阅读说明：本技术 化合物及包含其的有机发光元件 (Compound and organic light-emitting element comprising same ) 是由 车龙范 金振珠 尹洪植 洪性佶 洪玩杓 于 2019-06-12 设计创作，主要内容包括：本申请涉及由以下化学式1表示的化合物及包含其的有机发光元件。所述化学式1中,L1和L2彼此相同或不同,各自独立地为直接键合、或者取代或未取代的亚芳基,A和B中的至少一个为取代或未取代的胺基,其余为取代或未取代的芳基。[化学式1]<Image he="698" wi="700" file="DDA0002091709360000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(The present application relates to a compound represented by the following chemical formula 1 and an organic light emitting element including the same. In said chemical formula 1, L1 andl2 are the same or different from each other and are each independently a direct bond, or a substituted or unsubstituted arylene group, at least one of A and B is a substituted or unsubstituted amine group, and the remainder are substituted or unsubstituted aryl groups. [ chemical formula 1])

1. A compound represented by the following chemical formula 1:

chemical formula 1

In the chemical formula 1, the metal oxide is represented by,

l1 and L2, which are identical to or different from one another, are each independently a direct bond or a substituted or unsubstituted arylene group,

at least one of A and B is a substituted or unsubstituted amine group, and the remainder is a substituted or unsubstituted aryl group.

2. The compound of claim 1, wherein at least one of a and B is represented by the following chemical formula 2:

chemical formula 2

In the chemical formula 2, the first and second organic solvents,

ar1 and Ar2, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

3. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 101 to 103:

chemical formula 101

Chemical formula 102

Chemical formula 103

In the chemical formulae 101 to 103,

l1 and L2 are as defined in said chemical formula 1,

a1 and B1, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group,

ar3 to Ar6, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

4. The compound of claim 1, wherein L1 and L2, equal to or different from each other, are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

5. The compound of claim 1, wherein at least one of a and B is a substituted or unsubstituted amine group and the remainder are a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

6. The compound of claim 1, wherein at least one of a and B is an amine group substituted or unsubstituted with an aryl or heteroaryl group, and the remainder are a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

7. The compound of claim 2, wherein Ar1 and Ar2, equal to or different from each other, are each independently a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl.

8. The compound of claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the following structural formulas:

9. an organic light-emitting element comprising: a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound according to any one of claims 1 to 8.

10. The organic light-emitting element according to claim 9, wherein the organic layer comprises a light-emitting layer containing the compound.

11. The organic light-emitting element according to claim 9, wherein the organic layer comprises an electron-suppressing layer containing the compound.

12. The organic light-emitting element according to claim 9, wherein the organic layer comprises a hole injection layer or a hole transport layer containing the compound.

Technical Field

The present application claims priority based on korean patent application No. 10-2018-0068202 filed by 14.06.2018 to the korean patent office, the entire contents of which are incorporated herein by reference.

The present application relates to a compound represented by chemical formula 1 and an organic light emitting element including the same.

Background

In general, the organic light emission phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic substance. An organic light emitting element utilizing an organic light emitting phenomenon generally has a structure including an anode and a cathode, and an organic layer located between the anode and the cathode. Here, in order to improve the efficiency and stability of the organic light emitting element, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting element, if a voltage is applied between both electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned again to the ground state.

There is a continuing demand for the development of new materials for organic light emitting elements as described above.

Disclosure of Invention

Problems to be solved

The present application provides a compound represented by chemical formula 1 and an organic light emitting element including the same.

Means for solving the problems

The present application provides a compound represented by the following chemical formula 1.

[ chemical formula 1]

In the chemical formula 1 described above,

l1 and L2, which are identical to or different from one another, are each independently a direct bond or a substituted or unsubstituted arylene group,

at least one of A and B is a substituted or unsubstituted amine group, and the remainder is a substituted or unsubstituted aryl group.

In addition, the present application provides an organic light emitting element including: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include the compound.

Effects of the invention

An organic light-emitting element using the compound according to an embodiment of the present application can realize a low driving voltage, high light-emitting efficiency, or a long lifetime.

Drawings

Fig. 1 shows an example of an organic light-emitting element in which a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 9 are sequentially stacked.

Fig. 2 shows an example of an organic light-emitting element in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron suppression layer 5, a light-emitting layer 6, a hole suppression layer 7, an electron injection and transport layer 8, and a cathode 9 are stacked in this order.

Detailed Description

The present specification will be described in more detail below.

The present specification provides a compound represented by the above chemical formula 1.

According to an embodiment of the present application, the compound represented by the above chemical formula 1 has an advantage of being capable of adjusting triplet energy by having the above-described parent structure, and can exhibit characteristics of long life and high efficiency.

In the present specification, examples of the substituent are described below, but the substituent is not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from the group consisting of hydrogen, a halogen group, a nitrile group, a nitro group, a hydroxyl group, an ester group, a carbonyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or substituted with 2 or more substituents selected from the above-exemplified substituents, or having no substituent. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl can be aryl, and can also be interpreted as a substituent with 2 phenyl groups attached.

In the context of the present specification,refers to a site linked to another substituent or a binding moiety.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

In the present specification, the number of carbon atoms of the ester group is not particularly limited, but is preferably 1 to 50. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 50. Specifically, the compound may have the following structure, but is not limited thereto.

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 50. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethyl-propyl group, 1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl, 5-methylhexyl, etc., but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, and the number of carbon atoms is preferably 1 to 20. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, 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-methylbenzyloxy and the like, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples thereof include, but are not limited to, ethylene, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylmethylen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (diphenyl-1-yl) ethen-1-yl, stilbenyl, styryl and the like.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 24. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,And a fluorenyl group, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

When the above-mentioned fluorenyl group is substituted, it may be And the like, but is not limited thereto.

In the present specification, the heterocyclic group includes one or more heteroatoms other than carbon atoms, and specifically, the above-mentioned heteroatoms may include one or more atoms selected from O, N, Se, S and the like. The number of carbon atoms of the heterocyclic group is not particularly limited, but the number of carbon atoms is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl group,Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzopyrazinyl, pyrazinyl, triazinyl, pyrazinyl, carbazolyl, benzoxazolylAzolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoylAzolyl group,Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.

In the present specification, the aromatic hydrocarbon ring is not limited to 2-valent groups, and the above description of the aryl group can be applied.

In the present specification, the heterocyclic group can be applied to the above-mentioned explanation about the heterocyclic group, except that the heterocyclic group is a 2-valent group.

In the present specification, aryloxy, arylthio(s) ((R))Aryl thio), arylsulfonyl (C)Aryl group in Aryl sulfonyl), Aryl phosphino, aralkyl, aralkylamino, aralkenyl, and arylamino can be applied to the Aryl group described above.

In the present specification, alkylthio group(s) (ii)Alkyl thio xy), alkylsulfonyl(s) ((s) As the Alkyl group in Alkyl sulfoxy), an arylalkyl group, and an alkylamino group, the above description about the Alkyl group can be applied.

In the present specification, the alkenyl group in the aralkenyl group can be applied to the above-mentioned description about the alkenyl group.

In the present specification, the aryl group can be applied to the above-mentioned description of the aryl group, except that the arylene group is a 2-valent group.

In the present specification, the phrase "adjacent groups may be bonded to each other to form a ring" means that the adjacent groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, or a substituted or unsubstituted aromatic heterocyclic ring.

In the present specification, the aliphatic hydrocarbon ring means a non-aromatic ring and means a ring composed of only carbon and hydrogen atoms.

In the present specification, examples of the aromatic hydrocarbon ring include, but are not limited to, phenyl, naphthyl, and anthracenyl.

In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing 1 or more heteroatoms.

In the present specification, the aromatic heterocyclic ring means an aromatic ring containing 1 or more hetero atoms.

In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.

According to an embodiment of the present application, L1 and L2 are the same or different from each other and each independently is a direct bond, or a substituted or unsubstituted arylene group.

According to an embodiment of the present application, L1 and L2 are the same or different from each other and each independently represents a direct bond or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

According to an embodiment of the present application, L1 and L2 are the same or different from each other and each independently represents a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an embodiment of the present application, L1 and L2 are the same or different from each other and each independently represents a direct bond or a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.

According to an embodiment of the present application, L1 and L2 are the same as or different from each other, and each independently represents a direct bond, a phenylene group, a biphenylene group, a terphenylene group, a tetraphenylene group, a naphthylene group, a 2-valent anthracenyl group, a 2-valent fluorenyl group, a 2-valent phenanthrenyl group, a 2-valent pyrenyl group, or a 2-valent triphenylene group.

According to an embodiment of the present application, L1 and L2 are the same as or different from each other, and each is independently a direct bond or any one selected from the following structural formulae.

According to an embodiment of the present application, the above L1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

According to an embodiment of the present application, L1 and L2, equal to or different from each other, are each independently biphenylene, phenylene, or a direct bond.

According to one embodiment of the present application, L1 is biphenylene.

According to an embodiment of the present application, L1 is any one of the following structures.

According to an embodiment of the present application, L1 is phenylene.

According to an embodiment of the present application, L1 is any one of the following structures.

According to one embodiment of the present application, L1 is a direct bond.

According to one embodiment of the present application, L2 is biphenylene.

According to an embodiment of the present application, L2 is any one of the following structures.

According to an embodiment of the present application, L2 is phenylene.

According to an embodiment of the present application, L2 is any one of the following structures.

According to one embodiment of the present application, L2 is a direct bond.

According to an embodiment of the present application, at least one of a and B is a substituted or unsubstituted amine group, and the remainder are substituted or unsubstituted aryl groups.

According to an embodiment of the present application, at least one of a and B is an amine group substituted or unsubstituted with an aryl group or a heterocyclic group, and the remainder is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to an embodiment of the present application, at least one of a and B is an amine group substituted or unsubstituted with an aryl group having 6 to 60 carbon atoms or a heterocyclic group having 2 to 60 carbon atoms, and the remainder is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to an embodiment of the present application, at least one of a and B is an amine group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms or a heterocyclic group having 2 to 30 carbon atoms, and the remainder is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present application, at least one of a and B is an amine group substituted or unsubstituted with an aryl group having 6 to 15 carbon atoms or a heterocyclic group having 2 to 15 carbon atoms, and the remainder is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

According to an embodiment of the present application, at least one of a and B is a substituted or unsubstituted amine group, and the remainder is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

According to an embodiment of the present application, at least one of a and B is an amine group substituted or unsubstituted with an aryl group or a heteroaryl group, and the remainder is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

According to an embodiment of the present application, at least one of a and B is an amine group substituted or unsubstituted with 1 or more groups selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group, and the remainder is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

According to an embodiment of the present invention, at least one of a and B is an amine group substituted or unsubstituted with 1 or more groups selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group substituted with a phenyl group, and the remainder is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

According to an embodiment of the present application, at least one of a and B is represented by the following chemical formula 2.

[ chemical formula 2]

In the chemical formula 2 described above, the,

ar1 and Ar2, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present application, Ar1 and Ar2, which are the same as or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an embodiment of the present application, Ar1 and Ar2, which are the same as or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an embodiment of the present application, Ar1 and Ar2, which are the same as or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

According to an embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

According to an embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each is independently a phenyl group substituted or unsubstituted with an alkyl group or an aryl group; biphenyl substituted or unsubstituted with alkyl or aryl; a terphenyl group substituted or unsubstituted with an alkyl group or an aryl group; fluorenyl substituted or unsubstituted with alkyl or aryl; dibenzofuranyl substituted or unsubstituted with alkyl or aryl; dibenzothienyl substituted or unsubstituted with alkyl or aryl; or carbazolyl substituted or unsubstituted with alkyl or aryl.

According to an embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each is independently a phenyl group, a biphenyl group, a terphenyl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group substituted with a phenyl group.

According to an embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each is independently any one selected from the following structural formulae.

According to an embodiment of the present application, the chemical formula 1 may be represented by any one of the following chemical formulas 101 to 103.

[ chemical formula 101]

[ chemical formula 102]

[ chemical formula 103]

In the above-mentioned chemical formulas 101 to 103,

l1 and L2 are as defined in the above chemical formula 1,

a1 and B1, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group,

ar3 to Ar6, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present application, a1 and B1, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to an embodiment of the present application, a1 and B1, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present application, a1 and B1, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

According to an embodiment of the present application, a1 and B1, equal to or different from each other, are each independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl.

According to an embodiment of the present application, Ar3 to Ar6, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an embodiment of the present application, Ar3 to Ar6, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an embodiment of the present application, Ar3 to Ar6, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an embodiment of the present application, Ar3 to Ar6 are the same as or different from each other, and each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

According to an embodiment of the present application, Ar3 and Ar4 are the same as or different from each other, and each is independently a phenyl group substituted or unsubstituted with an alkyl group or an aryl group; biphenyl substituted or unsubstituted with alkyl or aryl; a terphenyl group substituted or unsubstituted with an alkyl group or an aryl group; fluorenyl substituted or unsubstituted with alkyl or aryl; dibenzofuranyl substituted or unsubstituted with alkyl or aryl; dibenzothienyl substituted or unsubstituted with alkyl or aryl; or carbazolyl substituted or unsubstituted with alkyl or aryl.

According to one embodiment of the present application, Ar3 and Ar4 are the same or different from each other and are each independently a phenyl group, a biphenyl group, a terphenyl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group substituted with a phenyl group.

According to an embodiment of the present application, Ar5 and Ar6 are the same as or different from each other, and each is independently a phenyl group substituted or unsubstituted with an alkyl group or an aryl group; biphenyl substituted or unsubstituted with alkyl or aryl; a terphenyl group substituted or unsubstituted with an alkyl group or an aryl group; fluorenyl substituted or unsubstituted with alkyl or aryl; dibenzofuranyl substituted or unsubstituted with alkyl or aryl; dibenzothienyl substituted or unsubstituted with alkyl or aryl; or carbazolyl substituted or unsubstituted with alkyl or aryl.

According to an embodiment of the present application, Ar5 and Ar6 are the same as or different from each other, and each is independently a phenyl group, a biphenyl group, a terphenyl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group substituted with a phenyl group.

According to an embodiment of the present application, the compound represented by the above chemical formula 1 is any one selected from the following structural formulae.

In addition, the present application provides an organic light emitting element including the above compound.

One embodiment of the present application provides an organic light emitting device, including: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound.

In the present application, when a member is referred to as being "on" another member, it includes not only a case where the member is in contact with the another member but also a case where the another member is present between the two members.

In the present application, when a part is referred to as "including" a certain component, unless otherwise specified, it means that the other component may be further included, but the other component is not excluded.

The organic layer of the organic light-emitting device of the present application may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light-emitting element is not limited to this, and a smaller number of organic layers may be included.

In one embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

In one embodiment of the present invention, the organic layer includes an electron-suppressing layer, and the electron-suppressing layer includes the compound.

In one embodiment of the present invention, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

In one embodiment of the present application, the organic light emitting device may further include 1 or 2 or more layers selected from a hole injection layer, a hole transport layer, an electron injection layer, an electron suppression layer, and a hole suppression layer.

The light emitting layer may include a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic condensed ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a dibenzofuran derivative and a ladder-type furan compoundPyrimidine derivatives, etc., but are not limited thereto.

In one embodiment of the present application, the organic layer including the compound of chemical formula 1 has a thickness ofTo

In one embodiment of the present application, the organic light emitting device includes: a first electrode, a second electrode provided so as to face the first electrode, a light-emitting layer provided between the first electrode and the second electrode, and 2 or more organic layers provided between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, wherein at least one of the 2 or more organic layers contains the compound. In one embodiment of the present application, the 2 or more organic layers may be 2 or more layers selected from among an electron suppression layer, a hole injection layer, and a hole transport layer.

In one embodiment of the present application, the organic layer includes a hole injection layer or a hole transport layer containing a compound including an arylamino group, a carbazolyl group, or a benzocarbazolyl group, in addition to the organic layer including the compound.

In another embodiment, the organic light emitting element may be a normal type (normal type) organic light emitting element in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

In another embodiment, the organic light emitting element may be an inverted (inverted) type organic light emitting element in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

For example, fig. 1 and 2 show an example of the structure of an organic light-emitting element according to an embodiment of the present application.

Fig. 1 illustrates an example of the structure of an organic light-emitting element in which a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 9 are sequentially stacked. In this structure, the above compound may be contained in the above light-emitting layer 3.

Fig. 2 illustrates a structure of an organic light-emitting element in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron suppression layer 5, a light-emitting layer 6, a hole suppression layer 7, an electron injection and transport layer 8, and a cathode 9 are sequentially stacked. In the structure described above, the compound may be contained in one or more of the hole injection layer 3, the hole transport layer 4, the light-emitting layer 6, and the electron suppression layer 5.

The organic light-emitting device of the present application can be produced by a material and a method known in the art, except that one or more layers of the organic layer contain the compound of the present application, that is, the compound.

When the organic light emitting element includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

The organic light emitting device of the present application may be manufactured using materials and methods known in the art, except that one or more layers of the organic layer include the compound described above, i.e., the compound represented by chemical formula 1.

For example, the organic light emitting element of the present application can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, the following production can be performed: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a Physical Vapor Deposition (PVD) method such as a sputtering method or an electron beam evaporation method, forming an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting element.

In addition, the compound of chemical formula 1 may be used not only for forming an organic layer by a vacuum deposition method but also for forming an organic layer by a solution coating method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light-emitting element can be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (international patent application publication No. 2003/012890). However, the production method is not limited thereto.

In one embodiment of the present application, the first electrode is an anode, and the second electrode is a cathode.

In another embodiment, the first electrode is a cathode and the second electrode is an anode.

The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the above-mentioned anode material that can be used in the present inventionMetals such as vanadium, chromium, copper, zinc, gold, etc., or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO: al or SnO₂: a combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.

The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO₂And a multilayer structure material such as Al, but not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: the organic light-emitting device has the ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film formation ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a material having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and a substance having a high quantum efficiency with respect to fluorescence or phosphorescence is preferable. As an example, there is 8-hydroxy-quinoline aluminum complex (Alq)₃) (ii) a An anthracene compound; a pyrene-based compound; a carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzo (b) isAzole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can inject electrons from the cathode well and transfer the electrons to the light emitting layer, and a substance having a high electron mobility is preferable. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.

The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: has an ability to transport electrons, an electron injection effect from a cathode, an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and is excellent in thin-film formability. Specifically, there are fluorenone, anthraquinone dimethane (Anthraquinodimethane), diphenoquinone, thiopyran dioxide, and,Azole,Oxadiazole, triazole, imidazole, triazine, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complexes include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.

The electron-inhibiting layer prevents electrons injected from the electron-injecting layer from entering the hole-injecting layer through the light-emitting layer, thereby improving the life and efficiency of the device. The known material may be used without limitation, and may be formed between the light-emitting layer and the hole-injecting layer or between the light-emitting layer and a layer which performs both hole injection and hole transport.

The hole-inhibiting layer is a layer that prevents holes from reaching the cathode and can be formed under the same conditions as those of the hole-injecting layer. Specifically, there areAn oxadiazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex (aluminum complex), and the like, but the present invention is not limited thereto.

The organic light emitting element according to the present application may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.

The production of the compound represented by the above chemical formula 1 and the organic light emitting device comprising the same is specifically described in the following examples. However, the following examples are provided to illustrate the present specification, and the scope of the present specification is not limited thereto.

< production example A >

Compound a was produced in the procedure described above.

< production example B >

Compound B was produced in the procedure described above.

< production example C >

Compound C was produced in the procedure described above.

< production example D >

Compound D was made in the procedure described above.

< production example 1> -production of Compound 1

In a 500ml round-bottomed flask under nitrogen atmosphere, after completely dissolving Compound A (8.45g,25.00mmol) and a-1(12.68g,28.75mmol) in 240ml of tetrahydrofuran, a 2M aqueous potassium carbonate solution (120ml) was added, tetrakis (triphenylphosphine) palladium (0.87g,0.75mmol) was added, and the mixture was stirred under heating for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 180ml of tetrahydrofuran to obtain compound 1(9.56g, 55%).

MS[M+H]⁺＝700

< production example 2> -production of Compound 2

After completely dissolving compound B (13.47g,19.33mmol) and a-2(3.82g,22.22mmol) in 220ml of tetrahydrofuran in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (110ml) was added, tetrakis (triphenylphosphine) palladium (0.67g,0.58mmol) was added, and the mixture was stirred under heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220ml of ethyl acetate to obtain Compound 2(11.34g, 74%).

MS[M+H]⁺＝790

< production example 3> -production of Compound 3

After completely dissolving compound C (8.64g,22.27mmol) and a-3(11.29g,25.61mmol) in 240ml of tetrahydrofuran in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, tetrakis (triphenylphosphine) palladium (0.77g,0.67mmol) was added, and the mixture was stirred under heating for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 280ml of ethyl acetate to obtain compound 3(11.24g, 67%).

MS[M+H]⁺＝750

< production example 4> -production of Compound 4

Compound D (10.34g,17.80mmol) and a-4(4.07g,20.47mmol) were completely dissolved in 260ml of tetrahydrofuran in a 500ml round-bottom flask under a nitrogen atmosphere, and then a 2M aqueous potassium carbonate solution (130ml) was added, followed by addition of tetrakis (triphenylphosphine) palladium (0.62g,0.53mmol), followed by stirring with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 270ml of ethyl acetate to obtain compound 4(7.75g, 58%).

MS[M+H]⁺＝700

< production example 5> -production of Compound 5

After completely dissolving Compound A (7.65g,22.63mmol) and a-5(10.28g,26.03mmol) in 240ml of tetrahydrofuran in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, tetrakis (triphenylphosphine) palladium (0.78g,0.68mmol) was added, and the mixture was stirred under heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 260ml of ethyl acetate to obtain compound 5(6.88g, 46%).

MS[M+H]⁺＝654

< production example 6> -production of Compound 6

After completely dissolving Compound C (6.54g,16.86mmol) and a-6(7.35g,19.38mmol) in 240ml of tetrahydrofuran in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, tetrakis (triphenylphosphine) palladium (0.58g,0.51mmol) was added, and the mixture was stirred under heating for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250ml of ethyl acetate to obtain Compound 6(5.44g, 47%).

MS[M+H]⁺＝688