阅读说明：本技术 有机发光化合物及其制备方法和器件 (Organic light-emitting compound, method for producing the same, and device ) 是由 汪康 孙向南 金成寿 张鹤 赵贺 孙峰 马晓宇 于 2019-09-26 设计创作，主要内容包括：本发明涉及一种有机发光化合物及其制备方法和器件,所述有机发光化合物的结构如化学式1所示：<Image he="616" wi="465" file="DDA0002216225650000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>本发明提供的有机发光化合物是具有蒽和胺结构的新型结构的有机发光化合物,含有该类化合物的有机电致发光器件具有较高的发光效率以及较长的寿命。本发明提供的有机发光化合物的制备方法,原料易得,合成步骤简单,产率较高。(The invention relates to an organic light-emitting compound, a preparation method and a device thereof, wherein the structure of the organic light-emitting compound is shown as a chemical formula 1: the organic luminescent compound provided by the invention is an organic luminescent compound with a novel structure of anthracene and amine structures, and an organic electroluminescent device containing the compound has high luminous efficiency and long service life. The invention provides a preparation method of an organic luminescent compoundThe raw materials are easy to obtain, the synthesis steps are simple, and the yield is high.)

1. An organic light emitting compound having a structure represented by chemical formula 1:

wherein Ar is₁、Ar₂Each independently is a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heterocyclic group, or are combined with each other to form a ring;

Ar₃hydrogen, deuterium, halogen, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combine with each other to form a ring;

r is hydrogen, deuterium, halogen, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylphosphino group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a ring;

l is a bond or is selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

2. The organic light-emitting compound according to claim 1, wherein Ar is Ar₃Selected from substituted or unsubstitutedPhenyl, biphenyl, terphenyl, naphthyl, fluorenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, pyrenyl, and phenanthryl.

3. The organic light-emitting compound according to claim 1, wherein Ar is Ar₃One selected from phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyrenyl and phenanthryl.

4. The organic light-emitting compound according to claim 1, wherein L is one of phenyl, biphenyl, terphenyl, naphthyl, pyrenyl, phenanthrenyl, fluorenyl, spiroyl, benzofuranyl, benzothienyl, dibenzofuranyl, and dibenzothiophenyl.

5. The organic light-emitting compound of claim 1, wherein L is phenyl or biphenyl.

6. An organic light-emitting compound according to claim 1, characterized in that it is selected from any one of the following structures:

7. a method for producing an organic light-emitting compound according to any one of claims 1 to 6, comprising the steps of:

adding the raw materials A, B, palladium tetratriphenylphosphine and potassium carbonate into toluene for coupling reaction to generate an intermediate C; brominating under the action of NBS to generate an intermediate D; forming a boric acid intermediate E by the intermediate D under the action of n-butyl lithium; the intermediate E and the raw material F form a compound shown in a chemical formula 1 under the action of palladium tetratriphenylphosphine and potassium carbonate;

the synthetic route is as follows:

wherein Hal represents halogen.

8. An organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer contains the organic luminescent compound according to any one of claims 1 to 6.

9. The organic electroluminescent device of claim 8, wherein the organic light-emitting compound is used as a hole transport layer material.

Technical Field

The invention relates to the technical field of luminescent materials, in particular to an organic luminescent compound and a preparation method and a device thereof.

Background

The organic semiconductor functional material of the OLED has been produced as a new generation of display technology, from information display to solid-state lighting devices, and the OLED has gradually advanced into the industrialization process along with the wide application prospect and the rapid advance of the technology.

The OLED is a hole and electron dual injection type light emitting device, and directly converts electric energy into light energy of organic semiconductor material molecules. OLEDs are typically of a double-layered structure, i.e. an organic functional layer sandwiched between a transparent conductive anode and a metal cathode. Under the drive of forward voltage that the anode is connected with the anode and the metal cathode is connected with the cathode, holes and electrons are respectively injected into the organic functional layer from the transparent anode and the metal cathode, are transmitted to the luminescent layer through other functional layers, approach to each other under the action of coulomb force, and are successfully captured to become electron-hole pairs, namely excitons, which are in the constraint energy level, and the excitons are radiated and excited to emit photons, namely, the organic semiconductor material emits light.

At present, the research of organic electroluminescent materials has been applied to many fields, many enterprises and talents have invested in the fields, and a large number of organic electroluminescent materials with excellent performance are developed successively, but the industrialization process of the technology still faces many key problems, and the development of more organic materials with higher efficiency is more important and urgent.

Disclosure of Invention

The object of the present invention is a novel organic light emitting compound having anthracene and amine structures, and a method and device for preparing the same. The organic electroluminescent device containing the material has higher luminous efficiency and longer service life.

In order to achieve the above purpose, the technical scheme of the invention is as follows:

the invention provides an organic light-emitting compound, the structure of which is shown in chemical formula 1:

wherein Ar is₁、Ar₂Each independently is a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heterocyclic group, or are combined with each other to form a ring;

Ar₃hydrogen, deuterium, halogen, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combine with each other to form a ring;

r is hydrogen, deuterium, halogen, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylphosphino group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a ring;

l is a bond or is selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

In the above technical scheme, Ar₃Preferred are self-aromatic substituent groups, and particularly preferred is one of substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, pyrenyl, and phenanthryl.

In the above technical scheme, Ar₃Further preferred is one of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, pyrenyl, and phenanthryl.

In the above technical solution, L is preferably one of phenyl, biphenyl, terphenyl, naphthyl, pyrenyl, phenanthrenyl, fluorenyl, spiroyl, benzofuranyl, benzothienyl, dibenzofuranyl, and dibenzothiophenyl.

In the above technical solution, L is further preferably phenyl or biphenyl.

The alkyl in the present invention preferably means a C1-C20 straight-chain alkyl group, branched-chain alkyl group, or cyclic alkyl group; the aryl group is an aryl group containing 6 to 60 carbon atoms; the heterocyclic group is a heterocycloalkyl group or a heteroaryl group having 3 to 20 carbon atoms.

In the present invention, the adjacent group may arbitrarily refer to a substituent which replaces an atom directly connected to an atom substituted with the corresponding substituent, a substituent which is disposed closest to the corresponding substituent in space, or another substituent which replaces an atom substituted with the corresponding substituent. The meaning of forming a ring by combining with an adjacent group is to combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted condensed ring thereof.

In the present invention, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: 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 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 heterocyclic group; or substituted with a substituent linked to two or more of the above exemplified substituents, or unsubstituted. For example, a substituent group "to which two or more substituent groups are attached may include a biphenyl group. In other words, a biphenyl group may be an aryl group, or may be interpreted as a substituent with two phenyl groups attached.

In the above technical solution, the organic light emitting compound of the present invention is optimally selected from any one of the following structures:

the invention also provides a preparation method of the organic luminescent compound, which comprises the following steps:

adding the raw materials A, B, palladium tetratriphenylphosphine and potassium carbonate into toluene for coupling reaction to generate an intermediate C; brominating under the action of NBS to generate an intermediate D; forming a boric acid intermediate E by the intermediate D under the action of n-butyl lithium; the intermediate E and the raw material F form a compound shown in a chemical formula 1 under the action of palladium tetratriphenylphosphine and potassium carbonate;

the synthetic route is as follows:

wherein Hal represents halogen, and the remaining substituent groups are as defined in chemical formula 1, and are not described herein again.

The present invention also provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer containing the compound represented by chemical formula 1 of the present invention.

In the above technical solution, the compound represented by chemical formula 1 of the present invention is used as a hole transport layer material.

The invention has the beneficial effects that:

the organic luminescent compound provided by the invention is an organic luminescent compound with a novel structure of anthracene and amine structures, and an organic electroluminescent device containing the compound has high luminous efficiency and long service life.

The preparation method of the organic luminescent compound provided by the invention has the advantages of easily available raw materials, simple synthesis steps and higher yield.

Detailed Description