[go: up one dir, main page]

CN113845467A - Compound with phenanthrocarbazole as core and application thereof - Google Patents

Compound with phenanthrocarbazole as core and application thereof Download PDF

Info

Publication number
CN113845467A
CN113845467A CN202111328559.3A CN202111328559A CN113845467A CN 113845467 A CN113845467 A CN 113845467A CN 202111328559 A CN202111328559 A CN 202111328559A CN 113845467 A CN113845467 A CN 113845467A
Authority
CN
China
Prior art keywords
compound
group
substituted
unsubstituted
organic electroluminescent
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
CN202111328559.3A
Other languages
Chinese (zh)
Inventor
孙军
胡宗学
张洋
袁江波
刘凯鹏
张宏科
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.)
Xi'an Manareco New Materials Co ltd
Original Assignee
Xi'an Manareco 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 Xi'an Manareco New Materials Co ltd filed Critical Xi'an Manareco New Materials Co ltd
Priority to CN202111328559.3A priority Critical patent/CN113845467A/en
Publication of CN113845467A publication Critical patent/CN113845467A/en
Pending legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • 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
    • C07D405/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D405/14—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 three or more hetero 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
    • C07D413/10—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
    • 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
    • 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • 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
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • 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
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • 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
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • C09K2211/1077—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms with oxygen
    • 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
    • C09K2211/1081—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms with sulfur

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)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention belongs to the technical field of organic electroluminescent functional materials and devices, and relates to a compound taking phenanthrocarbazole as a core, wherein the structural formula of the compound is shown as a formula (1). The novel compound formed by modifying the phenanthrocarbazole-based compound through introducing a specific electron-donating group into a specific position has higher glass transition temperature, and can obviously improve the efficiency and the service life of a luminescent device when being used as a hole transport material or a luminescent material in an organic electroluminescent device.
Figure DDA0003348040560000011

Description

Compound with phenanthrocarbazole as core and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescent functional materials and devices, and particularly relates to a compound taking phenanthrocarbazole as a core and application thereof.
Background
The luminous mechanism of display and lighting elements of Organic Light Emitting Diodes (OLEDs), which are self-luminous electronic elements, is a novel optoelectronic information technology that converts electrical energy directly into Light energy with the help of Organic semiconductor functional materials under the action of a direct current electric field. The light emission color can be red, green, blue, yellow alone or combined white. The biggest characteristics of the OLED light-emitting display technology are ultrathin, high response speed, ultralight weight, surface light-emitting and flexible display, can be used for manufacturing monochromatic or panchromatic displays, can be used as a novel light source technology, and can also be used for manufacturing illumination and display products or a novel backlight source technology for manufacturing liquid crystal displays.
OLEDs include two main categories of small molecule light emitting diodes and Polymer Light Emitting Diodes (PLEDs). Among them, a typical double heterostructure small molecule OLED consists of three organic layers sandwiched between electrodes. The organic layers close to the cathode and the anode are an Electron Transport Layer (ETL), a Hole Transport Layer (HTL), and sandwiched therebetween is an emission layer (EML), which is typically a host material doped with an emission material (Emitter). The PLED structure is relatively simple with a single solution processed layer combining a Light Emitting Polymer (LEP) layer and a host, charge transport function. The performance of the material plays a decisive role in the performance of the OLED luminescent device, and the excellent hole transport material can effectively improve the efficiency and prolong the service life of the device.
Common hole transport materials include carbazoles, organic amines and butadiene compounds, such as NPB, PVK, TPH, TAPC and the like. Phenanthrocarbazole has higher thermal stability due to a specific molecular conjugated structure in a molecule, and can obtain higher glass transition temperature (Tg) and higher hole mobility through electron-donating group modification. Blue light materials are always a hot point of concern in the industry, the blue light materials used in the current production line still completely depend on import and face the risk of being blocked by neck, and the homemade replacement task is very urgent. The material constructed by the invention can be used as a hole transport material or a luminescent material to improve the efficiency and the service life of an OLED device.
Disclosure of Invention
The invention aims to provide a material for improving the brightness efficiency of an OLED device and improving the performance of the device.
Based on the above purpose, the invention provides a phenanthrocarbazole-based compound, and a hole transport material or a luminescent material of an organic electroluminescent device prepared from the phenanthrocarbazole-based compound can effectively improve the luminance efficiency and the service life of the device.
In one aspect, the invention relates to a phenanthrocarbazole-core compound, wherein the structural formula of the phenanthrocarbazole-core compound is shown as formula (1):
Figure BDA0003348040540000021
wherein,
l represents one of a single bond or an aryl group; d represents an electron donating group selected from the group consisting of a substituted or unsubstituted amine group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted 10H spiro [ acridin-9, 9 '-fluorene ] group, a substituted or unsubstituted 10H spiro [ acridin-9, 9' -xanthene ] group, a substituted or unsubstituted 5-phenyl-5, 10-dihydrophenazinyl group, a substituted or unsubstituted 10H-phenothiazinyl group; preferably, the substituent of D is selected from one of aryl, carbazolyl, amine, furyl and thienyl.
Further, the L represents one of aryl and heteroaryl, and is selected from substituted or unsubstituted phenyl and substituted or unsubstituted naphthyl; preferably, said L is selected from the group consisting of:
Figure BDA0003348040540000031
further, D represents a group selected from:
Figure BDA0003348040540000032
wherein,
Ar1and Ar2Is represented as one of aryl and heteroaryl; r1And R2Is represented by one of aryl, alkyl and heteroaryl; x represents an oxygen atom, a sulfur atom, C-m1m2、Si-m1m2Or N-m3One of (1), m1、m2Each independently selected from hydrogen atom, methyl, phenyl or biphenyl, m3Is phenyl; y represents one of carbon atom, nitrogen atom and oxygen atom; preferably, Ar is1、Ar2Is represented by one of phenyl, biphenyl, carbazolyl and furyl, and R is1And R2Is represented by one of methyl, ethyl, tertiary butyl, phenyl, biphenyl, carbazolyl and furyl.
In particular, the compound of formula (1) is selected from:
Figure BDA0003348040540000041
Figure BDA0003348040540000051
Figure BDA0003348040540000061
Figure BDA0003348040540000071
Figure BDA0003348040540000081
further, it has been found that the compounds of formula (1) have outstanding optical properties and are particularly suitable for improving the luminance efficiency of organic electroluminescent display devices.
On the other hand, the invention also provides an organic electroluminescent device which comprises a hole transport layer, a luminescent layer, an electron transport layer and an electron injection layer, wherein the hole transport layer and the luminescent layer are made of the compound shown in the formula (1).
Compared with the prior art, the invention has the following beneficial effects or advantages:
(1) according to the compound of the formula (1), a specific electron-donating group is introduced to a specific position to modify phenanthrocarbazole to form a brand new compound, and the compound has remarkable optical property;
(2) the compound of the formula (1) improves the glass transition temperature (Tg) of a phenanthrocarbazole core structure, so that the compound is more suitable for being used as a preparation material of an organic electroluminescent device.
(3) The compound of formula (1) provided by the invention has excellent optical performance, and can be used as a hole transport layer and a light-emitting layer material, so that the efficiency and the service life of a device can be effectively improved.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device provided in an embodiment of the present invention.
In fig. 1, 1 is a substrate, 2 is an anode layer, 3 is a hole injection layer, 4 is a first hole transport layer, 5 is a second hole transport layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer.
Detailed Description
The following examples are given to illustrate the technical aspects of the present invention, but the present invention is not limited to the following examples.
Example 1
This example provides methods and procedures for preparing compound 2, compound 13, compound 16, compound 18, compound 29, compound 34, compound 40, compound 48, and compound 52, and testing their optical properties as follows:
(1) synthesis of intermediate 1-2
Figure BDA0003348040540000101
Adding 60g of the intermediate 1-1 into 1.5L of 1, 4-dioxane, dropwise adding 45ml of 8mol/L concentrated nitric acid at normal temperature, heating the reaction solution to 60 ℃ after dropwise adding, stirring for 30min, cooling to room temperature after the raw materials completely react, pouring the reaction solution into 3L of ice water, stirring to separate out a solid, filtering, leaching the solid with petroleum ether, and purifying with a silica gel column to obtain 16.8g of the intermediate 1-2, wherein the yield is 23.9%.
(2) Synthesis of intermediate 1
Figure BDA0003348040540000102
Under nitrogen flow, 10g of intermediate 1-2, 30g of triethyl phosphite and 300ml of 1, 2-dichlorobenzene are added, then the temperature is increased to 160 ℃ for reaction for 3 hours, the temperature is reduced to room temperature after the raw materials are completely reacted, the reaction solution is washed by water to be neutral, then anhydrous sodium sulfate is dried, and the intermediate 1 of 4.7g is obtained after the reaction solution is purified by silica gel column, and the yield is 52.9%.
(3) Synthesis of Compound 2
Figure BDA0003348040540000103
A250 ml three-necked flask was charged with 10g of intermediate 1, 14.6g of compound 2-1, 9.1g of sodium tert-butoxide, 150ml of toluene, purged with nitrogen, and then added with 86mg of tris (dibenzylideneacetone) dipalladium and 38mg of tri-tert-butylphosphine. Heating the reaction solution to 110 ℃, refluxing and stirring for reaction for 6h, monitoring by TLC (thin layer chromatography), cooling the raw materials to room temperature after complete reaction, washing the reaction solution to be neutral, drying an organic phase by using anhydrous sodium sulfate, concentrating the obtained crude product, purifying the crude product by using a silica gel column, and recrystallizing to obtain 12.6g of a compound 2 with the yield of 65.9%.
The structural characterization nuclear magnetic data for compound 1 was measured as follows:
1H NMR(400MHz,CDCl3)δ8.20(d,j＝7.2Hz,2H),7.62-7.69(m,6H),7.47(t,j＝7.2Hz,2H),7.39(d,j＝7.2Hz,2H),7.32(d,j＝6.4Hz,2H),7.24(d,j＝6.4Hz,4H),7.08(d,j＝6.4Hz,4H),7.00(d,j＝6.4Hz,2H)。
(4) synthesis of Compound 13
Figure BDA0003348040540000111
A250 ml three-necked flask was charged with 10g of intermediate 1, 19.6g of compound 13-1, 9.1g of sodium tert-butoxide, 150ml of toluene, purged with nitrogen, and then added with 86mg of tris (dibenzylideneacetone) dipalladium and 38mg of tri-tert-butylphosphine. Heating the reaction solution to 110 ℃, refluxing and stirring for reaction for 6h, monitoring by TLC (thin layer chromatography), cooling the raw materials to room temperature after complete reaction, washing the reaction solution to be neutral, drying an organic phase by using anhydrous sodium sulfate, concentrating the obtained crude product, purifying the crude product by using a silica gel column, and recrystallizing to obtain 15.7g of a compound 13, wherein the yield is 67.3%.
The structural characterization nuclear magnetic data for compound 13 was measured as follows:
1H NMR(400MHz,CDCl3)δ8.36(s,2H),8.20(d,j＝7.2Hz,2H),7.87(d,j＝6.4Hz,4H),7.62-7.69(m,8H),7.47-7.50(m,4H),1.43(s,18H)。
(5) synthesis of Compound 16
Figure BDA0003348040540000121
A250 ml three-necked flask was charged with 10g of intermediate 1, 18.6g of compound 16-1, 9.1g of sodium tert-butoxide, 150ml of toluene, purged with nitrogen, and then added with 86mg of tris (dibenzylideneacetone) dipalladium and 38mg of tri-tert-butylphosphine. Heating the reaction solution to 110 ℃, refluxing and stirring for reaction for 6h, monitoring by TLC (thin layer chromatography), cooling the raw materials to room temperature after complete reaction, washing the reaction solution to be neutral, drying an organic phase by using anhydrous sodium sulfate, concentrating the obtained crude product, purifying the crude product by using a silica gel column, and recrystallizing to obtain 13.8g of a compound 16 with the yield of 61.5%.
The structural characterization nuclear magnetic data for compound 16 was measured as follows:
1H NMR(400MHz,CDCl3)δ8.55(d,j＝7.2Hz,1H),8.20(d,j＝7.2Hz,2H),7.98(d,j＝7.2Hz,1H),7.94(d,j＝7.2Hz,1H),7.87(d,j＝6.4Hz,4H),7.62-7.66(m,4H),7.54(d,j＝7.2Hz,1H),7.49(s,1H),7.47(t,j＝7.2Hz,2H),7.42(s,1H),7.39(m,3H),7.35(t,j＝7.2Hz,1H),7.31(t,j＝7.2Hz,1H),7.16(t,j＝7.2Hz,1H)。
(6) synthesis of Compound 18
Figure BDA0003348040540000122
A250 ml three-necked flask was charged with 10g of intermediate 1, 14.5g of compound 18-1, 9.1g of sodium tert-butoxide, 150ml of toluene, purged with nitrogen, and then added with 86mg of tris (dibenzylideneacetone) dipalladium and 38mg of tri-tert-butylphosphine. Heating the reaction solution to 110 ℃, refluxing and stirring for reaction for 6h, monitoring by TLC (thin layer chromatography), cooling the raw materials to room temperature after complete reaction, washing the reaction solution to be neutral, drying an organic phase by using anhydrous sodium sulfate, concentrating the obtained crude product, purifying the crude product by using a silica gel column, and recrystallizing to obtain 13.9g of a compound 18 with the yield of 72.9%.
The structural characterization nuclear magnetic data for compound 18 was measured as follows:
1H NMR(400MHz,CDCl3)δ8.55(d,j＝7.2Hz,1H),8.20(d,j＝7.2Hz,2H),7.94(d,j＝7.2Hz,1H),7.72(d,j＝7.2Hz,1H),7.58-7.67(m,8H),7.47-7.50(m,4H),7.35-7.39(m,4H),7.16(t,j＝7.2Hz,1H)。
(7) synthesis of Compound 29
Figure BDA0003348040540000131
A250 ml three-necked flask was charged with 10g of intermediate 1, 20.3g of compound 29-1, 9.1g of sodium tert-butoxide, 150ml of toluene, purged with nitrogen, and then added with 86mg of tris (dibenzylideneacetone) dipalladium and 38mg of tri-tert-butylphosphine. Heating the reaction solution to 110 ℃, refluxing and stirring for reaction for 6h, monitoring by TLC (thin layer chromatography), cooling the raw materials to room temperature after complete reaction, washing the reaction solution to be neutral, drying an organic phase by using anhydrous sodium sulfate, concentrating the obtained crude product, purifying the crude product by using a silica gel column, and recrystallizing to obtain 16.1g of a compound 29, wherein the yield is 67.2%.
The structural characterization nuclear magnetic data for compound 29 was measured as follows:
1H NMR(400MHz,CDCl3)δ8.20(m,3H),8.15(d,j＝6.8Hz,1H),7.81(d,j＝6.8Hz,1H),7.75(d,j＝6.4Hz,2H),7.55-7.69(m,10H),7.47-7.50(m,6H),7.37-7.41(m,5H),7.32(d,j＝6.4Hz,2H)。
(8) synthesis of Compound 34
Figure BDA0003348040540000141
A250 ml three-necked flask was charged with 10g of intermediate 1, 22.1g of compound 34-1, 9.1g of sodium tert-butoxide, 150ml of toluene, purged with nitrogen, and then added with 86mg of tris (dibenzylideneacetone) dipalladium and 38mg of tri-tert-butylphosphine. Heating the reaction solution to 110 ℃, refluxing and stirring for reaction for 6h, monitoring by TLC (thin layer chromatography), cooling the raw materials to room temperature after complete reaction, washing the reaction solution to be neutral, drying an organic phase by using anhydrous sodium sulfate, concentrating the obtained crude product, purifying the crude product by using a silica gel column, and recrystallizing to obtain 16.1g of a compound 34 with the yield of 63.5%.
The structural characterization nuclear magnetic data for compound 34 was measured as follows:
1H NMR(400MHz,CDCl3)δ8.20(d,j＝7.2Hz,2H),7.98(d,j＝6.8Hz,1H),7.75(d,j＝6.4Hz,2H),7.62-7.69(m,7H),7.55(m,3H),7.47-7.49(m,4H),7.37-7.41(m,6H),7.28-7.32(m,4H),6.97(d,j＝6.8Hz,1H)。
(9) synthesis of Compound 40
Figure BDA0003348040540000142
A250 ml three-necked flask was charged with 10g of intermediate 1, 23.3g of compound 2-1, 9.1g of sodium tert-butoxide, 150ml of toluene, purged with nitrogen, and then added with 86mg of tris (dibenzylideneacetone) dipalladium and 38mg of tri-tert-butylphosphine. Heating the reaction solution to 110 ℃, refluxing and stirring for reaction for 6h, monitoring by TLC (thin layer chromatography), cooling the raw materials to room temperature after complete reaction, washing the reaction solution to be neutral, drying an organic phase by using anhydrous sodium sulfate, concentrating the obtained crude product, purifying the crude product by using a silica gel column, and recrystallizing to obtain 16.2g of a compound 40 with the yield of 61.2%.
The structural characterization of compound 40 was measured as follows:
1H NMR(400MHz,CDCl3)δ8.20(d,j＝7.2Hz,2H),7.90(d,j＝6.8Hz,1H),7.75(d,j＝6.4Hz,2H),7.62-7.69(m,6H),7.55(m,4H),7.47-7.49(m,4H),7.37-7.41(m,6H),7.28-7.34(m,4H),7.06(d,j＝6.8Hz,1H),1.69(s,6H)。
(10) synthesis of Compound 48
Figure BDA0003348040540000151
A250 ml three-necked flask was charged with 10g of intermediate 1, 15.2g of compound 48-1, 9.1g of sodium tert-butoxide, 150ml of toluene, purged with nitrogen, and then added with 86mg of tris (dibenzylideneacetone) dipalladium and 38mg of tri-tert-butylphosphine. Heating the reaction solution to 110 ℃, refluxing and stirring for reaction for 6h, monitoring by TLC (thin layer chromatography), cooling the raw materials to room temperature after complete reaction, washing the reaction solution to be neutral, drying an organic phase by using anhydrous sodium sulfate, concentrating the obtained crude product, purifying the crude product by using a silica gel column, and recrystallizing to obtain 14.4g of a compound 48 with the yield of 73.2%.
The structural characterization nuclear magnetic data for compound 48 was measured as follows:
1H NMR(400MHz,CDCl3)δ8.20(d,j＝7.2Hz,2H),7.62-7.69(m,6H),7.47(d,j＝7.2Hz,2H),7.39(d,j＝7.2Hz,2H),7.32(d,j＝6.4Hz,2H),7.14(d,j＝7.6Hz,2H),7.01(t,j＝7.6Hz,4H),6.96(d,j＝7.6Hz,2H)。
(11) synthesis of Compound 52
Figure BDA0003348040540000161
A250 ml three-necked flask was charged with 10g of intermediate 1, 22.0g of compound 52-1, 9.1g of sodium tert-butoxide, 150ml of toluene, purged with nitrogen, and then added with 86mg of tris (dibenzylideneacetone) dipalladium and 38mg of tri-tert-butylphosphine. Heating the reaction solution to 110 ℃, refluxing and stirring for reaction for 6h, monitoring by TLC (thin layer chromatography), cooling the raw materials to room temperature after complete reaction, washing the reaction solution to be neutral, drying an organic phase by using anhydrous sodium sulfate, concentrating the obtained crude product, purifying the crude product by using a silica gel column, and recrystallizing to obtain 16.0g of a compound 52, wherein the yield is 63.5%.
The structural characterization nuclear magnetic data for compound 52 was measured as follows:
1H NMR(400MHz,CDCl3)δ8.20(d,j＝7.2Hz,2H),7.90(d,j＝6.8Hz,2H),7.62-7.69(m,6H),7.56(d,j＝6.8Hz,2H),7.47(t,j＝7.2Hz,2H),7.38(m,4H),7.32(d,j＝6.4Hz,2H),7.28(d,j＝6.8Hz,2H),7.17-7.19(m,4H),7.14(d,j＝6.8Hz,2H),6.95(t,j＝6.8Hz,2H)。
(12) quantitative calculation of Tg, HOMO/LUMO and excited states
The compounds provided above and the conventional materials TCTA and BD01 were subjected to Tg, front track level, and excited state 1 tests, respectively, and the specific results are shown in table 1.
TABLE 1 HOMO, LUMO, Tg and excited state values of phenanthrocarbazole-based compounds
Compound (I) HOMO(eV) LUMO(eV) Excited state 1(eV) Tg(℃)
Compound 2 -4.84 -1.58 2.762 126
Compound 13 -4.98 -1.72 2.755 132
Compound 16 -4.99 -1.74 2.754 128
Compound 18 -4.77 -1.51 2.768 135
Compound 29 -4.84 -1.58 2.761 142
Compound 34 -4.84 -1.59 2.759 138
Compound 40 -4.85 -1.60 2.753 127
Compound 48 -4.91 -1.73 2.746 140
Compound 52 -4.98 -1.73 2.762 151
TCTA -5.20 -1.4 / 117
BD01 -4.69 -1.59 2.661 /
Note: the glass transition temperature Tg is determined by a differential scanning calorimeter (DSC, Mettler DSC3+ STAR), the temperature rise rate is 10 ℃/min; the energy level and energy of the front line orbit of the compound are obtained by quantitative calculation simulation software.
As can be seen from Table 1, the organic compound of the present invention has a higher HOMO value, and is useful for hole transport in an OLED device as a hole transport layer, thereby reducing the voltage of the device. The organic electroluminescent device may be a phosphorescent device or a device containing a TADF material or a fluorescent device without particular limitation. Therefore, when the compound taking phenanthrocarbazole as a donor is applied to an OLED device, the luminous efficiency of the device can be effectively improved.
Example 2
This example provides the application effect of the phenanthrocarbazole-based compound prepared in example 1 in an organic electroluminescent device. The structure of the organic electroluminescent device is specifically shown in fig. 1.
(1) Constitution of organic electroluminescent device
The organic electroluminescent device used in the present embodiment is constituted by including a substrate 1, an anode layer 2, a hole injection layer 3, a first hole transport layer 4, a second hole transport layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode layer 10, which are sequentially stacked.
Wherein, the anode layer 2 is made of Indium Tin Oxide (ITO) with high work function, the hole injection layer 3 is made of HAT-CN with the thickness of 5 nm; NPB is selected as the material of the first hole transport layer 4, and the thickness is 60 nm; the material of the second hole transport layer 5 is compound 2, and the thickness is 15 nm; the light-emitting layer 6 used BH1 as a host material and BD01 as a light-emitting material, and had a doping ratio of 5% and a thickness of 30 nm; TPBI is selected as the material of the hole blocking layer 7, and the thickness is 10 nm; the material of the electron transport layer 8 is ET-1, and the thickness is 35 nm; liq is selected as the material of the electron injection layer 9, and the thickness is 2 nm; the cathode layer is made of Al and has a thickness of 100 nm.
The structural formula of the basic material used by each functional layer in the device is as follows:
Figure BDA0003348040540000181
Figure BDA0003348040540000191
(2) preparation steps of organic electroluminescent device
The specific preparation steps of the organic electroluminescent device containing the compound 2 used in the present embodiment are as follows:
1) cleaning an ITO anode on transparent glass or a plastic substrate, respectively ultrasonically cleaning the ITO anode for 20 minutes by using deionized water, acetone and ethanol, and then carrying out Plasma (Plasma) treatment for 5 minutes in an oxygen atmosphere;
2) evaporating a hole injection layer material HAT-CN on the ITO anode layer in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HAT-CN is 5nm, and the hole injection layer is used as a hole injection layer;
3) evaporating a hole transport material NPB on the hole injection layer in a vacuum evaporation mode, wherein the thickness of the hole transport material NPB is 60nm, and the hole transport layer is used as a first hole transport layer;
4) evaporating a hole transport material compound 2 on the first hole transport layer NPB in a vacuum evaporation mode, wherein the thickness of the hole transport material compound 2 is 15nm, and the layer serves as a second hole transport layer;
5) co-evaporating a light-emitting layer on the second hole transport layer by a vacuum evaporation mode, wherein BH1 is used as a main material, BD01 is used as a light-emitting material, the doping amount ratio is 5%, and the thickness is 30 nm;
6) evaporating a hole blocking material TPBI on the light-emitting layer in a vacuum evaporation mode, wherein the thickness of the hole blocking material TPBI is 10nm, and the layer is used as a hole blocking layer;
7) evaporating an electron transport material ET-1 on the hole blocking layer in a vacuum evaporation mode, wherein the thickness of the electron transport material ET-1 is 35nm, and the electron transport material ET-1 serves as an electron transport layer;
8) evaporating an electron injection material Liq on the electron transport layer in a vacuum evaporation mode, wherein the thickness of the electron injection material Liq is 2nm, and the electron injection layer is used as an electron injection layer;
9) on the electron injection layer, a cathode Al was deposited by vacuum deposition to a thickness of 100nm, and the layer was used as a cathode conductive electrode.
The remaining prepared organic electroluminescent devices were the same as the organic electroluminescent device comprising compound 2, except that compound 3 was used as the second hole transport layer instead of compound 2; compound 5 as a second hole transport layer instead of compound 2; compound 11 as a second hole transport layer instead of compound 2; compound 40 as a second hole transport layer instead of compound 2; TCTA as the second hole transport layer, compound 4 as the light emitting material instead of BD 01; TCTA as the second hole transport layer, compound 6 as the light emitting material instead of BD 01; TCTA as the second hole transport layer, compound 13 as the light emitting material instead of BD 01; TCTA as the second hole transport layer, compound 16 as the light emitting material instead of BD 01; TCTA as the second hole transport layer, compound 18 as the light emitting material instead of BD 01; TCTA as the second hole transport layer and compound 29 as the light emitting material instead of BD 01; TCTA as the second hole transport layer, compound 34 as the light emitting material instead of BD 01; TCTA as the second hole transport layer and compound 48 as the light emitting material instead of BD 01; TCTA was used as the second hole transport layer, and compound 52 was used as the light emitting material instead of BD 01.
Based on the above-described preparation steps, the organic electroluminescent device constituent components of each device test group are shown in table 2.
TABLE 2 composition of organic electroluminescent devices of each group
Figure BDA0003348040540000211
(3) Performance testing of organic electroluminescent devices
The organic electroluminescent device prepared as described in (2) of example 2 was connected between the cathode and the anode using a driving circuit, and a Keithley2400 power supply in combination with a PR670 photometer by a standard methodTesting the voltage-efficiency-current density relation of the OLED device; the service life of the device is tested by a constant current method under the condition that the constant current density is 10mA/cm2The time for the test luminance to decay to 80% of the initial luminance is defined as the device LT80The life and the test results are shown in Table 3.
TABLE 3 Performance results for each group of organic electroluminescent devices
Figure BDA0003348040540000221
Figure BDA0003348040540000231
As can be seen from Table 3, the compound provided by the invention is used as a second hole transport layer material or a luminescent material in an OLED blue light emitter, and has excellent performance. Compared with the comparative group 1TCTA, the compound 3 in the experimental group 2 as the second hole transport layer has obviously improved luminous efficiency and service life, the luminous efficiency is improved by 22 percent, and the service life is improved by 23.8 percent; compared with BD01, compound 34 in test group 12 has 26.5% higher luminous efficiency and 32.9% longer service life as a luminescent material. Compared with the prior art that the compound is applied to the OLED device, the compound provided by the invention has good photoelectric properties such as luminous efficiency, service life and the like, has a great application value in the application of the OLED device, and has a good industrial prospect.
As described above, the present invention can be preferably implemented, and the above-mentioned embodiments only describe the preferred embodiments of the present invention, and do not limit the scope of the present invention, and various changes and modifications of the technical solution of the present invention made by those skilled in the art without departing from the design spirit of the present invention shall fall within the protection scope defined by the present invention.

Claims (10)

1. A phenanthrocarbazole-core compound is characterized in that the structural formula of the phenanthrocarbazole-core compound is shown as a formula (1):
Figure FDA0003348040530000011
wherein,
l represents one of a single bond or aryl; d represents an electron donating group selected from the group consisting of a substituted or unsubstituted amine group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted 10H spiro [ acridin-9, 9 '-fluorene ] group, a substituted or unsubstituted 10H spiro [ acridin-9, 9' -xanthene ] group, a substituted or unsubstituted 5-phenyl-5, 10-dihydrophenazinyl group, and a substituted or unsubstituted 10H-phenothiazinyl group.
2. The compound of claim 1, wherein D is selected from one of aryl, carbazolyl, amine, furyl, and thienyl.
3. A compound according to claim 1, wherein the aryl group represented by L is selected from the group consisting of:
Figure FDA0003348040530000012
4. a compound according to claim 1, wherein the electron donating group represented by D is selected from the group consisting of:
Figure FDA0003348040530000021
wherein,
Ar1and Ar2Is represented as one of aryl and heteroaryl; r1And R2Is represented by aryl, alkyl, heteroarylOne of the groups; x represents an oxygen atom, a sulfur atom, C-m1m2、Si-m1m2Or N-m3One of (1), m1、m2Each independently selected from hydrogen atom, methyl, phenyl or biphenyl, m3Is phenyl; y represents one of carbon atom, nitrogen atom and oxygen atom.
5. The compound of claim 4, wherein Ar is Ar1、Ar2Is represented by one of phenyl, biphenyl, carbazolyl and furyl, and R is1And R2Is represented by one of methyl, ethyl, tertiary butyl, phenyl, biphenyl, carbazolyl and furyl.
6. The compound of claim 1, having a structural formula selected from any one of compounds 1-52:
Figure FDA0003348040530000031
Figure FDA0003348040530000041
Figure FDA0003348040530000051
Figure FDA0003348040530000061
Figure FDA0003348040530000071
7. use of a compound according to any one of claims 1 to 6 in an organic electroluminescent device.
8. The use according to claim 7 for increasing the luminance efficiency of an organic electroluminescent device.
9. The use according to claim 7 for increasing the lifetime of an organic electroluminescent device.
10. An organic electroluminescent device, characterized in that one of the hole transport material or the light emitting material in the organic electroluminescent device comprises at least one compound according to any one of claims 1 to 6.
CN202111328559.3A 2021-11-10 2021-11-10 Compound with phenanthrocarbazole as core and application thereof Pending CN113845467A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202111328559.3A CN113845467A (en) 2021-11-10 2021-11-10 Compound with phenanthrocarbazole as core and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202111328559.3A CN113845467A (en) 2021-11-10 2021-11-10 Compound with phenanthrocarbazole as core and application thereof

Publications (1)

Publication Number Publication Date
CN113845467A true CN113845467A (en) 2021-12-28

Family

ID=78984204

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202111328559.3A Pending CN113845467A (en) 2021-11-10 2021-11-10 Compound with phenanthrocarbazole as core and application thereof

Country Status (1)

Country Link
CN (1) CN113845467A (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009059839A (en) * 2007-08-31 2009-03-19 Mitsui Chemicals Inc Organic transistor
CN102471262A (en) * 2009-08-12 2012-05-23 默克专利股份有限公司 Phenanthro[1,10,9,8-c,d,e,f,g]carbazole polymers and their use as organic semiconductors
CN112174969A (en) * 2020-10-30 2021-01-05 北京八亿时空液晶科技股份有限公司 Organic compound, organic electroluminescent material and organic electroluminescent element
CN112375002A (en) * 2021-01-18 2021-02-19 苏州久显新材料有限公司 2,4, 7-trisubstituted fluorene compound and electronic device thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009059839A (en) * 2007-08-31 2009-03-19 Mitsui Chemicals Inc Organic transistor
CN102471262A (en) * 2009-08-12 2012-05-23 默克专利股份有限公司 Phenanthro[1,10,9,8-c,d,e,f,g]carbazole polymers and their use as organic semiconductors
CN112174969A (en) * 2020-10-30 2021-01-05 北京八亿时空液晶科技股份有限公司 Organic compound, organic electroluminescent material and organic electroluminescent element
CN112375002A (en) * 2021-01-18 2021-02-19 苏州久显新材料有限公司 2,4, 7-trisubstituted fluorene compound and electronic device thereof

Similar Documents

Publication Publication Date Title
CN108586188B (en) Derivatives, materials containing the Derivatives, and organic electroluminescent devices
CN112038494B (en) Electroluminescent device based on chiral thermal activation delayed fluorescent material and preparation method thereof
CN111777633B (en) A boron-containing compound and an organic electroluminescent device containing the same
CN109608453B (en) Compound taking 4, 7-phenanthroline as receptor and application thereof
CN111808085B (en) Compound and application thereof, and organic electroluminescent device comprising compound
CN111574505B (en) Compound with benzo [ c ] cinnoline as receptor and application thereof
CN110526901A (en) A kind of luminous organic material and its application for preparing organic electroluminescence device
CN111689962A (en) Compound with benzimidazole pyridine as receptor and application thereof
WO2019085759A1 (en) Compound provided with an aza-spirofluorene and aryl ketone core, preparation method thereof, and application of same in oleds
CN111454251B (en) A pyrazine derivative and its application in OLED devices
CN112707894A (en) Acenaphthene imidazole compound and application thereof in organic electroluminescent device
CN113816909B (en) A kind of organic electroluminescent material containing phenanthrene structure and device thereof
CN109897029B (en) Terpyridyl derivative, and preparation method, application and device thereof
CN110294735B (en) Compound with anthracene and phenanthrene as core and application of compound in organic electroluminescent device
CN110776500B (en) Organic compound and application thereof
CN111018863B (en) Compound taking pyrrole [1, 2-a ] quinoxaline as receptor and application thereof
KR20170045426A (en) Azaboradibenzochrysene derivatives organic electroluminescent compound, ink composition and organic electroluminescent device
CN112358480A (en) Compound based on imidazo-cyclopent-isoquinoline as receptor and application thereof
CN107778219A (en) A kind of compound and its application using dibenzo hexatomic ring and nitrogenous hexa-member heterocycle as core
CN111377942B (en) Benzo five-membered fused heterocycle organic compound and application thereof
CN114644637A (en) Tris (1, 2-phenyl) diamine derivative organic photoelectric material and its use
CN113603665A (en) Organic electronic material containing dibenzo-heterocycle substituted phenanthrene and anthracene and application thereof
CN113845467A (en) Compound with phenanthrocarbazole as core and application thereof
CN113929692B (en) Compound taking benzofuroindole as donor and application thereof
CN105153193A (en) Organic electroluminescent diode 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