CN114507222A - Amine compound and application thereof in organic electroluminescent device - Google Patents

Amine compound and application thereof in organic electroluminescent device Download PDF

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CN114507222A
CN114507222A CN202210202047.0A CN202210202047A CN114507222A CN 114507222 A CN114507222 A CN 114507222A CN 202210202047 A CN202210202047 A CN 202210202047A CN 114507222 A CN114507222 A CN 114507222A
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王湘成
何睦
王鹏
何为
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Shanghai Yaoyi Electronic Technology Co ltd
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Abstract

The invention relates to the field of organic electroluminescent materials, in particular to an amine compound and application thereof in an organic electroluminescent device. The chemical structure of the amine compound is
Figure DDA0003529735370000011
The amine compound has extremely high stability, mobility, glass transition temperature and crystallization resistance, and obtains good device effect in OLED devices.

Description

Amine compound and application thereof in organic electroluminescent device
Technical Field
The invention relates to the field of organic electroluminescent materials, in particular to an amine compound and application thereof in an organic electroluminescent device.
Background
The OLED hole transport material requires high hole transport capacity, high glass transition temperature, strong crystallization resistance and stable molecular structure. Especially when the hole transport material is in contact with the light emitting layer, the requirements on molecular stability and glass transition temperature are higher. The hole transport material generally adopts aromatic amine compounds, can give out electrons well, and has high hole mobility. Spirofluorene compounds such as spiro [ fluorene-9, 9 '-xanthene ], spiro [ fluorene-9, 9' -thiaanthracene ] and the like have better hole transport and proper conjugation left effect, so that the spirofluorene compounds have better thermal stability and are used as hole transport materials, but when the spirofluorene compounds are used as hole transport materials, the molecular stability, the mobility and the crystallization temperature are still found to be not excellent enough.
Disclosure of Invention
In view of the above-mentioned drawbacks of the prior art, it is an object of the present invention to provide an amine compound and its use in an organic electroluminescent device, which solve the problems of the prior art.
To achieve the above and other related objects, the present invention provides, in one aspect, an amine compound having a chemical structure represented by formula (1):
Figure BDA0003529735350000011
wherein:
R1selected from substituted or unsubstituted straight chain or branched chain C1-C15 alkyl, substituted or unsubstituted C1-C15 cycloalkyl, substituted or unsubstituted C1-C15 heteroalkyl, substituted or unsubstituted C1-C15 heterocycloalkyl, substituted or unsubstituted C5-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, or substituted or unsubstituted C7-C40 aromatic and alkyl ring group;
R2、R3each independently selected from substituted or unsubstituted aryl of C5-C60, substituted or unsubstituted heteroaryl of C4-C60, or substituted or unsubstituted C7 ℃C60 aromatic and alkyl cyclic group;
R4～R15hydrogen, deuterium, substituted or unsubstituted straight-chain or branched-chain alkyl of C1-C15, substituted or unsubstituted C1-C15 cycloalkyl, substituted or unsubstituted C1-C15 heteroalkyl, substituted or unsubstituted C1-C15 heterocycloalkyl, substituted or unsubstituted C5-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, substituted or unsubstituted C7-C40 aromatic and alkyl ring radical; or R4～R15Any two adjacent groups combine to form a substituted or unsubstituted ring;
L1、L2each independently a direct bond, or a substituted or unsubstituted arylene group of C6 to C21;
X1selected from O, or S.
In another aspect, the present invention provides a hole transport layer material, which includes the amine compound of the present invention.
According to another aspect of the present invention, there is provided a use of the amine compound according to the present invention and/or the hole transport layer material according to the present invention in an organic electroluminescent device.
In another aspect, the present invention provides an organic electroluminescent device comprising the amine compound and/or the hole transport layer material as described above.
Another aspect of the present invention provides a display panel including the organic electroluminescent device according to the present invention.
Another aspect of the present invention provides a display device, including the display panel according to the present invention.
Compared with the prior art, the invention has the beneficial effects that:
r in the amine compound with the structural general formula (1) of the invention1The position of the corresponding C on the benzene ring is very important for the structural stability, anti-crystallization property, mobility and energy level adjustment of the hole transport material, and the main reason is that the substituent R is added into the position of the C1Especially, the addition of a group with certain electron donating property can well increase the mobility, increase the stability of a C-N bond and prolong the service life of the device. At the same time, because of the increaseAdded with steric hindrance, can draw energy level and improve glass transition temperature.
Drawings
Fig. 1 is a schematic view of one structure of an organic electroluminescent device (top emission device) in the example.
Fig. 2 is another schematic structural view of the organic electroluminescent device in the example (bottom emission device).
In the figure:
101 substrate
102 first electrode
103 hole injection layer
104 first hole transport layer
105 second hole transport layer
106 light emitting layer
107 hole blocking layer
108 electron transport layer
109 second electrode
110 coating
Detailed Description
Hereinafter, embodiments of the specifically disclosed amine-based compound and its application to an organic electroluminescent device will be described in detail. Other advantages and effects of the present invention will be readily apparent to those skilled in the art from the disclosure herein. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
Before the present embodiments are further described, it is to be understood that the scope of the invention is not limited to the particular embodiments described below; it is also to be understood that the terminology used in the examples is for the purpose of describing particular embodiments, and is not intended to limit the scope of the present invention; in the description and claims of the present application, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any value therebetween can be selected unless the invention otherwise indicated. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In addition to the specific methods, devices, and materials used in the examples, any methods, devices, and materials similar or equivalent to those described in the examples may be used in the practice of the invention in addition to the specific methods, devices, and materials used in the examples, in keeping with the knowledge of one skilled in the art and with the description of the invention.
The inventor of the invention provides a spirofluorenamine-based compound which is substituted at ortho-position or meta-position of spirofluorenamine through a great deal of research and study. The amine compound is found to have extremely high stability, mobility, glass transition temperature and crystallization resistance, and a good device effect is obtained in an OLED device. The present invention has been completed based on this finding.
Examples of the substituent in the present invention are described below, but the substituent is not limited thereto:
[ substituted or unsubstituted ] means substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boryl group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a heteroaryl group, or unsubstituted; or substituted with a substituent linking two or more of the substituents exemplified above, or unsubstituted. For example, "a substituent linking two or more substituents" may include a biphenyl group, i.e., the biphenyl group may be an aryl group, or a substituent linking two phenyl groups.
[ alkyl ] may be linear or branched, and the number of carbon atoms is not particularly limited. In some embodiments, alkyl includes, but is not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, n-butyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propyl, 2-pentyl, 2-dimethylheptyl, 1, 2-propyl, 2-pentyl, and mixtures thereof, Isohexyl, 4-methylhexyl, 5-methylhexyl.
The above description of alkyl groups also applies to alkyl groups in aralkyl, aralkylamino, alkylaryl, and alkylamino groups.
[ cycloalkyl ] may be cyclic, and the number of carbon atoms is not particularly limited. In some embodiments, cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.
[ heteroalkyl ] may be a linear or branched alkyl group containing a heteroatom, and the number of carbon atoms is not particularly limited. In some embodiments, heteroalkyl groups include, but are not limited to, alkoxy, alkylthio, alkylsulfonyl, and the like. The alkoxy group may include, for example, but not limited to, methoxy, ethoxy, n-propoxy, isopropoxy (isopropoxyxy), isopropoxy (i-propyloxy), n-butoxy, isobutoxy, t-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like. Alkylthio groups may include, for example, but are not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio, isopentylthio, n-hexylthio, 3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio, and the like.
[ heterocycloalkyl ] may be a cycloalkyl group containing a heteroatom, and the number of carbon atoms is not particularly limited. In some embodiments, heterocycloalkyl includes, but is not limited to
Figure BDA0003529735350000041
And the like.
[ aryl ] is not particularly limited, and the aryl group may be a monocyclic aryl group or a polycyclic aryl group. In some embodiments, monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, and the like. Polycyclic aryl groups include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, and the like. The fluorenyl group can be substituted, such as 9,9 '-dimethylfluorenyl, 9' -dibenzofluorenyl, and the like. Further, two of the substituents may be combined with each other to form a spiro ring structure, for example, 9' -spirobifluorenyl group and the like.
The above description of aryl groups applies to arylene groups, except that arylene groups are divalent.
The above description of aryl groups applies to aryl groups in aryloxy, arylthio, arylsulfonyl, arylphosphino, aralkyl, aralkylamino, aralkenyl, alkylaryl, arylamino, and arylheteroarylamino groups.
[ heteroaryl ] contains one or more of N, O, P, S, Si and Se as heteroatoms. Heteroaryl groups include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, oxazinyl, thiazinyl, dioxanyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, triazaindenyl, indolyl, indolinyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, and benzocarbazolyl, Dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, phenazinyl, imidazopyridinyl, phenazinyl, phenanthridinyl, phenanthrolinyl, phenothiazinyl, imidazopyridinyl, imidazophenanthridinyl, benzimidazoloquinazolinyl, benzimidazolophhenanthridinyl, spiro [ fluorene-9, 9' -xanthene ], benzidinaphthyl, dinaphthofuranyl, naphthobenzofuranyl, dinaphthothiophenyl, naphthobenzothienyl, triphenylphosphine oxide, triphenylborane, and the like.
The above description of heteroaryl groups applies to heteroaryl groups in heteroarylamino and arylheteroarylamino groups.
The above description of heteroaryl groups can be used for heteroarylenes, except that the heteroarylene group is divalent.
[ AROMATIC ALKYCYCLIC ] AROMATIC ALKYL GROUP is formed by the cyclization of an aryl group with an alkyl or heteroalkyl group. In some embodiments, aromatic and alkyl cyclic groups include, but are not limited to:
Figure BDA0003529735350000051
[ vicinal group ] may mean a substituent which replaces an atom directly bonded to an atom substituted with a corresponding substituent, a substituent which is located sterically closest to a corresponding substituent, or another substituent which replaces an atom substituted with a corresponding substituent. For example, R4And R5Is an "adjacent group".
Any two adjacent groups may be combined to form a substituted or unsubstituted ring, and may refer to, for example, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic heterocyclic ring.
An aliphatic hydrocarbon ring means a ring formed only of carbon and hydrogen atoms as a non-aromatic ring. The aliphatic hydrocarbon ring includes, but is not limited to, cycloalkylene, and specific examples may include cyclopropylene, cyclobutylene, cyclobutenyl, cyclopentylene, cyclopentenylene, cyclohexylene, cyclohexenylene, 1, 4-cyclohexadienylene, cycloheptenylene, cyclooctenylene, and the like.
The aromatic hydrocarbon ring is an aromatic ring formed only of carbon and hydrogen atoms. Specific examples of the aromatic hydrocarbon ring may include phenyl, naphthyl, anthryl, phenanthryl, perylenyl, anthryl, triphenylenyl, phenalkenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl, indenyl, acenaphthenyl, benzofluorenyl, spirofluorenyl, and the like, but are not limited thereto.
By aliphatic heterocycle is meant an aliphatic ring containing one or more heteroatoms. Specific examples of the aliphatic heterocyclic ring may include, but are not limited to, oxiranyl, tetrahydrofuryl, 1, 4-dioxaylethyl, pyrrolidinyl, piperidinyl, morpholinyl, oxetanyl, azocyclohexane (azoxane) group, and the like.
The aliphatic hydrocarbon ring may be monocyclic or polycyclic.
The invention provides an amine compound, wherein the chemical structure of the amine compound is shown as the formula (1):
Figure BDA0003529735350000061
wherein:
R1selected from substituted or unsubstituted straight chain or branched chain C1-C15 alkyl, substituted or unsubstituted C1-C15 cycloalkyl, substituted or unsubstituted C1-C15 heteroalkyl, substituted or unsubstituted C1-C15 heterocycloalkyl, substituted or unsubstituted C5-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, or substituted or unsubstituted C7-C40 aromatic and alkyl ring group;
R2、R3each independently selected from substituted or unsubstituted aryl of C5-C60, substituted or unsubstituted heteroaryl of C4-C60, or substituted or unsubstituted aromatic and alkyl cyclic group of C7-C60;
R4～R15independently of each other, hydrogen, deuterium, substituted or unsubstituted straight-chain or branched-chain alkyl of C1-C15, substituted or unsubstituted C1-C15 cycloalkyl, substituted or unsubstituted C1-C15 heteroalkyl, substituted or unsubstituted C1-C15, substituted or unsubstituted C5-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, substituted or unsubstituted C7-C40 aromatic and alkyl ring radical; or R4～R15Any two adjacent groups combine to form a substituted or unsubstituted ring;
L1、L2each independently a direct bond, or a substituted or unsubstituted arylene group of C6 to C21. The direct bond may be a single bond, for example.
X1Selected from O, or S.
In some embodiments, the amine compound has a chemical structure according to formula (2) or formula (3):
Figure BDA0003529735350000071
wherein R is1～R15、L1、L2、X1The definition is the same as in formula (1).
In the amine compound provided by the invention, R is1Selected from substituted or unsubstituted straight chain or branched chain C1-C10 alkyl, substituted or unsubstituted C1-C10 cycloalkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C1-C10 heterocycloalkyl, C6-C30 aryl, C6-C30 heteroaryl, alkyl substituted C7-C30 aryl; alkyl-substituted heteroaryl of C7 to C30; substituted or unsubstituted C7-C30 aromatic and alkyl ring radical.
In some embodiments, the R is1Selected from hydrogen, deuterium, methyl, isopropyl, tert-butyl,
Figure BDA0003529735350000072
Figure BDA0003529735350000073
Figure BDA0003529735350000081
Figure BDA0003529735350000082
or selected from aromatic and alkyl cyclic groups;
wherein, X2、X3Each is independently selected from O or S;
R16、R17each independently selected from hydrogen, deuterium, methyl, isopropyl, or tert-butyl.
It is further noted that
Figure BDA0003529735350000083
Figure BDA0003529735350000084
Indicating an arbitrary positional connection.
Further, the aromatic and alkyl ring group is formed by the cyclization of an aryl group and an alkyl or heteroalkyl group; preferably, the aryl group is selected from
Figure BDA0003529735350000085
(means that any of the two positions other than a, b, c, and d are connected together),
Figure BDA0003529735350000086
Figure BDA0003529735350000087
The alkyl group is selected from
Figure BDA0003529735350000088
Figure BDA0003529735350000089
The heteroalkyl group being selected from
Figure BDA0003529735350000091
Wherein, a, b, c, d in the aryl are respectively carbon, e and f are binding sites, and a, b or c, d are combined with e and f in the alkyl or heteroalkyl to form a ring. X4～X6Each is independentIndependently selected from O, S, atom or NR group; wherein R is selected from substituted or unsubstituted aryl of C6-C30 or substituted or unsubstituted heteroaryl of C6-C30.
More specifically, in some embodiments, a, b, c, d of the aryl group are combined with e, f of the alkyl or heteroalkyl group to form the following group:
Figure BDA0003529735350000092
wherein, X4～X6Each independently selected from O, S, or an NR group; wherein R is selected from substituted or unsubstituted aryl of C6-C30 or substituted or unsubstituted heteroaryl of C6-C30.
In the amine compound provided by the invention, R2、R3Each independently selected from aryl of C6-C30, heteroaryl of C6-C30 and aryl of C7-C60 substituted by alkyl; alkyl-substituted heteroaryl of C7 to C60; or substituted or unsubstituted C7-C30 aromatic and alkyl cyclic group.
In some embodiments, R2、R3Each independently selected from the group consisting of:
Figure BDA0003529735350000093
Figure BDA0003529735350000101
wherein, X7Each is independently selected from O or S; r is18、R19Each independently selected from hydrogen, deuterium, methyl, isopropyl, or tert-butyl.
In the amine compound provided by the invention, R4～R15Independently hydrogen, deuterium, substituted or unsubstituted straight chain or branched chain C1-C10 alkyl, substituted or unsubstituted C1-C10 cycloalkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C1-C10 heterocycloalkyl, and C6-C30 arylThe aryl group comprises C6-C30 heteroaryl, alkyl substituted aryl of C7-C30, alkyl substituted heteroaryl of C7-C30, and substituted or unsubstituted aromatic and alkyl ring group of C7-C30.
In some embodiments, R4～R15Each independently selected from hydrogen, deuterium, methyl, isopropyl, tert-butyl, alkoxy, phenyl, cyclohexyl, cyclopentyl, or, R4～R15Any two adjacent groups combine to form a benzene ring.
In the amine compound provided by the invention, L1、L2Each independently selected from a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene; preferably, the substituents are selected from methyl, isopropyl, tert-butyl, and the like.
In the amine compound provided by the present invention, the compound structure of formula (1) may be selected from any one of the following amine compounds, and the following amine compounds may be further substituted.
Figure BDA0003529735350000102
Figure BDA0003529735350000111
Figure BDA0003529735350000121
Figure BDA0003529735350000131
Figure BDA0003529735350000141
Specifically, the above structure may be unsubstituted or substituted with one or more substituents selected from the group consisting of the following. For example, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amine group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylheteroarylamino group, an arylphosphino group, a heteroaryl group and the like may be mentioned.
In another aspect, the present invention provides a hole transport layer material comprising the amine compound according to the first aspect of the present invention.
According to another aspect of the present invention, there is provided a use of the amine compound according to the first aspect and/or the hole transport layer material according to the second aspect of the present invention in an organic electroluminescent device.
In the organic electroluminescent device provided by the invention, the hole transport material layer material in the organic electroluminescent device, which is in direct contact with various luminescent layers such as red light, green light, blue light and the like, can be used in a top luminescent device, a bottom luminescent device or a series device.
The organic electroluminescent device provided by the invention comprises a first electrode, a second electrode and one or more organic material layers arranged between the first electrode and the second electrode, and is in a bottom or top light-emitting device structure (as shown in fig. 1 or 2), wherein the organic material layers can be in a single-layer structure, or in a multi-layer series structure formed by laminating two or more organic material layers, such as a structure comprising a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer and the like as the organic material layers, and can be prepared by using common methods and materials for preparing organic electroluminescent devices. The organic electroluminescent device adopts the amine compound 1 as a hole transport material layer material which is directly contacted with a luminescent layer in the red organic electroluminescent device.
In the organic electroluminescent device provided by the invention, the first electrode is used as an anode, and the anode material can be a material with a large work function, so that holes can be smoothly injected into the organic material layer. More examples are metals, metal oxides, combinations of metals and oxides, conductive polymers, and the like. The metal oxide may be, for example, Indium Tin Oxide (ITO), zinc oxide, Indium Zinc Oxide (IZO), or the like.
In the organic electroluminescent device provided by the invention, the second electrode is used as a cathode, and the cathode material can be a material with a small work function, so that electrons can be smoothly injected into the organic material layer. The cathode material may be, for example, a metal or a multilayer structure material. The metal may be, for example, magnesium, silver, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, tin, and lead, or alloys thereof. The cathode material is preferably selected from magnesium and silver.
In the organic electroluminescent device provided by the present invention, a material of the hole injection layer, preferably a material having a Highest Occupied Molecular Orbital (HOMO) between the work function of the anode material and the HOMO of the surrounding organic material layer, is used as a material that advantageously receives holes from the anode at a low voltage. The material of the hole injection layer 103 may be, for example
Figure BDA0003529735350000151
And combinations of one or more of the inventive chemicals of formula (1). In some embodiments, for example, compound a47 of the present invention may be
Figure BDA0003529735350000152
And the like. Or can be
Figure BDA0003529735350000153
The mixed material of (1).
In the organic electroluminescent device provided by the invention, the material of the hole transport layer is a material having high mobility to holes and is suitable for receiving the holes from the anode or the hole injection layer and transporting the holes to the light emitting layer. Materials for the hole transport layer include, but are not limited to, organic materials of arylamines, conductive polymers, block copolymers having both conjugated and non-conjugated moieties, and the like. In some embodiments, the material of the first hole transport layer may be, for example, an amine compound of formula (1) of the present invention or the like. In some embodiments, compound A47 of the present invention is evaporated
Figure BDA0003529735350000154
Obtaining a first hole transport layer 104, evaporating
Figure BDA0003529735350000161
The second layer hole transport layer 105 can be obtained. In another embodiment, the compound may also be evaporated
Figure BDA0003529735350000162
The first hole transporting layer 104 was obtained, and then the compound (1) of the present invention was evaporated to obtain the second hole transporting layer 105.
In the organic electroluminescent device provided by the present invention, the material of the light emitting layer may be generally selected from materials having good quantum efficiency for fluorescence or phosphorescence as materials capable of emitting light in the visible light region by receiving holes and electrons from the hole transport layer and from the electron transport layer, respectively, and combining the holes and the electrons. In some embodiments, the material of the light emitting layer 106 may be selected from, for example, the group consisting of
Figure BDA0003529735350000163
One or more of the above.
In the organic electroluminescent device provided by the present invention, in some embodiments, the hole blocking layer 107 may be selected from, for example, a group consisting of
Figure BDA0003529735350000164
In the organic electroluminescent device provided by the present invention, the material of the electron transport layer 108 is a material having high mobility to electrons and suitable as a material that advantageously receives electrons from the cathode and transports the electrons to the light emitting layer. In some embodiments, the material of the electron transport layer may be selected from, for example, the group consisting of
Figure BDA0003529735350000165
One or more of the above.
In the organic electroluminescent device provided by the invention, the material of the covering layer 110Generally has a high refractive index, and thus may contribute to an increase in light efficiency of the organic light emitting device, particularly external light emission efficiency. The cover layer 110 may be, for example
Figure BDA0003529735350000171
In another aspect, the invention provides a display panel comprising the organic electroluminescent device of the invention.
In another aspect, the invention provides a display device comprising the display panel of the invention.
The embodiments of the present invention are illustrated below by specific examples.
Synthesis examples:
the synthesis formula of the intermediate is as follows:
Figure BDA0003529735350000172
synthesis examples:
example 1: synthesis of Compound A1
Figure BDA0003529735350000181
The synthesis method of M1-3 comprises the following steps:
in a 2L reaction flask, M1-1(100g, 555mmol), M1-2(148g, 555mmol), tetrakistriphenylphosphine palladium (12.8g,11.1mmol) and potassium carbonate (153g,1110mmol) were weighed into a reaction flask, 700mL of toluene, 150mL of ethanol and 150mL of deionized water were added, the system was replaced with nitrogen 3 times, the reaction mixture was heated to reflux, and the reaction was stirred for 3 hours. Cooling the reaction mixed solution to 50 ℃, standing for layering, and washing an upper organic phase with 150mL of deionized water; the organic phase was passed through a column (toluene: petroleum ether: 1: 10). The solvent was concentrated, the remaining was passed through a silica gel column (toluene: petroleum ether ═ 1:10), and the solvent was concentrated to obtain 150g of a solid compound. The yield thereof was found to be 83%.
Synthesis of M1-4
A clean 1L reaction flask was charged with M1-3(100g, 309mmol) and trifluoromethanesulfonic acid (294g, 1960mmol) in this order, and the reaction mixture was heated to 160 ℃ and stirred for 3 hours. After the reaction is finished, cooling to room temperature, slowly adding 300mL of ethanol, stirring and crystallizing; after stirring for 4 hours, a yellow-green solid was obtained by filtration. Placing the solid in a 250mL flask, adding 100mL ethanol, pulping at room temperature, stirring for two hours, and filtering to obtain a light green solid. The solid was passed through a column (toluene: petroleum ether ═ 1:20), and the solvent was concentrated to give 55g of M1-4 as a solid, yield: 59%.
Synthesis of M1-6
A clean 500mL three-necked flask was charged with M1-5(25g, 100mmol), followed by addition of THF (200mL), and the system was purged with nitrogen 3 times and cooled to 0 ℃. n-BuLi (40mL,100mmol) was added dropwise to the reaction mixture, and after 20min addition, the reaction was stirred at 0 ℃ for 30 min. Under the protection of nitrogen, M1-4(29g, 100mmol) was added to the reaction solution in portions, and the reaction solution was warmed to room temperature of 25 ℃ for reaction for 1 hour. The reaction mixture was cooled to 0 ℃,100 mL of a saturated ammonium chloride solution was added, the mixture was separated, the aqueous phase was extracted once with EA, the organic phase was concentrated, and the mixture was passed through a silica gel column (mobile phase PE: EA ═ 20:1) to obtain 29g of a yellow solid with a yield of 62.9%.
Synthesis of M1:
a clean 500mL three-necked flask was charged with M1-6(25.0g,54mmol), and DCM (50mL) was added and the temperature was reduced to 0 ℃. Boron trifluoride diethyl etherate (17g, about 15mL) is added into the reaction solution drop by drop, and after the addition of the boron trifluoride diethyl etherate, the temperature of the reaction solution is raised to 25 ℃ and the reaction is carried out for 1h, and a large amount of solid is separated out. 200mL of petroleum ether was added to the reaction mixture, the mixture was stirred for 1 hour, and the mixture was filtered under suction to give an off-white solid, which was then passed through a silica gel column (mobile phase PE: EA: 10:1) to give 18g of a white solid with a yield of 75%.
Synthesis of compound a 1:
in a three-necked flask, M1(15g,33.8mmol), A1-1(7.6g, 33.8mmol), tris (dibenzylideneacetone) dipalladium (Pd2(dba)3, 0.3g, 3.38mmol, 1% eq), tri-tert-butylphosphine (t-Bu3P, 1mL,1.0mmol), sodium tert-butoxide (NaOBu-t, 6.4g, 67.7mmol), toluene (100mL) were added, the system was replaced with nitrogen, the reaction solution was heated to reflux, and the reaction was stirred for 180 min. The reaction solution was cooled to 70 ℃ and the hot silica gel column was superheated. The mother liquor was concentrated to 70mL, 30mL of ethanol was added, stirred at room temperature for 1h, and filtered. 120mL of toluene is added to the solid, the mixture is refluxed and dissolved, 100mL of petroleum ether is added, the mixture is stirred for 2 hours at room temperature, and the mixture is filtered. Toluene: the petroleum ether 2:1 chromatographic column separation is carried out, and the solution is dried by spinning to obtain 15g of white solid with the yield of 70 percent. LCMS (ESI ion source) M/Z: 631.4.
example 2: synthesis of compound a 21:
Figure BDA0003529735350000191
the synthesis method, auxiliary material types, raw and auxiliary material equivalent ratio and operation method of the compound A21 are completely consistent with those of A1, and the differences are that a reaction raw material M2-1 replaces M1-1, M2-2 replaces an M1-2 raw material, M2-3 replaces an M1-3 raw material, M2-4 replaces an M1-4 raw material, M2-5 replaces M1-5, M2-6 replaces an M1-6 raw material, and A21-1 replaces an A1-1 raw material. The total yield was 19.7%. The detailed description is as follows:
the synthesis method of M2-3 comprises the following steps:
in a 2L reaction flask, M2-1(100g, 555mmol), M2-2(175g, 555mmol), tetrakistriphenylphosphine palladium (12.8g,11.1mmol) and potassium carbonate (153g,1110mmol) were weighed into a reaction flask, toluene 700mL, ethanol 150mL and deionized water 150mL were added, the system was replaced with nitrogen 3 times, the reaction mixture was heated to reflux and the reaction was stirred for 3 hours. Cooling the reaction mixed solution to 50 ℃, standing for layering, and washing an upper organic phase with 150mL of deionized water; the organic phase was passed through a column (toluene: petroleum ether: 1: 10). The solvent was concentrated, and the remaining silica gel column (toluene: petroleum ether: 1:10) was passed through the solvent to concentrate the solvent, whereby 163g of a solid compound was obtained. The yield thereof was found to be 79%.
Synthesis of M2-4:
m2-3(100g, 268mmol) and trifluoromethanesulfonic acid (250g, 1667mmol) were added sequentially to a clean 1L reaction flask, and the reaction was heated to 160 ℃ and stirred for 3 hours. After the reaction is finished, cooling to room temperature, slowly adding 300mL of ethanol, stirring and crystallizing; after stirring for 4 hours, a yellow-green solid was obtained by filtration. Placing the solid in a 250mL flask, adding 100mL ethanol, pulping at room temperature, stirring for two hours, and filtering to obtain the solid. The solvent was concentrated by column chromatography (toluene: petroleum ether ═ 1:20) to give 62g of M2-4 as a solid, yield: 68%.
Synthesis of M2-6:
a clean 500mL three-necked flask was charged with M2-5(25g, 83mmol), followed by addition of THF (200mL), and the system was purged with nitrogen 3 times and cooled to 0 ℃. n-BuLi (33mL,83mmol) was added dropwise to the reaction mixture, and after 20min addition the reaction was stirred at 0 ℃ for 30 min. Under the protection of nitrogen, M2-4(28g, 83mmol) was added to the reaction solution in portions, and the reaction solution was warmed to room temperature of 25 ℃ for reaction for 1 hour. The reaction mixture was cooled to 0 ℃,100 mL of a saturated ammonium chloride solution was added, the mixture was separated, the aqueous phase was extracted once with EA, the organic phase was concentrated, and the mixture was passed through a silica gel column (mobile phase PE: EA ═ 20:1) to obtain 32g of a white solid with a yield of 70%.
Synthesis of M2:
a clean 500mL three-necked flask was charged with M2-6(25.0g,44mmol), and DCM (50mL) was added and the temperature was reduced to 0 ℃. Boron trifluoride diethyl etherate (17g, about 15mL) is added into the reaction solution drop by drop, and after the addition of the boron trifluoride diethyl etherate, the temperature of the reaction solution is raised to 25 ℃ and the reaction is carried out for 1h, and a large amount of solid is separated out. 200mL of petroleum ether was added to the reaction mixture, the mixture was stirred for 1 hour, and the mixture was filtered under suction to give an off-white solid, which was then passed through a silica gel column (mobile phase PE: EA: 10:1) to give 17g of a white solid with a yield of 72%.
Synthesis of compound a 21:
in a three-necked flask, M2(15g,27.6mmol), A21-1(15g, 27.6mmol), and tris (dibenzylideneacetone) dipalladium (Pd) were added2(dba)30.25g, 2.76mmol, 1% eq), tri-tert-butylphosphine (t-Bu)3P, 1mL,1.0mmol), sodium tert-butoxide (NaOBu-t, 5.2g, 55.2mmol), toluene (100mL) was added, the system was replaced with nitrogen, the reaction mixture was heated to reflux, and the reaction was stirred for 180 min. The reaction solution was cooled to 70 ℃ and the hot silica gel column was superheated. The mother liquor was concentrated to 70mL, 30mL of ethanol was added, stirred at room temperature for 1h, and filtered. 120mL of toluene was added to the solid, the mixture was refluxed and dissolved, 100mL of petroleum ether was added, and the mixture was stirred at room temperature for 2 hours and filtered. Toluene: petroleum ether 2:1 chromatographic column separation, solution spin drying to obtain white solid 17g, yield 73%. LCMS (ESI ion source) M/Z: 841.5.
example 3: synthesis of compound a 22:
Figure BDA0003529735350000201
the synthesis method, auxiliary material types, raw and auxiliary material equivalent ratio and operation method of the compound A22 are completely consistent with those of A1, and the differences are that a reaction raw material M3-1 replaces M1-1, M3-2 replaces an M1-2 raw material, M3-3 replaces an M1-3 raw material, M3-4 replaces an M1-4 raw material, M3-5 replaces M1-5, M3-6 replaces an M1-6 raw material, and A22-1 replaces an A1-1 raw material. The total yield was 21.1%. LCMS (ESI ion source) measured M/Z of Compound A22: 651.5.
example 4: synthesis of compound a 32:
Figure BDA0003529735350000211
the synthesis method, auxiliary material types, raw and auxiliary material equivalent ratio and operation method of the compound A32 are completely consistent with those of A1, and the differences are that a reaction raw material M4-1 replaces M1-1, M4-2 replaces an M1-2 raw material, M4-3 replaces an M1-3 raw material, M4-4 replaces an M1-4 raw material, M4-5 replaces M1-5, M4-6 replaces an M1-6 raw material, and A32-1 replaces an A1-1 raw material. The total yield was 21.5%. LCMS (ESI ion source) measured M/Z of Compound A32: 813.8.
example 5: synthesis of compound a 43:
Figure BDA0003529735350000212
the synthesis method, auxiliary material types, raw and auxiliary material equivalent ratio and operation method of the compound A43 are completely consistent with those of A1, and the differences are that a reaction raw material M5-1 replaces M1-1, M5-2 replaces an M1-2 raw material, M5-3 replaces an M1-3 raw material, M5-4 replaces an M1-4 raw material, M5-5 replaces M1-5, M5-6 replaces an M1-2 raw material, and A43-1 replaces an A1-1 raw material. The total yield is 20.1%. LCMS (ESI ion source) measured M/Z of Compound A43: 639.5.
example 6: synthesis of compound a 47:
Figure BDA0003529735350000213
the synthesis method, auxiliary material types, raw and auxiliary material equivalent ratio and operation method of the compound A47 are completely consistent with those of A1, and the differences are that a reaction raw material M6-1 replaces M1-1, M6-2 replaces an M1-2 raw material, M6-3 replaces an M1-3 raw material, M6-4 replaces an M1-4 raw material, M6-5 replaces M1-5, M6-6 replaces an M1-6 raw material, and A47-1 replaces an A1-1 raw material. The total yield is 20.8%. LCMS (ESI ion source) measured M/Z of Compound A47: 743.1.
example 7: synthesis of compound a 59:
Figure BDA0003529735350000214
the synthesis method, auxiliary material types, raw and auxiliary material equivalent ratio and operation method of the compound A59 are completely consistent with A1, and the differences are that a reaction raw material M7-1 replaces M1-1, M7-2 replaces M1-2 raw material, M7-3 replaces M1-3 raw material, M7-4 replaces M1-4 raw material, M7-5 replaces M1-5, M7-6 replaces M1-6 raw material, and A59-1 replaces A1-1 raw material. The total yield was 19.5%. LCMS (ESI ion source) measured M/Z of Compound A59: 839.7.
example 8: synthesis of compound a 78:
Figure BDA0003529735350000221
the synthesis method, auxiliary material types, raw and auxiliary material equivalent ratio and operation method of the compound A78 are completely consistent with those of A1, and the differences are that a reaction raw material M8-1 replaces M1-1, M8-2 replaces an M1-2 raw material, M8-3 replaces an M1-3 raw material, M8-4 replaces an M1-4 raw material, M8-5 replaces M1-5, M8-6 replaces an M1-6 raw material, and A78-1 replaces an A1-1 raw material. The total yield was 19.5%. LCMS (ESI ion source) measured M/Z of Compound A78: 941.8.
example 9: synthesis of compound a 81:
Figure BDA0003529735350000222
the synthesis method, auxiliary material types, raw and auxiliary material equivalent ratio and operation method of the compound A81 are completely consistent with those of A1, and the differences are that a reaction raw material M9-1 replaces M1-1, M9-2 replaces an M1-2 raw material, M9-3 replaces an M1-3 raw material, M9-4 replaces an M1-4 raw material, M9-5 replaces M1-5, M9-6 replaces an M1-6 raw material, and A81-1 replaces an A1-1 raw material. The total yield is 18.5%. LCMS (ESI ion source) measured M/Z of Compound A81: 981.6.
example 10: synthesis of compound a 92:
Figure BDA0003529735350000223
the synthesis method, auxiliary material types, raw and auxiliary material equivalent ratio and operation method of the compound A92 are completely consistent with those of A1, and the differences are that a reaction raw material M10-1 replaces M1-1, M10-2 replaces an M1-2 raw material, M10-3 replaces an M1-3 raw material, M10-4 replaces an M1-4 raw material, M10-5 replaces M1-5, M10-6 replaces an M1-6 raw material, and A92-1 replaces an A1-1 raw material. The total yield is 18.8%. LCMS (ESI ion source) measured M/Z of Compound A92: 946.4.
example 11: synthesis of compound a 99:
Figure BDA0003529735350000231
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M11 are completely consistent with those of M1, and the differences are that a reaction raw material M11-1 replaces M1-1, M11-2 replaces M1-2 raw material, M11-3 replaces M1-3 raw material, M11-4 replaces M1-4 raw material, M11-5 replaces M1-5, and M11-6 replaces M1-6 raw material. The overall yield was 25%. LCMS (ESI ion source) measured M/Z of Compound A99: 761.7.
example 12: synthesis of compound a 111:
Figure BDA0003529735350000232
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M12 are completely consistent with those of M1, and the differences are that a reaction raw material M12-1 replaces M1-1, M12-2 replaces M1-2 raw material, M12-3 replaces M1-3 raw material, M12-4 replaces M1-4 raw material, M12-5 replaces M1-5, and M12-6 replaces M1-6 raw material. The overall yield was 19%. LCMS (ESI ion source) measured M/Z of Compound A111: 771.3.
example 13: synthesis of compound a 119:
Figure BDA0003529735350000233
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M13 are completely consistent with those of M1, and the differences are that a reaction raw material M13-1 replaces M1-1, M13-2 replaces M1-2 raw material, M13-3 replaces M1-3 raw material, M13-4 replaces M1-4 raw material, M13-5 replaces M1-5, and M13-6 replaces M1-6 raw material. The total yield was 22%. LCMS (ESI ion source) to determine M/Z of Compound A119: 900.1.
example 14: synthesis of compound a 130:
Figure BDA0003529735350000241
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M14 are completely consistent with those of M1, and the differences are that a reaction raw material M14-1 replaces M1-1, M14-2 replaces M1-2 raw material, M14-3 replaces M1-3 raw material, M14-4 replaces M1-4 raw material, M14-5 replaces M1-5, and M14-6 replaces M1-6 raw material. The overall yield was 23%. LCMS (ESI ion source) measured M/Z of Compound A130: 733.5.
example 15: synthesis of compound a 134:
Figure BDA0003529735350000242
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M15 are completely consistent with those of M1, and the differences are that a reaction raw material M15-1 replaces M1-1, M15-2 replaces M1-2 raw material, M15-3 replaces M1-3 raw material, M15-4 replaces M1-4 raw material, M15-5 replaces M1-5, and M15-6 replaces M1-6 raw material. The overall yield was 19%. LCMS (ESI ion source) measured M/Z of Compound A134: 723.5.
example 16: synthesis of compound a 135:
Figure BDA0003529735350000243
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M16 are completely consistent with those of M1, and the differences are that a reaction raw material M16-1 replaces M1-1, M16-2 replaces M1-2 raw material, M16-3 replaces M1-3 raw material, M16-4 replaces M1-4 raw material, M16-5 replaces M1-5, and M16-6 replaces M1-6 raw material. The total yield was 24%. LCMS (ESI ion source) to determine M/Z of Compound A135: 823.5.
example 17: synthesis of compound a 155:
Figure BDA0003529735350000251
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M17 are completely consistent with those of M1, and the differences are that a reaction raw material M17-1 replaces M1-1, M17-2 replaces M1-2 raw material, M17-3 replaces M1-3 raw material, M17-4 replaces M1-4 raw material, M17-5 replaces M1-5, and M17-6 replaces M1-6 raw material. The total yield was 18%. LCMS (ESI ion source) measured M/Z of Compound A155: 667.2.
example 18: synthesis of compound a 158:
Figure BDA0003529735350000252
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M18 are completely consistent with those of M1, and the differences are that a reaction raw material M18-1 replaces M1-1, M18-2 replaces M1-2 raw material, M18-3 replaces M1-3 raw material, M18-4 replaces M1-4 raw material, M18-5 replaces M1-5, and M18-6 replaces M1-6 raw material. The overall yield was 19%. LCMS (ESI ion source) measured M/Z of Compound A158: 1029.8.
example 19: synthesis of compound a 162:
Figure BDA0003529735350000253
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M19 are completely consistent with those of M1, and the differences are that a reaction raw material M19-1 replaces M1-1, M19-2 replaces M1-2 raw material, M19-3 replaces M1-3 raw material, M19-4 replaces M1-4 raw material, M19-5 replaces M1-5, and M19-6 replaces M1-6 raw material. The total yield was 21%. LCMS (ESI ion source) measured M/Z of Compound A162: 901.7.
example 20: synthesis of compound a 165:
Figure BDA0003529735350000261
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M20 are completely consistent with those of M1, and the differences are that a reaction raw material M20-1 replaces M1-1, M20-2 replaces M1-2 raw material, M20-3 replaces M1-3 raw material, M20-4 replaces M1-4 raw material, M20-5 replaces M1-5, and M20-6 replaces M1-6 raw material. The total yield was 20%. LCMS (ESI ion source) M/Z of Compound A165: 885.6.
example 21: synthesis of compound a 169:
Figure BDA0003529735350000262
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M21 are completely consistent with those of M1, and the differences are that a reaction raw material M21-1 replaces M1-1, M21-2 replaces M1-2 raw material, M21-3 replaces M1-3 raw material, M21-4 replaces M1-4 raw material, M21-5 replaces M1-5, and M21-6 replaces M1-6 raw material. The overall yield was 23%. LCMS (ESI ion source) measured M/Z of Compound A169: 771.4.
example 22: synthesis of compound a 179:
Figure BDA0003529735350000263
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M22 are completely consistent with those of M1, and the differences are that a reaction raw material M22-1 replaces M1-1, M22-2 replaces M1-2 raw material, M22-3 replaces M1-3 raw material, M22-4 replaces M1-4 raw material, M22-5 replaces M1-5, and M22-6 replaces M1-6 raw material. The overall yield was 23%. LCMS (ESI ion source) measured M/Z of Compound A179: 943.5.
example 23: synthesis of compound a 209:
Figure BDA0003529735350000271
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M23 are completely consistent with those of M1, and the differences are that a reaction raw material M23-1 replaces M1-1, M23-2 replaces M1-2 raw material, M23-3 replaces M1-3 raw material, M23-4 replaces M1-4 raw material, M23-5 replaces M1-5, and M23-6 replaces M1-6 raw material. The overall yield was 19%. LCMS (ESI ion source) measured M/Z of Compound A209: 827.6.
example 24: synthesis of compound a 217:
Figure BDA0003529735350000272
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M24 are completely consistent with those of M1, and the differences are that a reaction raw material M24-1 replaces M1-1, M24-2 replaces M1-2 raw material, M24-3 replaces M1-3 raw material, M24-4 replaces M1-4 raw material, M24-5 replaces M1-5, and M24-6 replaces M1-6 raw material. The total yield was 22%. LCMS (ESI ion source) measured M/Z of Compound A217: 1041.7.
example 25: synthesis of compound a 239:
Figure BDA0003529735350000273
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M25 are completely consistent with those of M1, and the differences are that a reaction raw material M25-1 replaces M1-1, M25-2 replaces M1-2 raw material, M25-3 replaces M1-3 raw material, M25-4 replaces M1-4 raw material, M25-5 replaces M1-5, and M25-6 replaces M1-6 raw material. The total yield was 24%. LCMS (ESI ion source) measured M/Z of Compound A239: 797.5.
example 26: synthesis of compound a 256:
Figure BDA0003529735350000274
the synthesis method, the auxiliary material type, the equivalent ratio of raw materials and auxiliary materials and the operation method of the intermediate M26 are completely consistent with those of M1, and the differences are that a reaction raw material M26-1 replaces M1-1, M26-2 replaces M1-2 raw material, M26-3 replaces M1-3 raw material, M26-4 replaces M1-4 raw material, M26-5 replaces M1-5, and M26-6 replaces M1-6 raw material. The overall yield was 23%. LCMS (ESI ion source) measured M/Z of Compound A256: 856.7.
other compounds not described in the examples can be synthesized by the same method as described above.
Blue device example 1: blue light device manufacturing method (Top luminescence)
The preparation process comprises the following steps:
a transparent anode ITO film layer was formed on a glass substrate 101 to a film thickness of 150nm to obtain a first electrode 102 as an anode, and then vapor deposition was performed
Figure BDA0003529735350000281
With the Compound A47 of the present invention
Figure BDA0003529735350000282
Mixed material ofThe hole injection layer 103 was prepared by mixing the above materials at a ratio of 3:97 (mass ratio), and then evaporating a 100nm thick compound A47
Figure BDA0003529735350000283
A first hole transport layer 104 was obtained, and then a compound having a thickness of 20nm was evaporated
Figure BDA0003529735350000284
A second hole transport layer 105 was obtained and then evaporated at an evaporation rate of 95:5
Figure BDA0003529735350000285
And
Figure BDA0003529735350000286
30nm, fabricating a blue light emitting unit 106, and evaporating to deposit 10nm
Figure BDA0003529735350000291
A hole blocking layer 107 is formed, and then
Figure BDA0003529735350000292
And
Figure BDA0003529735350000293
an electron transport layer 108 having a thickness of 30nm was formed at a mixing ratio of 4:6 (mass ratio), followed by formation of a second electrode 109 comprising ytterbium having a thickness of 3nm and magnesium silver having a thickness of 10nm (mass ratio of 1: 9), followed by vapor deposition of a 70nm cover material thereon
Figure BDA0003529735350000294
A capping layer 110 is formed.
In blue light device examples 2-9, the compounds A59, A78, A134, A158, A162, A165, A169 and A179 are respectively adopted, and in blue light device comparative example 1, the compound D1 is adopted, and in blue light device comparative example 2, the compound D2 is adopted to replace the compound A47 in blue light device example 1 to be used as the first hole transport layer 104 to manufacture the blue light organic electroluminescent device.
Blue device comparative example 1:
Figure BDA0003529735350000295
blue device comparative example 2:
Figure BDA0003529735350000296
the efficiency is 10mA/cm at the current density2The efficiency of the invention is expressed by the numerical value of the current efficiency divided by the color coordinate CIEy (the unit is Cd/A/CIEy), and the service life is 50mA/cm2The time required for the brightness to decay to 95% of the initial brightness at current. The test results are detailed in table 1.
TABLE 1 relevant test data for voltage, efficiency, and lifetime of blue light device
Figure BDA0003529735350000301
Red device example 1: red light device manufacturing method (bottom lighting)
The preparation process comprises the following steps:
a transparent anode ITO film layer is formed on a glass substrate 101 to a film thickness of 150nm to obtain a first electrode 102 as an anode, and then vapor deposition is performed
Figure BDA0003529735350000311
With the compounds of the invention
Figure BDA0003529735350000312
The mixed material of (2) as the hole injection layer 103 was mixed at a ratio of 3:97 (mass ratio), and then a compound having a thickness of 100nm was deposited by evaporation
Figure BDA0003529735350000313
A first hole transport layer 104 was obtained, and then the compound (1) of the present invention was evaporated to a thickness of 100nm as required in the following table to obtain a second hole transport layer 105Then evaporating at the evaporation rate of 95:5
Figure BDA0003529735350000314
And
Figure BDA0003529735350000315
40nm, making red light emitting unit 106, and evaporating to deposit 10nm
Figure BDA0003529735350000316
A hole blocking layer 107 is formed, and then
Figure BDA0003529735350000317
And
Figure BDA0003529735350000318
an electron transport layer 108 having a thickness of 30nm was formed at a mixing ratio of 4:6 (mass ratio), and then magnesium silver having a thickness of 100nm (mass ratio of 1: 9) was formed as a second electrode 109.
In red device examples 2 to 18, the above-described compounds A1, a21, a22, a32, a43, a81, a92, a99, a111, a119, a130, a134, a135, a155, a209, a217, a239, and a256 were used, and in red device comparative example 1, compound D3 was used, and in red device comparative example 2, compound D4 was used instead of compound A1 in red device example 1 as the first hole transport layer 104, to fabricate a blue organic electroluminescent device, respectively.
Red device comparative example 1:
Figure BDA0003529735350000319
red device comparative example 2:
Figure BDA0003529735350000321
the efficiency is 10mA/cm at the current density2The efficiency of the invention is determined by dividing the current efficiency by the color coordinate CIEy numerical tableShows (in Cd/A/CIEy) that the lifetime is 50mA/cm2The time required for the brightness to decay to 95% of the initial brightness at current. The test results are detailed in table 2.
TABLE 2 relevant test data of voltage, efficiency and lifetime of red light device
Figure BDA0003529735350000322
Figure BDA0003529735350000331
The foregoing embodiments are merely illustrative of the principles and utilities of the present invention and are not intended to limit the invention. Any person skilled in the art can modify or change the above-mentioned embodiments without departing from the spirit and scope of the present invention. Accordingly, it is intended that all equivalent modifications or changes which can be made by those skilled in the art without departing from the spirit and technical spirit of the present invention be covered by the claims of the present invention.

Claims (15)

1. An amine compound, the chemical structure of which is shown in formula (1):
Figure FDA0003529735340000011
wherein:
R1selected from substituted or unsubstituted straight chain or branched chain C1-C15 alkyl, substituted or unsubstituted C1-C15 cycloalkyl, substituted or unsubstituted C1-C15 heteroalkyl, substituted or unsubstituted C1-C15 heterocycloalkyl, substituted or unsubstituted C5-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, or substituted or unsubstituted C7-C40 aromatic and alkyl ring group;
R2、R3each independently selected from substituted or unsubstituted aryl of C5-C60, and substituted or unsubstituted C4A heteroaryl of C60, or a substituted or unsubstituted aromatic and alkyl cyclic group of C7 to C60;
R4～R15hydrogen, deuterium, substituted or unsubstituted straight-chain or branched-chain alkyl of C1-C15, substituted or unsubstituted C1-C15 cycloalkyl, substituted or unsubstituted C1-C15 heteroalkyl, substituted or unsubstituted C1-C15 heterocycloalkyl, substituted or unsubstituted C5-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, substituted or unsubstituted C7-C40 aromatic and alkyl ring radical; or R4～R15Any two adjacent groups combine to form a substituted or unsubstituted ring;
L1、L2each independently a direct bond, or a substituted or unsubstituted arylene group of C6 to C21;
X1selected from O, or S.
2. The amine compound of claim 1, wherein R is1Selected from substituted or unsubstituted straight chain or branched chain C1-C10 alkyl, substituted or unsubstituted C1-C10 cycloalkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C1-C10 heterocycloalkyl, C6-C30 aryl, C6-C30 heteroaryl, alkyl substituted C7-C30 aryl; alkyl-substituted heteroaryl of C7 to C30; substituted or unsubstituted C7-C30 aromatic and alkyl cyclic radical;
and/or, R2、R3Each independently selected from aryl of C6-C30, heteroaryl of C6-C30 and aryl of C7-C60 substituted by alkyl; alkyl-substituted heteroaryl of C7 to C60; or substituted or unsubstituted C7-C30 aromatic and alkyl cyclic group; and/or, R4～R15Independently hydrogen, deuterium, substituted or unsubstituted straight-chain or branched-chain C1-C10 alkyl, substituted or unsubstituted C1-C10 cycloalkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C1-C10 heterocycloalkyl, C6-C30 aryl, C6-C30 heteroaryl, alkyl-substituted C7-C30 aryl, alkyl-substituted C7-C30 heteroaryl, and substituted or unsubstituted C7-C30 aromatic alkyl ring group.
3. The amine compound of claim 1 or 2, wherein the chemical structure of the amine compound is represented by formula (2) or formula (3):
Figure FDA0003529735340000021
wherein R is1～R15、L1、L2、X1The definition is the same as in formula (1).
4. The amine compound of claim 1 or 2, wherein R is1Selected from hydrogen, deuterium, methyl, isopropyl, tert-butyl,
Figure FDA0003529735340000022
Figure FDA0003529735340000023
Figure FDA0003529735340000031
Figure FDA0003529735340000032
Or selected from aromatic and alkyl cyclic groups;
wherein, X2、X3Each is independently selected from O or S;
R16、R17each independently selected from hydrogen, deuterium, methyl, isopropyl, or tert-butyl.
5. The amine compound of claim 4, wherein the aromatic and alkyl cyclic group is formed by the cyclization of an aryl group with an alkyl or heteroalkyl group; preferably, the aryl group is selected from
Figure FDA0003529735340000033
Figure FDA0003529735340000034
The alkyl group is selected from
Figure FDA0003529735340000035
The heteroalkyl group being selected from
Figure FDA0003529735340000036
Wherein, a, b, c, d in the aryl are respectively carbon, e and f are binding sites, and a, b or c, d are combined with e and f in the alkyl or heteroalkyl to form a ring; x4～X6Each independently selected from O, S, atoms or NR groups; wherein R is selected from substituted or unsubstituted aryl of C6-C30 or substituted or unsubstituted heteroaryl of C6-C30.
6. The amine compound of claim 5, wherein a, b, c, d of the aryl group are combined with e, f of the alkyl or heteroalkyl group to form the following group:
Figure FDA0003529735340000041
wherein, X4～X6Each independently selected from O, S, or an NR group; wherein R is selected from substituted or unsubstituted aryl of C6-C30 or substituted or unsubstituted heteroaryl of C6-C30.
7. The amine compound of claim 1 or 2, wherein R is2、R3Each independently selected from the group consisting of:
Figure FDA0003529735340000042
wherein, X7Each is independently selected from O or S; r18、R19Each independently selectsFrom hydrogen, deuterium, methyl, isopropyl, or tert-butyl.
8. The amine compound of claim 1 or 2, wherein R is4～R15Each independently selected from hydrogen, deuterium, methyl, isopropyl, tert-butyl, alkoxy, phenyl, cyclohexyl, cyclopentyl, or R4～R15Any two adjacent groups combine to form a benzene ring.
9. The amine compound of claim 1, wherein L is1、L2Each independently selected from a direct bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene; preferably, the substituents are selected from methyl, isopropyl, or tert-butyl.
10. The amine compound according to any one of claims 1 to 9, wherein the amine compound is selected from any one of the following chemical structures:
Figure FDA0003529735340000051
Figure FDA0003529735340000061
Figure FDA0003529735340000071
Figure FDA0003529735340000081
11. a hole transport layer material comprising the amine compound according to any one of claims 1 to 10.
12. Use of the amine compound according to any one of claims 1 to 10 and/or the hole transport layer material according to claim 11 in an organic electroluminescent device.
13. An organic electroluminescent device comprising the amine compound according to any one of claims 1 to 10 and/or the hole transport layer material according to claim 11.
14. A display panel comprising the organic electroluminescent device as claimed in claim 13.
15. A display device comprising the display panel according to claim 14.
CN202210202047.0A 2022-03-03 2022-03-03 Amine compound and application thereof in organic electroluminescent device Pending CN114507222A (en)

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