阅读说明：本技术 化合物及有机电致发光器件 (Compound and organic electroluminescent device ) 是由 段炼 高文正 邵爽 于 2018-08-08 设计创作，主要内容包括：本发明提供一种用于有机电致发光器件的新的有机电致发光材料,以及使用这种新的有机电致发光材料的有机电致发光器件。本发明的新的有机电致发光材料由下述式(I)表示。<Image he="366" wi="700" file="DDA0001758375870000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(The present invention provides a novel organic electroluminescent material for an organic electroluminescent device, and an organic electroluminescent device using the novel organic electroluminescent material. The novel organic electroluminescent material of the present invention is represented by the following formula (I).)

1. A compound of formula (I),

wherein the content of the first and second substances,

X¹～X⁵are identical to or different from each other, and X¹～X⁵Each independently represents a nitrogen atom or a carbon atom, wherein X¹～X⁵At least one of which is a nitrogen atom;

R¹represents a group selected from H, halogen, cyano, hydroxyl, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C3 to C30 heteroaryl, and when the alkyl, aryl, and heteroaryl are substituted, the substituents are each independently selected from one or more of halogen, cyano, hydroxyl, C1 to C10 alkyl, C3 to C10 cycloalkyl, C1 to C10 alkenyl, C1 to C6 alkoxy or thioalkoxy, C6 to C20 aryl, and C6 to C20 heteroaryl containing a heteroatom selected from N, O, S, Si;

m is an integer of 1 to 8, R¹In the case where there are plural, plural R¹Adjacent R, equal to or different from each other¹Condensed with the connected benzene ring to form C6-C30 aryl or C3-C30 heteroaryl or do not form a ring;

Ar¹is a group formed by connecting benzimidazolyl and aryl of C6-C20;

Ar²a group selected from: H. halogen, cyano, hydroxyl, substituted or unsubstituted amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, wherein when the alkyl, alkoxy, arylamino, heteroarylamino, aryl, and heteroaryl are substituted, the substituents are independently selected from one or more of halogen, cyano, hydroxyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C20 aryl, and C6-C20 heteroaryl containing a heteroatom selected from N, O, S, Si;

n is an integer of 1 to 4, Ar²In the case where plural Ar's are present, plural Ar' s²The same or different from each other.

2. The compound of claim 1,

X³or X⁵Is a nitrogen atom.

3. The compound of claim 1,

X¹～X⁵at least 2 of which are nitrogen atoms.

4. A compound according to any one of claims 1 to 3, wherein Ar is Ar¹Selected from the following groups:

the symbol "-" indicates the expression of the ring structure, indicating that the linking site is located at any position on the ring structure that can form a bond.

5. A compound according to any one of claims 1 to 3, wherein Ar is Ar²Selected from the following groups: H. halogen, cyano, hydroxy, substituted or unsubstituted amino, C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkyl groups as defined above, hydroxy, substituted or unsubstituted amino, substituted or unsubstituted C6-C12 heteroaryl, substituted or unsubstituted C3-C30 heteroaryl, hydroxy,when the aryl group or the heteroaryl group is substituted, the substituents are each independently selected from one or more of halogen, cyano, hydroxyl, methoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and phenyl.

6. A compound according to any one of claims 1 to 3, wherein Ar is Ar²Selected from the following groups:

the symbol denotes a position bonded to a six-membered ring attached to an anthracene ring, and the symbol "-" denotes an expression of a ring structure, and denotes that a bonding site is located at any position on the ring structure where bonding can be achieved.

7. The compound according to claim 1, wherein the compound of formula (I) is selected from the group consisting of:

8. use of a compound according to any one of claims 1 to 7 as an electron transport material or a hole blocking material.

9. Use of a compound according to any one of claims 1 to 7 in an organic electroluminescent device.

10. An organic electroluminescent element comprising a first electrode, a second electrode and an organic layer comprising at least one light-emitting layer interposed between the first electrode and the second electrode, the organic layer further comprising one or more layers selected from the group consisting of an electron-injecting layer, an electron-transporting layer, a hole-injecting layer, a hole-blocking layer and a hole-transporting layer, wherein the compound according to any one of claims 1 to 7 is contained in the organic layer.

11. The organic electroluminescent device according to claim 10, wherein the organic layer containing the compound is one or more layers selected from an electron transport layer, an electron injection layer, a hole blocking layer and a light emitting layer.

Technical Field

The invention relates to a novel organic heterocyclic compound which can be used as an organic electroluminescent material, in particular to a compound containing an anthracene structure and application thereof in an organic electroluminescent device.

Background

With the continuous advance of OLED technology in both display and lighting fields, much attention is paid to the research on the core materials of OLED technology. As core materials, common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like.

Various types of electron transport materials having high transport ability and high stability have been reported in the past. In general, electron transport materials are compounds having electron-deficient nitrogen-containing heterocyclic groups, most of which have a higher electron affinity and thus a stronger ability to accept electrons, but common electron transport materials such as AlQ are used as the electron transport material compared to hole transport materials₃The electron mobility of (aluminum octahydroxyquinoline) is much lower than that of a hole transport material, so that in an OLED device, on one hand, the recombination probability of holes and electrons caused by the imbalance of injection and transport of carriers is reduced, and thus the luminous efficiency of the device is reduced, and on the other hand, the electron transport material with lower electron mobility causes the working voltage of the device to be increased, so that the power efficiency is affected, and the energy saving is unfavorable.

In the current manufacturers of OLED screens, Liq (lithium octahydroxyquinoline) is widely used as a technical means for doping into an ET material layer, so as to achieve low voltage and high efficiency of devices, and have the effect of prolonging the service life of the devices. Liq mainly has the effect that a small amount of metal lithium can be reduced under the action of electrons injected from the cathode, so that the N-doping effect of the electron transport material is achieved, the injection effect of electrons is remarkably improved, and on the other hand, lithium ions can achieve the effect of improving the electron mobility of the ET material through the coordination effect of N atoms in the electron transport material, so that a device with the Liq doped with the ET has low working voltage and high luminous efficiency.

However, in order to further satisfy the increasing demand for the photoelectric properties of OLED devices and the demand for energy saving of mobile electronic devices, new and efficient OLED materials are continuously developed, wherein the development of new electron transport materials with high electron injection capability and high mobility is of great importance.

Disclosure of Invention

In view of the problems of the prior art, the present invention is to provide an electron transport material, which can be used in an organic electroluminescent device to meet the demand for increasing the photoelectric performance of an OLED device.

That is, the inventors of the present invention have found that a novel compound having an anthracene structure, and found that good electron injecting and transporting properties can be achieved by adjusting a substituent group of an electron transporting material having an anthracene structure and introducing the same into an organic electroluminescent device.

Specifically, as one aspect of the present invention, there is provided a compound represented by the following formula (I),

wherein the content of the first and second substances,

X¹～X⁵are identical to or different from each other, and X¹～X⁵Each independently represents a nitrogen atom or a carbon atom, wherein X¹～X⁵At least one of which is a nitrogen atom;

R¹represents a group selected from H, halogen, cyano, hydroxyl, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C1 to C12 alkoxy, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C3 to C30 heteroaryl, and when the alkyl, aryl, and heteroaryl are substituted, the substituents are each independently selected from halogen, cyano, hydroxyl, C1 to C10 alkyl, C3 to C10 cycloalkyl, C1 to C10 alkenyl, C1 to C6 alkoxy or thioalkoxy, C6 to C20 aryl, and C6 to C20 heteroaryl containing a heteroatom selected from N, O, S, Si;

m is an integer of 1 to 8, R¹In the case where there are plural, plural R¹Adjacent R, equal to or different from each other¹Condensed with the attached benzene ring to form a C6-C30 aromatic hydrocarbonOr a C3-C30 heteroaryl group or no ring;

Ar¹is a group formed by connecting benzimidazolyl and aryl of C6-C20;

Ar²a group selected from: H. halogen, cyano, hydroxyl, substituted or unsubstituted amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, in the case where the above alkyl, alkoxy, arylamino, heteroarylamino, aryl, and heteroaryl are substituted, the substituents are each independently selected from one or more of halogen, cyano, hydroxyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C20 aryl, and heteroaryl containing a heteroatom selected from N, O, S, Si and C6-C20;

n is an integer of 1 to 4, Ar²In the case where plural Ar's are present, plural Ar' s²The same or different from each other.

Among the compounds represented by the formula (I), X is preferred⁵Is a nitrogen atom, or preferably X³Is a nitrogen atom, or preferably X¹～X⁵At least 2 of which are nitrogen atoms.

As another aspect of the present invention, there is also provided a use of the compound as described above in an organic electroluminescent device. The compound has a larger conjugated structure, can realize good electron injection and transmission performance when being used as an electron transmission material, and further can obtain an organic electroluminescent device with low driving voltage and high luminous efficiency. Of course, since the compound of the present invention has a higher electron affinity, it can also be used as a material for a hole-blocking layer.

The compound can be independently used in a hole blocking layer and an electron transport layer, and can provide more excellent device performance compared with the existing material. The compound of the invention can also be used by being matched with the existing electron transport material or hole blocking material, and can also bring excellent device performance.

The use of the compound of the present invention as an electron transport material or a hole blocking material is not limited to the field of organic electroluminescence, and the compound can be applied to other electronic device fields, for example, a power storage element, a solar cell, a photoelectric sensor, and the like.

Detailed Description

In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below.

In the present specification, unless otherwise indicated, the following terms have the following meanings:

in the present invention, the expression of Ca to Cb means that the group has carbon atoms a to b, and the carbon atoms do not include the carbon atoms of the substituents unless otherwise specified. In the present invention, the expression of chemical elements includes the concept of chemically identical isotopes, such as the expression of "hydrogen", and also includes the concept of chemically identical "deuterium" and "tritium". In the present invention, "D" may be used to represent "deuterium".

In the present description, the expression "substituted or unsubstituted" means substituted by one or more substituents selected from: halogen, cyano, hydroxyl, alkoxy, alkyl, aryl, heteroaryl, preferably fluorine, cyano, methoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, quinolyl, phenylpyridinyl, pyridylphenyl, and the like; or no substituent.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 10. Specific examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, decyl, and the like.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms. Specific examples of aryl groups include phenyl, biphenyl, naphthyl, anthryl, phenanthryl, and the like.

Hereinafter, a material for an organic electroluminescent device according to an aspect of the present invention will be described.

The inventor finds that when the anthracene structure-containing compound is used as an organic layer material of an organic electroluminescent device, the anthracene structure-containing compound takes a heteroaromatic ring as a bridging bond, the device efficiency can be obviously improved compared with the prior art. Specifically, the material for an organic electroluminescent element of the present invention is a compound represented by the following formula (I).

Wherein the content of the first and second substances,

X¹～X⁵are identical to or different from each other, and X¹～X⁵Each independently represents a nitrogen atom or a carbon atom, wherein X¹～X⁵At least one of which is a nitrogen atom;

R¹represents a group selected from H, halogen, cyano, hydroxyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, and when the alkyl, aryl, and heteroaryl are substituted, the substituents are each independently selected from halogen, cyano, hydroxyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C20 aryl, and one or more C6-C20 heteroaryl containing a heteroatom selected from N, O, S, Si, and more preferably the substituent is selected from halogen, cyano, hydroxyl, methoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, dibenzofuranyl, One or more of pyridyl, quinolinyl, phenylpyridyl, pyridylphenyl;

m is an integer of 1 to 8, R¹In the case where there are plural, plural R¹Adjacent R, equal to or different from each other¹Condensed with the benzene ring to which they are attachedForm C6-C30 aryl or C3-C30 heteroaryl or do not form a ring;

Ar¹is a group formed by connecting benzimidazolyl and aryl of C6-C20;

Ar²a group selected from: H. halogen, cyano, hydroxyl, substituted or unsubstituted amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, in the case where the above alkyl, alkoxy, arylamino, heteroarylamino, aryl, and heteroaryl are substituted, the substituents are each independently selected from one or more of halogen, cyano, hydroxyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C20 aryl, and C6-C20 heteroaryl containing a heteroatom selected from N, O, S, Si, and further preferably the substituent is selected from halogen, cyano, hydroxyl, methoxy, and methoxy, One or more of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothienyl, pyridyl, quinolinyl, phenylpyridinyl, pyridylphenyl;

n is an integer of 1 to 4, Ar²In the case where plural Ar's are present, plural Ar' s²The same or different from each other.

Examples of C1-C12 alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and the like, among which methyl, ethyl, n-propyl, isopropyl are preferred, and methyl is more preferred;

examples of the C1-C12 alkoxy group include groups obtained by linking the above-mentioned C1-C12 alkyl group with-O-, such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, etc., among which methoxy, ethoxy, propoxy and more preferably methoxy are preferable;

examples of C6-C30 arylamino groups include: phenylamino, diphenylamino, biphenylylamino, terphenylamino, naphthylamino, anthrylamino, phenanthrylamino, fluorenylamino, pyrenylamino,

Arylamino, fluoranthenylamino, picrylamino, peryleneamino, etc., and among them, diphenylamino is preferable;

examples of C3-C30 heteroarylamino groups are: pyridylamino, pyrimidylamino, pyrazinylamino, pyridazinylamino, quinolylamino, isoquinolylamino, acridinylamino, pyrrolylamino, imidazolylamino, pyrazolylamino, indolylamino, benzimidazolylamino, carbazolylamino, furanylamino, thienylamino, thiazolylamino, benzofuranylamino, benzothienylamino, benzothiazolylamino, dibenzofuranylamino, dibenzothiophenylamino, piperidinylamino, pyrrolidinylamino and the like, with pyridylamino being preferred;

examples of C6-C30 aryl groups include: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, pyrenyl,

Fluoro, anthryl, benzo [ a ]]Anthracenyl, benzo [ c ]]Phenanthryl, triphenylene, benzo [ k ]]Fluoranthenyl, benzo [ g ]]

Radical, benzo [ b]Triphenylene, picene, perylene, etc., of which phenyl and naphthyl are preferred, and phenyl is more preferred;

the heteroaryl group having C3 to C30 may be a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, or the like, and specific examples thereof include: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, indolyl, benzimidazolyl, indazolyl, imidazopyridinyl, benzotriazolyl, carbazolyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, benzisoxazolyl, benzisothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzofuranyl, dibenzothienyl, piperidyl, pyrrolidinyl, piperazinyl, morpholinyl, phenazinyl, phenothiazinyl, phenoxazinyl, and the like are preferred among them, pyridyl, quinolyl, pyrrolidinyl, piperazinyl, morpholinyl, phenazinyl, phenothiazinyl, and the like, Dibenzofuranyl and dibenzothienyl, and more preferably pyridyl.

The compound of the present invention can provide very excellent performance as an electron transport material, and the specific reason is not clear, and the following reasons are presumed to be possible:

first, the structure of the present invention is selected to have a group with a strong electron affinity, such as Ar¹Comprising a phenylimidazolyl group, in the compound of the formula (I) of the present invention, X¹～X⁵At least 1 of the compounds is nitrogen atom, that is, the six-membered ring as a bridging bond is a nitrogen-containing heterocycle, so that the compound of the invention comprises groups such as pyridyl, pyrimidyl and triazinyl, and through the nitrogen-containing bridging bond, the electronegativity of the bridging part is improved, which is beneficial to the improvement of electron transport efficiency.

Secondly, the compound of the invention introduces a novel anthracene ring with a larger conjugated structure as a parent nucleus, and the parent nucleus is connected with Ar¹The inclusion of benzimidazolyl groups provides excellent compatibility with Ar, while the inclusion of such compounds as pyridine, pyrimidine, triazine as described above²The bridging bond between the two compounds makes the compound have higher electron affinity and is very suitable for the flow of electrons in the compound, and the bridging bond is closer to the work function of the cathode material, so that the material can easily obtain electrons from the cathode and has strong electron injection property.

Meanwhile, the compound has a very good coplanar conjugated structure, so that the compound molecules can fully generate pi-pi interaction between groups in a solid state, thereby being beneficial to the transmission of electrons among material molecules and enabling the material to have very high electron mobility.

Preferred among the compounds of formula (I) according to the invention is X³、X⁵At least one of which is a nitrogen atom. Specifically, the embodiment of the compound represented by formula (I) of the present invention can also be represented by the following formulae (II) and (III).

That is, when only one nitrogen atom is contained in the six-membered ring as a bridging bond, the nitrogen atom is located in the ortho-or para-position of the anthracycline, i.e., X in formula (I)³Or X⁵The inventor finds that the compound can provide better electron transport performance when being used in an organic electroluminescent device, and supposes that the nitrogen atom is positioned at the ortho-position or the para-position of an anthracene ring, and the electron absorption property of a six-membered ring is better exerted due to the arrangement of electron clouds, so that the compound has more favorable electron affinity and electron injection property as a whole, and the electron mobility of the organic electroluminescent material is favorably improved, the driving voltage is reduced, and the luminous efficiency is improved.

Further, in the present invention, when the structure of the compound represented by the above general formula is used, the compound is particularly preferable because not only excellent electron transport efficiency but also better life characteristics can be obtained when the compound is used in an organic electroluminescent device. The reason is presumed to be that when a nitrogen atom exists at the ortho position of the six-membered ring closer to the anthracene ring, on the one hand, the nitrogen atom is easy to generate more obvious pi-pi interaction with the anthracene ring with a larger conjugated structure, so that the electron mobility of the organic electroluminescent material is improved, the injection of electrons is facilitated, and the driving voltage is reduced; on the other hand, the nitrogen atom is close to the anthracene ring, and a hydrogen bond is formed between the hydrogen atom and the nitrogen atom on the anthracene ring, so that a larger coplanar conjugated structure is easily formed on the whole compound, the whole chemical property of the compound is more stable, the service life of the compound is prolonged, and the film forming performance of the compound in an organic layer can be improved possibly, so that the efficiency of an electron transport layer can be improved, the stability of the electron transport layer can be improved, and the device is efficient and durable.

Further, among the compounds represented by the formula (I) of the present invention, X is also preferable¹～X⁵At least 2 of which are nitrogen atoms, provide better electron transport properties. It is presumed that when 2 or more than 2 nitrogen atoms are present in the six-membered ring as a bridging bond, the compound as a whole has a higher electron affinity and a stronger electron accepting ability, and therefore contributes to further reduction in driving voltage and improvement in light emission efficiency. When X is present, X is¹～X⁵Is not limited by formula (II) or formula (III) when at least 2 of them are nitrogen atoms, i.e. X³Or X⁵May not be a nitrogen atom.

In the compound of the formula (I) of the present invention, Ar¹The aryl group is a group in which a benzimidazolyl group and an aryl group having 6 to 20 carbon atoms are bonded to each other, and is preferably a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, or the like, and more preferably a phenyl group. Ar (Ar)¹The aromatic group may contain 1 to 5 aromatic groups, and preferably 2 aromatic groups.

Further, Ar in the compound of the present invention¹Preferably selected from the following groups:

when Ar of the compound of the present invention is¹In the case of the above groups, the physical and chemical properties of the electron transport layer formed using the compound of the present invention are excellent, probably because the compound as a whole is more likely to form good crystals suitable for the flow of electrons in the electron transport layer.

In the compounds of the invention R¹Represents a group selected from H, halogen, cyano, hydroxyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, and when the alkyl, aryl, and heteroaryl groups are substituted, the substituents are each independentlyIs selected from halogen, cyano, hydroxyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C20 aryl and one or more of C6-C20 heteroaryl containing hetero atom selected from N, O, S, Si, more preferably the substituent is one or more selected from halogen, cyano, hydroxyl, methoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothienyl, pyridyl, quinolyl, phenylpyridinyl and pyridylphenyl, m is an integer of 1-8, R is an integer of 1-8¹In the case where there are plural, plural R¹Adjacent R, equal to or different from each other¹Condensed with the attached benzene ring to form a C6-C30 aryl group or a C3-C30 heteroaryl group or no ring, because the anthracene nucleus structure of the invention plays an important role in the physicochemical properties of the compounds of the invention.

Ar in the Compound of the present invention²Preferably selected from the following groups: H. halogen, cyano, hydroxyl, substituted or unsubstituted amino, C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, wherein when the alkyl, aryl, and heteroaryl are substituted, the substituents are each independently selected from one or more of halogen, cyano, hydroxyl, methoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and phenyl.

Ar in the Compound of the present invention²Preferably selected from the following groups:

the symbol indicates a position bonded to an anthracene ring as a mother nucleus or a six-membered ring as a bridging bond, and the symbol "-" indicates an expression of a ring structure indicating that a linking site is located at an arbitrary position on the ring structure capable of forming a bond.

Preferred structures of the compounds according to the present invention include, but are not limited to, the compounds having the following structures.

The compounds of the present invention are further preferably compounds having the following specific chemical structures,

the compound of the present invention can be applied to organic electronic devices, for example, organic electroluminescent devices, lighting devices, organic thin-film transistors, organic field-effect transistors, organic thin-film solar cells, large-area sensors such as information labels, electronic artificial skin sheets and sheet-type scanners, electronic paper, organic EL panels, and the like.

In addition, the invention also provides the application of the compound in an organic electroluminescent device. Wherein the compound can be used as, but not limited to, an electron transport layer material.

Specifically, one embodiment of the present invention provides an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layers comprise at least a light-emitting layer, and the organic layers comprise a compound of the present invention.

Further, as the organic layer between the first electrode and the second electrode, an electron injection layer, an electron transport layer, a light emitting layer, a hole transport layer, a hole injection layer, and the like are generally included, and among them, the organic layer containing the compound of the present invention can be used as, but not limited to, an electron transport layer.

Next, the organic electroluminescent device will be explained in detail.

The organic electroluminescent device includes first and second electrodes on a substrate, and an organic layer between the electrodes, which may be a multi-layered structure. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

As the substrate, a substrate used for a general organic light emitting display, for example: glass, polymer materials, glass with TFT components, polymer materials, and the like.

The anode material can be Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and tin dioxide (SnO)₂) Transparent conductive materials such as zinc oxide (ZnO), metal materials such as silver and its alloys, aluminum and its alloys, organic conductive materials such as PEDOT, and multilayer structures of these materials.

The cathode material can be selected from metals, metal mixtures and oxides such as magnesium silver mixture, LiF/Al, ITO and the like.

The organic electroluminescent device may further include a hole transport layer and a hole injection layer between the light emitting layer and the anode, and these layers may include one or more combinations of compounds HT1-HT34 listed below, but are not limited to the following compounds.

The light emitting layer of the organic electroluminescent device may include a host material and a light emitting dye, wherein the host may be one or a combination of more of the compounds BFH1-BFH14 listed below, but is not limited to the following compounds.

The luminescent dye may be a combination of one or more of the compounds BFD1-BFD9 listed below, but is not limited to the following compounds.

The organic layer of the organic electroluminescent device may include an electron transport layer, and a hole blocking layer between the light emitting layer and the electron transport layer. The compound can be independently used in a hole blocking layer and an electron transport layer, and can provide more excellent device performance compared with the existing material. The compound of the invention can also be used by being matched with the existing electron transport material or hole blocking material, and can also bring excellent device performance. For example, the compounds of the present invention can achieve very good device performance when complexed with liq. In addition, the hole blocking layer and the electron transport layer materials that can be used in combination with the compounds of the present invention may be one or a combination of more of the compounds ET1-ET57 listed below, but are not limited to the following compounds.

When the compound of the present invention is used in combination with other existing materials, the compounding ratio of the compound of the present invention may be 1 to 99% by weight, preferably 30 to 75% by weight, and more preferably 40 to 60% by weight.

An electron injection layer may be further included in the organic electroluminescent device between the electron transport layer and the cathode, and the electron injection layer material includes one or more combinations of the following listed materials, but is not limited to the following materials.

LiQ、LiF、NaCl、CsF、Li₂O、Cs₂CO₃、BaO、Na、Li、Ca。