CN113874366A

CN113874366A - Heterocyclic compound and organic light emitting device including the same

Info

Publication number: CN113874366A
Application number: CN202080038984.6A
Authority: CN
Inventors: 许瀞午; 洪性佶; 许东旭; 李在卓; 尹正民
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2019-09-11
Filing date: 2020-09-08
Publication date: 2021-12-31
Anticipated expiration: 2040-09-08
Also published as: KR102654051B1; KR20210031369A; WO2021049840A1; CN113874366B; KR20210031396A; KR102483545B1

Abstract

The present specification relates to a heterocyclic compound and an organic light-emitting device including the same.

Description

Heterocyclic compound and organic light emitting device including the same

Technical Field

The present specification claims priority of korean patent application No. 10-2019-0112880, which was filed in 2019, 09, 11 to the korean patent office, the entire contents of which are incorporated herein.

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed 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 device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.

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

Disclosure of Invention

Technical subject

The present specification provides heterocyclic compounds and organic light emitting devices comprising the same.

Means for solving the problems

The present specification provides heterocyclic compounds of the following chemical formula 1.

[ chemical formula 1]

In the above-described chemical formula 1,

at least one of X1 to X3 is N, and the remainder are CH,

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,

ar2 and Ar3, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group,

ar1 is a fluoranthenyl group substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; a fluorenyl group which is substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group and a heterocyclic group; or a polycyclic heterocyclic group containing O, N and S and substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group.

In addition, the present specification provides an organic light emitting device, including: the organic light-emitting device includes a first electrode, a second electrode provided to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include the heterocyclic compound.

Effects of the invention

An organic light-emitting device using the heterocyclic compound according to an embodiment of the present specification can achieve an improvement in efficiency.

An organic light emitting device using the heterocyclic compound according to an embodiment of the present specification can reduce a driving voltage.

An organic light-emitting device using the heterocyclic compound according to an embodiment of the present specification can achieve improvement in lifetime characteristics.

Drawings

Fig. 1 illustrates an organic light emitting device 10 according to an embodiment of the present description.

Fig. 2 illustrates an organic light emitting device 11 according to another embodiment of the present description.

Detailed Description

The present specification will be described in more detail below.

The present specification provides heterocyclic compounds of the above chemical formula 1.

The heterocyclic compound according to an embodiment of the present specification is a structure in which substituents are bonded to positions 1 and 5 of a naphthyl group as substituents connecting an electron donor and an electron acceptor through L1 and L2 as connecting groups. By appropriately adjusting the positions of the electron donor and the electron acceptor, which are separated from each other, it is possible to effectively manage the electron distribution and migration within the electron transport layer to maximize the efficiency and lifetime within the device.

In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.

In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the other member but also a case where the other member exists between the two members.

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 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.

In the present specification, the term "substituted or unsubstituted" means being substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, 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 alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylsulfoxy group (Alkyl thioaxy), a substituted or unsubstituted arylsulfoxy group (Aryl thioaxy), a substituted or unsubstituted alkylsulfonyl group (Alkyl sufoxy), a substituted or unsubstituted arylsulfonyl group (Aryl sufoxy), a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted Aryl group, and a substituted or unsubstituted heterocyclic group, or a substituent formed by connecting 2 or more substituents among the above-exemplified substituents, or does not have any substituent. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

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 30. 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, 4-methyl-2-pentyl 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, n-butyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylheptyl group, heptyl group, 1-methylhexyl group, 1-ethylhexyl group, 1-pentyl group, 2-pentyl group, and the like, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a2, 3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a2, 3-dimethylcyclohexyl group, a3, 4, 5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, 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, but the number of carbon atoms is preferably 1 to 30. 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 amine group may be selected from-NH₂The number of carbon atoms of the alkylamino group, the N-alkylarylamino group, the arylamine group, the N-arylheteroarylamino group, the N-alkylheteroarylamino group and the heteroarylamino group is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, an N-phenylnaphthylamino group, a ditolylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrylamino group, an N-phenylfluorenylamino group, an N-phenylterphenylamino group, an N-phenanthrenylfluorenylamino group, and an N-biphenylfluorenylamino group.

In the present specification, an N-alkylarylamino group means an amino group in which an alkyl group and an aryl group are substituted on the N of the amino group.

In this specification, an N-arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group on the N of the amine group.

In this specification, an N-alkylheteroarylamino group means an amino group substituted with an alkyl group and a heteroarylamino group on the N of the amino group.

In the present specification, the alkyl group in the arylalkyl group, arylamine group, N-arylalkylamine group, alkylsulfoxy group, alkylsulfonyl group, and N-alkylheteroarylamine group is the same as the above-mentioned alkyl group. Specifically, examples of the alkylsulfoxy group include methylsulfanyl group, ethylsulfanyl group, t-butylsulfanyl group, hexylsulfanyl group, and octylsulfanyl group, and examples of the alkylsulfonyl group include methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, and butylsulfonyl group, but the alkylsulfoxy group 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 30. Specific examples thereof include, but are not limited to, vinyl, 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-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.

In the present specification, arylalkenyl refers to alkenyl substituted with aryl.

In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

In the present specification, the boron group may be-BR₁₀₀R₁₀₁R is as defined above₁₀₀And R₁₀₁The same or different, may each be independently selected from the group consisting of hydrogen, deuterium, halogen, a nitrile group, a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group of carbon number 3 to 30, a substituted or unsubstituted linear or branched alkyl group of carbon number 1 to 30, a substituted or unsubstituted monocyclic or polycyclic aryl group of carbon number 6 to 30, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of carbon number 2 to 30.

In the present specification, specific examples of the phosphine oxide group include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group and the like, but the phosphine oxide group is not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be a monocyclic ring or a polycyclic ring.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. 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 30. Specifically, the polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a pyrenyl group, a phenalene group, a perylenel group, a perylene group, a light-emitting element, and a light-emitting element,

And a fluorenyl group, but is not limited thereto.

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

In the case where the above-mentioned fluorenyl group is substituted, it may be

And the like. However, the present invention is not limited thereto.

In the present specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent closest in steric structure to the substituent, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted in the ortho (ortho) position in the phenyl ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as groups "adjacent" to each other.

In the present specification, the aryl group in the arylalkyl group, the arylalkenyl group, the aryloxy group, the arylsulfenoxy group, the arylsulfonyl group, the N-arylalkylamino group, the N-arylheteroarylamino group and the arylphosphino group is exemplified by the same aryl groups as those described above. Specifically, the aryloxy group includes a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a3, 5-dimethyl-phenoxy group, a2, 4, 6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthracenyloxy, 2-anthracenyloxy, 9-anthracenyloxy, 1-phenanthrenyloxy, 3-phenanthrenyloxy, 9-phenanthrenyloxy and the like, and examples of the arylthioxy group include phenylthioxy, 2-methylphenylsulfenoxy, 4-tert-butylphenylsulfenoxy and the like, and examples of the arylsulfonyl group include phenylsulfonyl and p-toluenesulfonyl, but are not limited thereto.

In the present specification, as examples of the arylamine group, there are a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing 2 or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group can be selected from the examples of the aryl group described above.

In the present specification, the heterocyclic group contains 1 or more non-carbon atoms, i.e., heteroatoms, and specifically, the above-mentioned heteroatoms may contain 1 or more atoms selected from O, N, Se, S and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heterocyclic group may be monocyclic or polycyclic. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,

Azolyl group,

Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolylCarbazolyl, benzo

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl

Azolyl group,

Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, phenoxazinyl

Oxazinyl and dibenzofuranyl, but not limited thereto.

In the present specification, the heteroaryl group means an aromatic ring in the above-mentioned heteroaryl ring.

In the present specification, as examples of the heteroarylamino group, there are a substituted or unsubstituted monoheteroarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted triheteroarylamino group. The heteroarylamine group containing 2 or more heteroaryls may contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or may contain both a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the heteroarylamino group can be selected from the examples of the heteroaryl group described above.

In this specification, examples of the heteroaryl group in the N-arylheteroarylamino group and the N-alkylheteroarylamino group are the same as those of the above-mentioned heteroaryl group.

In the present specification, arylene means a group having two binding sites in an aryl group, i.e., a 2-valent group. The above description of aryl groups applies, except that they are each a 2-valent group.

According to an embodiment of the present description, at least one of X1 to X3 is N, and the others are CH.

According to an embodiment of the present description, any one of X1 to X3 is N, and the remainder are CH.

According to an embodiment of the present description, two of X1 to X3 are N, and the remainder are CH.

According to an embodiment of the present description, X1 to X3 are N.

According to an embodiment of the present specification, in the above chemical formula 1, L1 and L2, which are the same or different from each other, are each independently a direct bond, or a substituted or unsubstituted arylene group.

According to an embodiment of the present specification, in chemical formula 1 above, L1 and L2, which are the same or different from each other, are each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an embodiment of the present specification, in chemical formula 1 above, L1 and L2, which are the same or different from each other, are each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to an embodiment of the present specification, in the above chemical formula 1, L1 and L2, which are the same as or different from each other, are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

According to an embodiment of the present specification, in chemical formula 1 above, L1 and L2, which are the same or different from each other, are each independently a direct bond, a phenylene group substituted or unsubstituted with an alkyl group, a biphenylene group substituted or unsubstituted with an alkyl group, or a terphenylene group substituted or unsubstituted with an alkyl group.

According to an embodiment of the present disclosure, the chemical formula 1 is the following chemical formula 2.

[ chemical formula 2]

In the above chemical formula 2, Ar1 to Ar3 and X1 to X3 are the same as defined in chemical formula 1,

r1 and R2, which are the same or different from each other, are each independently hydrogen or alkyl,

a1 and a2 are each integers from 0 to 3.

According to an embodiment of the present disclosure, the chemical formula 1 is any one of the following chemical formulas 3 to 7.

[ chemical formula 3]

[ chemical formula 4]

[ chemical formula 5]

[ chemical formula 6]

[ chemical formula 7]

In the above chemical formulae 3 to 7, Ar1 to Ar3 and X1 to X3 are the same as defined in chemical formula 1,

r1 to R6, which are identical to or different from one another, are each independently hydrogen or alkyl,

a1 and a2 are each integers from 0 to 3,

a3 and a4 are each integers from 0 to 2.

According to an embodiment of the present specification, in the above chemical formula 1, Ar2 and Ar3, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group.

According to an embodiment of the present specification, in the above chemical formula 1, Ar2 and Ar3 are the same as or different from each other, and each is independently an aryl group.

According to an embodiment of the present specification, in the above chemical formula 1, Ar2 and Ar3 are the same as or different from each other, and each independently is an aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present specification, in the above chemical formula 1, Ar2 and Ar3 are the same as or different from each other, and each independently is an aryl group having 6 to 20 carbon atoms.

According to an embodiment of the present specification, in the above chemical formula 1, Ar2 and Ar3, which are the same or different from each other, are each independently 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 specification, in the above chemical formula 1, Ar2 and Ar3, which are the same or different from each other, are each independently a phenyl group substituted or unsubstituted with a substituent selected from the group consisting of an alkyl group, an aryl group and a heterocyclic group; a biphenyl group substituted or unsubstituted with a substituent selected from the group consisting of an alkyl group, an aryl group and a heterocyclic group; or naphthyl optionally substituted with substituents selected from alkyl, aryl and heterocyclyl.

According to an embodiment of the present specification, in the above chemical formula 1, Ar2 and Ar3, which are the same or different from each other, are each independently a phenyl group substituted or unsubstituted with a substituent selected from the group consisting of an alkyl group, a naphthyl group and an N-containing heterocyclic group; biphenyl substituted or unsubstituted with a substituent selected from the group consisting of alkyl, naphthyl, and an N-containing heterocyclic group; or naphthyl optionally substituted with a substituent selected from the group consisting of alkyl, naphthyl and N-containing heterocyclic group.

According to an embodiment of the present specification, in the above chemical formula 1, Ar2 and Ar3, which are the same or different from each other, are each independently a phenyl group substituted or unsubstituted with a substituent selected from the group consisting of an alkyl group, a naphthyl group and a pyridyl group; biphenyl substituted or unsubstituted with a substituent selected from the group consisting of alkyl, naphthyl and pyridyl; or naphthyl optionally substituted with a substituent selected from the group consisting of alkyl, naphthyl and pyridyl.

According to an embodiment of the present specification, in chemical formula 1 above, Ar1 is a fluoranthenyl group substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; a fluorenyl group substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group and a heterocyclic group; a polycyclic heterocyclic group containing O, N and 1 or more of S and substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group.

According to an embodiment of the present specification, in chemical formula 1 above, Ar1 is a polycyclic aryl group substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group.

According to an embodiment of the present specification, in chemical formula 1 above, Ar1 is a bicyclic to pentacyclic aryl group substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group.

According to an embodiment of the present specification, in chemical formula 1 above, Ar1 is a tricyclic to tetracyclic aryl group substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group.

According to an embodiment of the present specification, in chemical formula 1 above, Ar1 is a fluorenyl group substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group.

According to an embodiment of the present specification, in chemical formula 1, Ar1 is a fluorenyl group substituted or unsubstituted with 1 or more substituents selected from an alkyl group and an aryl group.

According to an embodiment of the present specification, in chemical formula 1 above, Ar1 is a fluorenyl group substituted or unsubstituted with 1 or more substituents selected from a methyl group and a phenyl group.

According to an embodiment of the present specification, in chemical formula 1, Ar1 is a fluoranthenyl group substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group.

According to an embodiment of the present specification, in chemical formula 1, Ar1 is a fluoranthenyl group.

According to an embodiment of the present specification, in chemical formula 1 above, Ar1 is a polycyclic heterocyclic group containing 1 or more of O, N and S and substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group.

According to an embodiment of the present specification, in chemical formula 1 above, Ar1 is a bicyclic or tricyclic heterocyclic group including 1 or more of O, N and S and substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group.

According to an embodiment of the present specification, in chemical formula 1 above, Ar1 is a benzimidazolyl group substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group.

According to an embodiment of the present specification, in chemical formula 1, Ar1 is a benzimidazolyl group which is substituted or unsubstituted with 1 or more substituents selected from an alkyl group, an aryl group and a heterocyclic group.

According to embodiment 1 of the present specification, in chemical formula 1 above, Ar1 is a benzimidazolyl group substituted or unsubstituted with 1 or more substituents selected from the group consisting of a methyl group, an ethyl group, a phenyl group and a pyridyl group.

According to an embodiment of the present specification, in chemical formula 1 above, Ar1 is a benzotriazole group substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group.

According to an embodiment of the present specification, in chemical formula 1 above, Ar1 is a benzothiazolyl group substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group.

According to the present wordsIn one embodiment of the present specification, in chemical formula 1, Ar1 is benzo unsubstituted or substituted with 1 or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group

An azole group.

According to an embodiment of the present specification, in chemical formula 1, Ar1 is a carbazolyl group substituted or unsubstituted with 1 or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a hetero ring.

According to an embodiment of the present disclosure, in chemical formula 1, Ar1 is benzotriazolyl, benzothiazolyl, or benzothiazolyl

An azole group or a carbazole group.

According to an embodiment of the present disclosure, the chemical formula 1 is selected from the following compounds.

According to an embodiment of the present specification, there is provided an organic light emitting device including: the organic light-emitting device includes a first electrode, a second electrode provided 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 heterocyclic compound.

According to one embodiment of the present description, the organic layer of the organic light-emitting device of the present description may be formed of a single layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the organic light emitting device is not limited thereto, and may include a smaller or greater number of organic layers.

For example, the organic light emitting device may have a stacked structure as shown below, but is not limited thereto.

(1) Anode/hole transport layer/light emitting layer/cathode

(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode

(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode

(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode

(5) Anode/hole transport layer/luminescent layer/electron transport layer/electron injection layer/cathode

(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode

(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode

(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(10) Anode/hole transport layer/electron inhibiting layer/light emitting layer/electron transport layer/cathode

(11) Anode/hole transport layer/electron inhibiting layer/light emitting layer/electron transport layer/electron injection layer/cathode

(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode

(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode

(14) Anode/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/cathode

(15) Anode/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode

(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode

(17) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode

(18) Anode/hole injection layer/hole transport layer/light-emitting layer/layer for simultaneous electron injection and transport/cathode

(19) Anode/hole injection layer/hole transport layer/electron suppression layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode

(20) Anode/hole injection layer/hole transport layer/electron suppression layer/light-emitting layer/hole blocking layer/electron transport layer/cathode

(21) Anode/hole injection layer/hole transport layer/electron suppression layer/light-emitting layer/hole blocking layer/cathode for simultaneous electron injection and transport

For example, the structure of the organic light emitting device of the present specification may have the structure shown in fig. 1 and 2, but is not limited thereto.

Fig. 1 illustrates a structure of an organic light emitting device 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. Fig. 1 is an exemplary structure of an organic light emitting device according to an embodiment of the present disclosure, and may further include other organic layers.

Fig. 2 illustrates a structure of an organic light emitting device in which a first electrode 30, a hole injection layer 60, a hole transport layer 70, a light emitting layer 40, an electron transport layer 80, an electron injection layer 90, and a second electrode 50 are sequentially stacked on a substrate 20. Fig. 2 is an exemplary structure according to an embodiment of the present disclosure, and may further include another organic layer.

According to one embodiment of the present disclosure, the organic layer includes an electron injection layer including the heterocyclic compound of chemical formula 1.

According to one embodiment of the present disclosure, the organic layer includes an electron transport layer including the heterocyclic compound of chemical formula 1.

According to an embodiment of the present disclosure, the organic layer includes a layer simultaneously performing electron injection and transport, and the layer simultaneously performing electron injection and transport includes the heterocyclic compound of chemical formula 1.

A hole-regulating layer or an electron-inhibiting layer may be provided between the hole-transporting layer and the light-emitting layer. The hole-adjusting layer or the electron-suppressing layer may be formed using the above-mentioned compounds or materials known in the art.

According to one embodiment of the present disclosure, the organic layer includes an electron-inhibiting layer, and the electron-inhibiting layer includes the heterocyclic compound of chemical formula 1.

An electron-regulating layer or a hole-blocking layer may be provided between the electron-transporting layer and the light-emitting layer. The electron adjusting layer or the hole blocking layer may be formed using the above-mentioned compounds or materials known in the art.

According to an embodiment of the present disclosure, the organic layer includes a hole blocking layer including the heterocyclic compound of chemical formula 1.

According to one embodiment of the present disclosure, the organic layer includes a light emitting layer including the heterocyclic compound of chemical formula 1 as a host of the light emitting layer.

According to an embodiment of the present disclosure, the organic layer includes the heterocyclic compound of chemical formula 1 as a main body, and may include other organic compounds, metals, or metal compounds as a dopant.

The dopant may be 1 or more selected from the following exemplified compounds, but is not limited thereto.

According to one embodiment of the present disclosure, the organic layer includes a light emitting layer including a compound of the following chemical formula 1-a.

[ chemical formula 1-A ]

In the above chemical formula 1-a,

n1 is an integer of 1 or more,

ar7 is substituted or unsubstituted benzofluorenyl with valency of more than 1, substituted or unsubstituted fluoranthenyl with valency of more than 1, substituted or unsubstituted pyrenyl with valency of more than 1, or substituted or unsubstituted pyrenyl with valency of more than 1

The base group is a group of a compound,

l4 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar8 and Ar9, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylalkyl group, or a substituted or unsubstituted hetero ring, or may be combined with each other to form a substituted or unsubstituted ring.

When n1 is 2 or more, the structures in parentheses of 2 or more are the same or different from each other.

According to one embodiment of the present disclosure, the organic layer includes a light emitting layer, and the light emitting layer includes the compound of formula 1-a as a dopant of the light emitting layer.

According to an embodiment of the present disclosure, L4 is a direct bond.

According to an embodiment of the present specification, n1 is 2.

According to an embodiment of the present specification, Ar7 mentioned above is a 2-valent pyrenyl group substituted or unsubstituted with deuterium, methyl, ethyl, isopropyl, or tert-butyl; or 2-valent substituted or unsubstituted by deuterium, methyl, ethyl, or tert-butyl

And (4) a base.

According to an embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present disclosure, Ar8 and Ar9 are the same or different from each other and each independently represents an aryl group substituted or unsubstituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group, or a silyl group substituted with an alkyl group.

According to an embodiment of the present specification, Ar8 and Ar9, which are the same or different from each other, are each independently an aryl group substituted or unsubstituted with an alkyl-substituted silyl group.

According to an embodiment of the present specification, Ar8 and Ar9, equal to or different from each other, are each independently an aryl group substituted or unsubstituted with a trimethylsilyl group.

According to an embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

According to an embodiment of the present disclosure, Ar8 and Ar9 are the same or different from each other and each independently represents a phenyl group substituted or unsubstituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group, or a trimethylsilyl group.

According to an embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently represents a biphenyl group substituted or unsubstituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group, or a trimethylsilyl group.

According to an embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently represents a terphenyl group substituted or unsubstituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group, or a trimethylsilyl group.

According to an embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently represents a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to an embodiment of the present disclosure, Ar8 and Ar9 are the same or different from each other, and each independently represents a hetero ring substituted or unsubstituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group, a silyl group substituted with an alkyl group, or a phenyl group.

According to an embodiment of the present disclosure, Ar8 and Ar9 are the same or different from each other and each independently represent a dibenzofuranyl group substituted or unsubstituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group, a trimethylsilyl group, or a phenyl group.

According to an embodiment of the present disclosure, the chemical formula 1-a is selected from the following compounds.

According to one embodiment of the present disclosure, the organic layer includes a light emitting layer including a compound of the following chemical formula 2-a.

[ chemical formula 2-A ]

In the above chemical formula 2-a,

ar11 and Ar12, which are the same or different from each other, are each independently a substituted or unsubstituted monocyclic aryl group or a substituted or unsubstituted polycyclic aryl group.

G1 to G8, which are the same or different from each other, are each independently hydrogen, a substituted or unsubstituted monocyclic aryl group, or a substituted or unsubstituted polycyclic aryl group.

According to one embodiment of the present disclosure, the organic layer includes a light emitting layer including the compound of chemical formula 2-a as a host of the light emitting layer.

According to an embodiment of the present disclosure, Ar11 and Ar12 are the same or different from each other, and each is independently a substituted or unsubstituted polycyclic aromatic group.

According to an embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently represents a substituted or unsubstituted polycyclic aromatic group having 10 to 30 carbon atoms.

According to an embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each is independently a substituted or unsubstituted naphthyl group.

According to an embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently represents a substituted or unsubstituted 1-naphthyl group.

According to an embodiment of the present specification, Ar11 and Ar12 are 1-naphthyl groups.

According to an embodiment of the present disclosure, G1 to G8 are hydrogen.

According to an embodiment of the present disclosure, the chemical formula 2-a is the following compound.

According to one embodiment of the present disclosure, the organic layer includes a light emitting layer, the light emitting layer includes the compound of chemical formula 1-a as a dopant of the light emitting layer, and includes the compound of chemical formula 2-a as a host of the light emitting layer.

According to an embodiment of the present disclosure, the organic layer may further include one or more layers selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

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

When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. This can be produced as follows: the organic el device is manufactured by forming a first electrode by depositing 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 (e-beam evaporation) method, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the first electrode, and then depositing a substance that can be used as a second electrode on the organic layer. In addition to this method, the second electrode material, the organic layer, and the first electrode material may be sequentially deposited on the substrate to manufacture the organic light emitting device. In addition, the heterocyclic compound of chemical formula 1 may form an organic layer not only by a vacuum evaporation method but also by a solution coating method in manufacturing 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.

According to an embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.

In another embodiment of the present disclosure, 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 anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO₂A 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 LiO₂Multilayer structure materials such as/Al, Mg/Ag, etc., but not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode as a hole injection substance, and the following compounds are preferable as the hole injection substance: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an excellent thin film-forming 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 substance is a substance 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 substance 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 electron inhibiting layer is a layer which prevents electrons injected from the electron injecting layer from entering the hole injecting layer through the light emitting layer, and can improve the life and efficiency of the device, and if necessary, can be formed at an appropriate portion between the light emitting layer and the hole injecting layer using a known material.

The light-emitting substance of the light-emitting layer 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 is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)₃) Carbazole-based compounds, dimerized styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is

Azole, 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 light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic fused 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 carbazole derivative, a dibenzofuran derivative, a ladder furan compound, a pyrimidine derivative, and the like, but is not limited thereto.

As the dopant material, there are aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,

And diindenopyrene, and the like, the styrylamine compound is a compound substituted with at least 1 arylvinyl group on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.

The hole blocking layer is a layer that prevents holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer, and can improve the life and efficiency of the device, and if necessary, can be formed at an appropriate portion between the light emitting layer and the electron injection layer using a known material.

The electron transport material in the electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport material is a material that can favorably receive electrons from the cathode and transfer the electrons to the light-emitting layer, and is preferably a material having a high mobility to electrons. The electron transport material of the electron transport layer may include the compound of formula 1, and may be formed as a layer alone or together with an additional electron transport material. When the electron transport layer is composed of a plurality of layers, at least one electron transport layer contains the compound of the above chemical formula 1, and the remaining electron transport layers may be formed of a known electron transport material. Specific examples of the electron-transporting substance 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 injected from electricityThe layer of the polar electrons is preferably a compound of the formula: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and having an excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,

Azole,

Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, 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 complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and 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 organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.

According to an embodiment of the present specification, the heterocyclic compound of chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to an organic light emitting device.

Modes for carrying out the invention

Hereinafter, in order to specifically explain the present specification, the detailed description will be given by referring to examples. However, the embodiments according to the present description may be modified into various forms, and the scope of the present description is not to be construed as being limited to the embodiments described in detail below. The embodiments of the present description are provided to more fully describe the present description to those skilled in the art.

Production example 1 Synthesis of chemical formula E1

The above-mentioned compound 2- ([1,1' -biphenyl ] -4-yl) -4-phenyl-6- (3- (5- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalen-1-yl) phenyl) -1,3, 5-triazine (10.0g, 15.7mmol) and 1- (4-bromophenyl) -2-ethyl-1H-benzo [ d ] imidazole (5.0g, 16.6mmol) were completely dissolved in tetrahydrofuran (100ml), potassium carbonate (7.4g, 53.7mmol) was dissolved in 100ml of water and added, tetrakis (triphenylphosphine) palladium (620mg, 0.537mmol) was added, and the mixture was stirred under heating for 4 hours. Cooling to normal temperature, removing potassium carbonate solution after the reaction is finished, and filtering the white solid. The filtered white solid was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to thereby produce the compound of the above chemical formula E1 (9.5g, yield 82%).

MS[M+H]⁺＝732

Production example 2 Synthesis of chemical formula E2

In production example 1, 9- (4- (5- (3- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) naphthalen-1-yl) phenyl) -9H-carbazole was used instead of 2- ([1,1 '-biphenyl ] -4-yl) -4-phenyl-6- (3- (5- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalen-1-yl) phenyl) -1,3, 5-triazine, 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1 was used, a compound of the above chemical formula E2 was produced in the same manner as in production example 1, except that 3, 5-triazine was used instead of 1- (4-bromophenyl) -2-ethyl-1H-benzo [ d ] imidazole.

MS[M+H]⁺＝753

Production example 3 Synthesis of chemical formula E3

A compound of the above chemical formula E3 was produced in the same manner as in production example 1 except that (5- (4- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) phenyl) naphthalen-1-yl) boronic acid was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-phenyl-6- (3- (5- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalen-1-yl) phenyl) -1,3, 5-triazine and 3-bromofluoranthene was used instead of 1- (4-bromophenyl) -2-ethyl-1H-benzo [ d ] imidazole in production example 1.

MS[M+H]⁺＝635

Production example 4 Synthesis of chemical formula E4

In production example 1, (4- (5- (4- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) phenyl) naphthalen-1-yl) phenyl) boronic acid was used in place of 2- ([1,1' -biphenyl ] -4-yl) -4-phenyl-6- (3- (5- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalen-1-yl) phenyl) -1,3, 5-triazine, and 2-bromo-9, 9-dimethyl-9H-fluorene was used in place of 1- (4-bromophenyl) -2-ethyl-1H-benzo [ d ] imidazole, except for this, the compound of the above chemical formula E4 was produced by the same method as in the above production example 1.

MS[M+H]⁺＝703

Production example 5 Synthesis of chemical formula E5

In production example 1,2, 4-diphenyl-6- (4- (4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalen-1-yl) phenyl) -1,3, 5-triazine was used in place of 2- ([1,1' -biphenyl]-4-yl) -4-phenyl-6- (3- (5- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalen-1-yl) phenyl) -1,3, 5-triazine with 2- (4-bromophenyl) benzo [ d]

Azole for 1- (4-bromophenyl) -2-ethyl-1H-benzo [ d ]]Except for imidazole, a compound of the above chemical formula E5 was produced by the same method as in the above production example 1.

MS[M+H]⁺＝628

Production example 6 Synthesis of chemical formula E6

Preparation example 5 used 2- (4-bromophenyl) benzo [ d]Thiazole for 2- (4-bromophenyl) benzo [ d]

Except for azole, a compound of the above chemical formula E6 was produced by the same method as in the above production example 5.

MS[M+H]⁺＝644

Example 1

Indium Tin Oxide (ITO) and a process for producing the same

The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone and methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode thus prepared as an anode, the compound HI1 and the compound HI2 were added in such a ratio that the molar ratio was 98:2 (molar ratio)

The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, a compound of the following chemical formula HT1

The hole transport layer is formed by vacuum evaporation. Then, on the hole transport layer, the film thickness

The compound of EB1 was vacuum-evaporated to form an electron suppression layer. Next, the electron inhibiting layer is formed on the substrate to a film thickness

A compound of the following chemical formula BH and a compound of the following chemical formula BD are subjected to vacuum evaporation at a weight ratio of 50:1 to form a light-emitting layer. On the light-emitting layer, the thickness of the film

The compound of the following chemical formula HB1 was vacuum-evaporated to form a hole-blocking layer. Next, on the hole-blocking layer, compound E1 synthesized in production example 1 and a compound of the following chemical formula LiQ were vacuum-evaporated at a weight ratio of 1:1 to obtain a hole-blocking layer

The thickness of (2) forms an electron transport layer. On the electron transport layer, lithium fluoride (LiF) is sequentially added

Thickness of aluminum and

the thickness of (3) is evaporated to form a cathode.

In the above process, the evaporation speed of the organic material is maintained

Lithium fluoride maintenance of cathode

Deposition rate of (3), aluminum maintenance

The vapor deposition rate of (2) is maintained at a vacuum degree of 2X 10 during vapor deposition^-7～5×10^-6And supporting to thereby fabricate an organic light emitting device.

Examples 2 to 6

An organic light-emitting device was produced in the same manner as in example 1 above, except that the compound described in table 1 below was used instead of compound E1 of example 1.

Comparative examples 1 to 9

An organic light-emitting device was produced in the same manner as in example 1 above, except that the compound described in table 1 below was used instead of compound E1 of example 1. The compounds of ET2 to ET10 used in table 1 below are shown below.

When a current was applied to the organic light emitting devices fabricated according to examples 1 to 6 and comparative examples 1 to 9, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown below [ table 1]]。T₉₅Refers to the time required for the brightness to decrease from the initial brightness (1600 nits) to 95%.

[ Table 1]

As shown in table 1 above, in the case of an organic light emitting device manufactured using the compound of the present invention as an electron transport layer, excellent characteristics are exhibited in terms of efficiency, driving voltage, and/or stability of the organic light emitting device.

The organic light emitting devices of examples 1 to 6 exhibited characteristics of low voltage, high efficiency, and long life, as compared to the organic light emitting devices manufactured using comparative examples 1 to 3, in which compounds ET2 to ET4 having substituents at the 1-and 4-positions of the naphthalene core were used as electron transport layers, respectively.

In addition, the organic light emitting devices of examples 1 to 6 exhibited low voltage, high efficiency, and long life characteristics, as compared to the organic light emitting devices manufactured using ET5 and ET6 having substituents at positions 1 and 5 of the naphthalene core and having a pyridine derivative as a substituent of Ar1, ET7 having a phenyl group substituted with a cyano group, ET8 having a triphenylene group, ET9 having a pyrimidine derivative, and ET10 having a triazine derivative, respectively, as electron transport layers.

The preferred embodiment (electron transport layer) of the present invention has been described above, but the present invention is not limited thereto, and may be modified into various forms and implemented within the scope of the claims and the scope of the detailed description of the invention, which also falls within the scope of the present invention.

Claims

1. A heterocyclic compound of the following chemical formula 1:

chemical formula 1

In the chemical formula 1, the first and second organic solvents,

at least one of X1 to X3 is N, and the remainder are CH,

ar1 is a fluoranthenyl group substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; a fluorenyl group which is substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group and a heterocyclic group; or a polycyclic heterocyclic group containing O, N and 1 or more of S and substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group.

2. The heterocyclic compound according to claim 1, wherein Ar2 and Ar3, which are the same or different from each other, are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

3. The heterocyclic compound according to claim 1, wherein the L1 and L2, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

4. The heterocyclic compound according to claim 1, wherein Ar1 is a fluorenyl group which is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; a fluoranthenyl group which is unsubstituted or substituted with one or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; benzimidazolyl substituted or unsubstituted with one or more substituents selected from deuterium, alkyl, alkenyl, cycloalkyl, aryl, arylalkyl, arylalkenyl, and heterocyclic; a benzotriazole group which is substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; benzothiazolyl which is substituted or unsubstituted with one or more substituents selected from deuterium, alkyl group, alkenyl group, cycloalkyl group, aryl group, arylalkyl group, arylalkenyl group, and heterocyclic group; is selected from deuterium, alkyl, alkeneBenzo unsubstituted or substituted by one or more substituents selected from the group consisting of cycloalkyl, aryl, arylalkyl, arylalkenyl and heterocyclyl

An azole group; or carbazolyl which is unsubstituted or substituted with 1 or more substituents selected from deuterium, alkyl group, alkenyl group, cycloalkyl group, aryl group, arylalkyl group, arylalkenyl group and heterocyclic group.

5. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is the following chemical formula 2:

chemical formula 2

In the chemical formula 2, Ar1 to Ar3 and X1 to X3 are the same as defined in chemical formula 1,

a1 and a2 are each integers from 0 to 3.

6. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is any one of the following chemical formulae 3 to 7:

chemical formula 3

Chemical formula 4

Chemical formula 5

Chemical formula 6

Chemical formula 7

In the chemical formulae 3 to 7, Ar1 to Ar3 and X1 to X3 are the same as defined in chemical formula 1,

a1 and a2 are each integers from 0 to 3,

a3 and a4 are each integers from 0 to 2.

7. The heterocyclic compound according to claim 1, wherein the compound of formula 1 is selected from the following compounds:

8. an organic light emitting device comprising:

a first electrode;

a second electrode provided to face the first electrode; and

one or more organic layers disposed between the first and second electrodes,

wherein one or more of the organic layers comprises the heterocyclic compound of any one of claims 1 to 7.

9. The organic light emitting device according to claim 8, wherein the organic layer comprises an electron injection layer, an electron transport layer, or a layer that performs electron injection and transport simultaneously, and the electron injection layer, the electron transport layer, or the layer that performs electron injection and transport simultaneously contains the heterocyclic compound.

10. The organic light emitting device of claim 8, wherein the organic layer comprises a hole blocking layer comprising the heterocyclic compound.

11. The organic light-emitting device according to claim 8, wherein the organic layer comprises a light-emitting layer containing the heterocyclic compound as a host of the light-emitting layer.