CN111499650A - Charge transport material and preparation method and application thereof - Google Patents
Charge transport material and preparation method and application thereof Download PDFInfo
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Abstract
The charge transport material has a structure shown as a formula I and is a compound with a spirofluorene fused mother core structure, and the charge transport material is endowed with excellent charge transfer capacity, higher glass transition temperature and thermal stability through the synergistic effect between the mother core structure and a plurality of substituents, so that the charge transport material is highly suitable for a hole transport material or an electron blocking material of an electroluminescent device, can effectively improve the luminous efficiency and brightness of the device, prolong the service life and reduce the driving voltage.
Description
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a charge transport material, and a preparation method and application thereof.
Background
Organic electroluminescent devices (Organic L light Emission Diodes, O L ED) are active light emitting display devices that emit light by recombination of electrons and holes in an Organic layer when current is applied to the Organic layer, have advantages such as light weight, simple component construction, excellent image quality, convenient manufacturing process, wide viewing angle, high color purity, and low power consumption, and are very suitable for portable electronic devices.
In order to realize excellent performance of the organic electroluminescent device, not only the structure and the manufacturing process of the electroluminescent device need to be optimized, but also the organic layer material constituting the device needs to be continuously developed and innovated. In a high-performance electroluminescent device, materials constituting the organic layer, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like, should be stable and have excellent efficiency. However, the development of organic layer materials currently applied to organic electroluminescent devices is still insufficient. Therefore, new materials are continuously developed and applied to appropriate positions of devices.
When the organic electroluminescent device is manufactured by a vacuum deposition method, the operation or storage is in a high temperature environment, so that the emitted light is changed, the luminous efficiency is reduced, the driving voltage is increased, and the lifetime is shortened. In order to prevent these problems, it is necessary to develop a novel charge transport material having a high glass transition temperature and capable of reducing a driving voltage.
CN105384764A discloses an organic charge transport material for O L ED display and a preparation method thereof, wherein the organic charge transport material takes tetraphenyl silicon as a main body, dibenzothiophene with hole transport capability is connected to the para position of the tetraphenyl silicon, and pentoxy with electron donating capability is introduced to the dibenzothiophene in order to better adjust the HOMO energy level.
CN110437085A discloses a hole transport material based on an ether structure and a preparation method and application thereof, the hole transport material takes oxygen or sulfur-linked bis-diphenylmethane as a core, takes alkoxy or alkylthio-substituted diphenylamine as a side group, more triphenylamine structures of the hole transport material can improve hole mobility, the hole transport material contains the ether or sulfur structure, has good planar stacking effect and improves hole transport capability, the alkoxy or alkylthio group is introduced at the tail end to regulate and control the performance of the material, and the hole transport material can be used as a charge transport material to be applied to photoelectric devices such as solar cells, O L ED and organic photosensitive drums.
CN110563724A discloses a hole transport material and a synthesis method thereof, and a display panel, wherein the hole transport material is a compound formed by combining planar dyadic acridine and electron-donating groups, the compound has a macrocyclic conjugated system with a rigid planar structure, so that molecules are orderly stacked in space, the hole transport capacity is enhanced, the hole transport rate is improved, meanwhile, the electron-donating groups are easy to generate hole migration under the action of an electric field, the hole transport rate of the material is improved, and the hole transport material of the existing O L ED display panel is improved.
Although the prior art discloses charge transport materials and application thereof in O L ED devices, the types of charge transport materials are still few, and the problems of poor thermal stability, low transport efficiency, influence on device life due to crystallization in the use process and the like exist, so that the preparation process requirements and the use performance requirements of the devices cannot be met.
Therefore, it is a research focus in the art to develop a wider variety of charge transport materials having excellent stability and high-efficiency transport properties to meet the needs of O L ED having low driving voltage, high efficiency, high luminance, and long lifetime.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a charge transport material, a preparation method and application thereof, wherein the charge transport material is endowed with excellent charge transfer capability and good thermal stability by the design of a compound parent nucleus structure and the introduction of a substituent group on a specific site, and the charge transport material can be used as a hole transport material or an electron blocking material of an electroluminescent device to effectively improve the luminous performance and the service life of the device.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a charge transport material having a structure as shown in formula I:
in the formula I, Z1、Z2Each independently selected from O or S.
In the formula I, X1、X2、X3、X4Each independently selected from C or N, and X1、X2、X3、X4At least 2 of which are C, e.g. X1、X2、X3、X4With 2, 3 or 4C.
In the formula I, Y has the structure
The dotted line represents the attachment site of the group.
L1、L2、L3Each independently selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C3-C30 heteroarylene.
R1、R2、R3、R4、R5、R6Each independently selected from any one of hydrogen, deuterium, halogen (such as fluorine, chlorine, bromine or iodine), substituted or unsubstituted C1-C30 linear or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and substituted or unsubstituted C6-C30 arylamine.
In the Y, R5、R6Not linked, or linked by chemical bonds to form a ring or fused to each other.
In the present invention, the phrase "form a ring by a chemical bond" means that R is5And R6The nitrogen-containing heterocyclic ring can be connected with each other through a chemical bond to form a ring, the formed ring can be a five-membered or six-membered nitrogen-containing heterocyclic ring, and the specific connecting ring forming mode is not limited; the term "fused to each other" means R5And R6May be fused to each other to form a fused ring structure, and the present invention is not limited to a specific fusion mode. The same description (connected to form a ring or fused to each other by a chemical bond) is referred to hereinafter with the same meaning.
The C6-C30 may be C6, C7, C8, C9, C10, C12, C15, C18, C20, C22, C24, C25, C27 or C29.
The C3-C30 may be C4, C5, C6, C8, C10, C12, C15, C18, C20, C22, C24, C25, C27 or C29.
The C1-C30 may be C2, C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25, C27 or C29.
The charge transport material provided by the invention is a compound with a spirofluorene condensed parent nucleus structure, the specific parent nucleus structure enables the charge transport material to have a macrocyclic conjugated effect, the introduction of an N-containing substituent Y (such as arylamine or carbazole structure) further improves the charge transport efficiency of the material, and the synergistic effect between the parent nucleus structure and a plurality of substituents endows the charge transport material with excellent charge transfer capability, higher glass transition temperature and thermal stability, so that the charge transport material is particularly suitable for a hole transport material or an electron blocking material of an electroluminescent device, can effectively improve the luminescence property and service life of the device, and reduces the driving voltage.
In the present invention, L1、L2、L3、R1、R2、R3、R4、R5、R6The substituted substituents in (1) are each independently selected from deuterium, C1 to C20 (e.g., C2, C4, C5, C6, C8, C10, C13, C15, C17, C19, etc.) straight-chain or branched alkyl, C3 to C30 (e.g., C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25, C27, C29, etc.) cycloalkyl, C1 to C20 (e.g., C2, C4, C5, C6, or C6, etc.) alkoxy, C6 to C6 (e.g., C6, or C6, at least one kind of bromine, C6, e.g., C6, bromine, C6, or C6, etc.), bromine, at least one of bromine, C6, and the like.
Preferably, said X1、X2、X3、X4Are all C.
Preferably, said X1、X2、X3、X4Each independently selected from C or N, and only 1 is N.
Preferably, said X1、X2、X4Are all C, X3Is N.
Preferably, said L1Is selected from a single bond and C6-C12 arylene, more preferably a single bond.
The C6-C12 arylene group may be C6, C10, C12 or the like, and exemplarily includes but is not limited to phenylene, biphenylene, naphthylene or the like.
Said "L1By "selected from a single bond" is meant that the N atom in the substituent Y is connected to the parent core structure in formula I by a single bond.
Preferably, said L2、L3Each independently selected from a single bond, and substituted or unsubstituted C6-C18 arylene.
Said "L2Selected from the group consisting of single bonds "means that the N atom and R in the substituent Y5By a single bond, "L3Selected from the group consisting of single bonds "means that the N atom and R in the substituent Y6Connected by a single bond.
The arylene group of C6 to C18 may be an arylene group of C6, C8, C9, C10, C12, C16, or C18, and the like, and exemplarily includes but is not limited to: phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrylene, fluorenylene, and the like.
L2、L3Wherein the substituted substituents are each independently at least one member selected from deuterium, C1 to C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9) straight-chain or branched alkyl, C1 to C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9) alkoxy, C6 to C18 (e.g., C7, C9, C10, C12, C14, C16, or C18) aryl, C3 to C20 (e.g., C4, C6, C7, C9, C10, C12, C14, C15, C17, or C19) heteroaryl, or halogen (e.g., fluorine, chlorine, bromine, or iodine).
Preferably, said L2、L3Each independently selected from a single bond, phenylene or biphenylene.
Preferably, said R is5、R6Each independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.
The C6-C30 aryl group may be an aryl group of C6, C7, C8, C9, C10, C12, C13, C15, C18, C20, C22, C24, C25, C27, or C29, etc., and exemplarily includes but is not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, or the like.
The heteroaryl group of C3-C30 may be a heteroaryl group of C4, C5, C6, C7, C8, C9, C10, C13, C15, C18, C20, C23, C25, C27, or C29, etc., and the heteroatoms of the heteroaryl group include N, O, S, etc., and exemplarily include but are not limited to: n-phenylcarbazolyl, furyl, thienyl, pyrrolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, carbazolyl, acridinyl, imidazolyl, oxazolyl, thiazolyl, indolyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, benzimidazolyl, quinolyl, isoquinolyl and the like.
R5、R6Wherein each of said substituted substituents is independently selected from at least one of deuterium, C-C (e.g., C, or C) straight or branched alkyl, C-C (e.g., C, or C, etc.) cycloalkyl, C-C (e.g., C, or C, etc.) alkoxy, C-C (e.g., C, or C, etc.) aryl, C-C (e.g., C, or C, etc.) heteroaryl, or halogen (e.g., fluorine, chlorine, bromine, or iodine).
Preferably, said R is5、R6Each independently selected from any one of hydrogen, deuterium, phenyl, biphenyl, fluorenyl, naphthyl, anthracenyl, phenanthrenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, acridinyl, furyl, thienyl, pyrrolyl, pyridyl, imidazolyl, oxazolyl, thiazolyl, indolyl, benzofuryl, dibenzofuryl, benzothienyl, dibenzothienyl, benzimidazolyl, quinolyl or isoquinolyl, or any one of the above groups substituted with a substituent; the R is5、R6Not linked, or linked by chemical bonds to form a ring or fused to each other.
The substituents are independently selected from deuterium, C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9) straight-chain or branched alkyl, C3-C20 (such as C4, C6, C7, C9, C10, C12, C14, C15, C17 or C19) cycloalkyl, C1-C10 (such as C2, C3, C4, C5, C6, C7, C8 or C9) alkoxy, C6-C20 (such as C7, C9, C10, C12, C14, C16, C18 or C20) aryl, C3-C20 (such as C4, C6, or C6) halogen, such as bromine, or at least one.
Preferably, Y is selected from any one of the following groups:
wherein the dotted line represents the attachment site of the group.
Preferably, said R is1、R2、R3、R4Each independently selected from hydrogen, deuterium, halogen (e.g., fluorine, chlorine, bromine, or iodine), substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C6-C18 arylamine.
The C1-C10 linear chain or branched chain alkyl can be C1, C2, C3, C4, C5, C6, C7, C8, C9 or C10 linear chain or branched chain alkyl, and exemplarily comprises but is not limited to: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl or the like.
The C6-C18 aryl group can be C6, C8, C9, C10, C12, C13, C14, C16 or C18 aryl group, and the like, and exemplarily comprises but is not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, or the like.
The C6-C18 arylamine group can be C6, C12, C18 and the like arylamine groups, and exemplarily comprises but is not limited to: a diphenylamino group, a triphenylamino group, and the like.
The substituted substituents are each independently selected from at least one of deuterium, C-C (e.g., C, or C) straight or branched alkyl, C-C (e.g., C, or C, etc.) cycloalkyl, C-C (e.g., C, or C, etc.) alkoxy, C-C (e.g., C, or C, etc.) aryl, C-C (e.g., C, or C, etc.) heteroaryl, or halogen (e.g., fluorine, chlorine, bromine, or iodine).
Preferably, said R is1、R2、R3、R4Each independently selected from hydrogen, deuterium, phenyl, triphenylaminyl or diphenylaminyl.
Preferably, the charge transport material comprises any one or a combination of at least two of the following compounds 1-6:
in another aspect, the present invention provides a method for preparing the charge transport material as described above, the method comprising:
and
and carrying out coupling reaction under the action of a catalyst to obtain the charge transport material.
Z1、Z2、X1、X2、X3、X4、L1、L2、L3、R1、R2、R3、R4、R5、R6Each independently having the same limitations as described above.
U is selected from halogen.
Preferably, said U is selected from chlorine or bromine.
Preferably, the catalyst is a palladium catalyst.
In another aspect, the present invention provides an O L ED device, the O L ED device comprising at least an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode, the material of the hole transport layer comprising a charge transport material as described above.
Preferably, the O L ED device further comprises an electron blocking layer, the material of the electron blocking layer comprising a charge transport material as described above.
In another aspect, the present invention provides an electronic device comprising an O L ED device as described above.
Compared with the prior art, the invention has the following beneficial effects:
the charge transport material provided by the invention is a compound with a spirofluorene condensed mother nucleus structure, and the charge transport material is endowed with excellent charge transfer capacity, higher glass transition temperature and thermal stability through the synergistic effect between the mother nucleus structure and a plurality of substituents, so that the charge transport material is highly suitable for a hole transport material or an electron blocking material of an electroluminescent device, can effectively improve the luminous efficiency and brightness of the device, prolong the service life and reduce the driving voltage, the glass transition temperature of the charge transport material reaches more than 110 ℃, the charge transport material is used as a hole transport layer material of an O L ED device, the luminous efficiency of the device reaches 62-80 Cd/A, the driving voltage can be as low as 4.3V, the L T95 service life reaches 170A.U, and the luminous performance of the O L ED device is obviously improved.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The compound starting materials (including compounds 1a, 2b, 3b, 4a, 4b) in the following examples of the present invention are commercially available.
Example 1
The present embodiment provides a charge transport material having the following structure:
the preparation method comprises the following steps:
4g of Compound 1a, 3g of anhydrous cesium carbonate powder, 0.4g of tris-dibenzylideneacetone dipalladium (Pd)2dba3) Sequentially adding the mixture into a 200m L three-necked bottle, adding 100m L anhydrous 1,4-dioxane (1,4-dioxane), uniformly stirring, vacuumizing while supplementing nitrogen in the process, keeping the vacuum for at least 30min, keeping the mixture in a nitrogen atmosphere, heating and keeping the temperature at 100 ℃, dropwise adding diphenylamine (2 g in total), carrying out light-shielding reflux reaction for 24h, tracking a point plate until the reaction is complete, cooling and recrystallizing, and carrying out chromatographic column chromatography to obtain 2.7g of the target product compound 1, wherein the yield is 52%.
Structural test of the target product: measurement of the glass transition temperature T by Differential Scanning Calorimetry (DSC)g110 deg.C, and high performance liquid chromatography (HP L C) to obtain purity of 99.9%;
1H NMR(400MHz，DMSO)：7.84(m,1H),7.55(m,1H),7.5(m,1H),7.48(m,2H),7.4(m,1H),7.38(m,1H),7.32(m,2H),7.28(m,1H),7.26(m,1H),7.22(m,1H),7.2(m,1H),7.1(m,1H),7.01(m,4H),6.9(m,1H),6.89(m,1H),6.7(m,1H),6.62(m,2H),6.61(m,1H),6.54(m,1H),6.46(m,4H)。
example 2
The present embodiment provides a charge transport material having the following structure:
the preparation process differs from example 1 only in that the diphenylamine used in example 1 is employed in an equimolar amount of compound 2b
Instead, 3.2g in total of the objective compound 2 was obtained in 56% yield.
Structural test of the target product: glass transition temperature T by DSCgThe purity was found to be 99.9% at 113 ℃ under HP L C;
1H NMR(400MHz，DMSO)：7.84(m,1H),7.55(m,1H),7.5(m,1H),7.48(m,6H),7.4(m,1H),7.38(m,1H),7.32(m,6H),7.28(m,1H),7.23(m,4H),7.26(m,1H),7.22(m,3H),7.2(m,1H),7.1(m,1H),6.90(m,1H),6.89(m,1H),6.70(m,1H),6.61(m,1H),6.54(m,1H),6.52(m,4H)。
example 3
The present embodiment provides a charge transport material having the following structure:
the preparation process differs from example 1 only in that the diphenylamine used in example 1 is employed in equimolar amounts of compound 3b
Instead, 3.6g in total of the objective compound 3 was obtained in a yield of 57%.
Structural test of the target product: glass transition temperature T by DSCgPurity was 99.9% as determined by HP L C at 114 deg.C;
1H NMR(400MHz，DMSO)：7.84(m,2H),7.55(m,2H),7.59(m,1H),7.5(m,1H),7.48(m,2H),7.4(m,1H),7.38(m,2H),7.32(m,2H),7.28(m,2H),7.26(m,1H),7.22(m,1H),7.2(m,1H),7.1(m,1H),7.01(m,2H),6.90(m,1H),6.89(m,1H),6.75(m,1H),6.70(m,1H),6.62(m,1H),6.61(m,1H),6.58(m,1H),6.54(m,1H),6.46(m,2H),1.67(s,6H)。
example 4
The present embodiment provides a charge transport material having the following structure:
the preparation method comprises the following steps:
4g of the compound 4a, 3g of anhydrous cesium carbonate powder, 0.4g of tris-dibenzylideneacetone dipalladium (Pd)2dba3) Sequentially adding the mixture into a 200m L three-necked bottle, adding 100m L anhydrous 1,4-dioxane (1,4-dioxane), uniformly stirring, vacuumizing while supplementing nitrogen in the process, keeping the mixture in a nitrogen atmosphere, heating and keeping the mixture at 100 ℃, dropwise adding a compound 4b (2.9 g in total), carrying out reflux reaction for 24 hours in a dark place, tracking a point plate until the reaction is complete, cooling and recrystallizing, and carrying out chromatography to obtain 4.2g of a target product compound 4, wherein the yield is 63%.
Structural test of the target product: glass transition temperature T by DSCgThe purity is 99.9 percent when measured by HP L C at 120 ℃;
1H NMR(400MHz，DMSO)：8.59(m,2H),7.84(m,1H),7.55(m,1H),7.48(m,4H),7.38(m,2H),7.32(m,4H),7.28(m,1H),7.23(m,2H),7.26(m,1H),7.22(m,2H),7.01(m,2H),6.90(m,1H),6.89(m,1H),6.70(m,1H),6.62(m,1H),6.61(m,1H),6.54(m,1H),6.52(m,2H),6.46(d,2H)。
application example 1
An O L ED device comprises an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer and a cathode in sequence, wherein the materials of the layers are as follows:
anode: indium Tin Oxide (ITO) with a thickness of 80 nm;
hole injection layer: the thickness is 10 nm; the material composition comprises a host material NPB, an object material F4-TCNQ and an object material, wherein the mass percentage of the object material is 3%;
hole transport layer: a charge transport material (compound 1) provided in example 1 of the present invention, having a thickness of 100 nm;
light-emitting layer: the thickness is 20 nm; the host material is TCTA and the guest material is Ir (ppy)3The mass percentage content of the guest material is 5 percent;
the electron transmission layer is 30nm thick, the host material is BPen, the guest material is L iQ, and the mass percentage content of the guest material is 50%;
cathode: a Mg/Ag electrode with a thickness of 20 nm;
the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer and the cathode of the O L ED device are prepared by an evaporation method.
Application example 2
An O L ED device differed from application example 1 only in that compound 1 in the hole transport layer was replaced with the charge transport material (compound 2) provided in example 2 of the present invention.
Application example 3
An O L ED device differed from application example 1 only in that compound 1 in the hole transport layer was replaced with the charge transport material (compound 3) provided in example 3 of the present invention.
Application example 4
An O L ED device differed from application example 1 only in that compound 1 in the hole transport layer was replaced with the charge transport material (compound 4) provided in example 4 of the present invention.
Application example 5
An O L ED device which differs from application example 1 only in that compound 1 in the hole transport layer was used as charge transport material compound 7 provided by the present invention
And (6) replacing.
Comparative example 1
An O L ED device which differs from application example 1 only in that compound 1 in the hole transport layer was replaced by a comparative compound NPB
And (6) replacing.
Comparative example 2
An O L ED device which differs from application example 1 only in that compound 1 in the hole transport layer was replaced with comparative compound 2
And (6) replacing.
Comparative example 3
An O L ED device which differs from application example 1 only in that compound 1 in the hole transport layer was replaced with comparative compound 3
And (6) replacing.
Performance testing of O L ED devices:
the O L ED devices provided in application examples 1-5 and comparative examples 1-3 were tested for luminous efficiency by measuring data of driving voltage V and luminous efficiency L E at 1000nits brightness, and L T95 lifetime data at a current density of 40mA/cm2Calculated under the condition.
The performance test results are shown in table 1:
TABLE 1
According to the data in table 1, the charge transport material provided by the invention is suitable for being used as a hole transport layer material in an O L ED device, compared with a hole transport material NPB commonly used in the prior art, the O L ED device using the charge transport material as a hole transport layer has the advantages that the luminous efficiency reaches 62-80 Cd/A, the service life of L T95 reaches 140-170 A.U., the driving voltage is reduced to 4.3-5.0V, the luminous efficiency of the device is effectively improved, the service life of the device is prolonged, and the driving voltage is reduced.
In the charge transport material provided by the invention, a specific parent-nucleus structure and a plurality of substituents are mutually cooperated, so that the charge transport material has excellent charge transfer capability, and the change of the parent-nucleus structure (comparative example 3) or the absence of the substituents (comparative example 2) can cause the reduction of the transport efficiency of the material and influence the performance of a device.
The applicant states that the present invention is illustrated by the above examples to a charge transport material of the present invention and a method of making and using the same, but the present invention is not limited to the above examples, i.e. it is not meant that the present invention must be implemented by the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. A charge transport material having a structure according to formula I:
wherein Z is1、Z2Each is independently selected from O or S;
X1、X2、X3、X4each independently selected from C or N, and X1、X2、X3、X4At least 2 of them are C;
y has the structure of
The dotted line represents the attachment site of the group;
L1、L2、L3each independently selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
R1、R2、R3、R4、R5、R6each independently selected from any one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C30 straight chain or branched chain alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl and substituted or unsubstituted C6-C30 arylamine;
R5、R6not linked, or linked by chemical bonds to form a ring or fused to each other.
2. A charge transport material as claimed in claim 1, wherein L1、L2、L3、R1、R2、R3、R4、R5、R6The substituted substituent groups are respectively and independently selected from at least one of deuterium, C1-C20 straight-chain or branched-chain alkyl, C3-C30 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl, C3-C30 heteroaryl or halogen.
3. The charge transport material of claim 1 or 2, wherein X is1、X2、X3、X4Are all C;
preferably, said X1、X2、X3、X4Each independently selected from C or N, and only 1 is N;
preferably, said X1、X2、X4Are all C, X3Is N.
4. A charge transport material according to any of claims 1 to 3 wherein L is present1Selected from single bond or C6-C12 arylene, preferably single bond;
preferably, said L2、L3Each independently selected from a single bond, substituted or unsubstituted C6-C18 arylene;
L2、L3wherein the substituted substituent groups are respectively and independently selected from at least one of deuterium, C1-C10 straight-chain or branched-chain alkyl, C1-C10 alkoxy, C6-C18 aryl, C3-C20 heteroaryl or halogen;
preferably, said L2、L3Each independently selected from a single bond, phenylene or biphenylene;
preferably, said R is5、R6Each independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstitutedC3-C30 heteroaryl;
R5、R6the substituted substituent groups are respectively and independently selected from at least one of deuterium, C1-C10 straight-chain or branched-chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C20 aryl, C3-C20 heteroaryl or halogen;
preferably, said R is5、R6Each independently selected from any one of hydrogen, deuterium, phenyl, biphenyl, fluorenyl, naphthyl, anthracenyl, phenanthrenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, acridinyl, furyl, thienyl, pyrrolyl, pyridyl, imidazolyl, oxazolyl, thiazolyl, indolyl, benzofuryl, dibenzofuryl, benzothienyl, dibenzothienyl, benzimidazolyl, quinolyl or isoquinolyl, or any one of the above groups substituted with a substituent; the R is5、R6Are not linked, or are linked by a chemical bond to form a ring or are fused to each other;
the substituents are respectively and independently selected from at least one of deuterium, C1-C10 straight chain or branched chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C20 aryl, C3-C20 heteroaryl or halogen;
preferably, Y is selected from any one of the following groups:
wherein the dotted line represents the attachment site of the group.
5. A charge transport material according to any of claims 1 to 4 wherein R is1、R2、R3、R4Each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C10 straight or branched chain alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C6-C18 arylamine;
the substituted substituent groups are respectively and independently selected from at least one of deuterium, C1-C10 straight-chain or branched-chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C20 aryl, C3-C20 heteroaryl or halogen;
preferably, said R is1、R2、R3、R4Each independently selected from hydrogen, deuterium, phenyl, triphenylaminyl or diphenylaminyl.
6. A charge transport material according to any of claims 1 to 5, comprising any one or a combination of at least two of the following compounds 1 to 14:
7. a method for producing a charge transport material according to any one of claims 1 to 6, comprising:
and
carrying out coupling reaction under the action of a catalyst to obtain the charge transport material;
Z1、Z2、X1、X2、X3、X4、L1、L2、L3、R1、R2、R3、R4、R5、R6each independently having the same limitations as in claim 1;
u is selected from halogen;
preferably, said U is selected from chlorine or bromine;
preferably, the catalyst is a palladium catalyst.
8. An O L ED device, characterized in that the O L ED device comprises at least an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode, the material of the hole transport layer comprises the charge transport material according to any one of claims 1 to 6.
9. The O L ED device according to claim 8, wherein the O L ED device further comprises an electron blocking layer, the material of the electron blocking layer comprising the charge transport material according to any one of claims 1 to 6.
10. An electronic device, characterized in that the electronic device comprises an O L ED device according to claim 8 or 9.
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| CN110818670A (en) * | 2018-08-07 | 2020-02-21 | 乐金显示有限公司 | Compound and organic light-emitting device |
| CN113402526A (en) * | 2021-07-26 | 2021-09-17 | 上海天马有机发光显示技术有限公司 | Organic compound, electroluminescent material and application thereof |
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| CN110818670A (en) * | 2018-08-07 | 2020-02-21 | 乐金显示有限公司 | Compound and organic light-emitting device |
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| CN110818670A (en) * | 2018-08-07 | 2020-02-21 | 乐金显示有限公司 | Compound and organic light-emitting device |
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