2 -、-Ge(R) 2 -、-Sn(R) 2 -、-C(＝O)-、-C(＝S)-、-C(＝Se)-、-P(＝O)(R)-、-S(＝O)-、-SO 2 -O-, -S-, or-C (=o) NR-, instead of the latter group;
5-60 membered, substituted or unsubstituted aryl or heteroaryl;
wherein the group R is-H, -D, -F, -Cl, -Br, -I, -CHO, -CN, an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, an aryl or heteroaryl group of 5 to 60 members.
The alkane may be a paraffin or a naphthene. It is easily understood that 1C atom cannot constitute a cycloalkane, and thus when the alkane is a cycloalkane, it has 3 to 40C atoms.
It should be noted that the term-D refers to deuterium atom.
R 1 、R 2 、R 3 、R 4 The energy level of the compound molecule can be adjusted by selecting different groups or atoms.
In the present application, the group R independently represents, for each occurrence, -H, -D, -F, -Cl, -Br, -I, -CHO, -CN, one of an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, an aryl or heteroaryl group having 5 to 60 members. The radicals R present in the differences may have the same molecular structure or may have different molecular structures.
In some embodiments of the application, R 1 、R 2 、R 3 、R 4 Each independently selected from one of the following groups or atoms:
an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, at least one H atom being substituted by a group R;
An alkyl group having 1 to 40C atoms, at least one H atom being substituted by a group R one-CH 2-group or any at least two non-adjacent-CH 2-groups of an alkoxy or thioalkyl group is substituted with-cr=rc-; C.ident.C-, -Si (R) 2 -、-Ge(R) 2 -、-Sn(R) 2 -、-C(＝O)-、-C(＝S)-、-C(＝Se)-、-P(＝O)(R)-、-S(＝O)-、-SO 2 -O-, -S-, or-C (=o) NR-, instead of the latter group;
aryl or heteroaryl groups having 5 to 60 members and at least one H atom substituted with a group R.
In some embodiments of the application, R is attached to adjacent carbon atoms 1 The groups are linked to each other; and/or the number of the groups of groups,
r being bound to adjacent carbon atoms 2 The groups are linked to each other.
As already mentioned above, R 1 May be a substituted alkyl, alkoxy or thioalkyl group having 1 to 40C atoms;
one of the substituted alkyl, alkoxy or thioalkyl groups-CH having 1 to 40C atoms 2 -a group or any at least two non-adjacent-CH 2 The radical is-CR=RC-, -C≡C-, -Si (R) 2 -、-Ge(R) 2 -、-Sn(R) 2 -、-C(＝O)-、-C(＝S)-、-C(＝Se)-、-P(＝O)(R)-、-S(＝O)-、-SO 2 -O-, -S-, or-C (=o) NR-, instead of the latter group;
5-60 membered, substituted aryl or heteroaryl.
As one of the substitution patterns, adjacent R 1 The groups may be substituted with one another to form an interconnecting relationship.
Similarly, adjacent R 2 Groups may also be substituted with one another to form an interconnecting relationship.
In some embodiments of the application, the first atom is one of B, C, si, O, S; and/or the number of the groups of groups,
the second atom is one of C, si, O, S, N, se.
In some embodiments of the present application, X is one of-O-, -S-, -Se-;
and/or the number of the groups of groups,
y is a direct bond and is a direct bond, or-O-, -S-; -Se-, -B (R) 0 )-、-C(R 0 ) 2 -、-Si(R 0 ) 2 -、-C(＝O)-、-C(R 0 )＝C(R 0 )-、-SO 2 -any of the groups;
wherein R is 0 Is a substituent.
The reason that X is one of-O-, -S-, -Se-is that X is on a five-membered ring, and no substituent is contained, so that the molecular stability of the compound is improved;
y mainly plays a role in connection and has a large selection range.
In some embodiments of the present application, G is one of G1, G2, G3, and G4, and the structural formulas of G1, G2, G3, and G4 are as follows:
wherein T is 1 ～T 8 Independently a C atom or an N atom, and T 1 ～T 8 At least one of which is an N atom;
T 9 ～T 11 independently C or N, and T 1 ～T 8 At least one of which is an N atom;
z is a group comprising a third atom, and the Z is attached to a non-Z part of the group G3 only through the third atom, the third atom being one of C, si, O, S, N;
Ar 1 、Ar 2 、Ar 3 、Ar 4 each independently selected from 5-23 membered, substituted or unsubstituted aryl or heteroaryl.
It is understood that each of G1, G2, G3, and G4 is an electron withdrawing group and has a low LUMO level. This facilitates electron transport by the compound, and when applied to an electron transport layer of an electroluminescent device, electrons can be efficiently transported into the light-emitting layer, so that the recombination probability of electrons and holes in the light-emitting layer is increased, and the device exhibits high light-emitting efficiency.
In some embodiments of the application, Z is-C (R 0 ) 2 -、-N(R 0 ) -any of-O-, -S-; and/or the number of the groups of groups,
Ar 1 、Ar 2 、Ar 3 、Ar 4 each independently selected from 5-23 membered and having at least one H atom bound to a group R 0 SubstitutedAn aryl group or a heteroaryl group,
wherein R is 0 Is a substituent.
In some embodiments of the application, R 0 Is one of the following groups or atoms:
-D，-F，-Cl，-Br，-I，-CN；
an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, substituted or unsubstituted;
one of the-CH groups having 1 to 40C atoms, substituted or unsubstituted alkyl, alkoxy or thioalkyl groups 2 -a group or any at least two non-adjacent-CH 2 The radical is-CR=RC-, -C≡C-, -Si (R) 2 -、-Ge(R) 2 -、-Sn(R) 2 -、-C(＝O)-、-C(＝S)-、-C(＝Se)-、-P(＝O)(R)-、-S(＝O)-、-SO 2 -O-, -S-, or-C (=o) NR-, instead of the latter group;
5-60 membered, substituted or unsubstituted aryl or heteroaryl;
Wherein the group R is-H, -D, -F, -Cl, -Br, -I, -CHO, -CN, an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, an aryl or heteroaryl group of 5 to 60 members.
In some embodiments of the application, R 0 Is one of the following groups or atoms:
an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, at least one H atom being substituted by a group R;
one-CH 2-group or any at least two non-adjacent-CH groups of alkyl, alkoxy or thioalkyl groups having 1 to 40C atoms, at least one H atom being replaced by a radical R 2 The radical is-CR=RC-, -C≡C-, -Si (R) 2 -、-Ge(R) 2 -、-Sn(R) 2 -、-C(＝O)-、-C(＝S)-、-C(＝Se)-、-P(＝O)(R)-、-S(＝O)-、-SO 2 -O-, -S-, or-C (=o) NR-, instead of the latter group;
aryl or heteroaryl groups having 5 to 60 members and at least one H atom substituted with a group R.
In some embodiments of the application, the compound is one of the following having the molecular structure:
/>
/>
/>
/>
/>
/>
/>
in a second aspect, embodiments of the present application provide an electron transport material comprising a compound according to any of the embodiments of the first aspect.
The electron transport material refers to a material used for an electron transport layer of an OLED or a QLED.
It will be appreciated by those skilled in the art that the electron transport material is implemented based on the compound according to the first aspect, and specific embodiments of the electron transport material may refer to the embodiments of the first aspect, and since the electron transport material adopts some or all of the technical solutions of the embodiments of the first aspect, at least all of the beneficial effects brought by the technical solutions of the embodiments of the first aspect are not described herein again.
In a third aspect, referring to fig. 1 and 2, an embodiment of the present application provides an electroluminescent device, where the electroluminescent device includes:
an anode 2;
a light-emitting layer 6;
an electron transport layer 8, wherein the material of the electron transport layer 8 is the electron transport material according to any embodiment of the second aspect;
and a cathode 10.
The electroluminescent device comprises an OLED device and a QLED device.
It will be appreciated by those skilled in the art that electroluminescent devices typically also include a substrate. Referring to fig. 1, the electroluminescent device of the present application may be a front-end device in which an anode 2 is disposed on a substrate 1. The positive device includes:
a substrate 1;
an anode 2 disposed on the substrate 1;
A light-emitting layer 6 provided on the anode 2;
an electron transport layer 8 disposed on the light emitting layer 6;
a cathode 10 disposed on the electron transport layer 8.
Referring to fig. 2, the electroluminescent device according to the present application may be an inverted device in which a cathode 10 is disposed on a substrate 1. The inverted device includes:
a substrate 1;
a cathode 10 disposed on the substrate 1;
an electron transport layer 8 disposed on the cathode 10;
a light-emitting layer 6 disposed on the electron transport layer 8;
an anode 2 arranged on the light emitting layer 6.
It will be appreciated by those skilled in the art that the light emitting device may be a top emitting device or a bottom emitting device.
It will be appreciated by those skilled in the art that the substrate 1 may be a transparent rigid or flexible material, such as glass, polyimide, etc., which enables both rigid substrate display and flexible display.
Those skilled in the art will appreciate that the materials of the anode 2 and cathode 10 may be, for example, one or more of a metal, a carbon material, and a metal oxide, and that the metal may be, for example, one or more of Al, ag, cu, mo, au, ba, ca and Mg. The carbon material may be, for example, one or more of graphite, carbon nanotubes, graphene, and carbon fibers; the metal oxide may be a doped or undoped metal oxide, including one or more of ITO, FTO, ATO, AZO, GZO, IZO, MZO and AMO, and also including a composite electrode of doped or undoped transparent metal oxide with a metal sandwiched therebetween.
In some embodiments of the present application, the light emitting device further comprises at least one of a hole injection layer 3, a hole transport layer 4, and an electron injection layer 9.
It will be appreciated by those skilled in the art that the material of the hole injection layer 3 may be an inorganic oxide, such as an oxide of a metal such as molybdenum, titanium, vanadium, rhenium, ruthenium, chromium, zirconium, hafnium, tantalum, silver, tungsten, manganese, or a dopant of a strong electron-withdrawing system, for example, F4TCNQ, HAT-CN, or the like, or may be a material obtained after P-type doping of the hole transport material. The thickness of the hole injection layer 3 may be 5 to 30nm.
As will be appreciated by those skilled in the art, the material of the hole transport layer 4 may be an arylamine or carbazole material, such as NPB, TPD, BAFLP, DFLDPBi. The thickness of the hole transport layer 4 may be 300 to 100nm.
It will be appreciated by those skilled in the art that the light-emitting layer 6 may be a red phosphorescent host and a red phosphorescent dopant, a green phosphorescent host and a green phosphorescent dopant, or a fluorescent host and a fluorescent dopant, and the host material of the light-emitting layer 6 may include one material or a mixture of two or more materialsThe host material of the blue light emitting layer 6 can be selected from anthracene derivatives ADN, MADN, etc., and the dopant can be pyrene derivatives, fluorene derivatives, perylene derivatives, styrylamine derivatives, metal complexes, etc., such as TBPe, BDAVBi, DPAVBi, FIrpic, etc.; the host material of the green luminescent layer 6 can be selected from coumarin dyes, quinacridone derivatives, polycyclic aromatic hydrocarbons, diamine anthracene derivatives, carbazole derivatives, such as DMQA, BA-NPB, alq 3 Etc., the dopant may be a metal complex, etc., such as Ir (ppy) 3 、Ir(ppy) 2 (acac) and the like; the red light-emitting host material can be selected from DCM series materials such as DCM, DCJTB, DCJTI, etc., and the dopant can be metal complex such as Ir (piq) 2 (acac)、PtOEP、Ir(btp) 2 (acac), etc., the thickness of the light emitting layer 6 may be 20 to 100nm.
It will be appreciated by those skilled in the art that the thickness of the electron transport layer 8 may be 20nm to 100nm.
As will be appreciated by those skilled in the art, the electron injection layer 9 material includes Li 2 O、K 2 SiO 3 At least one of LiF, yb, mg, ca. The thickness of the electron injection layer 9 may be 1nm to 10nm.
In some embodiments of the present application, the light emitting device further comprises at least one of a hole blocking layer 7, an electron blocking layer 5.
It will be appreciated by those skilled in the art that the electron blocking layer 5 has hole transport properties, and may be a red light emitting auxiliary layer, a green light emitting auxiliary layer, or a blue light emitting auxiliary layer, and the material of the electron blocking layer 5 may be an arylamine or carbazole material, such as CBP, PCzPA, etc., and the thickness of the electron blocking layer 5 may be 5 to 50nm.
It is understood by those skilled in the art that the hole blocking layer 7 includes at least one of an aromatic heterocyclic compound, such as imidazole derivatives such as benzimidazole derivatives, imidazopyridine derivatives, and benzimidazolofhenanthridine derivatives, and oxazine derivatives such as pyrimidine derivatives and triazine derivatives, and a compound having a nitrogen-containing six-membered ring structure such as quinoline derivatives, isoquinoline derivatives, and phenanthroline derivatives, and a compound having a phosphine oxide substituent on a heterocycle, such as OXD-7, TAZ, p-EtTAZ, BPhen, BCP, and an electron transport material according to the present application. The thickness of the hole blocking layer 7 may be 5 to 100nm.
It can be appreciated by those skilled in the art that the electroluminescent device according to the third aspect of the present application is implemented based on the electron transport material according to the second aspect, and specific embodiments of the electroluminescent device may refer to the embodiment of the second aspect, and since the electroluminescent device adopts some or all of the technical solutions of the embodiment of the second aspect, at least all of the beneficial effects brought by the technical solutions of the embodiment of the second aspect are not described herein in detail.
The application will be further illustrated with reference to specific examples. It is to be understood that these examples are illustrative of the present application and are not intended to limit the scope of the present application. The experimental procedures, which are not specified in the following examples, are generally determined according to national standards. If the corresponding national standard does not exist, the method is carried out according to the general international standard, the conventional condition or the condition recommended by the manufacturer.
Example 1
The structural formula of each material related to this embodiment is as follows:
referring to fig. 1, the present embodiment provides an electroluminescent device having the following structure:
glass substrate 1/anode 2 (ITO)/hole injection layer 3 (5 nm)/hole transport layer 4 (30 nm)/electron blocking layer 5 (10 nm)/light emitting layer 6 (20 nm)/hole blocking layer 7 (10 nm)/electron transport layer 8 (40 nm)/electron injection layer 9 (1 nm)/cathode 10 (100 nm)
Wherein the hole injection layer 3 is made of HAT-CN, the hole transport layer 4 is made of NPB, the electron blocking layer 5 is made of TCTA, the hole blocking layer 7 is made of DPEPO, the electron injection layer 9 is made of LiF,
the material of the luminescent layer 6 consists of a blue host material AND a blue dopant, the blue host material is AND, the blue dopant material is DPAVBi,
the material of the electron transport layer 8 is material i.
The light emitting device described in this embodiment is prepared by the steps of:
the preparation process of the light emitting device is as follows:
ultrasonically treating the glass substrate 1 provided with ITO in a cleaning agent, flushing in deionized water, ultrasonically degreasing in an acetone-ethanol mixed solvent, and baking in a clean environment until water is completely removed;
placing a glass plate provided with ITO into a vacuum cavity, vacuumizing to 1X 10-5-1X 10-6, and vacuum evaporating a hole injection material on one side of the ITO far away from the glass plate to form a hole injection layer 3;
evaporating a hole transport material on one side of the hole injection layer 3 far away from the ITO to form a hole transport layer 4;
vacuum evaporating an electron blocking material on one side of the hole transport layer 4 far away from the hole injection layer 3 to form an electron blocking layer 5;
the light-emitting layer 6 is formed by vacuum evaporation of a light-emitting material on the side of the electron blocking layer 5 far away from the hole transport layer 4, wherein the light-emitting material comprises a blue light main body material and a blue light doping agent material, and the weight ratio of the blue light main body material to the blue light doping agent material is 95:5, a step of;
Vacuum evaporating a hole blocking material on one side of the light-emitting layer 6 far away from the electron blocking layer 5 to form a hole blocking layer 7;
an electron transport layer 8 is formed by vacuum evaporation of an electron transport material on the side of the hole blocking layer 7 remote from the light emitting layer 6. An electron injection layer 9 is formed by vacuum vapor deposition of an electron injection material on the side of the electron transport layer 8 remote from the hole blocking layer 7. And plating an Al layer on the electron injection layer 9 far away from the vapor electron transport layer 8 to form a cathode 10, thus obtaining the electroluminescent device.
Example 2
This embodiment differs from embodiment 1 only in that:
the material of the electron transport layer 8 is material ii.
Example 3
This embodiment differs from embodiment 1 only in that:
the material of the electron transport layer 8 is material iii.
Example 4
This embodiment differs from embodiment 1 only in that:
the material of the electron transport layer 8 is material iv.
Example 5
This embodiment differs from embodiment 1 only in that:
the material of the electron transport layer 8 is material v.
Example 6
This embodiment differs from embodiment 1 only in that:
the material of the electron transport layer 8 is material vi.
Example 7
This embodiment differs from embodiment 1 only in that:
the material of the electron transport layer 8 is material vii.
Example 8
This embodiment differs from embodiment 1 only in that:
The material of the electron transport layer 8 is material viii.
Comparative example 1
This comparative example differs from example 1 only in that:
the material of the electron transport layer 8 is material ix.
Related experiment and effect data:
the structural formulas and the relevant properties of the materials of the electron transport layer 8 used in examples 1 to 8 and comparative examples are shown in table 1:
/>
TABLE 1
Wherein LUNO/HOMO refers to a molecular front line orbit simulated by a Gaussian model molecule, and is obtained through calculation.
The synthesis method of the material can be carried out in the following way:
material I:
synthesis of intermediate M1: 9-bromo-11H-benzo [ a ]]Fluorenone (3.74 g,12.14 mmol), 2- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) -1, 10-phenanthroline (3.80 g,12.5 mmol), pd (PPh 3) 4 (0.7 g,0.6 mmol), potassium carbonate (2.76 g,20 mmol) and THF/H2O (60 mL/12 mL) were added to a 200mL pressure-resistant bottle and heated to 100deg.C under argon for pressurizing reaction for 12H. After completion of the reaction, the reaction mixture was cooled to room temperature, a large amount of solid was precipitated, the reaction mixture was filtered, and the filtered solid was washed with ethanol (100 mL) and dried to give a white powdery solid (4.21 g,10.32 mmol). Yield: 85%. 1 HNMR(500MHz,Chloroform)δ9.28(s,1H),8.88(s,1H),8.80(s,1H),8.45(s,1H),8.39(s,1H),8.28(m,2H),8.05(m,2H),7.89(d,J＝10.0Hz,2H),7.55(m,4H),7.34(s,1H).
Synthesis of material I: 3-bromo-2-phenylfuran (1.10 g,5 mmol) was dissolved in 30mL anhydrous tetrahydrofuran, added to a two-necked flask under argon atmosphere, cooled to-78deg.C, stirred for 10min, n-butyllithium (1.6 mol/L, THF,3.5 mL) was slowly added dropwise with a syringe, stirred for 1h at 78deg.C, then intermediate M1 (2.04 g,5 mmol) was weighed, dissolved in anhydrous tetrahydrofuran, and added to the flask. And (3) heating to room temperature, and continuing stirring and reacting for 24 hours under the protection of argon. The reaction was monitored to completion by TLC plates, the reaction was dried by spin-drying and stirred. Intermediate 2 was isolated as a solid powder (1.82 g,3.4 mmol) using a chromatography silica gel column in 68% yield. 1H NMR (500 MHz, chloroform) delta 8.80 (s, 1H), 8.66 (s, 1H), 8.44 (d, J=10.0 Hz, 2H), 8.38 (m, 2H), 8.07 (s, 1H), 7.97 (s, 1H), 7.92 (s, 1H), 7.88 (s, 1H), 7.76 (s, 1H), 7.65-7.51 (m, 3H), 7.48-7.20 (m, 7H), 6.41 (s, 1H).
Material II:
synthesis of intermediate M2: the synthesis of intermediate M2 is similar to that of intermediate M1, except that 9-bromo-11H-benzo [ a ] fluorenone is replaced with 2-bromo-11H-benzo [ a ] fluorenone, to afford intermediate M2. Yield: 82%.1H NMR (500 MHz, chloroform) delta 8.88 (s, 1H), 8.79 (d, J=10.0 Hz, 2H), 8.63 (s, 1H), 8.45 (s, 1H), 8.39 (s, 1H), 8.26 (s, 1H), 8.18 (s, 1H), 8.06 (s, 1H), 7.93 (s, 1H), 7.88 (s, 1H), 7.67 (m, 2H), 7.57 (d, J=10.0 Hz, 2H), 7.34 (s, 1H).
Synthesis of material II: the synthesis of material II is similar to that of material I, except that M1 is replaced by M2 to obtain material II. Yield: 62%. 1 H NMR(500MHz,Chloroform)δ8.80(s,1H),8.67(s,1H),8.44(d,J＝10.0Hz,2H),8.38(d,J＝15.0Hz,2H),8.15(d,J＝7.6Hz,2H),7.98(s,1H),7.88(s,1H),7.82(s,1H),7.76(s,1H),7.64-7.51(m,3H),7.48-7.22(m,6H),6.41(s,1H).
Material III:
synthesis of intermediate M3: the synthesis of intermediate M3 is similar to that of intermediate M1, except that 9-bromo-11H-benzo [ a ] fluorenone is replaced with 9-bromo-7H-benzo [ a ] fluorenone, to afford intermediate M3. Yield: 79%.1H NMR (500 MHz, chloroform) δ9.01 (s, 1H), 8.88 (s, 1H), 8.80 (s, 1H), 8.45 (s, 1H), 8.39 (s, 1H), 8.26 (s, 1H), 8.13 (s, 1H), 8.06 (s, 1H), 7.98 (s, 1H), 7.88 (s, 1H), 7.82 (s, 1H), 7.66-7.48 (m, 3H), 7.40 (s, 1H), 7.34 (s, 1H).
Synthesis of material III: the synthesis of material III is similar to that of material I, except that M1 is replaced by M3 to obtain material II. The yield thereof was found to be 66%. 1 H NMR(500MHz,Chloroform)δ8.90(s,1H),8.80(s,1H),8.68(s,1H),8.44(d,J＝10.0Hz,2H),8.38(m,2H),7.88(s,1H),7.77(d,J＝10.0Hz,2H),7.67-7.50(m,3H),7.49-7.22(m,7H),7.09(s,1H),6.41(s,1H).
Material IV:
synthesis of intermediate M4: the synthesis of intermediate M4 is similar to the synthesis of intermediate M2, except that 2- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) -1, 10-phenanthroline is replaced by 2, 4-diphenyl-6- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) -1,3, 5-triazine, thus obtaining intermediate M4. Yield: 80%.1H NMR (500 MHz, chloroform) delta 8.78 (s, 1H), 8.63 (s, 1H), 8.36 (s, 4H), 8.16 (d, J=15.0 Hz, 2H), 8.06 (s, 1H), 7.93 (s, 1H), 7.87 (s, 1H), 7.67 (m, 2H), 7.50 (s, 6H).
Synthesis of material IV: the synthesis of material IV is similar to that of material I, except that M1 is replaced with M4 to obtain material IV. The yield thereof was found to be 65%. 1 H NMR(500MHz,Chloroform)δ8.47(s,1H),8.43(s,1H),8.36(s,4H),8.15(d,J＝10.4Hz,2H),7.97(d,J＝5.0Hz,2H),7.82(s,1H),7.76(s,1H),7.57(s,1H),7.50(s,6H),7.47-7.34(m,4H),7.29(s,1H),6.41(s,1H).
Material V:
synthesis of intermediate M5: the synthesis of intermediate M5 is similar to the synthesis of intermediate M2, except that 2- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) -1, 10-phenanthroline is replaced by 2, 4-phenyl-6- (3- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) phenyl) -1,3, 5-triazine, thus obtaining intermediate M5. Yield: 67%.1H NMR (500 MHz, chloroform) delta 8.78 (s, 1H), 8.63 (s, 1H), 8.43-8.29 (m, 6H), 8.18 (s, 1H), 8.06 (s, 1H), 7.93 (s, 1H), 7.87 (s, 1H), 7.66 (m, 4H), 7.47 (m, 7H).
Synthesis of material V: synthesis of Material V and Material I is synthesized similarly, except that M1 is replaced by M5 to obtain material V. Yield: 61%. 1 H NMR(500MHz,Chloroform)δ8.43(s,1H),8.37(dd,J＝7.5,2.5Hz,7H),8.15(d,J＝13.6Hz,2H),7.97(d,J＝5.0Hz,2H),7.82(s,1H),7.76(s,1H),7.70(s,1H),7.59(m,2H),7.50(s,6H),7.46-7.35(m,4H),7.29(s,1H),6.41(s,1H).
Material VI:
synthesis of intermediate M6: the synthesis of intermediate M6 is similar to that of intermediate M4, except that 9-bromo-11H-benzo [ a ] fluorenone is replaced with 3-bromo-11H-benzo [ a ] fluorenone, to afford intermediate M6. Yield: 78%.1H NMR (500 MHz, chloroform) δ9.21 (s, 1H), 8.78 (s, 1H), 8.63 (s, 1H), 8.57 (s, 1H), 8.35 (d, J=10.0Hz, 5H), 8.26 (s, 1H), 8.00 (s, 1H), 7.76 (s, 1H), 7.63 (s, 1H), 7.50 (s, 6H).
Synthesis of material VI: the synthesis of material VI is similar to that of material I, except that M1 is replaced with M6 to obtain material VI. Yield: 60%. 1 H NMR(500MHz,Chloroform)δ9.10(s,1H),8.45(s,1H),8.36(s,4H),8.24(d,J＝3.6Hz,2H),8.14(s,1H),7.85(s,1H),7.80(s,1H),7.76(s,1H),7.52(m,7H),7.46-7.25(m,5H),6.41(s,1H).
Material VII:
synthesis of intermediate M7: the synthesis of intermediate M7 is similar to that of intermediate M1, except that 2- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) -1, 10-phenanthroline is replaced by 2,2' - (5- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) -1, 3-phenylene) diphenyl [ d ] oxazole, and intermediate M7 can be obtained. Yield: 80%.1H NMR (500 MHz, chloroform) delta 8.43 (s, 1H), 8.36 (s, 1H), 8.30 (s, 2H), 8.19 (s, 1H), 8.14 (s, 1H), 8.04 (s, 1H), 7.97 (d, J=5.0 Hz, 2H), 7.82 (s, 1H), 7.74 (s, 4H), 7.57 (s, 1H), 7.43 (s, 1H), 7.38 (s, 4H).
Synthesis of material VII: material and method for producing the sameThe synthesis of material VII is similar to that of material I, except that M1 is replaced by M7 to give material VI. Yield: 59%. 1 H NMR(500MHz,Chloroform)δ8.43(s,1H),8.35(s,1H),8.30(d,J＝4.4Hz,3H),8.07(s,1H),7.97(s,2H),7.92(s,1H),7.75(d,J＝10.0Hz,5H),7.62(s,1H),7.48-7.24(m,10H),6.41(s,1H).
Material VIII:
synthesis of intermediate M8: the synthesis of intermediate M8 is similar to that of intermediate M1, except that 2- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) -1, 10-phenanthroline is replaced by diphenyl (4- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) phenyl) phosphine oxide, and intermediate M8 can be obtained. Yield: 74%.1H NMR (500 MHz,Chloroform) δ8.78 (s, 1H), 8.63 (s, 1H), 8.18 (s, 1H), 8.06 (s, 1H), 7.97 (s, 4H), 7.93 (s, 1H), 7.87 (s, 1H), 7.78 (s, 4H), 7.67 (d, J=20.0 Hz, 2H), 7.51 (s, 6H), 7.44 (s, 1H).
Synthesis of material VIII: the synthesis of material VIII is similar to that of material I, except that M1 is replaced with M8 to obtain material VIII. Yield: 55%. 1 H NMR(500 MHz,Chloroform)δ8.43(s,1H),8.23(s,1H),8.07(s,1H),7.94(d,J＝25.0 Hz,7H),7.77(d,J＝10.0 Hz,5H),7.62(s,1H),7.51(s,6H),7.47-7.22(m,6H),6.41(s,1H).
The electroluminescent devices obtained in examples 1 to 8 had a current density of 15mA/cm 2 The test items comprise a starting voltage, brightness, external quantum efficiency and service life.
The test results are shown in Table 2.
TABLE 2
The specific test data of the comparative example are:
the starting voltage is 3.96V, and the brightness is 37325Cd/m 2 An external quantum efficiency of 7.75, The service life LT95@1000nit is 306h.
As can be seen from the specific test data of table 2 and comparative examples, the compounds of examples 1 to 8 are electron transport materials having good device properties, and the OLED devices using them as electron transport layers all exhibit high efficiency, low driving voltage, long-life electroluminescent properties.
Various embodiments of the application may exist in a range of forms; it should be understood that the description in a range format is merely for convenience and brevity and should not be construed as a rigid limitation on the scope of the application; it is therefore to be understood that the range description has specifically disclosed all possible sub-ranges and individual values within that range. For example, it should be considered that a description of a range from 1 to 6 has specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the range, such as 1, 2, 3, 4, 5, and 6, wherever applicable. In addition, whenever a numerical range is referred to herein, it is meant to include any reference number (fractional or integer) within the indicated range.
In the present application, unless otherwise specified, terms such as "upper" and "lower" are used specifically to refer to the orientation of the drawing in the figures. In addition, in the description of the present specification, the terms "include", "comprising" and the like mean "including but not limited to". Moreover, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. Without further limitation, an element defined by the phrase "comprising … …" does not exclude the presence of other like elements in a process, method, article or apparatus that comprises the element. Relational terms such as "first" and "second", and the like may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Herein, "and/or" describing an association relationship of an association object means that there may be three relationships, for example, a and/or B, may mean: a alone, a and B together, and B alone. For the association relation of more than three association objects described by the "and/or", it means that any one of the three association objects may exist alone or any at least two of the three association objects exist simultaneously, for example, for a, and/or B, and/or C, any one of the A, B, C items may exist alone or any two of the A, B, C items exist simultaneously or three of the three items exist simultaneously. Herein, "at least one" means one or more, and "a plurality" means two or more. "at least one", "at least one" or the like refer to any combination of these items, including any combination of single item(s) or plural items(s). For example, "at least one (individual) of a, b, or c," or "at least one (individual) of a, b, and c," may each represent: a, b, c, a-b (i.e., a and b), a-c, b-c, or a-b-c, wherein a, b, c may be single or plural, respectively.
The foregoing is only a specific embodiment of the application to enable those skilled in the art to understand or practice the application. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the application. Thus, the present application is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims (13)

1. A compound, characterized in that the compound has a molecular structure represented by formula (i):
wherein said X is a group comprising a first atom and said X is attached to a non-X moiety of said compound through only one of said first atoms;
the Y is a direct bond and is a direct bond,
or,
the Y is a group comprising a second atom, and the Y is attached to a non-Y moiety of the compound through only one of the second atoms;
a1 is an aromatic or heteroaromatic ring structure of 4 to 50 members, or 4 to 50 members, at least one H atom being bound by a radical R 3 Substituted aromatic or heteroaromatic ring structures;
l is one of a direct bond, an arylene group of 6 to 40 carbon atoms, a heteroarylene group of 3 to 40 carbon atoms, or L is a group R having at least one H atom 4 One of a substituted arylene group of 6 to 40 carbon atoms or a heteroarylene group of 3 to 40 carbon atoms;
g is an electron withdrawing group;
R 1 、R 2 、R 3 、R 4 is substituent, m is R 1 The number of groups, n is R 2 The number of groups, m and n are each independently selected from the interval [0,4 ]]An integer of (a) is provided.
2. A compound according to claim 1, wherein R 1 、R 2 、R 3 、R 4 Each independently selected from one of the following groups or atoms:
-D，-F，-Cl，-Br，-I，-CHO，-CN，-C(＝O)Ar，-P(＝O)(Ar) 2 ，-S(＝O)Ar，-S(＝O) 2 Ar，-N(R) 2 ，-N(Ar) 2 ，-NO 2 ，-Si(R) 2 ，-B(OR) 2 ，-OSO 2 R；
an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, substituted or unsubstituted;
one of the-CH groups having 1 to 40C atoms, substituted or unsubstituted alkyl, alkoxy or thioalkyl groups 2 -a group or any at least two non-adjacent-CH 2 The radical is-CR=RC-, -C≡C-, -Si (R) 2 -、-Ge(R) 2 -、-Sn(R) 2 -、-C(＝O)-、-C(＝S)-、-C(＝Se)-、-P(＝O)(R)-、-S(＝O)-、-SO 2 -O-, -S-, or-C (=o) NR-, instead of the latter group;
5-60 membered, substituted or unsubstituted aryl or heteroaryl;
wherein the group R is-H, -D, -F, -Cl, -Br, -I, -CHO, -CN, an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, an aryl or heteroaryl group of 5 to 60 members.
3. A compound according to claim 2, wherein R 1 、R 2 、R 3 、R 4 Each independently selected from one of the following groups or atoms:
An alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, at least one H atom being substituted by a group R;
an alkyl group having 1 to 40C atoms, at least one H atom being substituted by a group R one-CH 2-group or any at least two non-adjacent-CH 2-groups of an alkoxy or thioalkyl group is substituted with-cr=rc-; C.ident.C-, -Si (R) 2 -、-Ge(R) 2 -、-Sn(R) 2 -、-C(＝O)-、-C(＝S)-、-C(＝Se)-、-P(＝O)(R)-、-S(＝O)-、-SO 2 -O-, -S-, or-C (=o) NR-, instead of the latter group;
aryl or heteroaryl groups having 5 to 60 members and at least one H atom substituted with a group R.
4. A compound according to claim 3, wherein R is attached to adjacent carbon atoms 1 The groups are linked to each other; and/or the number of the groups of groups,
r being bound to adjacent carbon atoms 2 The groups are linked to each other.
5. The compound of claim 1, wherein the first atom is one of B, C, si, O, S; and/or the number of the groups of groups,
the second atom is one of C, si, O, S, N, se.
6. The compound of claim 4, wherein X is one of-O-, -S-, -Se-; and/or the number of the groups of groups,
y is a direct bond and is a direct bond, or-O-, -S-; -Se-, -B (R) 0 )-、-C(R 0 ) 2 -、-Si(R 0 ) 2 -、-C(＝O)-、-C(R 0 )＝C(R 0 )-、-SO 2 -any of the groups;
wherein R is 0 Is a substituent.
7. The compound of claim 1, wherein G is one of G1, G2, G3, G4, and the structural formula of G1, G2, G3, G4 is as follows:
Wherein T is 1 ～T 8 Independently a C atom or an N atom, and T 1 ～T 8 At least one of which is an N atom;
T 9 ～T 11 independently C or N, and T 1 ～T 8 At least one of which is an N atom;
z is a group comprising a third atom, and the Z is attached to a non-Z part of the group G3 only through the third atom, the third atom being one of C, si, O, S, N;
Ar 1 、Ar 2 、Ar 3 、Ar 4 each independently selected from 5-23 membered, substituted or unsubstituted aryl or heteroaryl.
8. The compound of claim 7, wherein Z is-B (R 0 )-、-C(R 0 ) 2 -、-Si(R 0 ) 2 -、-C(＝O)-、-C＝N R 0 -、-C＝C(R 0 ) 2 -、-O-、-S-、-S(＝O)-、-SO 2 -any of the groups; and/or the number of the groups of groups,
Ar 1 、Ar 2 、Ar 3 、Ar 4 each independently selected from 5-23 membered and having at least one H atom bound to a group R 0 A substituted aryl or heteroaryl group, and a substituted aryl or heteroaryl group,
wherein R is 0 Is a substituent.
9. A compound according to claim 6 or 8, wherein R 0 Is one of the following groups or atoms:
-D，-F，-Cl，-Br，-I，-CN；
an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, substituted or unsubstituted;
one of the-CH groups having 1 to 40C atoms, substituted or unsubstituted alkyl, alkoxy or thioalkyl groups 2 -a group or any at least two non-adjacent-CH 2 The radical is-CR=RC-, -C≡C-, -Si (R) 2 -、-Ge(R) 2 -、-Sn(R) 2 -、-C(＝O)-、-C(＝S)-、-C(＝Se)-、-P(＝O)(R)-、-S(＝O)-、-SO 2 -O-, -S-, or-C (=o) NR-, instead of the latter group;
5-60 membered, substituted or unsubstituted aryl or heteroaryl;
wherein the group R is-H, -D, -F, -Cl, -Br, -I, -CHO, -CN, an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, an aryl or heteroaryl group of 5 to 60 members.
10. The compound of claim 9, wherein R 0 Is one of the following groups or atoms:
an alkyl, alkoxy or thioalkyl group having 1 to 40C atoms, at least one H atom being substituted by a group R;
one-CH 2-group or any at least two non-adjacent-CH groups of alkyl, alkoxy or thioalkyl groups having 1 to 40C atoms, at least one H atom being replaced by a radical R 2 The radical is-CR=RC-, -C≡C-, -Si (R) 2 -、-Ge(R) 2 -、-Sn(R) 2 -、-C(＝O)-、-C(＝S)-、-C(＝Se)-、-P(＝O)(R)-、-S(＝O)-、-SO 2 -O-, -S-, or-C (=o) NR-, instead of the latter group;
aryl or heteroaryl groups having 5 to 60 members and at least one H atom substituted with a group R.
11. The compound of claim 1, wherein the compound is one of the following having the molecular structure:
12. an electron transporting material, characterized in that the electron transporting material comprises the compound according to any one of claims 1 to 11.
13. An electroluminescent device, comprising:
an anode;
a light emitting layer;
an electron transport layer, the electron transport layer being made of the electron transport material according to claim 12;
and a cathode.
CN202311062671.6A 2023-08-22 2023-08-22 Compound, electron transport material, and electroluminescent device Pending CN117088870A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202311062671.6A CN117088870A (en) 2023-08-22 2023-08-22 Compound, electron transport material, and electroluminescent device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202311062671.6A CN117088870A (en) 2023-08-22 2023-08-22 Compound, electron transport material, and electroluminescent device

Publications (1)

Publication Number Publication Date
CN117088870A true CN117088870A (en) 2023-11-21

Family

ID=88771101

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202311062671.6A Pending CN117088870A (en) 2023-08-22 2023-08-22 Compound, electron transport material, and electroluminescent device

Country Status (1)

Country Link
CN (1) CN117088870A (en)

Similar Documents

Publication Publication Date Title
KR101115036B1 (en) Compound Containing Thianthrene And Organic Electronic Element Using The Same, Terminal Thereof
KR101153910B1 (en) Chemical Comprising Indole Derivatives and Organic Electronic Element using the same, Terminal thereof
KR101305934B1 (en) Chemical and Organic Electronic Element using the same, Terminal thereof
KR20110066763A (en) Compound containing indoloacridine and organic electronic element using the same, terminal thereof
KR20110034103A (en) Compound containing heterocyclic 5-membered ring derivative condensed aryl ring and organic electronic element using the same, terminal thereof
KR20200004266A (en) Multicyclic compound and organic light emitting device comprising the same
JPWO2018173598A1 (en) Organic electroluminescent device
KR101968213B1 (en) Heterocyclic compound and organic light emitting device comprising the same
KR20110092262A (en) Compound containing 5-membered heterocycle and organic electronic element using the same, terminal thereof
KR101181277B1 (en) Compound Containing Indoloacridine And Organic Electronic Element Using The Same, Terminal Thereof
KR101147318B1 (en) Compound Containing 5-Membered Heterocycle And Organic Electronic Element Using The Same, Terminal Thereof
KR101270505B1 (en) Amine Compound Having Three Carbazole And Organic Electronic Element Using The Same, Terminal Thereof
KR20110044587A (en) Chemical comprising dibenzocarbazole and organic electroric element using the same, terminal thererof
KR101181276B1 (en) Compound Containing Indoloacridine And Organic Electronic Element Using The Same, Terminal Thereof
KR101379765B1 (en) Asymmetric aryl amine structure of the blue light-emitting material containing meta-substituted phenyl and organic electroluminescent device using the same
KR101181278B1 (en) Compound Containing Indoloacridine And Organic Electronic Element Using The Same, Terminal Thereof
KR101146929B1 (en) Compound Containing At Least Two 5-Membered Heterocycle And Organic Electronic Element Using The Same, Terminal Thereof
CN108164496B (en) Compound and organic electronic device thereof
KR101415730B1 (en) Aromatic compound derivatives and organic electroluminescent device using the same
KR101181270B1 (en) Compound Containing Indoloacridine And Organic Electronic Element Using The Same, Terminal Thereof
CN117088870A (en) Compound, electron transport material, and electroluminescent device
KR101163050B1 (en) Chemical Comprising Benzo Anthracene Have a Heterocyclic Ring and Organic Electronic Element using the same, Terminal thereof
KR102594848B1 (en) Organic light emitting device
KR20190106503A (en) Compound and organic light emitting device comprising the same
KR20190013149A (en) Organic luminescent compound, producing method of the same and organic electroluminescent device including the same

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination