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CN111808085B - Compound and application thereof, and organic electroluminescent device comprising compound - Google Patents

Compound and application thereof, and organic electroluminescent device comprising compound Download PDF

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CN111808085B
CN111808085B CN201910295805.6A CN201910295805A CN111808085B CN 111808085 B CN111808085 B CN 111808085B CN 201910295805 A CN201910295805 A CN 201910295805A CN 111808085 B CN111808085 B CN 111808085B
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CN111808085A (en
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李之洋
邢其峰
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Beijing Eternal Material Technology Co Ltd
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Beijing Eternal Material Technology Co Ltd
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Abstract

The invention provides a compound and application thereof, and an organic electroluminescent device comprising the compound, wherein the compound has a structure shown in a formula (I), the compound is used as a luminescent material in the organic electroluminescent device, the organic electroluminescent device comprises a substrate, a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode, and any one or at least two of the compounds are contained in the organic layer; the compound has better electron transmission capability, can realize carrier balance, is used for an organic electroluminescent device, can effectively reduce the starting voltage and improves the luminous efficiency.

Description

Compound and application thereof, and organic electroluminescent device comprising compound
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound and application thereof, and an organic electroluminescent device comprising the compound.
Background
The organic electroluminescent display (OLED) has the advantages of self-luminescence, low voltage DC drive, full solidification, wide viewing angle, light weight, simple composition and process, and the like, compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, has large viewing angle and low power, has response speed which can be 1000 times that of the liquid crystal display, and has lower manufacturing cost than that of the liquid crystal display with the same resolution, so the organic electroluminescent device has wide application prospect.
With the continuous advancement of OLED technology in illumination and display fields, people pay more attention to research on efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is usually the result of optimized collocation of device structures and various organic materials. In the most common OLED device structures, the following classes of organic materials are typically included: a hole injection material, a hole transport material, an electron transport material, a light emitting material (dye or doped guest material) of each color, a corresponding host material, and the like. Phosphorescent host materials currently in use tend to have a single carrier transport capability, such as hole-type transport hosts as well as electron-type transport hosts.
CN104884444a provides a condensed ring amine compound represented by formula (1) having an antipyran ring or a ouinone ring: and an organic electroluminescent element comprising a cathode, an anode, and an organic thin film layer comprising one or more layers sandwiched between the cathode and the anode, wherein the organic thin film layer comprises a light-emitting layer, at least 1 layer of the organic thin film layer contains at least 1 kind of the amine compound (n is an integer of 1 to 4, B is a structure represented by the following formula (2), A is a gene represented by the following formula (4) 1 -R 8 At least one group of the 2 adjacent genes is bonded to each other to form a group having a valence of 2 represented by the following formula (3). X is an oxygen atom or a sulfur atom: wherein when X is a sulfur atom, n is an integer of 2 to 4. Ar (Ar) 1 、Ar 2 Aryl groups having 6 to 30 ring-forming carbon atoms which are substituted or unsubstituted, and the like. L, L 1 L and L 2 Is a single bond, an arylene group having 6 to 30 ring-forming carbon atoms, or the like. Wherein Ar is 1 Ar and Ar 2 When both are substituted or unsubstituted aryl groups having 6 to 30 ring-forming carbon atoms, L is a single bond. The condensed ring amine compound has higher luminous efficiency and lower driving voltage, but the luminous efficiency is still to be further improved.
CN104045623a discloses a novel compound, a method for producing the same, and an organic electronic element using the same. The novel compounds of the present invention are capable of allowing hole injection, hole transport, electron injection and electron transport, or as luminescent materials in organic electronic elements or organic light emitting elements; the novel compound takes naphthobenzofuran or naphthobenzothiophene as a mother nucleus, and by introducing substituent groups, the organic electronic element has lower driving voltage and better stability, but the stability of the organic electronic element is still to be further improved.
Therefore, a wider variety of higher performance luminescent materials are desired to be developed.
Disclosure of Invention
In view of the deficiencies of the prior art, it is an object of the present invention to provide a compound having the structure of formula (I):
formula (I);
in formula (I), X is independently O or S;
in the formula (I), R 1 And R is 2 Independently represents a single substituent to a maximum permissible substituent, and each is independently selected from any one of hydrogen, C1-C12 alkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxy, silyl, amino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
in the formula (I), A 1 Is thatAnd A is 2 Is->
Or, A 1 Is thatAnd A is 2 Is->
Wherein L is 1 And L 2 Each independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group,
Ar 1 is a substituted or unsubstituted C3-C30 electron-deficient heteroaryl,
Ar 2 and Ar is a group 3 Each independently selected from any one of substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl;
a＝1，b＝1，A 1 substituted in the 5-position in the compound of formula (I) and A 2 Substituted at the 8-position and 9-position in the compound of formula (I)Or 10 bits of the total number of the bits,
or a=1, b=1, a 1 Substituted in the compound of the formula (I) at the 1-, 2-, 3-, 4-or 6-position and A 2 Substituted at the 7-, 8-, 9-or 10-position in the compound of the structure of formula (I),
or a=2, b=1, a 1 Is thatAnd A is 2 Is->A 1 And (A) 2 ) 2 Respectively substituting any three of 1, 2, 3,4, 5, 6, 7, 8, 9 or 10 positions in the compound of the structure of the formula (I),
or a=1, b=2, a 1 Is thatAnd A is 2 Is->(A 1 ) 2 And A 2 Respectively substituting any three of 1, 2, 3,4, 5, 6, 7, 8, 9 or 10 positions in the compound with the structure shown in the formula (I);
". Times" represents the site of attachment to the parent nucleus;
the substituent group of the substituent is selected from any one of halogen, C1-C10 alkyl or cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon group, and C3-C30 monocyclic heteroaromatic hydrocarbon or condensed ring heteroaromatic hydrocarbon group.
According to the compound provided by the invention, naphthobenzofuran or naphthobenzothiophene is taken as a parent nucleus, excellent chemical property and physical property of benzene ring, naphthalene ring and five-membered aromatic heterocycle are integrated, and hetero atoms on the five-membered aromatic heterocycle have high electron-rich property, so that the compound has good charge transmission performance and electron donating performance, the compound has good stability, and is matched with a specific electron-withdrawing group and an aromatic amine electron-withdrawing group to be used at a specific substitution site, or matched with two electron-withdrawing groups and an aromatic amine electron-withdrawing group to be used, so that the balance of carriers is realized, and the maximally effective exciton is formed on a luminescent layer, so that the compound has the effects of low starting voltage, high luminous efficiency and long service life, the starting voltage is less than or equal to 4.6V, the current efficiency is more than or equal to 18cd/A, and the LT95 service life is more than or equal to 60h in an organic electroluminescent device; the electron donating group adopts a specific arylamine structure, and the introduction of the electron donating group of the arylamine structure is considered to obviously improve the HOMO of the molecule, so that the voltage of the device is reduced; compared with dibenzofuran or thiophene, the naphthobenzofuran or thiophene has the advantages that the conjugated structure of molecules is enlarged, the rigid structure of the molecules is increased, the molecules show better electrochemical stability, and the service life of devices is prolonged.
The "substituted substituent" referred to in the present invention is explained as follows: when the "substituted or unsubstituted" group is a substituted group, the substituent on the group is a "substituted substituent", and the range of the substituent is as described in the preceding paragraph, and the same meaning applies when the same expression is referred to below. Exemplary, when Ar 1 When the group is selected from C3-C30 electron-deficient heteroaryl substituted by cyano, the cyano group on the C3-C30 electron-deficient heteroaryl is a substituent substituted.
Preferably, when a=1 and b=1, the compound is selected from the structures (2-1) or (2-2):
substituted at the 5-position of the compound of formula (2-1), and +.>Substitution atThe 8, 9 or 10 positions of the compound,
or alternatively, the first and second heat exchangers may be,substituted at the 1-, 2-, 3-, 4-or 6-position of the compound of formula (2-1) and +.>Substitution at the 7, 8, 9 or 10 position of the compound;
substituted at the 7-position of the compound of formula (2-2) and +.>Substituted in the 1-, 2-, 3-, 4-or 6-position of the compound,
or alternatively, the first and second heat exchangers may be,substituted at the 8-, 9-or 10-position of the compound of formula (2-2) and +.>
Substitution at the 1-, 2-, 3-, 4-, 5-or 6-position of the compound;
preferably, the a=1, b=2, a 1 Is thatAnd A is 2 Is->The compound is selected from the structures (2-3):
preferably, the a=2, b=1, a 1 Is thatAnd A is 2 Is->The compound is selected from the structures (2-4):
wherein L is 1 、L 2 、Ar 1 、Ar 2 、Ar 3 、R 1 、R 2 And X each independently has the same definition as claim 1.
Preferably, said R 1 And R is 2 Are all hydrogen.
Preferred R of the invention 1 、R 2 The hydrogen is adopted, because the introduction of excessive functional group substitution increases unstable factors in the molecular electrochemical environment, influences the service life of the device, and the compound with larger molecular weight is not easy to vapor deposition, so that the compound is designed into the compound with simple structure as far as possible on the premise of not influencing the carrier balance and the luminous efficiency of the compound.
Preferably, the heteroatom in the substituted or unsubstituted C3 to C30 electron-deficient heteroaryl is N;
preferably, the Ar 1 Independently is any one of a substituted or unsubstituted quinazolinyl group and a derivative thereof, a substituted or unsubstituted triazinyl group and a derivative thereof, a substituted or unsubstituted pyrimidinyl group and a derivative thereof, a substituted or unsubstituted quinoxalinyl group and a derivative thereof, a substituted or unsubstituted pyridinyl group and a derivative thereof.
The substituent group of the substituent is selected from any one of halogen, C1-C10 alkyl or cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon group, and C3-C30 monocyclic heteroaromatic hydrocarbon or condensed ring heteroaromatic hydrocarbon group.
Preferably, the Ar 2 And Ar is a group 3 Each independently selected from any one of substituted or unsubstituted C6-C30 aryl, C3-C30 heteroaryl with a substituted or unsubstituted heteroatom of S or O;
preferably, the Ar 2 And Ar is a group 3 Each independently selected from substituted or unsubstituted C6-C30 aryl;
preferably, the Ar 2 And Ar is a group 3 Each independently selected from any one of phenyl, naphthyl or biphenyl.
The substituent group of the substituent is selected from any one of halogen, C1-C10 alkyl or cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon group, and C3-C30 monocyclic heteroaromatic hydrocarbon or condensed ring heteroaromatic hydrocarbon group.
Preferably, the L 1 And L 2 Each independently selected from any one of a single bond, a substituted or unsubstituted C6-C18 arylene group, and a substituted or unsubstituted C3-C18 heteroarylene group.
The substituent group of the substituent is selected from any one of halogen, C1-C10 alkyl or cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon group, and C3-C30 monocyclic heteroaromatic hydrocarbon or condensed ring heteroaromatic hydrocarbon group.
Preferably, the L 2 Is a single bond.
Preferably, a is 1 and b is 1.
In the invention, a is preferably 1, and b is preferably 1, because the introduction of excessive electricity absorption or supply groups can cause unbalance of molecular carriers, so that the comprehensive performance of molecules is reduced, and the compound with larger molecular weight is not easy to evaporate, so that the compound is designed to be a compound with a simple structure as far as possible on the premise of not influencing the carrier balance and the luminous efficiency of the compound.
Preferably, the compound has any one of the following structures (3-1) to (3-10):
wherein L is 1 、L 2 、Ar 1 、Ar 2 、Ar 3 、R 1 、R 2 And X each independently has the same defined range as described above;
in the formula (3-2),substituted in the 5-position of the compound, +.>Substitution at the 8-, 9-or 10-position of the compound;
in the formula (3-7),substituted in the 7-position of the compound, +.>Substitution is at the 1-, 2-, 3-, 4-or 6-position of the compound.
Preferably, the compound has any one of the following structures (4-1) to (4-10):
wherein L is 1 、L 2 、Ar 1 、Ar 2 、Ar 3 、R 1 、R 2 And X each independently has the same defined range as described above;
in the formula (4-4),substituted in the 7-position of the compound, +.>Substitution at the 1-, 2-, 3-, 4-or 6-position of the compound;
in the formula (4-9),substituted in the 5-position of the compound, +.>Substitution is at the 8, 9 or 10 position of the compound.
Preferably, the A 1 Substituted in the 5-position in the compound of formula (I) and A 2 Substitution at position 8, 9 or 10 in the compound of formula (I);
preferably, the A 1 Substituted in the 5-position in the compound of formula (I) and A 2 Substituted at the 9-position in the compound of formula (I).
Preferably, the compound has the following (6-1) structure:
wherein L is 1 、L 2 、Ar 1 、Ar 2 、Ar 3 Each of X and X independently has the same defined range as described above.
Preferably, the compound has any one of the following structures P1-P79:
it is a second object of the present invention to provide the use of a compound according to one of the objects as a material for a light-emitting layer 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 an organic layer between the first electrode and the second electrode, the organic layer comprising any one or a combination of at least two of the compounds according to one of the objects.
The organic electroluminescent device provided by the invention comprises a first electrode, a second electrode and an organic material layer positioned between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In particular embodiments, a substrate may be used below the first electrode or above 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 ) Zinc oxide(ZnO) and the like, and any combinations 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 material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material 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 such as the compounds shown below HT-1 to HT-34, or any combination thereof.
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 HI1 through HI3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1 to HI3 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 host material is selected from, but not limited to, one or more of GPH-1 to GPH-80.
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 OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. 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.
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 compounds:
LiQ、LiF、NaCl、CsF、Li 2 O、Cs 2 CO 3 、BaO、Na、Li、Ca。
compared with the prior art, the invention has the following beneficial effects:
according to the compound provided by the invention, naphthobenzofuran or naphthobenzothiophene is taken as a parent nucleus, excellent chemical property and physical property of benzene ring, naphthalene ring and five-membered aromatic heterocycle are integrated, and hetero atoms on the five-membered aromatic heterocycle have high electron-rich property, so that the compound has good charge transmission performance and electron donating performance, the compound has good stability, and is matched with a specific electron-withdrawing group and an aromatic amine electron-withdrawing group to be used at a specific substitution site, or matched with two electron-withdrawing groups and an aromatic amine electron-withdrawing group to be used, so that the balance of carriers is realized, and the maximally effective exciton is formed on a luminescent layer, so that the compound has the effects of low starting voltage, high luminous efficiency and long service life, the starting voltage is less than or equal to 4.6V, the current efficiency is more than or equal to 18cd/A, and the LT95 service life is more than or equal to 60h in an organic electroluminescent device; the electron donating group adopts a specific arylamine structure, and the introduction of the electron donating group of the arylamine structure is considered to obviously improve the HOMO of the molecule, so that the voltage of the device is reduced; compared with dibenzofuran or thiophene, the naphthobenzofuran or thiophene has the advantages that the conjugated structure of molecules is enlarged, the rigid structure of the molecules is increased, the molecules show better electrochemical stability, and the service life of devices is prolonged.
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 synthetic route of the compounds of formula (I) according to the invention:
the compound M1 and the compound A1 are subjected to Suzuki coupling reaction to generate M2, and the M2 and the compound A2 are subjected to Buchwald-Hartwig coupling reaction to generate the compound of the formula (I), wherein the sequence of the two steps of reaction can be adjusted according to actual needs;
wherein X is independently O or S;
Y 1 and Y 2 Each independently selected from any one of chlorine, bromine and iodine;
A 1 is thatAnd A is 2 Is->Or, A 1 Is->And A is 2 Is->
Wherein L is 1 And L 2 Each independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group,
Ar 1 independently a substituted or unsubstituted C3 to C30 electron-deficient heteroaryl electron-deficient group,
Ar 2 and Ar is a group 3 Each independently selected from any one of substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl;
the substituent group of the substituent is selected from any one of halogen, C1-C10 alkyl or cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon group, and C3-C30 monocyclic heteroaromatic hydrocarbon or condensed ring heteroaromatic hydrocarbon group.
a＝1，b＝1，Y 1 Substituted in(I) In the compound of the structure at position 5, and Y 2 Substituted at the 8-, 9-or 10-position in the compounds of the structure of formula (I),
or a=1, b=1, y 1 Substituted in the compound of the formula (I) at the 1-, 2-, 3-, 4-or 6-position and Y 2 Substituted at the 7-, 8-, 9-or 10-position in the compound of the structure of formula (I),
or a=2, b=1, y 1 And (Y) 2 ) 2 Respectively substituting any three of 1, 2, 3,4, 5, 6, 7, 8, 9 or 10 positions in the compound of the structure of the formula (I),
or a=1, b=2, (Y) 1 ) 2 And Y 2 Respectively substituted for any three of the 1, 2, 3,4, 5, 6, 7, 8, 9 or 10 positions in the compound of the structure of formula (I).
The specific preparation method of the above novel compound of the present invention will be described in detail below by taking a plurality of preparation examples as examples, but the preparation method of the present invention is not limited to these preparation examples.
Preparation example 1
(1) Preparation of Compound P3-1:
raw material S1 (31.2 g,100 mmol), S2 (31.5 g,100 mmol), potassium carbonate (20.7 g,150 mmol) and tetrakis (triphenylphosphine) palladium (0.5 g) are added into a single-port bottle, 300mL of dioxane and 50mL of water are added, the mixture is heated to reflux for 10h, the reaction of the raw material is detected by Thin Layer Chromatography (TLC), dichloromethane is added for extraction after water quenching, and an organic phase is concentrated and then purified by column chromatography to obtain a product of a target compound P3-1.
(2) Preparation of Compound P3
Compound P3-1 (27.3 g,50 mmol), diphenylamine (10.1 g,60 mmol), sodium t-butoxide (9.6 g,100 mmol), tris (dibenzylideneacetone) dipalladium 0.5g and 2-dicyclohexylphosphine-2 ',6' -dimethoxy-biphenyl 0.5g were added to a flask containing toluene (300 mL), heated to reflux for 5 hours, monitored by Thin Layer Chromatography (TLC) to complete the reaction, cooled, and concentrated over silica gel to give a brown oil, which was purified by column chromatography to give pale yellow solid P3.
Characterization of the structure of P3 obtained in step (2) with nuclear magnetism gave the following results:
nuclear magnetism 1 H NMR(500MHz，Chloroform)δ:9.03-8.90(m，2H)，8.54(s，1H)，8.17-8.09(m，2H)，8.03(dd，J＝14.8，3.1Hz，1H)，7.94(dt，J＝14.7，3.1Hz，1H)，7.85–7.65(m，4H))，7.64–7.34(m，9H)，7.32–7.15(m，4H)，7.14–6.92(m，7H)。
Preparation example 2
(1) Preparation of Compound P9-1:
raw materials S1 (100 mmol), S3 (100 mmol), potassium carbonate (20.7 g,150 mmol) and tetrakis (triphenylphosphine) palladium (0.5 g) are added into dioxane (300 mL), water (50 mL) and heated to reflux reaction for 10h, the raw materials are detected to be reacted by Thin Layer Chromatography (TLC), water quenching is carried out, dichloromethane extraction is carried out, and an organic phase is concentrated and then column chromatography is carried out to purify the product, thus obtaining the target compound P9-1.
(2) Preparation of Compound P9
Compound P9-1 (60 mmol), triphenylamine 3-borate (60 mmol), potassium carbonate (100 mmol), tris (dibenzylideneacetone) dipalladium 0.5g and 2-dicyclohexylphosphine-2 ',6' -dimethoxy-biphenyl 0.5g are added into a flask with 300mL dioxane and 50mL water, heated to reflux reaction for 10h, monitored by Thin Layer Chromatography (TLC) to complete the reaction, quenched by water, extracted by dichloromethane, and the organic phase is concentrated and purified by column chromatography to obtain product P9.
Characterization of the structure of P9 obtained in step (2) with nuclear magnetism gave the following results:
nuclear magnetic 1H NMR (500 mhz, chloroform) delta 9.05-8.88 (m, 2H), 8.75 (d, j=2.9 hz, 1H), 8.50 (s, 1H), 8.13 (ddd, j=15.0, 4.4,3.0hz, 2H), 8.05-7.94 (m, 2H), 7.85-7.73 (m, 3H), 7.71-7.60 (m, 2H), 7.60-7.40 (m, 5H), 7.32-7.12 (m, 7H), 7.12-6.91 (m, 6H).
Preparation example 3
(1) Preparation of Compound P34-1:
a single-necked flask was charged with S4 (100 mmol), S5 (110 mmol), sodium t-butoxide (150 mmol), 0.5g of tris (dibenzylideneacetone) dipalladium and 0.5g of 2-dicyclohexylphosphine-2 ',6' -dimethoxy-biphenyl, and the mixture was heated to reflux for 5 hours, after completion of the reaction, the reaction was detected by Thin Layer Chromatography (TLC), and after cooling, the reaction mixture was concentrated over silica gel to give a brown oil, and the pale yellow solid P34-1 was purified by column chromatography.
(2) Preparation of Compound P34-2
Compound P34-1 (60 mmol), potassium acetate 100mmol, bippinacol borate 120mmol, tris (dibenzylideneacetone) dipalladium 0.5g and 2-dicyclohexylphosphine-2 ',6' -dimethoxy-biphenyl 0.5g are added into 300ml dioxane, the reaction is carried out for 6h under reflux, the reaction of the raw materials is detected by Thin Layer Chromatography (TLC), after-treatment, extraction is carried out by adding water and ethyl acetate, separation is carried out, and the organic phase is concentrated to obtain white solid P34-2.
(3) Preparation of Compound P34
The compound P34-2 (50 mmol), S6 (50 mmol), potassium carbonate (70 mmol) and tetra (triphenylphosphine) palladium (0.5 g) are added into a flask with dioxane (300 mL) and water (50 mL), and the mixture is heated to reflux reaction for 10h, the reaction is monitored by Thin Layer Chromatography (TLC), after water quenching, dichloromethane extraction is carried out, and the organic phase is concentrated and then purified by column chromatography, thus obtaining the product P34.
Characterization of the structure of P34 obtained in step (3) by nuclear magnetism gave the following results:
nuclear magnetic 1H NMR (500 mhz, chloride) delta 9.09 (t, j=3.0 hz, 1H), 9.04-8.90 (m, 1H), 8.52 (ddd, j=29.9, 14.9,3.0hz, 2H), 8.42-8.28 (m, 2H), 8.22-8.04 (m, 4H)), 8.04-7.94 (m, 1H), 7.81-7.68 (m, 2H), 7.68-7.32 (m, 16H), 7.30-7.15 (m, 2H), 7.13-6.93 (m, 3H).
Synthesis example 4
The difference from synthesis example 2 is only that S3 is replaced by an equivalent amount of triphenylamine 3-borate, giving product P42.
The structure of the obtained P42 was characterized by nuclear magnetism, and the result was as follows:
nuclear magnetic 1H NMR (500 mhz, chloride) delta 9.09 (t, j=3.0 hz, 1H), 9.04-8.90 (m, 1H), 9.03-8.91 (m, 2H), 8.63 (d, j=2.9 hz, 1H), 8.13 (dd, j=15.0, 3.1hz, 1H), 7.87-7.73 (m, 4H), 7.73-7.59 (m, 4H), 7.59-7.41 (m, 5H), 7.33-7.13 (m, 7H), 7.13-6.91 (m, 6H).
Synthesis example 5
The difference from synthesis example 1 is only that S1 is replaced with an equal amount of S7 and S2 is replaced with an equal amount of S8, to obtain the product P46.
The structure of the obtained P46 was characterized by nuclear magnetism, and the result was as follows:
nuclear magnetic 1H NMR (500 mhz, chloroform) delta 9.09-8.87 (m, 3H), 8.54 (dd, j=15.0, 3.1hz, 1H), 8.33 (s, 1H), 8.22 (d, j=3.1 hz, 1H), 8.15-7.93 (m, 3H), 7.87-7.74 (m, 2H), 7.74-7.63 (m, 2H), 7.62-7.52 (m, 2H), 7.52-7.41 (m, 3H), 7.30-7.18 (m, 5H), 7.14-6.93 (m, 6H).
Synthesis example 6
The compound P50 obtained in this synthesis example was synthesized in the same manner as P9, except that S1 was replaced with equivalent S9 and triphenylamine-3-boric acid was replaced with equivalent triphenylamine-2-boric acid.
The structure of P50 obtained in this synthesis example was characterized by nuclear magnetism, and the results were as follows:
nuclear magnetic 1H NMR (500 mhz, chloride) delta 9.06-8.89 (m, 2H), 8.43-8.28 (m, 4H), 8.19 (s, 1H), 8.05 (ddd, j=30.0, 15.0,3.0hz, 2H), 7.16-7.42 (m, 10H), 7.42-7.31 (m, 3H), 7.31-7.16 (m, 4H), 7.14-6.93 (m, 6H).
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 above glass substrate with anode in vacuum chamber, and vacuumizing to 1×10 -5 ～9×10 -3 Pa, vacuum evaporating HI-3 as a hole injection layer on the anode layer film, wherein the evaporation rate is 0.1nm/s, and the thickness of the evaporation film is 10nm;
vacuum evaporation HT-4 is carried out on the hole injection layer to serve as a hole transmission layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 80nm;
vacuum evaporating a luminescent layer of the device on the hole transport layer, wherein the luminescent layer comprises a main material and a dye material, the evaporation rate of P3 is regulated to be 0.1nm/s by utilizing a multi-source co-evaporation method, the evaporation rate of dye RPD-8 is set to be 5% in proportion, and the total film thickness of evaporation is 30nm;
vacuum evaporating electron transport layer material ET-46 of the device on the luminescent layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 30nm;
LiF with the thickness of 0.5nm is vacuum evaporated on an Electron Transport Layer (ETL) to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
So that it has the following structure:
ITO/HI-3(10nm)/HT-4(80nm)/P3:5％RPD-8(30nm)/ET-46(30nm)/LiF(0.5nm)/Al(150nm)。
example 2
The difference from example 1 is that P3 is replaced by P9.
Example 3
The difference from example 1 is that P3 is replaced by P34.
Example 4
The difference from example 1 is that P3 is replaced by P42.
Example 5
The difference from example 1 is that P3 is replaced by P46.
Example 6
The difference from example 1 is that P3 is replaced by P50.
Example 7
The difference from example 1 is that P3 is replaced by P61.
Example 8
The difference from example 1 is that P3 is replaced by P60.
Example 9
The difference from example 1 is that P3 is replaced by P73.
Comparative example 1
The difference from example 1 is that P3 is replaced by compound C-1.
Comparative example 2
The difference from example 1 is that P3 is replaced by compound C-2.
Performance testing
The driving voltage and current efficiency and the lifetime of the organic electroluminescent devices prepared in examples and comparative examples were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the luminance of the organic electroluminescent device was measured to reach 10000cd/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 lifetime test of LT95 is as follows: using a luminance meter at 10000cd/m 2 Under the condition of brightness, constant current is kept, and the brightness of the organic electroluminescent device is measured to be reduced to 9500cd/m 2 Time in hours.
The results of the performance test are shown in Table 1:
TABLE 1
As can be seen from Table 1, the OLED devices in the examples have starting voltages of less than or equal to 4.6V, maximum external quantum efficiencies of more than or equal to 18%, and have higher luminous efficiency and lower starting voltage; the luminescent material of the device of comparative example 1 is replaced by C-1, the turn-on voltage and the maximum external quantum efficiency are obviously poor, because the molecule contains quinoline which absorbs electricity, but the molecule has weaker electricity absorption and lower electron mobility, and furthermore, the molecule contains a biaryl amine structure, so that the electricity supply is strong, the hole transmission is quick, and the formation of effective excitons in a luminescent layer is greatly reduced due to the mismatch of the hole and the electron transmission, so that the performance of the molecule is lower than that of the material of the invention; the light emitting material of the device of comparative example 2 was replaced with C-2 containing no electron-deficient heteroaryl group, which does not contain an electron withdrawing group, and such a structure is difficult to efficiently inject electrons, and excitons cannot be efficiently formed, resulting in significant deterioration of the turn-on voltage and maximum external quantum efficiency;
the results prove that when the compound provided by the invention is used as a luminescent layer material of an OLED device, the luminescent efficiency of the device can be improved, and the starting voltage is reduced, because the compound provided by the invention takes naphthobenzofuran or naphthobenzothiophene as a parent nucleus and is matched with specific arylamine electron-donating groups and specific C3-C30 electron-deficient heteroaryl groups, the compound has good charge transmission performance and electron-donating performance, and has better stability, and the compound is matched with the electron-donating groups and electron-deficient groups of the arylamine structure to be used together, and the compound is used in the organic electroluminescent device to have the effects of low starting voltage, high luminescent efficiency and long service life by selecting proper substitution sites.
The applicant declares that the above is only a specific embodiment of the present invention, but the scope of the present invention is not limited thereto, and it should be apparent to those skilled in the art that any changes or substitutions that are easily conceivable within the technical scope of the present invention disclosed by the present invention fall within the scope of the present invention and the disclosure.

Claims (13)

1. A compound, characterized in that the compound has the structure of formula (I):
in formula (I), X is independently O or S;
in the formula (I), R 1 And R is 2 Independently represents a single substituent to a maximum permissible substituent, and each is independently selected from any one of hydrogen, C1-C12 alkyl, halogen, cyano;
in the formula (I), A 1 Is thatAnd A is 2 Is->
Or, A 1 Is thatAnd A is 2 Is->
Wherein L is 1 And L 2 Each independently selected from any one of a single bond, a C6-C18 arylene group,
Ar 1 is any one of substituted or unsubstituted quinazolinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, and substituted or unsubstituted quinoxalinyl;
Ar 2 and Ar is a group 3 Each independently selected from the group consisting of substituentsOr any one of unsubstituted C6-C30 aryl groups;
a＝1，b＝1，A 1 substituted in the 5-position in the compound of formula (I) and A 2 Substituted at the 10-position in the compound of formula (I),
or a=1, b=1, x is S, a 1 Is thatAr 1 For substituted or unsubstituted triazinyl, A 1 Substituted in the 5-position in the compound of formula (I) and A 2 Is->Which is substituted in the 8-position or 10-position in the compound of the structure of formula (I);
or a=1, b=1, a 1 Is thatAr 1 Is any one of substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinoxalinyl, A 1 Substituted in the 5-position in the compound of formula (I) and A 2 Is->Which is substituted in the compound of the structure of formula (I) in position 8, 9 or 10,
or a=1, b=1, a 1 Is thatWhich is substituted in the 5-position in the compound of the formula (I) and A 2 Is thatAr 1 Is any one of substituted or unsubstituted quinoxalinyl, A 2 Substituted at the 8-, 9-or 10-position in the compounds of the structure of formula (I),
or alternatively, the first and second heat exchangers may be,a＝1，b＝1，A 1 substituted in the 1-, 2-, 3-, 4-position in the compound of the structure of formula (I), and A 2 Substituted at the 7-, 8-, 9-or 10-position in the compound of the structure of formula (I),
or a=1, b=1, a 1 Substituted in the 6-position in the compound of formula (I) and A 2 Substituted at the 10-position in the compound of formula (I),
or a=1, b=1, a 1 Is thatWhich is substituted in the 6-position in the compound of the formula (I) and A 2 Is thatAr 1 A is a substituted or unsubstituted quinazolinyl group 2 Substituted at the 8-or 10-position in the compound of formula (I),
or a=1, b=1, a 1 Is thatWhich is substituted in the 6-position in the compound of the formula (I) and A 2 Is thatAr 1 Is any one of substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinoxalinyl, A 2 Substituted at the 7-, 8-, 9-or 10-position in the compound of the structure of formula (I),
or a=1, b=1, a 1 Is thatAr 1 Is any one of substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinoxalinyl, A 1 Substituted in the 6-position in the compound of formula (I) and A 2 Is->Which is substituted in the compound of the structure of formula (I) in position 7, 8, 9 or 10,
or a=2, b=1, a 1 Is thatAnd A is 2 Is->A 1 And (A) 2 ) 2 Respectively substituting any three of 1, 2, 3,4, 5, 6, 7, 8, 9 or 10 positions in the compound of the structure of the formula (I),
or a=1, b=2, a 1 Is thatAnd A is 2 Is->(A 1 ) 2 And A 2 Respectively substituting any three of 1, 2, 3,4, 5, 6, 7, 8, 9 or 10 positions in the compound with the structure shown in the formula (I);
". Times" represents the site of attachment to the parent nucleus;
the substituent group of the substituent is selected from any one of halogen, C1-C10 alkyl, C6-C30 monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon group.
2. The compound according to claim 1, wherein the compound has any one of the following structures (2-1) to (2-4):
wherein L is 1 、L 2 、Ar 1 、Ar 2 、Ar 3 、R 1 、R 2 And X each independently has the same definition as claim 1;
substituted at the 5-position of the compound of formula (2-1), and +.>Instead of being in the 10-position of the compound,
or alternatively, the first and second heat exchangers may be,substituted at the 5-position of the compound of formula (2-1), ar 1 Is any one of substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinoxalinyl, and +.>Substitution at the 8-, 9-or 10-position in the compound of the structure of formula (2-1);
or alternatively, the first and second heat exchangers may be,substitution of the 1-, 2-, 3-, 4-position of the compound of formula (2-1) and +.>Substitution at the 7, 8, 9 or 10 position of the compound;
or alternatively, the first and second heat exchangers may be,substituted at the 6-position of the compound of formula (2-1), and +.>Instead of being in the 10-position of the compound,
or alternatively, the first and second heat exchangers may be,substituted at the 6-position of the compound of formula (2-1), ar 1 Is any one of substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinoxalinyl, and +.>Substituted at the 7-, 8-, 9-or 10-position of the compound,
substituted at the 7-position of the compound of formula (2-2) and +.>Substituted at 1 position, 2 position, 3 position and 4 position of the compound,
or alternatively, the first and second heat exchangers may be,substituted at the 7-position of the compound of formula (2-2), ar 1 Is any one of substituted or unsubstituted pyrimidinyl and substituted or unsubstituted quinoxalinyl; and->Substituted in the 6-position of the compound;
or alternatively, the first and second heat exchangers may be,substituted at the 8-, 9-or 10-position of the compound of formula (2-2) and +.>Substituted at 1 position, 2 position, 3 position, 4 position and 5 position of the compound,
or alternatively, the first and second heat exchangers may be,substitution in formula (2-2)10 th position of the compound, and->The substitution is at the 6-position of the compound,
or alternatively, the first and second heat exchangers may be,substituted at the 8-position of the compound of formula (2-2), ar 1 Is a substituted or unsubstituted quinazolinyl group, andsubstituted in the 6-position of the compound.
3. The compound of claim 1, wherein R 1 And R is 2 Are all hydrogen.
4. The compound of claim 1, wherein Ar 2 And Ar is a group 3 Each independently selected from any one of substituted or unsubstituted phenyl, naphthyl or biphenyl.
5. The compound of claim 1, wherein L 2 Is a single bond.
6. The compound of claim 1, wherein a is 1 and b is 1.
7. The compound according to claim 1, wherein the compound has any one of the following structures (3-1) to (3-10):
wherein L is 1 、L 2 、Ar 1 、Ar 2 、Ar 3 、R 1 、R 2 And X each independently has the same definition as claim 1;
in the formula (3-1),instead of being in the 10-position of the compound,
or, ar 1 Is a substituted or unsubstituted quinazolinyl group, andsubstitution at the 7, 8 or 9 position of the compound;
in the formula (3-2),substituted in the 5-position of the compound, +.>Substituted in the 10-position of the compound;
in the formula (3-7),substituted in the 7-position of the compound, +.>Substituted at 1 position, 2 position, 3 position and 4 position of the compound,
or alternatively, the first and second heat exchangers may be,substituted in the 7-position, ar, of the compounds 1 Is any one of substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinoxalinyl,/or->Substituted in the 6-position of the compound;
in the formula (3-8),substituted in the 8-position of the compound, +.>Substituted in the 1-, 2-, 3-or 4-position of the compound,
or alternatively, the first and second heat exchangers may be,substituted in the 8-position of the compound, ar 1 Is a substituted or unsubstituted quinoxalinyl, -/->Substituted in the 5-position of the compound.
8. The compound according to claim 1, wherein the compound has any one of the following structures (4-1) to (4-10):
wherein L is 1 、L 2 、Ar 1 、Ar 2 、Ar 3 、R 1 、R 2 And X each independently has the same definition as claim 1;
in the formula (4-2),substituted in the 9-position of the compound, +.>Substituted in the 1-, 2-, 3-or 4-position of the compound,
in the formula (4-3),substituted in the 8-position of the compound, +.>Substituted in the 1-, 2-, 3-or 4-position of the compound,
in the formula (4-4),substituted in the 7-position of the compound, +.>Substitution at positions 1, 2, 3,4 of the compound;
in the formula (4-9),substituted in the 5-position of the compound, +.>Substituted in position 8, 9 or 10, ar 1 Is any one of substituted or unsubstituted quinoxalinyl,
in the formula (4-10),substituted in the 6-position of the compound, +.>Instead of being in the 10-position of the compound,
or alternatively, the first and second heat exchangers may be,substitution ofIn the 6-position of the compound,/->Substituted in position 7, 8, 9 or 10, ar 1 Is any one of substituted or unsubstituted pyrimidinyl and substituted or unsubstituted quinoxalinyl,
or alternatively, the first and second heat exchangers may be,substituted in the 6-position of the compound, +.>Substituted in the 8-or 10-position, ar, of the compounds 1 Is a substituted or unsubstituted quinazolinyl group.
9. The compound of claim 1, wherein a is 1 Substituted in the 5-position in the compound of formula (I) and A 2 Substituted at the 10-position in the compound of formula (I).
10. The compound of claim 1, wherein the compound has the following (6-1) structure:
wherein L is 1 、L 2 、Ar 2 、Ar 3 And X each independently has the same definition as claim 1;
Ar 1 is any one of substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrimidinyl and substituted or unsubstituted quinoxalinyl;
the substituent group of the substituent is selected from any one of halogen, C1-C10 alkyl, C6-C30 monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon group.
11. A compound, characterized in that the compound has any one of the following structures:
12. use of a compound according to any one of claims 1-11, characterized in that the use is as a material for a light-emitting layer in an organic electroluminescent device.
13. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode;
the organic layer comprises any one or a combination of at least two of the compounds of any one of claims 1-11.
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