CN113444093B - Compound and application thereof - Google Patents

Compound and application thereof Download PDF

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CN113444093B
CN113444093B CN202010231011.6A CN202010231011A CN113444093B CN 113444093 B CN113444093 B CN 113444093B CN 202010231011 A CN202010231011 A CN 202010231011A CN 113444093 B CN113444093 B CN 113444093B
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CN113444093A (en
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李之洋
张辉
曾礼昌
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Beijing Eternal Material Technology Co Ltd
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    • 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
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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    • 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
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    • 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
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • 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

Abstract

The invention relates to a compound and application thereof, the compound has a structure shown in a formula I, the compound provided by the invention takes carbazole derivatives as a mother nucleus structure, wherein the substituent groups must contain substitution of 7-membered aromatic rings, the purpose of the design is that carbazole guarantees corresponding HOMO energy level, good hole transmission capacity is provided, the addition of 7-membered aromatic rings provides larger plane conjugated groups, carrier mobility of the whole molecule is increased, and furthermore, the rigid structure is introduced, so that the material has high vitrification temperature and excellent thermal stability, and can effectively improve device efficiency, reduce driving voltage and prolong service life when being applied to OLED devices.

Description

Compound and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound and application thereof.
Background
In recent years, organic Light Emitting Diodes (OLEDs) have been developed rapidly, and have been in the spotlight in the field of information display, which is mainly benefited by that OLED devices can use three primary colors of high saturation red, green and blue to prepare a full-color display device, and the color gorgeous, light, thin and soft performance can be achieved without an additional backlight source.
The OLED device plays an important role in a thin layer structure containing various organic functional materials, including a light emitting layer material, an electron blocking layer material, an electron transporting layer material, a hole blocking layer material, a hole transporting layer material, and the like. After the power is turned on, electrons and holes are respectively injected and transmitted to the light emitting layer, and are recombined to generate excitons, so that light emission is realized. Therefore, research into organic functional materials in OLED devices is an important research topic for those skilled in the art.
At present, researchers have developed various organic functional materials for various specific device structures, and the effects of improving carrier mobility, regulating carrier balance, breaking through electroluminescent efficiency and delaying device attenuation are achieved.
Common fluorescent emitters emit light mainly using singlet excitons generated by recombination of holes and electrons, and such emitters are still used in various OLED devices. Further, phosphorescent emitters, i.e., a material that can emit light using both triplet and singlet excitons, such as iridium complexes, etc., are also included. The thermal excitation delayed fluorescence (TADF) technique can achieve higher luminous efficiency by promoting transition of triplet excitons to singlet excitons, and still effectively utilizing triplet excitons without using a metal complex. The thermal excitation sensitized fluorescence (TASF) technology adopts a TADF material to sensitize a luminous body in an energy transfer mode, so that higher luminous efficiency is realized, and the TADF material has wide application prospect in the OLED field.
Although a wide variety of organic functional layer materials have been developed, the requirements of OLED devices are increasingly higher nowadays, and the existing organic functional materials are not suitable for new OLED devices with higher performance.
Therefore, there is a need in the art to develop a larger variety of organic functional materials, which can improve the light emitting efficiency, reduce the driving voltage, and prolong the service life when applied to OLED devices.
Disclosure of Invention
An object of the present invention is to provide a compound capable of improving luminous efficiency, reducing driving voltage, and prolonging service life when applied to an OLED device.
To achieve the purpose, the invention adopts the following technical scheme:
the invention provides a compound, which has a structure shown in a formula I;
in the formula I, the A has a structure shown in the formula II;
in formula II, the X 1 ～X 14 Independently selected from CR 1 Or N, the R 1 Independently selected from hydrogen, takenSubstituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C3-C30 heteroaryl, said R 1 Independently linked to the linked aromatic ring to form a ring or not; preferably not linked into a ring; when two or more R are present in formula II 1 When the two or more R are 1 May be the same or different;
in formula II, represents a bond of a group;
in the formula I, the ring B and the ring C independently represent a substituted or unsubstituted C6-C30 aromatic ring condensed with a five-membered ring or a substituted or unsubstituted C3-C30 heteroaromatic ring;
in the formula I, the L 1 One selected from single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C3-C30 heteroarylene;
R 1 、L 1 the substituted groups in ring B and ring C are independently selected from one or a combination of at least two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 fused ring aryl, C3-C30 monocyclic heteroaryl, C6-C30 fused ring heteroaryl. The above "substituted or unsubstituted" group may be substituted with one substituent or may be substituted with a plurality of substituents, and when the number of substituents is plural, the substituents may be selected from different substituents, and the same meaning is given in the present invention when the same expression mode is referred to, and the selection ranges of the substituents are shown above and are not repeated.
In the above substituent, the carbon number of the C1-C10 chain alkyl group may be C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.; the carbon number of the C3-C10 cycloalkyl group can be C4, C5, C6, C7, C8, C9, C10 and the like; the carbon number of the C1-C10 alkoxy group may be C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.; the carbon number of the C1-C10 thioalkoxy group can be C2, C3, C4, C5, C6, C7, C8, C9, C10 and the like; the carbon number of the C6-C30 monocyclic aryl can be C10, C12, C14, C16, C18, C20, C26, C28 and the like; the carbon number of the C10-C30 condensed ring aryl group can be C10, C12, C14, C16, C18, C20, C26, C28 and the like; the carbon number of the C3-C30 monocyclic heteroaryl group can be C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28 and the like; the carbon number of the C6-C30 fused ring heteroaryl group may be C10, C12, C14, C16, C18, C20, C26, C28, etc. More preferably, the substituent is selected from any one of C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl, C6-C30 condensed ring heteroaryl, and specifically phenyl, naphthyl, biphenyl, pyridyl, pyrimidinyl, quinolinyl, quinoxalinyl, quinazolinyl, dibenzofuranyl, dibenzothienyl, and the like are preferable.
The compound provided by the invention takes 7-membered conjugated aromatic ring as a parent nucleus structure (a structure shown as a formula II), wherein a substituted group must contain carbazole and derivative groups thereofThe purpose of this design is that carbazole guarantees the corresponding HOMO level, providing good hole transport capability. The addition of the structure shown in the formula II provides larger plane conjugated groups, the carrier mobility of the whole molecule is increased, and the introduction of the rigid structure ensures that the material has high glass transition temperature and excellent thermal stability, and can effectively improve the efficiency of the device, reduce the driving voltage and prolong the service life when being applied to OLED devices.
In the present invention, the heteroatom of the heteroaryl group is generally selected from N, O, S.
The atomic names described in the present invention, including the corresponding isotopes thereof, for example, hydrogen (H) includes 1 H (protium or H), 2 H (deuterium or D), etc.; carbon (C) then comprises 12 C、 13 C, etc.
In the present invention, the expression "ring structure" means that the linking site is located at any position on the ring structure that can be bonded.
In the present invention, the carbon number of the C1-C10 chain alkyl group may be C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.; the carbon number of the C3-C10 cycloalkyl group can be C4, C5, C6, C7, C8, C9, C10 and the like; the carbon number of the C1-C10 alkoxy group may be C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.; the carbon number of the C1-C10 silane group can be C2, C3, C4, C5, C6, C7, C8, C9, C10 and the like; the carbon number of the C6-C30 aryl group can be C10, C12, C14, C16, C18, C20, C26, C28 and the like; the carbon number of the C6-C30 arylamino group can be C10, C12, C14, C16, C18, C20, C26, C28 and the like; the carbon number of the C3-C30 heteroaryl amino group can be C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28 and the like; the carbon number of the C3-C30 heteroaryl group may be C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, etc. The number of carbons is merely illustrative and is not limited to the above.
Preferably, in formula II, the X 1 ～X 14 Are all CR 1 。
Preferably, said R 1 Is hydrogen.
Preferably, the ring B and the ring C are independently selected from one of a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, and a substituted or unsubstituted group represented by formula III;
in the formula III, the ring D represents a substituted or unsubstituted C6-C24 aromatic ring or a substituted or unsubstituted C3-C24 heteroaromatic ring;
in formula III, X and Y are independently selected from a single bond, S, O or N-L 2 -Ar 2 And X and Y are not simultaneously single bonds;
the L is 2 One selected from single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C3-C30 heteroarylene;
the Ar is as follows 2 Selected from substituted or unsubstituted C3 to C30 electron-deficient heteroaryl or substituted or unsubstituted C6 to C30 aryl;
in formula III, the dotted line on the benzene ring represents the fused position with the five-membered ring in formula I;
ring D, L 2 And Ar is a group 2 The substituted groups of (3) are independently selected from one or a combination of at least two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl.
Preferably, at least one of the rings B and C is a substituted or unsubstituted group of formula III.
The invention preferably contains at least one condensed group shown in a formula III, the introduction of the structure can provide good hole transmission performance, and furthermore, an electricity absorbing group can be introduced at the position of X or Y to adjust the electron transmission performance of the molecule, so that the molecule has bipolar property, and the transmission of carriers is balanced, thereby further improving the performance of the device.
Preferably, the ring B is a substituted or unsubstituted group of formula III, and the ring C is a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthyl group.
Preferably, in formula III, the ring D represents a substituted or unsubstituted benzene ring.
Preferably, in formula III, at least one of X and Y is N-L 2 -Ar 2 。
Preferably, in formula III, the X and Y are independently selected from a single bond or N-L 2 -Ar 2 。
Preferably, in formula III, X is a single bond and Y is N-L 2 -Ar 2 。
Preferably, the compound has a structure represented by formula I-1;
in formula I-1, the A, L 1 Having the same meaning as in formula I, said D, X, Y having the same meaning as in formula III.
Preferably, the compound has a structure represented by the formulas (a) to (f):
preferably the structures of formula (a) and formula (b);
the A and L 1 Has the same meaning as in formula I, ar 2 And L 2 Has the same meaning as in formula III.
Specifically, the compounds of formula (a) include (a-1), (a-1) and (a-3);
specifically, the compounds of formula (b) include (b-1), (b-1) and (b-3);
specifically, the compounds of formula (c) include (c-1), (c-1) and (c-3);
specifically, the compounds of formula (d) include (d-1), (d-1) and (d-3);
specifically, the compounds of formula (e) include (e-1), (e-1) and (e-3);
specifically, the compounds of formula (f) include (f-1), (f-1) and (f-3);
preferably, the Ar 2 Any one selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, and a substituted or unsubstituted quinolinyl group.
Preferably, the Ar 2 Selected from substituted or unsubstituted C3 to C30 electron-deficient heteroaryl groups, preferably nitrogen-containing substituted or unsubstituted C3 to C30 electron-deficient heteroaryl groups.
Preferably, the Ar 2 Has one of the following structures (3-1) to (3-4):
in the formula (3-1), the Z 1 、Z 2 、Z 3 、Z 4 And Z 5 Each independently selected from CR 3 Or N atom, and Z 1 、Z 2 、Z 3 、Z 4 And Z 5 At least one of which is an N atom,
in the formula (3-2), the Z 6 、Z 7 、Z 8 、Z 9 、Z 10 、Z 11 、Z 12 And Z 13 Each independently selected from CR 3 Or N atom, and Z 6 、Z 7 、Z 8 、Z 9 、Z 10 、Z 11 、Z 12 And Z 13 At least one of which is an N atom,
in the formula (3-3), the Z 14 、Z 15 、Z 16 、Z 17 、Z 18 、Z 19 、Z 20 、Z 21 、Z 22 And Z 23 Each independently selected from CR 3 Or N atom, and Z 14 、Z 15 、Z 16 、Z 17 、Z 18 、Z 19 、Z 20 、Z 21 、Z 22 And Z 23 At least one of which is an N atom,
in the formula (3-4), Z 24 、Z 25 、Z 26 、Z 27 、Z 28 、Z 29 、Z 30 、Z 31 、Z 32 And Z 33 Each independently selected from CR 3 Or N atom, and Z 24 、Z 25 、Z 26 、Z 27 、Z 28 、Z 29 、Z 30 、Z 31 、Z 32 And Z 33 At least one of which is an N atom,
the R is 3 One selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C10 silane, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
wherein, represents the access bond of the group.
Preferably, the Ar 2 Has the structure shown in (3-1) or (3-2).
Preferably, the Ar 2 One selected from the following substituted or unsubstituted groups: pyridyl, quinolinyl, quinazolinyl, triazinyl, pyrimidinyl or quinoxalinyl.
Preferably, the Ar 2 Has a structure as shown in (3-1) or (3-2);
in the formula (3-1), Z 1 、Z 2 、Z 3 、Z 4 And Z 5 At least two of which are N atoms; and/or, in the formula (3-2), Z 6 、Z 7 、Z 8 、Z 9 、Z 10 、Z 11 、Z 12 And Z 13 At least two of which are N atoms.
Preferably, the method comprises the steps of,the Ar is as follows 2 One selected from the following substituted or unsubstituted groups: preferred quinazolines, quinoxalines and triazines
Preferably, the L 2 Selected from any one of single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, and substituted or unsubstituted pyridylene.
Preferably, the L 1 Selected from single bonds or substituted or unsubstituted phenylene groups.
Preferably, the compound has any one of the structures shown in the following P1 to P109:
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it is a second object of the present invention to provide the use of a compound according to one of the objects, which is applied to an organic electroluminescent device.
Preferably, the compound is used as a light-emitting layer material, preferably as a light-emitting layer host material, in an organic electroluminescent device.
It is a further object of the present invention to provide an organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode, the organic layer comprising at least one compound according to one of the objects.
Preferably, the organic layer comprises a light-emitting layer containing at least one compound of one of the purposes.
Preferably, the compound serves as a host material of the light emitting layer.
In one embodiment, the organic layer may further include a hole transport region and an electron transport region.
In one embodiment, a substrate may be used under the first electrode or over the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) 2 ) An oxide transparent conductive material such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) and any combination thereof can be used.
The organic layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives including compounds as shown below HT-1 to HT-34; or any combination thereof.
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The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-34 described above, or one or more of the compounds HI-1 through HI-3 described below; one or more compounds of HT-1 through HT-34 may also be used to dope one or more compounds of HI-1 through HI-3 described below.
The luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise Host materials (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light emitting layer may be a single color light emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of the RPD-1 through RPD-28 listed below.
The electron transport region may be an Electron Transport Layer (ETL) of a single layer structure including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, combinations of one or more of ET-1 through ET-57 listed below.
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An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following.
Liq、LiF、NaCl、CsF、Li 2 O、Cs 2 CO 3 、BaO、Na、Li、Ca。
The cathode is magnesium-silver mixture, liF/Al, ITO and other metals, metal mixtures and oxides.
Compared with the prior art, the invention has the following beneficial effects:
the compound provided by the invention takes 7-membered conjugated aromatic ring as a parent nucleus structure (a structure shown as a formula II), wherein a substituted group must contain carbazole and derivative groups thereofThe carbazole guarantees the corresponding HOMO energy level, provides good hole transmission capacity, provides a larger plane conjugated group, increases carrier mobility of the whole molecule, and has high glass transition temperature and excellent thermal stability due to the introduction of the rigid structure, so that the device efficiency can be effectively improved, the driving voltage can be reduced, and the service life can be prolonged when the carbazole is applied to an OLED device. />
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
The representative synthesis method of the compound shown in the general formula I is as follows:
the symbols mentioned above have the same meaning as in formula I and formula II.
The compounds of the synthesis processes of the invention not mentioned in the following synthesis examples are all starting products obtained commercially. The solvents and reagents used in the invention, such as methylene dichloride, ethanol, 1, 8-dibromonaphthalene, phenylboronic acid, carbazole and other chemical reagents, can be purchased from domestic chemical product markets, such as national drug group reagent company, TCI company, shanghai Bi De medicine company, carboline reagent company and the like. In addition, the person skilled in the art can synthesize the compounds by known methods.
Synthesis of intermediates M1-M4:
1, 8-dibromonaphthalene (0.1 mol,1 eq), phenylboronic acid (0.1 mol,1 eq), potassium carbonate (0.2 mol,2 eq), tetrakis (triphenylphosphine) palladium (0.001 mol,0.01 eq), dioxane (300 mL), and water (50 mL) were added to a three-necked flask. The reaction was heated to 90℃in an oil bath for 6 hours, and TLC was monitored to complete the reaction. The reaction solution was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure. thecrudeproductispurifiedbycolumnchromatographytoobtainanintermediateM-A.
M-A(0.08mol,1eq),pinacolo-aminophenylborate(0.1mol,1.2eq),potassiumcarbonate(0.12mol,1.5eq),tetrakis(triphenylphosphine)palladium(0.0008mol,0.01eq),dioxane(250mL)andwater(40mL)wereaddedtoathree-neckedflask. The reaction was heated to 110℃in an oil bath for 6 hours, and monitored by Thin Layer Chromatography (TLC) for completion. And cooling the reaction liquid to room temperature, and performing column chromatography purification on the crude product obtained by removing the solvent by rotary evaporation under reduced pressure to obtain an intermediate M-B.
M-B (0.05 mol) was added to 200mL of acetic acid, sulfuric acid (0.25 mol) was added, the temperature was lowered to 10℃and then an aqueous solution of sodium nitrite (0.1 mol) was added dropwise, the reaction was allowed to proceed to room temperature for 4 hours after completion of the dropwise addition, and the completion of the reaction was confirmed by gas chromatography-mass spectrometry (GC-MS) detection, followed by column chromatography purification of intermediate M.
The same procedure as described above was followed substituting only the pinacol o-aminophenylborate with an equivalent of chloro-ortho-aminophenylborate to give the following intermediate:
synthesis of intermediate M5:
m (0.05 mol) was added to 200mL of Dimethylformamide (DMF), the temperature was lowered to 0℃and then a DMF solution (0.075 mol) of N-bromosuccinimide (NBS) was added dropwise, the reaction was allowed to proceed to room temperature for 4 hours after completion of the dropwise addition, and the completion of the reaction was confirmed by GC-MS detection, followed by column chromatography purification of intermediate M5.
Synthesis of intermediate M6:
(0.1 mol) of 2-nitro-1-naphthol is added into 300mL of dichloromethane, triethylamine (0.15 mol) is added, the temperature is reduced to 0 ℃, 0.2mol of trifluoromethanesulfonic anhydride is added dropwise, the reaction is carried out for 2 hours at room temperature after the dropwise addition is finished, TLC (thin layer chromatography) monitors the reaction to be complete, organic phase is slowly added into water for separation, and the organic phase is concentrated to obtain brown oily matter, and yellow solid is obtained after petroleum ether is heated and boiled and washed.
M6-A (0.1 mol,1 eq), 2'- (pinacol ester-2-yl) -1, 1' -biphenyl ] -2-amine (0.12 mol,1.2 eq), potassium carbonate (0.15 mol,1.5 eq), tetrakis (triphenylphosphine) palladium (0.001 mol,0.01 eq), dioxane (250 mL), and water (40 mL) were added to a three-necked flask. The reaction was heated to 110℃in an oil bath for 6 hours, and TLC was monitored to complete the reaction. And cooling the reaction liquid to room temperature, and performing column chromatography purification on the crude product obtained by removing the solvent by rotary evaporation under reduced pressure to obtain an intermediate M6-B.
M6-B (0.05 mol,1 eq), sulfuric acid (0.1 mol), acetic acid (200 mL) were added to a three-necked flask. Cooling to 10 ℃, dropwise adding an aqueous solution (0.1 mol) of sodium nitrite, reacting for 2 hours at room temperature after the dropwise adding is finished, and monitoring the reaction by TLC. Adding water and ethyl acetate for extraction, and performing column chromatography purification on the crude product obtained by removing the solvent by rotary evaporation under reduced pressure to obtain an intermediate M6-C.
M6-C (0.04 mol,1 eq), iron powder (0.2 mol) and ethanol (200 mL) are added into a three-neck flask, the mixture is heated and refluxed for 24h, the ethanol is directly dried after the reaction is completed, and after washing residues with dichloro, the organic phase is concentrated to obtain brown oily matter M6-D.
M6-D (0.04 mol), cuprous bromide (0.1 mol) and hydrochloric acid (0.1 mol) are added into 200mL of acetonitrile, tert-butyl nitrite (0.1 mol) is added dropwise after the temperature is reduced to 0 ℃, the reaction is carried out for 4 hours at 50 ℃ after the dropwise addition, the reaction is complete by GC-MS monitoring, and the intermediate M6 is obtained by column chromatography.
Synthesis example 1
Synthesis of Compound P6
Indolo [2,3-A ] carbazole (10 mmol), M5 (10 mmol), sodium tert-butoxide (20 mmol), tris (dibenzylideneacetone) dipalladium (0.1 mmol), tri-tert-butylphosphine (0.2 mmol) and xylene (200 mL) are added into a reaction bottle, the mixture is heated to 120 ℃ for reaction for 6h, TLC monitors the reaction completion, water and methylene dichloride are added after cooling, and the organic phase is separated, concentrated and purified by column chromatography to obtain the compound P6-A.
P6-A (6 mmol), 2-chloro-4-phenylquinazoline (6 mmol), sodium tert-butoxide (10 mmol), tris (dibenzylideneacetone) dipalladium (0.1 mmol), tri-tert-butylphosphine (0.2 mmol) and xylene (150 mL) are added into a reaction bottle, the mixture is heated to 150 ℃ for reaction for 8 hours, TLC monitors the reaction completion, water and methylene dichloride are added after the temperature is reduced, and the organic phase is separated, concentrated and purified by column chromatography to obtain the compound P6.
Synthesis example 2:
synthesis of Compound P34
Indolo [2,3-B ] carbazole (10 mmol), M5 (10 mmol), sodium tert-butoxide (20 mmol), tris (dibenzylideneacetone) dipalladium (0.1 mmol), tri-tert-butylphosphine (0.2 mmol) and xylene (200 mL) are added into a reaction bottle, the mixture is heated to 120 ℃ for reaction for 6h, TLC monitors the reaction completion, water and methylene dichloride are added after cooling, and the organic phase is separated, concentrated and purified by column chromatography to obtain the compound P34-A.
34-A (6 mmol), 2-chloro-3-phenylquinoxaline (6 mmol), sodium tert-butoxide (10 mmol), tris (dibenzylideneacetone) dipalladium (0.1 mmol), tri-tert-butylphosphine (0.2 mmol) and xylene (150 mL) are added into a reaction bottle, the mixture is heated to 150 ℃ for reaction for 8 hours, TLC monitors the reaction completion, water and methylene dichloride are added after cooling, and the organic phase is separated, concentrated and purified by column chromatography to obtain the compound P34.
Synthesis example 3:
synthesis of Compound P54
The difference from synthesis example 1 is that indolo [2,3-C ] carbazole is substituted with an amount of indolo [2,3-C ] carbazole of the same species to give compound P54.
Synthesis example 4:
synthesis of Compound P62
The difference from synthesis example 3 is that 2-chloro-4-phenylquinazoline is replaced with an equivalent mass of 2-chloro-3-phenylquinoxaline to give compound P62.
Synthesis example 5:
synthesis of Compound P74
Indolo [2,3-C ] carbazole (10 mmol), M3 (10 mmol), sodium tert-butoxide (20 mmol), tris (dibenzylideneacetone) dipalladium (0.1 mmol), tri-tert-butylphosphine (0.2 mmol) and xylene (200 mL) are added into a reaction bottle, the mixture is heated to 150 ℃ for reaction for 6h, TLC monitors the reaction completion, water and methylene dichloride are added after cooling, and the organic phase is separated, concentrated and purified by column chromatography to obtain the compound P74-A.
P74-A (6 mmol), 2-chloro-4-phenylquinazoline (6 mmol), sodium tert-butoxide (10 mmol), tris (dibenzylideneacetone) dipalladium (0.1 mmol), tri-tert-butylphosphine (0.2 mmol) and xylene (150 mL) are added into a reaction bottle, the mixture is heated to 150 ℃ for reaction for 8 hours, TLC monitors the reaction completion, water and methylene dichloride are added after the temperature is reduced, and the organic phase is separated, concentrated and purified by column chromatography to obtain the compound P74.
Synthesis example 6:
synthesis of Compound P94
Indolo [3,2-B ] carbazole (10 mmol), M6 (10 mmol), sodium tert-butoxide (20 mmol), tris (dibenzylideneacetone) dipalladium (0.1 mmol), tri-tert-butylphosphine (0.2 mmol) and xylene 200mL are added into a reaction bottle, heated to 120 ℃ for reaction for 6h, TLC monitors that the reaction is complete, direct filtration is carried out after cooling, and a filter cake is recrystallized by xylene to obtain a compound P94-A.
P94-A (6 mmol), 2-chloro-4, 6-diphenyl- (1, 3, 5) triazine (6 mmol), sodium tert-butoxide (10 mmol), tris (dibenzylideneacetone) dipalladium (0.1 mmol), tri-tert-butylphosphine (0.2 mmol) and 200mL of dimethylbenzene are added into a reaction bottle, the mixture is heated to 150 ℃ for reaction for 8h, TLC monitors that the reaction is complete, the mixture is directly filtered after being cooled, and a filter cake is recrystallized by using dimethylbenzene to obtain a compound P94.
Synthesis example 7:
synthesis of Compound P105
Indolo [3,2-A ] carbazole (10 mmol), 2-chloro-4-phenylquinazoline (10 mmol), sodium tert-butoxide (20 mmol), tris (dibenzylideneacetone) dipalladium (0.1 mmol), tri-tert-butylphosphine (0.2 mmol) and xylene 200mL are added into a reaction bottle, the mixture is heated to 120 ℃ for reaction for 6h, TLC monitors that the reaction is complete, the mixture is directly filtered after being cooled, and a filter cake is recrystallized by using xylene to obtain a compound P105-A.
P105-A (6 mmol), M4 (6 mmol), sodium tert-butoxide (10 mmol), tris (dibenzylideneacetone) dipalladium (0.1 mmol), tri-tert-butylphosphine (0.2 mmol) and 200mL of xylene are added into a reaction bottle, the mixture is heated to 150 ℃ for 8h, the reaction is monitored by TLC, the mixture is directly filtered after being cooled, and a filter cake is recrystallized by the xylene to obtain a compound P105.
The specific synthetic methods of the above compounds are given in an exemplary manner, and the compounds not given in the following examples are prepared by similar methods, and can be obtained by replacing raw materials, which are not described herein, or can be prepared by other methods in the prior art by a person skilled in the art.
In order to verify the certainty of the molecular structure of the compound of formula I synthesized by the present invention, we confirmed it by elemental analysis (Siemens FLASH 2000 CHNS/O organic element analyzer) and mass spectrometry information (ZAB-HS type mass spectrometer manufactured by Micromass Co., UK), and the results are shown in Table 1.
TABLE 1
Compounds of formula (I) Elemental analysis (%) Mass spectrum (M/Z)
P6 C,88.02；H,4.38；N,7.60 736.26
P34 C,88.02；H,4.38；N,7.60 736.26
P54 C,88.02；H,4.38；N,7.60 736.26
P62 C,88.02；H,4.38；N,7.60 736.26
P74 C,86.48；H,4.35；N,9.17 763.27
P94 C,88.02；H,4.38；N,7.60 736.26
P105 C,88.02；H,4.38；N,7.60 736.26
Example 1
The embodiment provides an organic electroluminescent device, which is prepared by the following steps:
the glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
placing the glass substrate with ITO anode into a vacuum chamber, and vacuumizing to<1×10 -5 Pa, vacuum thermal evaporation is carried out on the anode layer film in sequence, wherein 10nm of HT-4:HI-3 (97/3,w/w) mixture is used as a hole injection layer, 60nm of compound HT-4 is used as a hole transmission layer, 40nm of compound P6:RPD-8 (100:3, w/w) is used as a light-emitting layer, 25nm of compound ET-46:ET-57 (50/50, w/w) mixture is used as an electron transmission layer, 1nm of LiF is used as an electron injection layer, and 150nm of metallic aluminum is used as a cathode. The total evaporation rate of all organic layers and LiF was controlled at 0.1 nm/sec, and the evaporation rate of the metal electrode was controlled at 1 nm/sec.
Examples 2 to 11, comparative examples 1 to 2 differ from example 1 only in that the light-emitting layer host material P6 was replaced with the light-emitting layer host material shown in table 2.
The structure of the host material of the light-emitting layer in comparative examples 1 to 2 is as follows:
of these, compound C1 was synthesized with reference to patent CN107200743a, and compound C2 was synthesized with reference to patent CN107434809 a.
Performance test:
(1) The driving voltage and current efficiency and the lifetime of the organic electroluminescent devices prepared in examples and comparative examples were measured using a Photo Research company PR 750 type optical radiometer, an ST-86LA type brightness meter (university of Beijing photoelectric instrumentation Co., ltd.) and a Keithley4200 test system at the same brightness. Specifically, the luminance of the organic electroluminescent device was measured to reach 3000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time is the driving voltage, and the current density at the time is measured; the ratio of brightness to current density is the current efficiency; the current efficiency of comparative example 1 was recorded as 1, and the remainder were ratios to the current efficiency of comparative example 1.
The results of the performance test are shown in Table 2.
TABLE 2
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The results in table 2 show that the novel organic material of the present invention is used in an organic electroluminescent device, so that the device has both a lower driving voltage and a higher current efficiency.
Compared with comparative examples 1 and 2, the host material of the light-emitting layer used in the examples introduces a novel large conjugated aromatic ring, improves the plane type of molecules, improves the mobility of molecules, facilitates the transmission of carriers, increases the efficiency of the device, and reduces the driving voltage.
The present invention is described in detail by the above examples, but the present invention is not limited to the above detailed methods, i.e., it does not mean that the present invention must be practiced depending on the above detailed methods. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.

Claims (21)

1. A compound, characterized in that the compound has a structure represented by formula I-1;
the A has a structure shown in a formula II;
in formula II, the X 1 ～X 14 Independently selected from CR 1 The R is 1 Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C3-C30 heteroaryl, said R 1 Independently linked to the linked aromatic ring to form a ring or not;
in formula II, represents a bond of a group;
ring D represents a substituted or unsubstituted C6-C24 aromatic ring or a substituted or unsubstituted C3-C24 heteroaromatic ring;
the X and Y are independently selected from single bond, S, O or N-L 2 -Ar 2 One of X and Y is N-L 2 -Ar 2 ；
The L is 1 、L 2 Independently selected from one of single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C3-C30 heteroarylene;
the Ar is as follows 2 Selected from substituted or unsubstituted C3 to C30 electron-deficient heteroaryl groups;
R 1 、L 1 ring D, L 2 And Ar is a group 2 The substituted groups of (3) are independently selected from one or a combination of at least two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl.
2. The compound of claim 1, wherein R 1 Is hydrogen.
3. A compound according to claim 1, wherein ring D represents a substituted or unsubstituted benzene ring.
4. The compound of claim 1, wherein X and Y are independently selected from a single bond or N-L 2 -Ar 2 。
5. The compound of claim 1 wherein X is a single bond and Y is N-L 2 -Ar 2 。
6. The compound according to claim 1, wherein the compound has a structure represented by formulae (a) to (f):
said A, L 1 、Ar 2 And L 2 All having the same limitations as in claim 1.
7. The compound of claim 6, wherein the compound has the structures of formula (a) and formula (b).
8. The compound of claim 1, wherein Ar 2 Any one selected from a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, and a substituted or unsubstituted quinolinyl group.
9. The compound of claim 1, wherein Ar 2 Has one of the following structures (3-1) to (3-4):
in the formula (3-1), the Z 1 、Z 2 、Z 3 、Z 4 And Z 5 Each independently selected from CR 3 Or N atom, and Z 1 、Z 2 、Z 3 、Z 4 And Z 5 At least one of which is an N atom,
in the formula (3-2), the Z 6 、Z 7 、Z 8 、Z 9 、Z 10 、Z 11 、Z 12 And Z 13 Each independently selected from CR 3 Or N atom, and Z 6 、Z 7 、Z 8 、Z 9 、Z 10 、Z 11 、Z 12 And Z 13 At least one of which is an N atom,
in the formula (3-3), the Z 14 、Z 15 、Z 16 、Z 17 、Z 18 、Z 19 、Z 20 、Z 21 、Z 22 And Z 23 Each independently selected from CR 3 Or N atom, and Z 14 、Z 15 、Z 16 、Z 17 、Z 18 、Z 19 、Z 20 、Z 21 、Z 22 And Z 23 At least one of which is an N atom,
in the formula (3-4), Z 24 、Z 25 、Z 26 、Z 27 、Z 28 、Z 29 、Z 30 、Z 31 、Z 32 And Z 33 Each independently selected from CR 3 Or N atom, and Z 24 、Z 25 、Z 26 、Z 27 、Z 28 、Z 29 、Z 30 、Z 31 、Z 32 And Z 33 At least one of which is an N atom,
the R is 3 One selected from hydrogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, halogen, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl;
wherein, represents the access bond of the group.
10. The compound of claim 9, wherein Ar 2 Has the structure shown in (3-1) or (3-2).
11. The compound of claim 9, wherein Ar 2 Has a structure as shown in (3-1) or (3-2):
in the formula (3-1), Z 1 、Z 2 、Z 3 、Z 4 And Z 5 At least two of which are N atoms; and/or, in the formula (3-2), Z 6 、Z 7 、Z 8 、Z 9 、Z 10 、Z 11 、Z 12 And Z 13 At least two of which are N atoms.
12. The compound of claim 1, wherein Ar 2 One selected from the following substituted or unsubstituted groups: quinazoline, quinoxaline and triazine.
13. The compound of claim 1, wherein L 2 Selected from any one of single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, and substituted or unsubstituted pyridylene.
14. The compound of claim 1, wherein L 1 Selected from single bonds or substituted or unsubstituted phenylene groups.
15. A compound, characterized in that the compound has any one of the structures shown below:
16. use of a compound according to any one of claims 1 to 15, wherein the compound is used in an organic electroluminescent device.
17. Use according to claim 16, characterized in that the compound is used as a light-emitting layer material in an organic electroluminescent device.
18. The use according to claim 17, wherein the compound is used as a host material for a light emitting layer in an organic electroluminescent device.
19. An organic electroluminescent device, characterized in that it comprises a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode, the organic layer comprising at least one compound according to any one of claims 1 to 15.
20. The organic electroluminescent device of claim 19, wherein the organic layer comprises a light-emitting layer comprising at least one compound according to any one of claims 1 to 15.
21. The organic electroluminescent device of claim 20, wherein the compound serves as a host material for the light-emitting layer.
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