CN114907359B - Organic compound and application thereof in organic electroluminescent device - Google Patents

Organic compound and application thereof in organic electroluminescent device Download PDF

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CN114907359B
CN114907359B CN202210726540.2A CN202210726540A CN114907359B CN 114907359 B CN114907359 B CN 114907359B CN 202210726540 A CN202210726540 A CN 202210726540A CN 114907359 B CN114907359 B CN 114907359B
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CN114907359A (en
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王湘成
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 organic compound and application thereof in an organic electroluminescent device. The chemical structure of the organic compound is shown as a formula I:

Description

Organic compound and application thereof in organic electroluminescent device
Technical Field
The invention relates to the field of organic electroluminescent materials, in particular to an organic compound and application thereof in an organic electroluminescent device.
Background
Organic Light Emitting Diodes (OLED) are widely used in various displays because of their self-luminescence, solid state, bendable, high efficiency and other characteristics. Phosphorescent materials theoretically have 100% internal quantum luminous efficiency, whereas common fluorescent materials have only 25% luminous efficiency, and are therefore commonly used in OLEDs. The phosphorescent light-emitting material is mainly formed by mixing a light-emitting host material and a light-emitting guest material. Holes and electrons are respectively injected from the anode and the cathode, are injected into a main body of the light-emitting layer through the hole transmission layer and the electron transmission layer and are combined to form excitons, and the energy of the excitons is transferred to a light-emitting object from the light-emitting main body to emit light. In general, the mass ratio of the light-emitting main body to the light-emitting layer is 99% -85%. The properties of the material of the light-emitting body are therefore critical for the performance of the OLED.
Phosphorescent light-emitting host materials are required to have a relatively suitable triplet energy level, well-balanced hole and electron mobility, and good thermal stability. The existing phosphorescent light-emitting main body material is mainly prepared from carbazole or carbazole-derived varieties, and particularly a compound containing a plurality of aromatic rings is a preferable material of the phosphorescent light-emitting main body, and the compound has very suitable triplet energy level and can well regulate the energy level. However, the rigidity of the material is strong, the conjugation area is large, and the evaporation temperature of the material is generally higher. The C-N structure of carbazole is unstable, and C-N bond is easy to break in long-term evaporation process, thus leading to cracking of material. To solve this problem, one method is to reduce the molecular weight and the conjugated area, and the other is to replace the hydrogen atom on the aromatic ring with an alkyl group or a heteroalkyl group. However, the adoption of the reduction of molecular weight and conjugate area can cause difficult regulation and control of energy level, and the triplet state is very high, which is unfavorable for the collocation of devices; the alkyl or heteroalkyl is used for replacing hydrogen atoms on the aromatic ring, so that the material evaporation temperature can be reduced, and the material service time can be prolonged, but the alkyl can be affected by a large amount of rotational vibration, telescopic vibration and the like, and the energy transfer to the dopant luminescent molecules can be affected, so that the efficiency is low.
The OLED display panel is composed of red light, green light and blue light in an array mode. When one color is lightened by power on, the other two colors keep a dark state if not electrified. In practice, two other colors appear, and although the power is not applied, a slightly bright state appears, so that the color is not pure. This color purity reduction is particularly severe just when it is on, a condition which may be referred to as pixel crosstalk. The red light and the green light have the theoretically lowest starting voltage, so that the crosstalk is more serious. Currently, panel factories make some effort from device or panel pixel designs, but still have limited effectiveness.
Disclosure of Invention
In view of the above-mentioned drawbacks of the prior art, an object of the present invention is to provide an organic compound and its application in an organic electroluminescent device for solving the problems in the prior art.
To achieve the above and other related objects, in one aspect, the present invention provides an organic compound having a chemical structure as shown in formula i:
at least two adjacent carbon atoms in formula i form a non-aromatic ring by linking with other carbon atoms and/or heteroatoms selected from O, S, or N;
x is selected from O, S, NR a, or CR aRb, wherein R a、Rb is independently selected from hydrogen, deuterium, substituted or unsubstituted straight or branched chain alkyl with C1-C10, substituted or unsubstituted cycloalkyl with C3-C20, substituted or unsubstituted heteroalkyl with C1-C10, substituted or unsubstituted aryl with C6-C60, substituted or unsubstituted heteroaryl with C5-C30, substituted or unsubstituted amino with C6-C30, or Ra, rb are linked to form a substituted or unsubstituted ring;
y is selected from the group consisting of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl, Wherein R c is attached to the nitrogen atom of formula I and R c is selected from the group consisting of substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C5-C30 heteroarylene; r d、Re and R f are each independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C30 amino, or any two of R c、Rd、Re and R f are joined to form a substituted or unsubstituted ring;
R 1～R3 is each independently selected from hydrogen, deuterium, fluorine, carbon trifluoride, cyano, nitro, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or wherein two or more adjacent groups are joined to each other to form a substituted or unsubstituted ring;
m is selected from 0 to 6, n is selected from 0 to 2, and q is selected from 0 to 4.
In another aspect, the present invention provides a composition comprising the aforementioned organic compound of the present invention and a second host compound selected from one or more of the following chemical structures:
in another aspect, the present invention provides a light-emitting host material comprising the aforementioned organic compound, and/or the aforementioned composition.
In another aspect, the present invention provides an organic layer comprising the aforementioned light-emitting host material.
In another aspect, the present invention provides the use of an organic compound, a composition as described above, and/or a light-emitting host material as described above in an organic electroluminescent device.
In another aspect, the present invention provides an organic electroluminescent device, including a first electrode, a second electrode, and an organic layer, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, or an electron transport layer, and the organic layer includes the aforementioned organic compound, composition, and/or light emitting host material.
In another aspect, the present invention provides a display or lighting device comprising an organic electroluminescent device as described above.
Compared with the prior art, the invention has the beneficial effects that:
the organic compound disclosed by the invention is applied to the field of organic electroluminescence, can reduce the use temperature, prolong the service life and can reduce the problem of luminous crosstalk of a luminous panel.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device (top-emission device) in an embodiment.
Fig. 2 is another structural schematic diagram of an organic electroluminescent device (bottom light-emitting device) in the embodiment.
In the figure:
101. Substrate
102. First electrode
103. Hole injection layer
104. First layer hole transport layer
105. A second hole transport layer
106. Light-emitting layer
107. Hole blocking layer
108. Electron transport layer
109. Second electrode
110. Cover layer
Detailed Description
Embodiments of the specifically disclosed organic compounds and their use in organic electroluminescent devices are described in detail below. Other advantages and effects of the present invention will be readily apparent to those skilled in the art from the present disclosure. The invention may be practiced or carried out in other embodiments that depart from the specific details, and the details of the present description may be modified or varied from the spirit and scope of the present invention.
Before the embodiments of the invention are explained in further detail, it is to be understood that the invention is not limited in its scope to the particular embodiments described below; it is also to be understood that the terminology used in the examples of the invention is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the invention; in the description and claims of the invention, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise.
Where numerical ranges are provided in the examples, it is understood that unless otherwise stated herein, both endpoints of each numerical range and any number between the two endpoints are significant both in the numerical range. 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, materials used in the embodiments, any methods, devices, and materials of the prior art similar or equivalent to those described in the embodiments of the present invention may be used to practice the present invention according to the knowledge of one skilled in the art and the description of the present invention.
Through a great deal of research and study, the inventor provides a novel material design scheme which can perfectly solve two types of problems in the prior art at the same time. According to the technical scheme, a non-aromatic ring is added into a carbazole-derived aromatic ring-containing molecular structure, and the non-aromatic ring can be cycloalkyl or heterocycloalkyl, for example. The cycloalkyl or heterocycloalkyl can reduce the vapor deposition temperature of the material as the alkyl substituted hydrogen atom, and meanwhile, the molecular rotation and vibration of the cycloalkyl can be limited, so that adverse effects and reduction of luminous efficiency can be avoided in the process of transferring host energy to a guest. And the addition of the cycloalkyl or the heterocycloalkyl can effectively improve the dielectric constant of the material, so that the starting voltage is improved, and the pixel crosstalk problem can be solved to a great extent. On this basis, the present application has been completed.
Phosphorescent host materials in order to balance the number of holes and electrons, two methods are generally used, one is to add a hole-transporting type of light-emitting host and an electron-transporting type of light-emitting host material at the same time. Secondly, a hole transport group and an electron transport group are simultaneously introduced on the same molecule. Both methods are often found in practical applications. The solution of the invention is applicable to both carrier transport balancing methods.
Examples of the substituents in the present invention are described below, but the substituents are not limited thereto:
by [ substituted or unsubstituted ] is meant a substitution with one or more substituents selected from the group consisting of: deuterium, halogen groups, cyano groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfonyl groups, arylsulfonyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups, arylphosphine groups, and heteroaryl groups, acenaphthylene derivative groups, 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.
The "alkyl group" may be linear or branched, and the number of carbon atoms is not particularly limited. In some embodiments, alkyl groups include, but are 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, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like.
The above description of alkyl groups also applies to alkyl groups in aralkyl groups, aralkylamine groups, alkylaryl groups, and alkylamino groups.
The [ cycloalkyl ] group 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-t-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.
The "heteroalkyl" group may be a straight-chain 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, can be alkoxy, alkylthio, alkylsulfonyl, and the like. Alkoxy groups may include, for example, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy (i-propyloxy), n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzoxy, and the like. Alkylthio groups may include, for example, but are not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, t-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 toEtc.
The "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, tetrabiphenyl, pentabiphenyl, and the like. Polycyclic aryl groups include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, and the like. Fluorenyl groups can be substituted, such as 9,9 '-dimethylfluorenyl, 9' -dibenzofluorenyl, and the like. In addition, two of the substituents may combine with each other to form a spiro structure, for example, 9' -spirobifluorenyl, 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, arylphosphinyl, 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, diazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, oxazinyl, thiazinyl, dioxanyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, triazaindenyl, indolyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl pyrazinopyrazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, phenazinyl, imidazopyridinyl, phenazinyl, phenanthridinyl, phenanthrolinyl, phenothiazinyl, imidazopyridinyl, imidazophenanthridinyl, benzimidazolazolyl, benzimidazolophenidinyl, spiro [ fluorene-9, 9' -xanthene ], benzobinaphthyl, dinaphthyl, naphthyfuranyl, dinaphthylthiophenyl, naphthybenzothiophenyl, triphenylphosphine oxide, triphenylborane, and the like.
The above description of heteroaryl groups applies to heteroaryl groups in heteroaryl amine groups and arylheteroaryl amine groups.
The above description of heteroaryl groups applies to heteroarylene groups, except that the heteroarylene group is divalent.
An amine group is an organic compound in which the hydrogen atom of ammonia is replaced with an alkyl group. For example, the number of carbon atoms in the alkyl group may be 6 to 30.
[ Adjacent group ] may mean a substituent substituted for an atom directly connected to an atom substituted with a corresponding substituent, a substituent located spatially closest to the corresponding substituent, or another substituent substituted for an atom substituted with a corresponding substituent.
The term "attached to form a substituted or unsubstituted ring" 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.
Aliphatic hydrocarbon ring means a ring formed of only carbon and hydrogen atoms as a non-aromatic ring. Specific examples of the aliphatic hydrocarbon ring include, but are not limited to, cycloalkylene, cyclobutene, cyclopentene, cyclohexylene, cyclohexenylene, 1, 4-cyclohexanediene, cycloheptylene, cyclooctane, and the like.
The aromatic hydrocarbon ring is an aromatic ring formed only from carbon and hydrogen atoms. Specific examples of the aromatic hydrocarbon ring may include phenyl, naphthyl, anthracenyl, phenanthryl, perylenyl, fluoranthracenyl, triphenylenyl, phenalkenyl, pyrenyl, naphthacene, pentacenyl, fluorenyl, indenyl, acenaphthylenyl, benzofluorenyl, spirofluorenyl, and the like, but are not limited thereto.
Aliphatic heterocyclic ring means an aliphatic ring comprising one or more heteroatoms. Specific examples of the aliphatic heterocycle may include, but are not limited to, oxiranyl, tetrahydrofuranyl, 1, 4-dioxanyl, pyrrolidinyl, piperidinyl, morpholinyl, oxetanyl, azocyclohexane (azoxane) yl, and the like.
The aliphatic hydrocarbon ring may be monocyclic or polycyclic.
The first aspect of the invention provides an organic compound, wherein the chemical structure of the organic compound is shown as a formula I: the chemical structure of the organic compound is shown as a formula I:
at least two adjacent carbon atoms in formula i form a non-aromatic ring by linking with other carbon atoms and/or heteroatoms selected from O, S, or N.
X is selected from O, S, NR a, or CR aRb, wherein R a、Rb is independently selected from hydrogen, deuterium, substituted or unsubstituted straight or branched chain alkyl with C1-C10, substituted or unsubstituted cycloalkyl with C3-C20, substituted or unsubstituted heteroalkyl with C1-C10, substituted or unsubstituted aryl with C6-C60, substituted or unsubstituted heteroaryl with C5-C30, substituted or unsubstituted amino with C6-C30, or Ra, rb are linked to form a substituted or unsubstituted ring;
y is selected from the group consisting of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl, (The foregoing structural formula may be abbreviated as N(RcRdRe)、C(＝O)RcRd、Si(RcRdReRf)、P(＝O)(RcRdRe)、B(RcRdRe)、S(＝O)2(RcRd)), wherein R c is attached to a nitrogen atom in formula I, R c is selected from the group consisting of substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C5-C30 heteroarylene, R d、Re and R f are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C30 amine, or any two of R c、Rd、Re and R f are attached to form a substituted or unsubstituted ring;
R 1～R3 is each independently selected from hydrogen, deuterium, fluorine, carbon trifluoride, cyano, nitro, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or wherein two or more adjacent groups are joined to each other to form a substituted or unsubstituted ring;
m is selected from 0 to 6, n is selected from 0 to 2, and q is selected from 0 to 4.
In some embodiments, m, n, q are integers, and m may have a value of, for example, 0 to 3, 3 to 6, 0, 1,2, 3,4, 5, 6. The value of n may be, for example, 0 to 1, 1 to 2, 0, 1, or 2.q may be, for example, 0 to 2, 2 to 4, 0, 1,2, 3, or 4.
For example, C1 to C10 means that the number of carbon atoms is 1 to 10. C6-C30 means that the number of carbon atoms is 6-30. The other places where this occurs are explained before.
In the organic compound provided by the invention, the non-aromatic ring is selected from cycloalkyl or heterocycloalkyl. The non-aromatic ring is preferably selected from a substituted or unsubstituted C3 to C12 cycloalkyl group, or a substituted or unsubstituted C3 to C10 heterocycloalkyl group. In some embodiments, the number of cycloalkyl groups may be, for example, 3 to 5, 5 to 10, or 10 to 12, etc. The number of heterocycloalkyl groups may be, for example, 3 to 5, 5 to 8, or 8 to 10.
More preferably, the non-aromatic ring is selected from any one of the following groups: the non-aromatic ring is selected from any one of the following groups:
any two adjacent carbon atom positions on the above groups coincide with any two adjacent carbon atom positions in formula i.
At least two adjacent carbon atoms in formula i form a non-aromatic ring by linking to:
The asterisk carbon atom positions on the above groups coincide with any two adjacent asterisk carbon atom positions in formula i.
In the organic compound provided by the invention, Y is selected from any one group or a combination of any two or more groups selected from the following groups:
wherein,
Ar is selected from a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C5-C30 heteroaryl group;
Each of A 1 and A 2 is independently selected from hydrogen, deuterium, fluorine, carbon trifluoride (-CF 3), cyano (-CN), nitro (-NO 2), substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C5-C20 heteroaryl;
X 1～X7 is each independently selected from O, S or CR eRf, wherein R e、Rf is each independently selected from hydrogen, deuterium, fluorine, carbon trifluoride, cyano, nitro, straight or branched C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl;
Z 1～Z8 are each independently selected from C, or N;
any of the above positions on the group may serve as a site of attachment to the nitrogen atom of formula I.
By way of illustration, in some embodiments,For example, it may be/>Etc. Specific choices of other groups can be made with reference to this variant.
In the organic compound provided by the invention, R a is selected from any one of the following groups or a combination of more than two groups:
Methyl, ethyl,
Any position on the above-mentioned group may be used as a site for attachment of a group adjacent thereto in formula I. For example, where X is selected from NR a, any of the positions on the above groups may serve as a point of attachment to the nitrogen atom on NR a. For another example, where X is selected from CR aRb, any of the positions on the above groups may be used as the attachment site to a carbon atom on CR aRb.
By way of example, in some embodiments,For example, it may be/>Specific choices of other groups can be made with reference to this variant.
In the organic compound provided by the invention, R b is selected from methyl, ethyl or phenyl.
In the organic compound provided by the invention, in R a or R b, the hetero atom in the hetero alkyl or heteroaryl is independently selected from O, N, S, P, si, se or B.
In the organic compound provided by the invention, in R a or R b, the substituted or unsubstituted C5-C30 heteroaryl is selected from substituted or unsubstituted C6-C30 carbazolyl.
In the organic compound provided by the invention, R a、Rb is connected to form in CR aRb R a、Rb is linked to form a ring, specifically, R a、Rb is bonded to form a ring together with C in CR aRb.
In the organic compound provided by the invention, each R 1～R3 is independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tertiary butyl, fluorine, carbon trifluoride, cyano, nitro or phenyl.
In the organic compound provided by the invention, in R c, the hetero atom in the heteroarylene is selected from O, N, S, P, si, se or B.
In the organic compound provided by the invention, in R d、Re and R f, the hetero atoms in the heteroaryl are respectively and independently selected from O, N, S, P, si, se or B.
In the organic compound provided by the invention, the substituted or unsubstituted C5-C30 heteroaryl is selected from substituted or unsubstituted C6-C30 carbazolyl.
Among the organic compounds provided by the present invention, the organic compound is selected from any one of the following chemical structures:
/>
/>
/>
/>
/>
/>
Specifically, the above structure may be unsubstituted or substituted with one or more substituents selected from the group consisting of. Examples of the group include deuterium, halogen group, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amine group, phosphine oxide group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamino group, aralkylamino group, heteroarylamino group, arylamino group, arylheteroarylamino group, arylphosphine group, and heteroaryl group.
The second aspect of the present invention provides a composition comprising an organic compound according to the first aspect of the present invention and a second host compound. The second host compound is selected from one or more of the following chemical structures:
The organic compound according to the first aspect of the present invention may be used as a first host compound and may be used together with a second host compound as a light-emitting host material.
A third aspect of the present invention provides a light-emitting host material comprising an organic compound according to the first aspect of the present invention, and/or a composition according to the second aspect of the present invention.
A fourth aspect of the invention provides an organic layer comprising a light-emitting host material according to the first aspect of the invention.
A fifth aspect of the invention provides the use of an organic compound according to the first aspect of the invention, a composition according to the second aspect of the invention, and/or an organic layer according to the third aspect of the invention in an organic electroluminescent device.
A sixth aspect of the present invention provides an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, which may be a single-layer structure or a multi-layer tandem structure in which two or more organic layers are laminated, such as having at least one layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, or an electron transport layer, as a bottom or top light emitting device structure. Can be prepared using common methods and materials for preparing organic electroluminescent devices. The organic layer comprises an organic compound according to the first aspect of the invention, a composition according to the second aspect of the invention, and/or a light-emitting host material according to the third aspect of the invention.
The light-emitting layer comprises the organic compound according to the first aspect of the invention and/or the composition according to the second aspect of the invention. The organic electroluminescent device adopts the organic compound and the composition as a luminescent main material of the organic electroluminescent device.
In the organic electroluminescent device provided by the invention, the first electrode is used as the anode layer, and the anode material can be a material with a large work function, for example, so that holes are smoothly injected into the organic layer. More for example, 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 the cathode layer, and the cathode material can be a material with a small work function, for example, so that electrons are smoothly injected into the organic layer. The cathode material may be, for example, a metal or a multi-layer structural 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 a work function of the anode material and a HOMO of the surrounding organic layer, is used as a material that advantageously receives holes from the anode at a low voltage.
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 as a material for receiving holes from the anode or the hole injection layer and transporting the holes to the light emitting layer. The material of the hole transport layer includes, but is not limited to, an organic material of arylamine, a conductive polymer, a block copolymer having both conjugated and non-conjugated portions, and the like.
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 transporting layer and from the electron transporting layer, respectively, and combining the holes and electrons.
In the organic electroluminescent device provided by the present invention, the material of the electron transport layer is a material having high mobility for electrons, and is suitable as a material that advantageously receives electrons from the cathode and transports the electrons to the light emitting layer.
In the organic electroluminescent device provided by the invention, the material of the cover layer generally has a high refractive index, so that the light efficiency of the organic electroluminescent device can be improved, and the improvement of external luminous efficiency is particularly facilitated.
In the organic electroluminescent device provided by the invention, the organic electroluminescent device is an organic photovoltaic device, an organic luminescent device, an organic solar cell, electronic paper, an organic photoreceptor, an organic thin film transistor and the like.
In another aspect, the invention provides a display or lighting device comprising an organic electroluminescent device according to the invention.
Embodiments of the present invention are described below by way of specific examples.
Synthetic examples:
the synthesis of the compounds of the invention has the following 3 schemes:
general formula 1:
General formula 2:
general formula 3:
the detailed synthesis procedure is as follows:
Example 1
The synthesis method of the compound A1 comprises the following steps:
synthesis of intermediate A1-3:
A1-1 (30 g,71.2mmol, A1-2 (14.6 g,85.4 mmol), K 2CO3 (29.4 g,213.6 mmol), pd acetate (OAc) 2 (0.16 g,0.7 mmol), triphenylphosphine pph 3 (56.0 g,213.6 mmol) and 300mL dichlorobenzene were added sequentially to a three-necked flask, the reaction mixture was warmed to reflux (180 ℃ C.), stirred for 24 hours, cooled, concentrated in vacuo, and the remaining solution was separated by column chromatography with toluene and petroleum ether as a flushing liquid for 2 times, the collected liquid was evaporated in vacuo, and toluene was recrystallized to give a solid, which was dried to give 14g of an intermediate compound, yield 45% LCMS (ESI ion source) measured M/Z:436.3.
Synthesis of compound A1:
In a three-necked flask, A1-3 (10 g,22.9 mmol), A1-4 (4.3 g,22.9 mmol), tris (dibenzylideneacetone) dipalladium (Pd 2(dba)3, (0.4 g,0.46 mmol), tri-tert-butylphosphine t-Bu 3 P (0.5 g,2.29 mmol), sodium tert-butoxide NaOBu-t (6.6 g,68.7 mmol) were added, and the mixture was stirred in toluene solvent (tolene) under nitrogen atmosphere, the reaction solution was warmed to 110℃and stirred for 3 hours, the reaction solution was cooled to room temperature, extracted with toluene and water, the toluene phase was evaporated, the solid was purified by column chromatography with toluene-petroleum ether, then concentrated in vacuo, and the concentrate was recrystallized and purified with toluene to give 9.4g of the A1 compound, yield 70%. S (ESI ion source) was measured M/Z：588.4.1H NMR(DMSO-d6):δ,9.00(d,1H),8.58–8.49(m,1H),7.94–7.81(m,3H),7.79(d,1H),7.71–7.62(m,2H),7.62–7.34(m,15H),7.32(d,1H),2.78–2.64(m,4H),1.75(m,4H).
Example 2
The synthesis method of the compound A9 comprises the following steps:
synthesis of Compound A9-3:
A9-1 (20 g,48.4 mmol), A9-2 (10 g,48.4 mmol), tris (dibenzylideneacetone) dipalladium (Pd 2(dba)3, (0.4 g,0.96 mmol), tri-tert-butylphosphine t-Bu 3 P (1.04 g,4.8 mmol), sodium tert-butoxide NaOBu-t (13.9 g,145.2 mmol) were added to a three-necked flask, stirred in a toluene solvent (tolene) under nitrogen atmosphere, the reaction mixture was warmed to 110℃and stirred for 3 hours, the reaction mixture was cooled to room temperature, extracted with toluene and water, the toluene phase was evaporated to dryness, the solid was purified by column chromatography using toluene-petroleum ether, then concentrated in vacuo, and the concentrate was recrystallized and purified with a toluene-ethanol mixed solvent to give 17.4g of the compound A9-3, yield 67%. LCMS (ESI ion source) was measured M/Z:538.2.
Synthesis of Compound A9-4:
A9-3 (15 g,27.8mmol, K 2CO3 (11.5 g,83.4 mmol), pd acetate (OAc) 2 (0.06 g,0.27 mmol), tricyclohexylphosphine tetrafluoroborate pcy3-HBF4 (0.1 g,2.8 mmol) and 300mL of N, N-Dimethylacetamide (DMA) were sequentially added to a three-necked flask, the reaction mixture was heated to 130℃and stirred for 8 hours, after cooling after completion of the reaction, vacuum concentration was performed, and the remaining solution was purified by column chromatography using toluene and petroleum ether as a flushing liquid, and after the collected liquid was evaporated in vacuo, recrystallized from toluene to give a solid, which was dried to give 10g of an intermediate compound A9-4 in a yield of 74% LCMS (ESI ion source) as measured M/Z502.2.
Synthesis of compound A9:
In a three-necked flask, A9-4 (10 g,19.9 mmol), A9-5 (3.7 g,19.9 mmol), tris (dibenzylideneacetone) dipalladium (Pd 2(dba)3, (0.17 g,0.2 mmol), tri-tert-butylphosphine t-Bu 3 P (0.43 g,2.0 mmol), sodium tert-butoxide NaOBu-t (5.7 g,59.7 mmol) were added, and the mixture was stirred in toluene solvent (tolene) under nitrogen atmosphere, the reaction solution was warmed to 110℃and stirred for 3 hours, the reaction solution was cooled to room temperature, extracted with toluene and water, the toluene phase was evaporated, the solid was purified by column chromatography with toluene-petroleum ether, then concentrated in vacuo, and the concentrate was recrystallized and purified with toluene to give 9.3g of the A9 compound, yield 72%. S (ESI ion source) was measured M/Z：654.8.1H NMR(DMSO-d6):δ,8.98(s,1H),8.30–8.23(m,1H),8.07(m,1H),7.99–7.92(m,1H),7.85(d,1H),7.76–7.49(m,10H),7.49–7.27(m,12H),6.92(d,1H),5.93(s,2H).
Example 3
The synthesis method of the compound A14 comprises the following steps:
Synthesis of intermediate A14-3:
the synthesis method of A14-3 is the same as that of A1, except that A1-1 is replaced with A14-1, and A1-2 is replaced with A14-2. The yield thereof was found to be 48%. LCMS (ESI ion source) measured M/Z:436.3.
Synthesis of compound a 14:
The synthesis method of A14 is the same as that of A1 except that A1-3 is replaced with A14-3, and A1-4 is replaced with A14-4. The yield thereof was found to be 73%. LCMS (ESI ion source) measurement M/Z：602.4.1H NMR(DMSO-d6)δ,8.09–7.98(m,2H),7.82(d,1H),7.68(d,1H),7.63–7.56(m,3H),7.56–7.48(m,5H),7.48–7.37(m,7H),7.34–7.23(m,2H),7.13(d,1H),2.99–2.90(t,2H),2.76–2.67(t,2H),1.82–1.65(m,4H).
The remaining compounds can be obtained according to the same method as the above three syntheses, except that the corresponding raw materials are substituted. The list of the intermediates of the first step reaction of the compounds of the same preparation method as A1 is shown in Table 1:
TABLE 1
/>
/>
The second-step reaction results of the compounds produced by the same method as A1 are shown in Table 2:
TABLE 2
/>
/>
The list of the intermediates of the first step reaction of the compounds of the same preparation method as A9 is shown in Table 3:
TABLE 3 Table 3
The list of the intermediates of the second reaction for the compounds of the same preparation as A9 is shown in Table 4:
TABLE 4 Table 4
The list of the intermediates of the third step reaction of the compounds of the same preparation method as A9 is shown in Table 5:
TABLE 5
The results of the nuclear magnetism test are shown in Table 6:
TABLE 6
/>
/>
/>
/>
The light emitting dopant materials that can be matched can be selected from, but not limited to, the following compounds:
Device example:
the compounds of the invention used in the device are all purified by sublimation, and the purity is over 99.98 percent.
The single-color device structure adopts the following molecular of the invention for the host material of the phosphorescence light-emitting layer or the light-emitting body material of the green light-emitting layer. As a host material for the light-emitting layer. The compounds of the present invention may be used in top-emitting, bottom-emitting or two or more light emitting layer devices.
The top light emitting device is shown in fig. 1 and the bottom light emitting device is shown in fig. 2.
Device example 1: as a host material for the red light emitting layer, a bottom emission manufacturing method is exemplified
The preparation process comprises the following steps:
Forming a transparent anode ITO film layer with a film thickness of 150nm on a glass substrate 101 to obtain a first electrode 102 as anode, and evaporating PD1 And hole transport material HT1/>As the hole injection layer 103, the mixed material was mixed at a ratio of 3:97 (mass ratio), and then HT1/>, 100nm thick was evaporatedA first hole transport layer 104 was obtained, and then 100nm thick compound RP1/>, was evaporatedA second hole transport layer 105 was obtained, and then the compound A1/> of the present invention was evaporated at an evaporation rate of 55:40:5Electron-transporting luminescent host material NH1/>And a luminescent doping material D1/>40Nm, a red light emitting unit 106 was fabricated, and 10nm HB1/>, was evaporatedHole blocking layer 107 is formed and then ET1/>, is evaporatedAnd Liq/>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 the second electrode 109.
The device test was performed using keithley power supply, MS-75 spectrometer combined test equipment. The voltage was 10mA/cm 2, the efficiency was expressed as the current efficiency at 10mA/cm 2 divided by the color coordinate CIEy value (in Cd/A), and the lifetime was the time required for the luminance to decay to 95% of the initial luminance at 10mA/cm 2 current. The present invention is expressed in terms of relative values with reference to comparative example 1 as 100%.
Device examples 2 to 20 compound A1 in example 1 was replaced with A9, a14, a31, a38, a46, a57, a71, a81, a90, a98, a114, a125, a131, a135, a145, a150, a166, a180, a200 compound, respectively. As in table 7.
TABLE 7
/>
Comparative compound 1:
device example 21: as a host material for the red light emitting layer, a top emission manufacturing method is exemplified
The preparation process comprises the following steps:
Forming an anode Ag/ITO film layer with a film thickness of 100nm/15nm on a glass substrate 101 to obtain a first electrode 102 as anode, and evaporating PD1 And hole transport material HT1/>As the hole injection layer 103, the mixed material was mixed at a ratio of 3:97 (mass ratio), and then HT1 was vapor deposited at a thickness of 100nmA first hole transport layer 104 was obtained, and then 100nm thick compound RP1 was evaporatedA second hole transport layer 105 was obtained, and then the compound B2/> of the present invention was evaporated at an evaporation rate of 95:5And a luminescent doping material D1/>40Nm, a red light emitting unit 106 was fabricated, and 10nm HB1/>, was evaporatedHole blocking layer 107 is formed and then ET1/>, is evaporatedWith LiqAn electron transport layer 108 having a thickness of 30nm was formed at a mixing ratio of 4:6 (mass ratio), and then a magnesium silver layer having a thickness of 15nm (mass ratio of 1:9) was formed as the second electrode 109, followed by evaporation of a 70nm optical coupling layer CP1/>
The device test was performed using keithley power supply, MS-75 spectrometer combined test equipment. The voltage was 10mA/cm 2, the efficiency was expressed as the current efficiency at 10mA/cm 2 divided by the color coordinate CIEy value (in Cd/A), and the lifetime was the time required for the luminance to decay to 95% of the initial luminance at 10mA/cm 2 current. The present invention is expressed in relative values with reference to comparative example 2 as 100%.
Device examples 21 to 41 the compound B2 in example 21 was replaced with a compound of B11, B18, B28, B39, B46, B58, B66, B81, B90, B99, B109, B115, B122, B133, B137, B152, B164, B170, B181, B189, respectively. As in table 8.
TABLE 8
/>
Comparative compound 2:
Some device configurations differ from the embodiments of the present invention, but remain effective.
Thermal stability experiments:
In a chamber for simulating production of vapor deposition, the chamber has a vacuum system, a heating system, and a rate detection system. Vacuumizing the cavity to 10-7torr according to the following steps After heating for 200 hours, the cavity was opened and the material in the material container was taken out, and the purity of the remaining material was measured by HPLC. The material was confirmed to be resistant to high temperature by comparing the initial material purity before heating with the material purity after heating for 200 hours. The test results are shown in Table 8:
TABLE 8
From the results, it can be seen that the compounds of the present invention have better heat stability.
The foregoing is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art, who is within the scope of the present invention, should make equivalent substitutions or modifications according to the technical scheme of the present invention and the inventive concept thereof, and should be covered by the scope of the present invention.

Claims (8)

1. An organic compound, characterized in that the organic compound is selected from any one of the following chemical structures:
2. A composition comprising the organic compound of claim 1 and a second host compound selected from one or more of the following chemical structures:
3. A light-emitting host material comprising the organic compound according to claim 1, and/or the composition according to claim 2.
4. An organic layer comprising the light-emitting host material according to claim 3.
5. Use of an organic compound according to claim 1, a composition according to claim 2, a light-emitting host material according to claim 3, and/or an organic layer according to claim 4 in an organic electroluminescent device.
6. An organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, or an electron transport layer, and the organic layer comprises the organic compound according to claim 1, the composition according to claim 2, and/or the light emitting host material according to claim 3.
7. The organic electroluminescent device according to claim 6, wherein the light-emitting layer comprises the organic compound according to claim 1 and/or the composition according to claim 2.
8. A display or lighting device, characterized in that it comprises an organic electroluminescent device as claimed in claim 7.
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CN112812119A (en) * 2020-05-20 2021-05-18 陕西莱特光电材料股份有限公司 Organic compound, and electronic element and device using same
KR102373387B1 (en) * 2021-11-26 2022-03-11 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
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CN111269078A (en) * 2018-12-05 2020-06-12 三星显示有限公司 Condensed-cyclic compound, composition comprising the same, and organic light-emitting device
CN112812119A (en) * 2020-05-20 2021-05-18 陕西莱特光电材料股份有限公司 Organic compound, and electronic element and device using same
KR102398180B1 (en) * 2021-08-31 2022-05-17 덕산네오룩스 주식회사 An organic electronic element comprising compound for organic electronic element and an electronic device thereof
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