CN110872298A - Condensed ring aryl compound, organic electronic device and application thereof - Google Patents

Condensed ring aryl compound, organic electronic device and application thereof Download PDF

Info

Publication number
CN110872298A
CN110872298A CN201911121013.3A CN201911121013A CN110872298A CN 110872298 A CN110872298 A CN 110872298A CN 201911121013 A CN201911121013 A CN 201911121013A CN 110872298 A CN110872298 A CN 110872298A
Authority
CN
China
Prior art keywords
substituted
unsubstituted
group
ring
aryl
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
CN201911121013.3A
Other languages
Chinese (zh)
Inventor
谢坤山
蔡烨
丁欢达
魏定纬
陈志宽
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.)
Ningbo Lu Milan New Materials Co Ltd
Original Assignee
Ningbo Lu Milan New Materials 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 Ningbo Lu Milan New Materials Co Ltd filed Critical Ningbo Lu Milan New Materials Co Ltd
Priority to CN201911121013.3A priority Critical patent/CN110872298A/en
Publication of CN110872298A publication Critical patent/CN110872298A/en
Pending legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • C07D471/12—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 three hetero rings
    • C07D471/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • 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
    • H10K50/15—Hole 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electromagnetism (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention relates to a condensed ring aryl compound, an organic electronic device and application thereof, wherein the condensed ring aryl compound has a structure shown in a formula (I),
Figure DDA0002275467580000011
wherein n is an integer of 0 to 5, X1、X2、Y1、Y2Each independently selected from the group consisting of a bond, N and CR5A combination of R1‑R5Either group is independently connected to ring A or ring B by a single bond, a double bond, and/or R1‑R5Any two adjacent rings form a ring C, the ring C is an electron-withdrawing ring, and R is1‑R5Are electron withdrawing groups. The structure is a non-planar structure, so that annihilation generated by high-energy excitons is reduced, holes are promoted to be injected into the hole transport layer by the anode, stacking and crystallization of molecules of the hole transport layer are avoided, and the service life of the device is prolonged; the parent nucleus is a rigid structure, which is beneficial to improving the stability of the device, the substituent group is an electron-withdrawing group, the LUMO energy level of the compound is between-4.6 and-6.0 eV, and the compound can be used as a P-doped material.

Description

Condensed ring aryl compound, organic electronic device and application thereof
Technical Field
The invention relates to the technical field of photoelectric materials, in particular to a condensed ring aryl compound, an organic electronic device and application thereof.
Background
Compared with an inorganic electroluminescent device (ELD), an organic light-emitting device (OLED) has the advantages of high brightness, fast response, wide viewing angle, simple process, high color purity, capability of realizing full-color display from blue light to red light, flexibility and the like, has wide application prospect in the fields of display and illumination, and is more and more emphasized by people.
An OLED device in the prior art generally includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and is matched with appropriate electrodes, and each of the layers is respectively composed of the following materials: hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials. When the OLED device is electrified, holes enter the device from the anode and then pass through the hole injection layer and the hole transport layer, electrons enter the device from the cathode and then pass through the electron injection layer and the electron transport layer, and when the holes and the electrons are combined in the light emitting layer, the light emitting material is excited to emit light. Therefore, for the OLED device, the injection and transport of charges are the first step of converting electric energy into light, and this process plays a crucial role in the turn-on voltage, the light emitting efficiency and the lifetime of the device. The injection and transmission efficiency of charges can be effectively improved by improving the concentration and the mobility of carriers, so that the starting voltage of the device is reduced, the luminous efficiency is improved, and the service life is prolonged. In the aspect of the hole transport layer, small molecules with hole properties, namely a hole injection layer material (P-doped material), are doped into the hole transport material, so that the concentration of holes can be effectively increased, and the hole transport efficiency is improved. If an electron is moved from the HOMO level of the hole transport material to the LUMO level of the dopant, a hole is formed, referred to as P-type doping, and the dopant is the P-doped material.
Although the P-doped material used in the prior art has a low LUMO level, which can be matched with the HOMO level of the hole transport layer material, the P-doped material still has a series of defects, especially defects in the aspect of service life, which seriously affect the commercial application of the material.
Disclosure of Invention
Therefore, the technical problem to be solved by the present invention is to overcome the defect of short life of P-doped material in the prior art, and to provide a fused ring aryl compound.
Another object of the present invention is to provide an organic electronic device.
Another object of the present invention is to provide an application of an organic electronic device.
The invention provides a condensed ring aryl compound which has a structure shown in a formula (I),
Figure BDA0002275467560000021
wherein n is an integer of 0 to 5, X1、X2、Y1、Y2Each independentlySelected from the group consisting of a bond, N and CR5A combination of R1-R5Either group is independently connected to ring A or ring B by a single bond, a double bond, and/or R1-R5Any two adjacent rings form a ring C, the ring C is an electron-withdrawing ring, and R is1-R5Are electron withdrawing groups.
Further, said R1-R5Either group is singly bound to ring A or ring B, and R is1-R5Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, R6Substituted or unsubstituted C1-C10Alkyl of R6Substituted or unsubstituted C2-C10Alkenyl of R6Substituted or unsubstituted C2-C10Alkynyl of (A), R6Substituted or unsubstituted C6-C30Aryl and R6Substituted or unsubstituted C2-C30A heteroaryl group of (a);
the R is6The substituent is selected from deuterium, halogen, cyano, nitro and R7Substituted or unsubstituted C1-C4Alkyl of R7Substituted or unsubstituted C2-C4Alkenyl of R7Substituted or unsubstituted C2-C4Alkynyl of (A), R7Substituted or unsubstituted C6-C20Aryl and R7Substituted or unsubstituted C2-C20The heteroaryl of (a), the R7Selected from the group consisting of deuterium, halogen, cyano and nitro.
Further, said R1-R5Either group is doubly bonded to ring A or ring B and is independently selected from the group consisting of oxygen, sulfur and
Figure BDA0002275467560000031
combinations of the above.
Further, said R1-R5Either group being doubly-bound to ring A or ring B, and
Figure BDA0002275467560000032
is composed of
Figure BDA0002275467560000033
Wherein two R are1’The same or different; and/or
Figure BDA0002275467560000034
Is composed of
Figure BDA0002275467560000035
Wherein two R are2’The same or different; and/or
Figure BDA0002275467560000036
Is composed of
Figure BDA0002275467560000037
Wherein two R are3’The same or different; and/or
Figure BDA0002275467560000038
Is composed of
Figure BDA0002275467560000039
Wherein two R are4’The same or different; and/or
Figure BDA00022754675600000310
Is composed of
Figure BDA00022754675600000311
Wherein two R are5’Are the same or different, and R1’-R5’Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, R6Substituted or unsubstituted C1-C10Alkyl of R6Substituted or unsubstituted C2-C10Alkenyl of R6Substituted or unsubstituted C4-C20Cycloalkenyl group of (A), R6Substituted or unsubstituted C4-C20Cycloalkenone group of, R6Substituted or unsubstituted C4-C20Of cycloalkenylthioketone group, R6Substituted or unsubstituted C2-C10An alkynyl group of,R6Substituted or unsubstituted C6-C30Aryl of (2), R6Substituted or unsubstituted C6-C30Aryl ketone group of (A) and R6Substituted or unsubstituted C2-C30Or two adjacent substituents on ring A and/or ring B are connected and form a ring C 'together with the carbon atom bonded with the substituents, wherein the ring C' is selected from the group consisting of R6Substituted or unsubstituted C4-C30Cycloalkenyl group of (A), R6Substituted or unsubstituted C6-C30Aryl of (2), R6Substituted or unsubstituted C2-C30Heteroaryl of (A), R6Substituted or unsubstituted C4-C20Cycloalkenone group of and R6Substituted or unsubstituted C4-C20A combination of cyclic thioketonic groups of (a);
the R is6The substituent is selected from deuterium, halogen, cyano, nitro and R7Substituted or unsubstituted C1-C4Alkyl of R7Substituted or unsubstituted C2-C4Alkenyl of R7Substituted or unsubstituted C2-C4Alkynyl of (A), R7Substituted or unsubstituted C6-C20Aryl and R7Substituted or unsubstituted C5-C20The heteroaryl of (a), the R7Selected from the group consisting of deuterium, halogen, cyano and nitro.
Further, the ring C is selected from R6Substituted or unsubstituted C4-C20Cycloalkenyl of (a), R6Substituted or unsubstituted C6-C30Aryl and R6Substituted or unsubstituted C2-C30A heteroaryl group of (a);
the R is6The substituent is selected from deuterium, halogen, cyano, nitro and R7Substituted or unsubstituted C1-C4Alkyl of R7Substituted or unsubstituted C2-C4Alkenyl of R7Substituted or unsubstituted C2-C4Alkynyl of (A), R7Substituted or unsubstituted C6-C20Aryl of (2)And R7Substituted or unsubstituted C2-C20The heteroaryl of (a), the R7Selected from the group consisting of deuterium, halogen, cyano and nitro.
Further, the alkyl group is C1-C4The alkenyl group is C2-C4The alkynyl group is C2-C4Aryl selected from the group consisting of phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthyl, anthracenyl, phenalenyl, phenanthrenyl, fluorenyl, pyrenyl, chicory, perylenyl and azulenyl, heteroaryl selected from the group consisting of dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoselenophenyl, carbazolyl, indocarbazolyl, pyridylindolyl, pyridimidyl, pyrrolopyridyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, oxatriazolyl, dioxazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, oxazinyl, oxathiazinyl, oxadiazodiazinyl, indolyl, benzimidazolyl, indazolyl, indenozinyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, phenanthryl, phenanthrenyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phthalazinyl, pteridinyl, xanthenyl, acridinyl, phenazinyl, phenothiazinyl, benzothienopyridyl, thienodipyridyl, benzoselenophenopyridyl, selenobenzodipyridyl, phenanthroline, pyrazinyl, thiophenonyl, benzothiazolyl and pyrazinyl
Figure BDA0002275467560000051
Combinations of compounds wherein "" is a connecting position.
Further, the cycloalkenone group or the cycloalkenone group is selected from the following groups:
Figure BDA0002275467560000052
wherein,T1、T2each independently is O or S; "" is a connection location.
Further, the compound has a structure shown in one of the following:
Figure BDA0002275467560000061
wherein m is an integer of 0-4; z1、Z2Each independently a single bond, N or CR5，R1-R5、R8-R15Each independently an electron withdrawing group, and the compound does not contain a hydrogen atom.
Further, said R1-R5、R8-R15Each independently selected from the group consisting of a bond, oxygen, sulfur,
Figure BDA0002275467560000062
Figure BDA0002275467560000063
Deuterium, fluoro, trifluoromethyl, cyano, nitro, R16Fully substituted phenyl, R16Fully substituted pyrazinyl, R16Fully substituted pyrimidinyl, R16Fully substituted pyridyl, R16Fully substituted triazinyl radical, R16Fully substituted cyclopentadienyl, R16Fully substituted vinyl, R16Fully substituted benzyl ketone group, R16Fully substituted
Figure BDA0002275467560000064
R16Fully substituted
Figure BDA0002275467560000065
R16Fully substituted
Figure BDA0002275467560000066
R16Fully substituted
Figure BDA0002275467560000071
And R16Get allIs of generation
Figure BDA0002275467560000072
Combinations of the compounds, or R1-R15Wherein two adjacent groups are linked and taken together with the carbon atom to which the substituent is bonded form a ring D, each ring D is independently selected from R16Fully substituted
Figure BDA0002275467560000073
R16Fully substituted pyrazinyl and R16Combinations of fully substituted naphthyl radicals, R16The substituent is selected from the group consisting of deuterium, fluorine, cyano, nitro and trifluoromethyl, R1-R15Each being substituted by a plurality of R16When substituted, R16May be the same or different, "+", "or,
Figure BDA0002275467560000074
Is the attachment location.
Further, the compound has a structure shown in one of the following:
Figure BDA0002275467560000075
Figure BDA0002275467560000081
Figure BDA0002275467560000091
Figure BDA0002275467560000101
Figure BDA0002275467560000111
the present invention also provides an organic electronic device comprising at least a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer, the hole injection layer comprising any of the compounds described above.
Further, the organic electronic device is selected from the group consisting of an organic light emitting diode, an organic solar cell, an organic photoconductor, an organic transistor, and a lighting element.
The invention also provides the application of the organic electronic device in a display device or a lighting device.
The technical scheme of the invention has the following advantages:
1. the condensed ring aryl compound provided by the invention has a non-planar structure (three-dimensional structure), and has no stacking among molecules, so that annihilation generated by high-energy excitons is reduced, a hole is promoted to be injected into a hole transport layer by an anode, joule heat is avoided, stacking and crystallization of molecules of the hole transport layer are avoided, and the service life of a device is prolonged; the parent nucleus is a rigid structure, the stability is good, the stability of the device is favorably improved, and the substituent is an electron-withdrawing group, so that the LUMO energy level of the compound is between-4.6 and-6.0 eV, and the compound can be used as a P-doped material.
2. The condensed ring aryl compound provided by the invention does not contain active hydrogen in a mother-nucleus structure, and does not contain hydrogen atoms in a substituent group, so that the deterioration caused by chemical reaction in the device preparation engineering is avoided, and the service life of the device is prolonged.
3. According to the condensed ring aryl compound provided by the invention, fluorine atoms are introduced into the compound, the compound has high thermal stability and good film forming property and can enhance the electron injection and transmission capability of molecules, and the condensed ring aryl compound is used as a hole injection layer material and is beneficial to prolonging the service life of a device; the compound is small molecule with molecular weight less than 1000, and can be used for preparing devices in an evaporation mode, so that quenching caused by pi-pi accumulation is avoided, and efficiency is improved.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are some embodiments of the present invention, and other drawings can be obtained by those skilled in the art without creative efforts.
FIG. 1 is a schematic view of the structure of an organic electroluminescent device in example 26 of the present invention;
reference numerals:
1-an anode layer; 2-a hole injection layer;
3-a hole transport layer; 4-a light-emitting layer;
5-Electron transport layer 6-Electron injection layer
7-cathode layer.
Detailed Description
The following examples are provided to further understand the present invention, not to limit the scope of the present invention, but to provide the best mode, not to limit the content and the protection scope of the present invention, and any product similar or similar to the present invention, which is obtained by combining the present invention with other prior art features, falls within the protection scope of the present invention.
The examples do not show the specific experimental steps or conditions, and can be performed according to the conventional experimental steps described in the literature in the field. The reagents or instruments used are not indicated by manufacturers, and are all conventional reagent products which can be obtained commercially.
Example 1
Figure BDA0002275467560000131
Synthesis of intermediate 1-P-1: 1-bromo-2, 3,5, 6-tetrafluoro-4-nitrobenzene (27.3 g, 1 equivalent, 0.1mol), 2, 3-diaminomaleonitrile (21.60 g, 2 equivalents, 0.2mol), sodium tert-butoxide (4 equivalents, 0.4mol), ethanol (80 ml) are added into a 250 ml three-necked bottle under the protection of nitrogen, reflux and stirring are carried out for 12 hours, after the reaction is finished, the temperature is reduced to room temperature, 10ml of ice water is added for quenching, dichloromethane is added for extraction, the concentrate is subjected to rotary evaporation, ethanol is recrystallized, and acetonitrile is beaten for 3 times to obtain an intermediate 1-P-1(16.2 g, the yield is 40%).
Intermediate 2-P-1: in a 100 ml three-neck bottle, under the protection of nitrogen and absolute anhydrous environment, adding an intermediate 1-P-1(4.40 g, 1 equivalent, 0.01mol), 4-bromo-2, 3,5, 6-tetrafluoropyridine (4.58 g, 2 equivalent), tetrahydrofuran (THF, 20 ml), slowly adding n-butyl lithium (2 equivalent) at 78 ℃, heating to room temperature after the addition is finished, stirring for 4 hours, dropwise adding 10ml of water after the reaction is finished, quenching, extracting dichloromethane, performing rotary evaporation on a concentrate, recrystallizing the obtained mixture by using ethanol, and pulping the mixture for three times (n-hexane: acetonitrile ═ 5:2) to obtain an intermediate 2-P-1(2.3 g, yield of 48%).
Intermediate 3-P-1: adding the intermediate 2-P-1(4.8 g, 0.01mol), 5% Pd/C (5mmol) and tetrahydrofuran (10 ml) into a 50 ml three-neck flask under the protection of nitrogen, removing air, closing the nitrogen, introducing hydrogen, stirring for 2 hours, filtering to remove solids after the reaction is finished, and removing methanol by rotary evaporation to obtain a solid.
In a 50 mL three-necked flask, the solid product obtained in the previous step, sulfuric acid (2mol/L,10mL), an aqueous solution (1 mL) of sodium nitrite (0.01mol) was slowly added at 0 ℃, after the addition, cuprous bromide (0.01mol) was added, the mixture was stirred at room temperature for 30 minutes, the crude product was extracted with dichloromethane, and the solid product obtained by concentration was slurried 3 times with (n-hexane: acetonitrile ═ 5:1) to obtain intermediate 3-P-1(2.1 g, yield 42%).
Synthesis of P-1: in a 50 ml three-neck bottle, under the protection of nitrogen and absolute anhydrous environment, adding an intermediate 3-P-1(5.1 g, 1 equivalent, 0.01mol), 4-bromo-2, 3,5, 6-tetrafluoropyridine (4.58 g, 2 equivalent), tetrahydrofuran (THF, 20 ml), slowly adding n-butyl lithium (2 equivalent) at 78 ℃, heating to room temperature after the addition is finished, stirring for 4 hours, dropwise adding 10ml of water after the reaction is finished, quenching, extracting dichloromethane, performing rotary evaporation on a concentrate, and pulping the obtained mixture for 3 times by using (n-hexane: dichloromethane: acetonitrile 10:1:3) to obtain P-1(2.2 g, yield 38%) after the acetonitrile is pulped for one time.
Elemental analysis: c24N10F8Theoretical value: c, 49.67; n, 24.14; measured value: c, 49.71; n, 24.11; HRMS (ESI) m/z (M): theoretical value: 580.0180, respectively; measured value: 580.0186.
example 2
Figure BDA0002275467560000151
Synthesis of P-2: the same as the synthesis of intermediate 1-P-1, except that 1,2,4, 5-tetrafluoro-3, 6-dinitrobenzene (24 g, 1 eq, 0.1mol) was substituted for the compound 1-bromo-2, 3,5, 6-tetrafluoro-4-nitrobenzene, to give compound P-2(19.0 g, 51% yield).
Elemental analysis: c14N10F4Theoretical value: c, 45.18; n, 37.63; measured value: c, 45.21; n, 37.60; HRMS (ESI) m/z (M): theoretical value: 372.0104, respectively; measured value: 372.0109.
example 3
Figure BDA0002275467560000152
Synthesis of P-3: the same intermediate, 1-P-1, was synthesized except that 1,2,4, 5-tetrafluoro-3, 6-dicyanobenzene (20 g, 1 eq, 0.1mol) was substituted for compound 1-bromo-2, 3,5, 6-tetrafluoro-4-nitrobenzene to give compound P-3(14.6 g, 44% yield).
Elemental analysis: c16N10Theoretical value: c, 57.84; n, 42.16; measured value: c, 57.87; n, 42.13; HRMS (ESI) m/z (M): theoretical value: 332.0307, respectively; measured value: 332.0312.
example 4
Figure BDA0002275467560000161
Synthesis of P-4: the same intermediate, 1-P-1, was synthesized except that 1,2,3, 4-tetrafluoro-5, 6-dicyanobenzene (20 g, 1 eq, 0.1mol) was substituted for compound 1-bromo-2, 3,5, 6-tetrafluoro-4-nitrobenzene to give compound P-4(12.6 g, 38% yield).
Elemental analysis: c16N10Theoretical value: c, 57.84; n, 42.16; measured value: c, 57.82; n, 42.18; HRMS (ESI) m/z (M): theoretical value: 332.0307, respectively; measured value: 332.0315.
example 5
Figure BDA0002275467560000162
Synthesis of intermediate 1-P-6: 4-bromo-2, 3,5, 6-tetrafluoropyridine (2.29 g, 1 equivalent, 0.01mol), diaminomaleonitrile (2.16 g, 2 equivalents), sodium tert-butoxide (0.04mol), ethanol (15 ml) are added into a 50 ml three-necked bottle under the protection of nitrogen, the mixture is stirred under reflux for 5 hours, after the reaction is finished, the temperature is reduced to room temperature, 10ml of ice water is added for quenching, dichloromethane is extracted, a concentrate is subjected to rotary evaporation, and n-hexane: acetonitrile: 5:2 is beaten for three times to obtain an intermediate 1-P-6(1.55 g, yield 43%).
Synthesis of P-6: adding an intermediate 1-P-6(3.61 g, 1 equivalent, 0.01mol), 5-bromo-2, 4, 6-trifluoropyrimidine (2.12 g, 1 equivalent) and THF (30 ml) into a 100 ml three-neck bottle under the protection of nitrogen, slowly adding n-butyllithium at-78 ℃, then heating to room temperature, stirring for 2 hours, dropwise adding 10ml of water, quenching, extracting with dichloromethane, performing rotary evaporation on a concentrate, recrystallizing the obtained mixture with ethanol, pulping for 3 times (n-hexane: acetonitrile: 5:2), and performing 1-time acetonitrile distillation to obtain P-6(2.0 g, 48% yield)
Elemental analysis: c17N11F3Theoretical value: c, 49.17; n, 37.10; measured value: c, 49.21; n, 37.07; HRMS (ESI) m/z (M): theoretical value: 415.0290, respectively; measured value: 415.0286.
example 6
Figure BDA0002275467560000171
Synthesis of P-7: the same intermediate, 1-P-6, was synthesized except that perfluoropyrazine (15.2 g, 1 eq) was used instead of 4-bromo-2, 3,5, 6-tetrafluoropyridine to give P-7(20.73 g, 73% yield).
Elemental analysis: c12N10Theoretical value: c, 50.71; n, 49.29; measured value: c, 50.68; n, 49.32; HRMS (ESI) m/z (M): theoretical value: 284.0307, respectively; measured value: 284.0301.
example 7
Figure BDA0002275467560000172
Synthesis of P-8: in a 100 ml three-necked flask, perfluoronaphthalene (2.72 g, 1 equivalent, 0.01mol), diaminomaleic cyanide 2.16 g, 2 equivalents, DMF (20 ml) were added under nitrogen protection, sodium tert-butoxide (4 equivalents) was slowly added at room temperature, after the addition, the temperature was from room temperature to 80 ℃, stirred for 6 hours, after the reaction was completed, water was added to quench, dichloromethane was extracted, anhydrous sodium sulfate was dried, and the solvent was evaporated, (n-hexane: acetonitrile 5:2) slurried three times and recrystallized once from acetonitrile to give intermediate P-8(2.5 g, 43% yield).
Elemental analysis: c18N8F4Theoretical value: c, 53.48; n, 27.72; measured value: c, 53.51; n, 27.70; HRMS (ESI) m/z (M): theoretical value: 404.0182, respectively; measured value: 404.0189.
example 8
Figure BDA0002275467560000181
The synthesis of compound P-10 was identical to that of P-8 except that the temperature was raised to 150 ℃ and the reaction was carried out by beating (n-hexane: dichloromethane: acetonitrile: 10:1:1) three times and recrystallizing (acetonitrile: n-hexane: 10:1) once to obtain compound P-10(0.9 g, 22% yield).
Elemental analysis: c18N8F4Theoretical value: c, 53.48; n, 27.72; measured value: c, 53.51; n, 27.71; HRMS (ESI) m/z (M): theoretical value: 404.0182, respectively; measured value: 404.0186.
example 9
Figure BDA0002275467560000191
Synthesis of P-11: adding P-8(4.0 g, 1 equivalent, 0.01mol), perfluorotriazine (2.7 g, 2 equivalents), pyridine (20 ml) and tris (diethylamino) phosphine (2 equivalents) into a 50 ml three-neck bottle under the protection of nitrogen, stirring at 100 ℃ for 2 hours, cooling to room temperature after the reaction is finished, dropwise adding 10ml of water to quench, extracting by dichloromethane, rotationally evaporating a concentrate, pulping the obtained mixture for 3 times by using (n-hexane: acetonitrile ═ 5:2), and recrystallizing by using acetonitrile to obtain P-11(2.4 g, the yield is 40%)
Elemental analysis: c24N14F6Theoretical value: c, 48.18; n, 32.77; measured value: c, 48.21; n, 32.74; HRMS (ESI) m/z (M): theoretical value: 598.0335, respectively; measured value: 598.0339.
example 10
Figure BDA0002275467560000192
Synthesis of P-12: the synthesis was identical to that of P-11 except that perfluorotriazine was replaced with 1,2,3,4, 5-pentafluoro-6-cyanobenzene (3.9 g, 2 eq.) to give P-12(2.5 g, 35% yield).
Elemental analysis: c32N10F10Theoretical value: c, 53.80; n, 19.61; measured value: c, 53.84; n, 19.58; HRMS (ESI) m/z (M): theoretical value: 714.0148, respectively; measured value: 714.0153.
example 11
Figure BDA0002275467560000201
Synthesis of P-13: perfluoronaphthalene (2.72 g, 1 equivalent, 0.01mol), cis-1, 1,1,4,4, 4-hexafluorobut-2-ene-2, 3-diamine (3.88 g, 2 equivalents), DMF (20 ml) were added to a 50 ml three-necked flask under nitrogen protection, sodium tert-butoxide (4 equivalents) was slowly added at room temperature, after the addition was completed, the mixture was stirred at room temperature to 80 ℃ for 6 hours, after the reaction was completed, water was added to quench, dichloromethane was extracted, anhydrous sodium sulfate was dried, the solvent was evaporated, n-hexane: acetonitrile ═ 5:1 was beaten for 3 times, and acetonitrile was recrystallized once to obtain P-13(2.48 g, 43% yield).
Elemental analysis: c18N4F16Theoretical value: c, 37.52; n, 9.72; measured value: c, 37.55; n, 9.70; HRMS (ESI) m/z (M): theoretical value: 575.9867, respectively; measured value: 575.9873.
example 12
Figure BDA0002275467560000202
Synthesis of P-17: the same intermediate, 1-P-6, was synthesized except that 2,3,6, 7-tetrafluoro-1, 4,5, 8-deuterated benzene (20.41 g, 1 eq.) was used instead of 4-bromo-2, 3,5, 6-tetrafluoropyridine to give P-17(21.51 g, 64% yield).
Elemental analysis: c18N8D4Theoretical value: c, 64.29; d, 2.40; n, 33.32; measured value: c, 64.32; d, 2.41; n, 33.28; HRMS (ESI) m/z (M): theoretical value: 336.0810, respectively; measured value: 336.0818.
example 13
Figure BDA0002275467560000211
Synthesis of P-18: the difference from P-8 was that cis-1, 1,1,4,4, 4-hexafluorobut-2-ene-2, 3-diamine was replaced with 5, 6-diamino-2, 3-dicyano-pyrazine (16.00 g, 2 eq) to give P-18(19.30 g, 38% yield).
Elemental analysis: c22N12F4Theoretical value: c, 51.98; n, 33.07; measured value: c, 51.95; n, 33.11; HRMS (ESI) m/z (M): theoretical value: 508.0305, respectively; measured value: 508.0112.
example 14
Figure BDA0002275467560000212
Synthesis of P-19: the difference from intermediate 1-P-6 was that 2,3,6, 7-tetrafluoro-1, 4,5, 8-tetrakis (trifluoromethyl) naphthalene (47.20 g, 1 eq) was used instead of 4-bromo-2, 3,5, 6-tetrafluoropyridine to give P-19(28.4 g, 47% yield).
Elemental analysis: c22N8F12Theoretical value: c, 43.73; n, 18.54; measured value: c, 43.77; n, 18.51; HRMS (ESI) m/z (M): theoretical value: 604.0054, respectively; measured value: 604.0049.
example 15
Figure BDA0002275467560000213
Synthesis of P-21: under the protection of nitrogen, adding P-8(4.04 g, 1 equivalent), diaminomaleonitrile (2.16 g, 2 equivalents) and DMF (60 ml), adding sodium tert-butoxide (4 equivalents) at room temperature, stirring for 4 hours at 120 ℃ after the addition is finished, removing the solvent after the reaction is finished, recrystallizing the product twice with acetonitrile, and pulping twice with acetonitrile to obtain P-21(1.93 g, 36% yield).
Elemental analysis: c26N16Theoretical value: c, 58.22; n, 41.78; measured value: c, 58.25; n, 41.75; HRMS (ESI) m/z (M): theoretical value: 536.0492, respectively; measured value: 536.0486.
example 16
Figure BDA0002275467560000221
Synthesis of P-22: the synthesis of P-21 was identical except that P-8 was replaced with P-10(4.04 g, 1 eq, 0.01mol) to give compound P-22(2.04 g, 38% yield).
Elemental analysis: c26N16Theoretical value: c, 58.22; n, 41.78; measured value: c, 58.26; n, 41.75; HRMS (ESI) m/z (M): theoretical value: 536.0492, respectively; measured value: 536.0498.
example 17
Figure BDA0002275467560000231
Synthesis of P-23: in a 50 ml three-necked bottle, P-8(4.0 g, 1 eq), 4-cyano-2, 3,5, 6-tetrafluorobenzonitrile (4.3 g, 2 eq) and tetrahydrofuran (20 ml) are added under the protection of nitrogen, sodium tert-butoxide (2 eq) is added at 0 ℃, reflux and stirring is carried out for 8 hours after the completion of dropwise addition, the temperature is reduced to room temperature, 10ml of ice water is added for quenching, dichloromethane is used for extraction, and a concentrate is subjected to rotary evaporation, wherein n-hexane, dichloromethane and acetonitrile are 10: 2: 2, and the mixture is beaten for 3 times and acetonitrile is beaten for one time to obtain P-23(3.3 g, the yield is 42%).
Elemental analysis: c36N12F10Theoretical value: c, 54.70; n, 21.26; measured value: c, 54.74; n, 21.23; HRMS (ESI) m/z (M): theoretical value: 790.0209, respectively; measured value: 790.0214.
example 18
Figure BDA0002275467560000232
Synthesis of P-24: the difference from P-23 is that 2- (tetrafluoropyridin-4-) acetonitrile (38 g, 2 eq) was substituted for 4-cyano-2, 3,5, 6-tetrafluorophenethyl cyanide, yielding P-24(23 g, 31% yield).
Elemental analysis: c32N12F10Theoretical value: c, 51.77; n, 22.64; measured value: c, 51.81; n, 22.62; HRMS (ESI) m/z (M): theoretical value: 742.0209, respectively; measured value: 742.0216.
example 19
Figure BDA0002275467560000241
Synthesis of P-25: the difference from P-23 was that 1,2,3, 4-tetrafluorocyclopenta-1, 3-diene (27.60 g, 2 eq.) was used instead of 4-cyano-2, 3,5, 6-tetrafluorophenylacetonitrile to give P-25(20.42 g, 32% yield).
Elemental analysis: c28N8F10Theoretical value: c, 52.68; n, 17.55; measured value: c, 52.72; n, 17.52; HRMS (ESI) m/z (M): theoretical value: 638.0086, respectively; measured value: 638.0089.
example 20
Figure BDA0002275467560000242
Synthesis of P-26: the difference from P-23 was that 4,5,6, 7-tetrafluoro-1H-indene-1, 3(2H) -dione (43.60 g, 2 eq.) was substituted for 4-cyano-2, 3,5, 6-tetrafluorobenzonitrile to give P-26(23.94 g, 30% yield).
Elemental analysis: c36N8F10O4Theoretical value: c, 54.16; n, 14.03; measured value: c, 54.12; n, 14.05; HRMS (ESI) m/z (M): theoretical value: 797.9883, respectively; measured value: 793.9879.
example 21
Figure BDA0002275467560000251
Synthesis of P-29: the difference from P-8 was that perfluoroanthracene (8.43 g, 1 eq.) was used instead of perfluoronaphthalene and diaminomaleonitrile (4.32 g, 4 eq.) to give P-29(1.93 g, 31% yield).
Elemental analysis: c30N16F2Theoretical value: c, 57.89; n, 36.01; measured value: c, 57.93; n, 36.08; HRMS (ESI) m/z (M): theoretical value: 622.0460, respectively; measured value: 622.0467.
example 22
Figure BDA0002275467560000252
Synthesis of P-30: under the protection of nitrogen, 1,2,3,4,5, 6,7, 8-octafluoro-4 a,8 b-biphenylene (2.98 g, 1 equivalent), diaminomaleic cyanide (5.40 g, 5 equivalents), DMSO (20 ml), potassium tert-butoxide (5 equivalents) are refluxed for 12 hours, after the reaction is finished, dichloromethane is extracted, and the crude product is beaten with acetonitrile for 3 times to obtain P-30(2.58 g, 46% yield).
Elemental analysis: c28N16Theoretical value: c, 60.01; n, 39.99; measured value: c, 59.98; n, 40.02; HRMS (ESI) m/z (M): theoretical value: 560.0492, respectively; measured value: 560.0499.
example 23
Figure BDA0002275467560000261
Synthesis of P-31: the difference from P-30 was that 1,2,3,4,5, 6,7, 8-octafluoroanthracene-9, 10-dione (3.52 g, 1 eq.) was used instead of 1,2,3,4,5, 6,7, 8-octafluoro-4 a,8 b-biphenylene and diaminodicyan-amide (5 eq.) to give P-31(2.53 g, 41% yield).
Elemental analysis: c30N16O2Theoretical value: c, 58.45; n, 36.36; measured value: c, 58.48; n, 36.34; HRMS (ESI) m/z (M): theoretical value: 616.0390, respectively; measured value: 616.0396.
example 24
Figure BDA0002275467560000262
Synthesis of P-32: the difference from P-30 was that 1,2,3,4,5, 6,7, 8-octafluoroanthracene-9, 10-dithione (3.84 g, 1 eq.) was used instead of 1,2,3,4,5, 6,7, 8-octafluoro-4 a,8 b-biphenylene, diaminomaleonitrile (5 eq.) to give P-32(2.59 g, 40% yield).
Elemental analysis: c30N16S2Theoretical value: c, 55.56; n, 34.56; s, 9.89; measured value: c, 55.59; n, 34.54; s, 9.88; HRMS (ESI) m/z (M): theoretical value: 647.9933, respectively; measured value: 647.9936.
example 25
Figure BDA0002275467560000271
Synthesis of P-34:
the first step is as follows: in a 50 ml three-necked flask, P-8(4.0 g, 0.01mmol), urea (2.4 g, 4 equiv.) and ethanol (10 ml) were added under nitrogen for 10 hours, and after completion of the reaction, after cooling to room temperature, quenching was performed by adding 10ml of water, extraction was performed with ethyl acetate (20 ml × 3), dried over anhydrous sodium sulfate, and spun-dried, and the crude product was purified by chromatography (dichloromethane/hexane, 1/5) to give 1-P-34(2.1 g, yield 63%).
The second step is that: in a 50 ml three-necked flask, 1-P-34(3.36 g, 1 eq, 0.01mol), malononitrile (1.3 g, 2 eq), potassium carbonate (4 eq), ethanol (15 ml) were added under nitrogen atmosphere and stirred at room temperature for 10 hours, after the reaction was completed, after cooling to room temperature, 5 ml of water was added and quenched, ethyl acetate (20 ml × 3) was extracted, dried over anhydrous sodium sulfate, spun-dried, and the crude product was purified by chromatography (dichloromethane/hexane, 1/5) to obtain compound P-34(2.7 g, 51% yield).
Elemental analysis: c26N16Theoretical value: c, 58.22; n, 41.78; measured value: c, 58.26; n, 41.74; HRMS (ESI) m/z (M): theoretical value: 536.0492, respectively; measured value: 536.0487.
example 26
Preparing an organic electroluminescent device:
an ITO transparent substrate was placed in an evaporation apparatus in which ITO (indium tin oxide) was used as an anode layer 1, a 10nm hole injection layer 2, a 100nm hole transport layer 3(HTL), a 50nm organic light emitting layer 4(EML), a 40nm electron transport layer 5(ETL), a 1nm electron injection layer 6(EIL), and an 80nm cathode layer 7 were sequentially evaporated, in which N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine was used as a hole transport layer 3, 3 wt% Ir (piq)3: CBP as the organic light emitting layer 4, BPhen as the electron transport layer 5, LiF as the electron injection layer 6, and Al as the cathode layer 7 allow the device to be formed into the specific structure shown in fig. 1.
The method comprises the following steps:
(1) substrate cleaning: carrying out ultrasonic treatment on the ITO-coated transparent motor substrate in an aqueous cleaning agent (the components and concentration of the aqueous cleaning agent are that ethylene glycol solvent is less than or equal to 10wt percent and triethanolamine is less than or equal to 1wt percent), washing in deionized water, and carrying out ultrasonic treatment in a water-based solvent system under the conditions of acetone: ultrasonic degreasing is carried out in an ethanol mixed solvent (volume ratio is 1:1), baking is carried out in a clean environment until water is completely removed, and then ultraviolet light and ozone are used for cleaning.
(2) Vapor deposition of organic light-emitting functional layer
Placing the glass substrate with anode layer 1 in a vacuum chamber, and vacuumizing to 1 × 10-6To 2X 10-4Pa, vacuum evaporating a hole injection layer material (P-doping material) on the anode layer 1 film to form a hole injection layer 2, wherein the evaporation rate is 0.1nm/s, and the evaporation thickness is 10 nm;
n, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine is evaporated on the hole injection layer 2 to be used as a hole transmission layer 3, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 100 nm;
an organic light emitting layer 4 is evaporated on the hole transport layer 3, and the organic light emitting layer 4 is made of (3 wt% Ir (piq) 3: CBP) as the material of the organic light emitting layer. The preparation method comprises the following steps: vacuum evaporating a luminescent main material doping material in a co-evaporation mode, wherein the evaporation rate of the main material is 0.09nm/s, the evaporation rate of the doping dye is 0.01nm/s, and the total evaporation film thickness is 50 nm;
a layer (BPhen) is evaporated on the organic light-emitting layer 4 in vacuum to be used as an electron transport layer 5 of the device, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 40 nm;
a layer of LiF is evaporated on the electron transport layer 5 in vacuum, and is used as an electron injection layer 6 of the device, the evaporation rate is 0.05nm/s, and the total film thickness of the evaporation is 1 nm;
al is deposited on the electron injection layer 6 as a cathode layer 7 of the device at a deposition rate of 0.1nm/s and a total deposition thickness of 80 nm.
Wherein, in a comparison test, the common HAT (CN) is selected6As hole injection layer material, HAT (CN)6Has the following chemical structure:
Figure BDA0002275467560000291
in the remaining experimental examples, the compound of the present invention was used as a hole injection layer material.
The structural formula of the hole transport layer material is as follows:
Figure BDA0002275467560000292
the organic light-emitting layer comprises the following materials:
Figure BDA0002275467560000301
the structural formula of the electron transport layer material is as follows:
Figure BDA0002275467560000302
table 1 shows the thermal decomposition temperatures (T) of the compounds described in the present applicationd) And the LUMO energy level.
TABLE 2 shows the compounds described in the present application and HAT (CN)6Performance parameters of the organic electroluminescent device as a hole injection layer material.
Test conditions
(1) Thermal decomposition temperature: thermal decomposition temperature measurements of samples were performed using a thermogravimetric analyzer (TGA, US TA TGA55)The test is carried out in the test range of room temperature to 600 ℃, the heating rate is 10 ℃/min, and the temperature with 5 percent weight loss under the nitrogen atmosphere is defined as the decomposition temperature Td；
(2) And (4) energy level testing: the LUMO energy levels of the compounds obtained in examples 1 to 25 of the present invention were measured by cyclic voltammetry (CV shanghai chenhua CHI-600E) using an electrochemical workstation, with platinum wire (Pt) as a counter electrode and silver/silver chloride (Ag/AgCl) as a reference electrode. Under the nitrogen atmosphere, the test is carried out in methylene chloride electrolyte containing 0.1M tetrabutylammonium hexafluorophosphate at the scanning rate of 100mV/s, the potential calibration is carried out by ferrocene, and the absolute energy level of the potential of the ferrocene in the vacuum state is set as-4.8 eV:
Figure BDA0002275467560000311
wherein,
Figure BDA0002275467560000312
represents a reduction potential; eFc/Fc+Indicates the ferrocene potential.
(3) Testing the characteristics of the device such as current, brightness, service life and the like: synchronously testing by adopting a PR 650 spectral scanning luminance meter and a KeithleyK 2400 digital source meter system; and (3) testing conditions are as follows: the current density is 10mA/cm2The temperature was 25 ℃.
TABLE 1
Figure BDA0002275467560000313
TABLE 2
Figure BDA0002275467560000321
Figure BDA0002275467560000331
Compared with the device prepared by the compound of comparative example 1, the service life of the device prepared by the compound of the invention is prolonged, the compound of the invention has a non-planar structure (three-dimensional structure) and no intermolecular stacking, the annihilation generated by high-energy excitons is reduced, the injection of holes into a hole transport layer by an anode is promoted, the generation of joule heat is avoided, the stacking and crystallization of molecules of the hole transport layer are avoided, and the service life of the device is prolonged.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.

Claims (13)

1. A fused ring aryl compound characterized by having a structure represented by the formula (I),
Figure FDA0002275467550000011
wherein n is an integer of 0 to 5, X1、X2、Y1、Y2Each independently selected from the group consisting of a bond, N and CR5A combination of R1-R5Either group is independently connected to ring A or ring B by a single bond, a double bond, and/or R1-R5Any two adjacent rings form a ring C, the ring C is an electron-withdrawing ring, and R is1-R5Are electron withdrawing groups.
2. A fused ring aryl compound as claimed in claim 1, wherein R is1-R5Either group is singly bound to ring A or ring B, and R is1-R5Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, R6Substituted or unsubstituted C1-C10Alkyl of R6Substituted or unsubstituted C2-C10Alkenyl of R6Substituted or unsubstituted C2-C10Alkynyl of (A), R6Substituted or unsubstituted C6-C30Aryl and R6Substituted or unsubstituted C2-C30A heteroaryl group of (a);
the R is6The substituent is selected from deuterium, halogen, cyano, nitro and R7Substituted or unsubstituted C1-C4Alkyl of R7Substituted or unsubstituted C2-C4Alkenyl of R7Substituted or unsubstituted C2-C4Alkynyl of (A), R7Substituted or unsubstituted C6-C20Aryl and R7Substituted or unsubstituted C2-C20The heteroaryl of (a), the R7Selected from the group consisting of deuterium, halogen, cyano and nitro.
3. A fused ring aryl compound as claimed in claim 1, wherein R is1-R5Either group is doubly bonded to ring A or ring B and is independently selected from the group consisting of oxygen, sulfur and
Figure FDA0002275467550000021
combinations of the above.
4. A fused ring aryl compound as claimed in claim 1, wherein R is1-R5Either group being doubly-bound to ring A or ring B, and
Figure FDA0002275467550000022
is composed of
Figure FDA0002275467550000023
Wherein two R are1’The same or different; and/or
Figure FDA0002275467550000024
Is composed of
Figure FDA0002275467550000025
Wherein two R are2’The same or different; and/or
Figure FDA0002275467550000026
Is composed of
Figure FDA0002275467550000027
Wherein two R are3’The same or different; and/or
Figure FDA0002275467550000028
Is composed of
Figure FDA0002275467550000029
Wherein two R are4’The same or different; and/or
Figure FDA00022754675500000210
Is composed of
Figure FDA00022754675500000211
Wherein two R are5’Are the same or different, and R1’-R5’Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, R6Substituted or unsubstituted C1-C10Alkyl of R6Substituted or unsubstituted C2-C10Alkenyl of R6Substituted or unsubstituted C4-C20Cycloalkenyl group of (A), R6Substituted or unsubstituted C4-C20Cycloalkenone group of, R6Substituted or unsubstituted C4-C20Of cycloalkenylthioketone group, R6Substituted or unsubstituted C2-C10Alkynyl of (A), R6Substituted or unsubstituted C6-C30Aryl of (2), R6Substituted or unsubstituted C6-C30Aryl ketone group of (A) and R6Substituted or unsubstituted C2-C30Or two adjacent substituents on ring A and/or ring B are connected and form a ring C 'together with the carbon atom bonded with the substituents, wherein the ring C' is selected from the group consisting of R6Substituted or unsubstituted C4-C30Cycloalkenyl group of (A), R6Substituted or unsubstituted C6-C30Aryl of (2), R6Substituted or unsubstituted C2-C30Heteroaryl of (A), R6Substituted or unsubstituted C4-C20Cycloalkenone group of and R6Substituted or unsubstituted C4-C20A combination of cyclic thioketonic groups of (a);
the R is6The substituent is selected from deuterium, halogen, cyano, nitro and R7Substituted or unsubstituted C1-C4Alkyl of R7Substituted or unsubstituted C2-C4Alkenyl of R7Substituted or unsubstituted C2-C4Alkynyl of (A), R7Substituted or unsubstituted C6-C20Aryl and R7Substituted or unsubstituted C5-C20The heteroaryl of (a), the R7Selected from the group consisting of deuterium, halogen, cyano and nitro.
5. A fused ring aryl compound as claimed in claim 1, wherein ring C is selected from R6Substituted or unsubstituted C4-C20Cycloalkenyl of (a), R6Substituted or unsubstituted C6-C30Aryl and R6Substituted or unsubstituted C2-C30A heteroaryl group of (a);
the R is6The substituent is selected from deuterium, halogen, cyano, nitro and R7Substituted or unsubstituted C1-C4Alkyl of R7Substituted or unsubstituted C2-C4Alkenyl of R7Substituted or unsubstituted C2-C4Alkynyl of (A), R7Substituted or unsubstituted C6-C20Aryl and R7Substituted or unsubstituted C2-C20The heteroaryl of (a), the R7Selected from the group consisting of deuterium, halogen, cyano and nitro.
6. A fused ring aryl compound as claimed in claim 2,4 or 5, wherein said alkyl is C1-C4The alkenyl group is C2-C4The alkynyl group is C2-C4Aryl selected from the group consisting of phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthyl, anthracenyl, phenalenyl, phenanthrenyl, fluorenyl, pyrenyl, chicory, perylenyl and azulenyl, heteroaryl selected from the group consisting of dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoselenophenyl, carbazolyl, indocarbazolyl, pyridylindolyl, pyridimidyl, pyrrolopyridyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, oxatriazolyl, dioxazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, oxazinyl, oxathiazinyl, oxadiazodiazinyl, indolyl, benzimidazolyl, indazolyl, indenozinyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, phenanthryl, phenanthrenyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phthalazinyl, pteridinyl, xanthenyl, acridinyl, phenazinyl, phenothiazinyl, benzothienopyridyl, thienodipyridyl, benzoselenophenopyridyl, selenobenzodipyridyl, phenanthroline, pyrazinyl, thiophenonyl, benzothiazolyl and pyrazinyl
Figure FDA0002275467550000031
Combinations of compounds wherein "" is a connecting position.
7. A fused ring aryl compound according to claim 4, wherein said cycloalkenone group or cycloalkenone group is selected from the group consisting of:
Figure FDA0002275467550000041
wherein, T1、T2Each independently is O or S; "" is a connection location.
8. A fused ring aryl compound as claimed in claim 1, having a structure represented by one of:
Figure FDA0002275467550000042
Figure FDA0002275467550000051
wherein m is an integer of 0-4; z1、Z2Each independently a single bond, N or CR5，R1-R5、R8-R15Each independently an electron withdrawing group, and the compound does not contain a hydrogen atom.
9. A fused ring aryl compound as claimed in claim 8, wherein R is1-R5、R8-R15Each independently selected from the group consisting of a bond, oxygen, sulfur,
Figure FDA0002275467550000052
Deuterium, fluoro, trifluoromethyl, cyano, nitro, R16Fully substituted phenyl, R16Fully substituted pyrazinyl, R16Fully substituted pyrimidinyl, R16Fully substituted pyridyl, R16Fully substituted triazinyl radical, R16Fully substituted cyclopentadienyl, R16Fully substituted vinyl, R16Fully substituted benzyl ketone group, R16Fully substituted
Figure FDA0002275467550000053
R16Fully substituted
Figure FDA0002275467550000054
R16Fully substituted
Figure FDA0002275467550000055
R16Fully substituted
Figure FDA0002275467550000058
And R16Fully substituted
Figure FDA0002275467550000059
Combinations of the compounds, or R1-R15Wherein two adjacent groups are linked and taken together with the carbon atom to which the substituent is bonded form a ring D, each ring D is independently selected from R16Fully substituted
Figure FDA0002275467550000061
R16Fully substituted pyrazinyl and R16Combinations of fully substituted naphthyl radicals, R16The substituent is selected from the group consisting of deuterium, fluorine, cyano, nitro and trifluoromethyl, R1-R15Each being substituted by a plurality of R16When substituted, R16May be the same or different, "+", "or,
Figure FDA0002275467550000062
Is the attachment location.
10. A fused ring aryl compound as claimed in claim 9, having a structure as shown in one of:
Figure FDA0002275467550000063
Figure FDA0002275467550000071
Figure FDA0002275467550000081
Figure FDA0002275467550000091
11. an organic electronic device comprising at least a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer, wherein the hole injection layer comprises a compound according to any one of claims 1 to 9.
12. The organic electronic device according to claim 11, wherein the organic electronic device is selected from the group consisting of organic light emitting diodes, organic solar cells, organic photoconductors, organic transistors and lighting elements.
13. Use of the organic electronic device of claim 11 or 12 in a display device or a lighting device.
CN201911121013.3A 2019-11-15 2019-11-15 Condensed ring aryl compound, organic electronic device and application thereof Pending CN110872298A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201911121013.3A CN110872298A (en) 2019-11-15 2019-11-15 Condensed ring aryl compound, organic electronic device and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201911121013.3A CN110872298A (en) 2019-11-15 2019-11-15 Condensed ring aryl compound, organic electronic device and application thereof

Publications (1)

Publication Number Publication Date
CN110872298A true CN110872298A (en) 2020-03-10

Family

ID=69718016

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201911121013.3A Pending CN110872298A (en) 2019-11-15 2019-11-15 Condensed ring aryl compound, organic electronic device and application thereof

Country Status (1)

Country Link
CN (1) CN110872298A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111454265A (en) * 2020-05-07 2020-07-28 宁波卢米蓝新材料有限公司 Fused heterocyclic compound and preparation method and application thereof
CN114874418A (en) * 2022-04-24 2022-08-09 广东聚石科技研究有限公司 Conjugated polymer based on trifluoromethyl substituted quinoxaline and preparation method and application thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107833974A (en) * 2017-07-12 2018-03-23 北京鼎材科技有限公司 A kind of novel electroluminescent device
CN110407859A (en) * 2019-07-18 2019-11-05 清华大学 A kind of luminescent material and its organic electroluminescence device using and comprising it

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107833974A (en) * 2017-07-12 2018-03-23 北京鼎材科技有限公司 A kind of novel electroluminescent device
CN110407859A (en) * 2019-07-18 2019-11-05 清华大学 A kind of luminescent material and its organic electroluminescence device using and comprising it

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
边照阳等: "《QuEChERS技术及应用》", 30 November 2017 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111454265A (en) * 2020-05-07 2020-07-28 宁波卢米蓝新材料有限公司 Fused heterocyclic compound and preparation method and application thereof
CN111454265B (en) * 2020-05-07 2021-08-24 宁波卢米蓝新材料有限公司 Fused heterocyclic compound and preparation method and application thereof
CN114874418A (en) * 2022-04-24 2022-08-09 广东聚石科技研究有限公司 Conjugated polymer based on trifluoromethyl substituted quinoxaline and preparation method and application thereof
CN114874418B (en) * 2022-04-24 2023-12-19 广东聚石科技研究有限公司 Conjugated polymer based on trifluoromethyl substituted quinoxaline, and preparation method and application thereof

Similar Documents

Publication Publication Date Title
CN110862381B (en) Organic electroluminescent compound and preparation method and application thereof
KR101791276B1 (en) Compound having a substituted anthracene ring structure and pyridoindole ring structure, and organic electroluminescent element
KR101544237B1 (en) Organic electroluminescent device
KR101650595B1 (en) Compound having substituted anthracene ring structure and pyridoindole ring structure and organic electroluminescence device
KR101773363B1 (en) Organic compound and composition and organic optoelectric device and display device
WO2011105373A1 (en) Substituted pyridyl compound and organic electroluminescent element
CN106661038B (en) Organic compound, organic photoelectric device and display device
CN112625032B (en) Organic compound and application thereof
CN111718355B (en) Nitrogen-containing heterocyclic compound and application thereof
CN112159412B (en) Organic nitrogen-containing heterocyclic compound and application thereof
WO2020133833A1 (en) Dibenzo heterocyclic compound, preparation method therefor and use thereof
KR101966468B1 (en) Compound having pyridoindole ring structure and substituted bipyridyl group, and organic electroluminescent element
CN106432078A (en) Novel compound and organic electronic device using the same
KR102616374B1 (en) Composition, organic electroluminescent device comprising same and method of manufacturing same
CN110872298A (en) Condensed ring aryl compound, organic electronic device and application thereof
KR102546867B1 (en) Organic light emitting device
CN114380836B (en) Organic nitrogen-containing heterocyclic compound and application thereof
CN109836421B (en) A compound of general formula and its application
CN111777614B (en) Organic electroluminescent compound and application thereof
CN111454265B (en) Fused heterocyclic compound and preparation method and application thereof
CN111574505B (en) Compound with benzo [ c ] cinnoline as receptor and application thereof
CN111675714B (en) Organic electroluminescent compound with balanced carrier transmission performance and application thereof
CN110483533A (en) A kind of compound and its preparation method and application
CN110872310A (en) Condensed ring aryl compound, organic electronic device and application thereof
CN111763223B (en) Organic compound, thermal activation delay fluorescent material and application thereof

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
RJ01 Rejection of invention patent application after publication

Application publication date: 20200310

RJ01 Rejection of invention patent application after publication