CN116438946A

CN116438946A - Organic light emitting device

Info

Publication number: CN116438946A
Application number: CN202280007125.XA
Authority: CN
Inventors: 尹正民; 洪性佶; 许东旭; 韩美连; 李在卓; 尹喜敬; 朴浒润
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2021-03-26
Filing date: 2022-03-08
Publication date: 2023-07-14
Also published as: KR20220134124A; WO2022203245A1

Abstract

The present specification relates to an organic light emitting device including a compound represented by chemical formula 1.

Description

Organic light emitting device

Technical Field

The present application claims priority from korean patent application No. 10-2021-0039370, filed to the korean patent office on 3 months 26 of 2021, the entire contents of which are incorporated herein.

The present specification relates to organic light emitting devices.

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 and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, 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. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition to the ground state again.

There is a continuing need to develop new materials for use in organic light emitting devices as described above.

Prior art literature

(patent document 1) korean laid-open patent No. 10-2013-0049276

Disclosure of Invention

Technical problem

An organic light emitting device is provided in the present specification.

Solution to the problem

An embodiment of the present specification provides an organic light emitting device including: an anode, a cathode, and 1 or more organic layers provided between the anode and the cathode, wherein 1 or more of the organic layers contains a compound represented by the following chemical formula 1.

[ chemical formula 1]

In the above-mentioned chemical formula 1,

x1 and X2 are the same or different from each other and are each independently O or S,

r1 to R4 are the same or different from each other and are each independently a substituted or unsubstituted aryl group or are combined with each other with the adjacent groups to form a substituted or unsubstituted naphthalene ring.

Ar, L1 and L2 are the same or different from each other and each independently is a monocyclic to tricyclic or more than pentacyclic arylene group,

m and n are each integers from 0 to 3,

when m and n are each 2 or more, 2 or more L1 s and L2 s are each the same or different from each other,

m+n is 1 or more.

Effects of the invention

The organic light emitting device described in the present specification exhibits effects of low driving voltage, high efficiency and/or long life by including the compound represented by chemical formula 1 in the organic layer.

Drawings

Fig. 1 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 5, and a cathode 9 are stacked in this order.

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

Fig. 3 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4-1, a second hole transport layer 4-2, a light-emitting layer 5, an electron transport and injection layer 8, and a cathode 9 are stacked in this order.

[ description of the symbols ]

1: substrate board

2: anode

3: hole injection layer

4: hole transport layer

4-1: a first hole transport layer

4-2: a second hole transport layer

5: light-emitting layer

6: electron transport layer

7: electron injection layer

8: electron transport and injection layers

9: cathode electrode

Detailed Description

The present specification will be described in more detail below.

In the present specification, when a certain component is referred to as "including/comprising" a certain component, unless otherwise specified, it means that other components may be further included, rather than excluded.

In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is connected to the other member but also the case where another member exists between the two members.

In the present description of the invention,

or the dotted line indicates the location of the binding to the chemical formula or compound.

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

The term "substituted" as used herein means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" means substituted with a member selected from deuterium, halogen group, cyano (-CN), nitro, hydroxy, alkyl, cycloalkyl, alkoxy, phosphorus oxide, aryloxy, alkylthio

Arylthio->

Alkylsulfonyl->

Arylsulfonyl group

1 or 2 or more substituents selected from the group consisting of alkenyl, silyl, boron, amino, aryl and heterocyclic groups, or a substituent obtained by linking 2 or more substituents selected from the above-described substituents, or a substituent not having any substituent. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.

In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, halogen group, cyano group, nitro group, hydroxyl group, amino group, silyl group, boron group, alkoxy group, aryloxy group, alkyl group, cycloalkyl group, aryl group, and heterocyclic group, or substituted with a substituent in which 2 or more substituents among the above exemplified substituents are linked, or does not have any substituent.

In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, cyano, alkyl, aryl, and heterocyclic groups, or substituted with a substituent in which 2 or more substituents out of the above-exemplified substituents are linked, or does not have any substituent.

In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, cyano, alkyl, and aryl, or substituted with a substituent in which 2 or more substituents out of the above-exemplified substituents are linked, or does not have any substituent.

Examples of the above substituents are described below, but are not limited thereto.

In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).

In the present specification, the silyl group may be represented by-SiY _a Y _b Y _c The chemical formula of (A) is shown in the specification, Y is shown in the specification _a 、Y _b And Y _c Each may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group is specifically, but not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.

In the present specification, the boron group may be represented BY-BY _d Y _e The chemical formula of (A) is shown in the specification, Y is shown in the specification _d And Y _e Each may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Examples of the boron group include trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but are not limited thereto.

In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the above alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, and the like.

In this specification, the above description of the alkyl group may be applied to an arylalkyl group other than an aryl group.

In the present specification, the above-mentioned alkoxy group may be a straight chain, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy and the like are possible, but not limited thereto.

The alkyl groups, alkoxy groups, and other substituents containing an alkyl moiety described in this specification are all included in straight or branched chain forms.

In the present specification, the alkenyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include 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 (diphenyl-1-yl) ethen-1-yl, styryl and the like, but are not limited thereto.

In the present specification, the alkynyl group is a substituent group including a triple bond between carbon atoms, and may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkynyl group has 2 to 20 carbon atoms. According to another embodiment, the above alkynyl group has 2 to 10 carbon atoms.

In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like, but not limited thereto.

In the present specification, the amine group is-NH ₂ The amine group may be substituted with the alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, a combination thereof, or the like. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the amine group has 1 to 20 carbon atoms. According to one embodiment, the amine group has 1 to 10 carbon atoms. Specific examples of the substituted amine group include, but are not limited to, methylamino group, dimethylamino group, ethylamino group, diethylamino group, phenylamino group, 9-dimethylfluorenylphenylamino group, pyridylphenylamino group, diphenylamino group, phenylpyridylamino group, naphthylamino group, biphenylamino group, anthracenyl amino group, dibenzofuranylphenylamino group, 9-methylanthracenylamino group, diphenylamino group, phenylnaphthylamino group, xylylamino group, phenyltolylamino group, and diphenylamino group.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms.

In the present specification, the aryl group may be an aryl group formed of a single ring, or a polycyclic aryl group (an aryl group having two or more rings). The aryl group having a single ring may be a phenyl group or a group formed by connecting 2 or more phenyl groups. The aryl group having a single ring may be a phenyl group, a biphenyl group, a terphenyl group, a tetrabiphenyl group, or the like, but is not limited thereto. Polycyclic aryl may refer to a group formed by fusing two or more single rings such as naphthyl and phenanthryl. As the polycyclic aryl group, there may be mentioned naphthyl, anthryl, phenanthryl and pyrenylPerylene radical,

A group, a fluorenyl group, a triphenylene group, and the like, but is not limited thereto.

In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

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

An isospirofluorenyl group; />

(9, 9-dimethylfluorenyl) and +.>

(9, 9-diphenylfluorenyl) and the like. However, the present invention is not limited thereto.

In the present specification, the aryl group in the aryloxy group may be applied to the above description about the aryl group.

In the present specification, the above-mentioned alkyl groups in the alkylthio group and the alkylsulfonyl group may be applied to the above-mentioned explanation about the alkyl group.

In the present specification, the above-described aryl groups in the arylthio group and the arylsulfonyl group can be applied to the above-described description about the aryl group.

In the present specification, the heterocyclic group is a ring group containing 1 or more heteroatoms in N, O, P, S, si and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to one embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarzolyl, triazinyl, and the like.

In this specification, the heteroaryl group is aromatic, and the above description of the heterocyclic group can be applied thereto.

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

In this specification, the above description of the heterocyclic group may be applied to a heterocyclic group other than the 2-valent heterocyclic group.

In this specification, the above description of heteroaryl groups may be applied, except that heteroaryl groups are 2-valent.

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a hydrocarbon ring or a heterocyclic ring.

The hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic group and an aliphatic ring, and may be selected from the examples of cycloalkyl groups and aryl groups.

In the present specification, the meaning of forming a ring by bonding adjacent groups to each other means that a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or condensed rings thereof are formed by bonding adjacent groups to each other. The hydrocarbon ring refers to a ring composed of only carbon and hydrogen atoms. The heterocyclic ring is a ring containing 1 or more elements selected from N, O, P, S, si and Se. 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.

In the present specification, the aliphatic hydrocarbon ring means a ring which is not aromatic and is composed of only carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1, 4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like.

In the present specification, an aromatic hydrocarbon ring means an aromatic ring composed of only carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, peryleneFluoranthene, triphenylene, phenalene, pyrene, naphthacene, and combinations thereof,

Pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, and the like, but is not limited thereto. In the present specification, an aromatic hydrocarbon ring can be interpreted as having the same meaning as an aryl group.

In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing 1 or more hetero atoms. Examples of aliphatic heterocycles include ethylene oxide (oxalane), tetrahydrofuran, and 1, 4-di-

Alkyl (1, 4-dioxane), pyrrolidine, piperidine, morpholine, oxepane>

Azacyclooctane->

Thiacyclooctane

And the like, but is not limited thereto.

In the present specification, an aromatic heterocycle means an aromatic ring containing 1 or more hetero atoms. Examples of the aromatic heterocyclic ring include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, and the like,

Azole, i->

Oxazole, thiazole, isothiazole, triazole, < >>

Diazoles for treating diabetesThiadiazole, dithiazole, tetrazole, pyran, thiopyran, pyridazine, and +.>

Oxazine, thiazide, di->

Alkene, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, naphthyridine, triazaindene, indole, indolizine, benzothiazole, benzo->

Oxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, pheno->

Oxazine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiment of the present invention may be modified into various forms, and the scope of the present invention is not limited to the embodiment described below.

The compound represented by chemical formula 1 according to the present invention is prepared by reacting a compound represented by chemical formula 1 with an aromatic group

An azole and/or thiazole ring, thereby increasing +.>

The thermal stability of the azole and thiazole rings allows smooth injection and transfer of electrons, and thus when the compound represented by the above chemical formula 1 is applied to an organic light-emitting device, an organic light-emitting device having high efficiency, low voltage and/or long life characteristics can be obtained.

Chemical formula 1 will be described in detail below.

[ chemical formula 1]

In the above-mentioned chemical formula 1,

r1 to R4 are identical to or different from each other and are each independently a substituted or unsubstituted aryl group or are combined with each other with the adjacent groups to form a substituted or unsubstituted naphthalene ring,

m and n are each integers from 0 to 3,

when m and n are each 2 or more, 2 or more L1 s and L2 s are each the same or different from each other, and m+n is 1 or more.

In one embodiment of the invention, X1 and X2 are O.

In one embodiment of the invention, X1 and X2 are S.

In one embodiment of the present invention, X1 is O and X2 is S.

In one embodiment of the invention, X1 is S and X2 is O.

In one embodiment of the invention, R1 to R4 are identical to or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or are bonded to each other with adjacent groups to form a substituted or unsubstituted naphthalene ring.

In one embodiment of the invention, R1 to R4 are identical to or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or are bonded to each other with adjacent groups to form a substituted or unsubstituted naphthalene ring.

In one embodiment of the invention, R1 to R4 are identical to or different from each other and are each independently an aryl group having 6 to 30 carbon atoms or are bonded to each other with adjacent groups to form a naphthalene ring.

In one embodiment of the invention, R1 to R4 are phenyl groups or are bonded to each other with adjacent groups to form a naphthalene ring.

In one embodiment of the invention, R1 and R2 combine with each other to form a naphthalene ring.

In one embodiment of the invention, R3 and R4 combine with each other to form a naphthalene ring.

In one embodiment of the invention, R1 to R4 are bonded to each other with the adjacent groups to form a naphthalene ring,

are the same as or different from each other, and are each independently represented by any one of the following structural formulas.

In the above-mentioned structural formula, the water-soluble polymer,

represents the binding site to L1 or L2.

In one embodiment of the invention Ar, L1 and L2 are the same or different from each other and are each independently a monocyclic to tricyclic or more than pentacyclic arylene group.

In one embodiment of the present invention, ar, L1 and L2 are the same or different from each other and each independently is a monocyclic to tricyclic or more than pentacyclic arylene group having 6 to 60 carbon atoms.

In one embodiment of the present invention, ar, L1 and L2 are the same or different from each other and each independently is a monocyclic to tricyclic or pentacyclic or higher arylene group having 6 to 30 carbon atoms.

In one embodiment of the invention Ar, L1 and L2 are the same or different from each other and are each independently a monocyclic to tricyclic or hexacyclic arylene group.

In one embodiment of the invention, ar is a monocyclic to tricyclic or hexacyclic arylene group.

In one embodiment of the invention, L1 and L2 are identical to or different from each other and are each independently monocyclic to tricyclic arylene.

In one embodiment of the present invention, L1 and L2 are the same or different from each other, and are each independently an arylene group constituted of a single ring or a bicyclic arylene group.

In one embodiment of the invention Ar, L1 and L2 are the same or different from each other and are each independently phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, or spirobifluorenylene.

In one embodiment of the invention, ar is phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, or spirobifluorenylene.

In one embodiment of the invention, L1 and L2 are the same or different from each other and are each independently phenylene, biphenylene, or naphthylene.

In one embodiment of the invention, L1 and L2 are identical to or different from each other and are each independently phenylene or biphenylene.

In an embodiment of the present specification, ar, L1 and L2 are the same or different from each other, and each is independently represented by any one of the following structures.

In the above structure, the broken line indicates the bonding position.

In the above structure, the broken line indicates the bonding position.

In an embodiment of the present specification, L1 and L2 are the same or different from each other, and each is independently represented by any one of the following structures.

In the above structure, the broken line indicates the bonding position.

In one embodiment of the invention, when m is 0, - (L1) m-represents a direct bond.

In one embodiment of the invention, when n is 0, - (L2) n-represents a direct bond.

In one embodiment of the invention, - (L1) m-and- (L2) n-are the same or different from each other and are each independently a monocyclic to tricyclic or hexacyclic arylene group having 6 to 30 carbon atoms, and at least one of- (L1) m-and- (L2) n-is a monocyclic to tricyclic or hexacyclic arylene group having 6 to 30 carbon atoms.

In one embodiment of the invention, - (L1) m-is a direct bond, phenylene, or biphenylene.

In one embodiment of the invention, - (L2) n-is a direct bond, phenylene, or biphenylene.

In one embodiment of the invention, - (L1) m-is a direct bond, - (L2) n-is phenylene or biphenylene.

In one embodiment of the invention, - (L2) n-is a direct bond, - (L1) m-is phenylene or biphenylene.

In one embodiment of the invention, m and n are each integers from 0 to 3.

In one embodiment of the invention, m and n are each integers from 0 to 2.

In one embodiment of the invention, m is an integer from 0 to 2.

In one embodiment of the invention, n is an integer from 0 to 2.

In one embodiment of the present invention, m+n is 1 or more.

In one embodiment of the invention, m+n is 1 to 4.

In one embodiment of the present invention, the above chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3.

[ chemical formula 1-1]

[ chemical formulas 1-2]

[ chemical formulas 1-3]

In the above chemical formulas 1-1 to 1-3, the definitions of X1, X2, ar, L1, L2, m and n are the same as those in the above chemical formula 1.

In one embodiment of the present invention, the above chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-3.

[ chemical formula 2-1]

[ chemical formula 2-2]

[ chemical formulas 2-3]

In the above chemical formulas 2-1 to 2-3, the definitions of R1 to R4, ar, L1, L2, m and n are the same as those in the above chemical formula 1.

In one embodiment of the present invention, the above chemical formula 1 is represented by the following chemical formula 3-1 or 3-2.

[ chemical formula 3-1]

[ chemical formula 3-2]

In the above chemical formulas 3-1 and 3-2, the definitions of R1 to R4, X1, X2, L1 and L2 are the same as those in the above chemical formula 1,

a1 and a2 are each an integer of 1 to 3, and when a1 and a2 are each 2 or more, L1 and L2 are each the same or different from each other.

In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following compounds.

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The compound represented by chemical formula 1 according to an embodiment of the present specification may manufacture a core structure by a method shown in the following formula 1. The substituents may be bonded by methods known in the art, and the kinds, positions or numbers of the substituents may be changed according to techniques known in the art.

[ general formula 1]

/>

In the above formula 1, Y1 and Y2 are the same or different from each other and are each independently halogen or-SO ₃ C ₄ F ₉ Preferably chlorine, bromine, or-SO ₃ C ₄ F ₉ 。

At this time, the compound belonging to the range of the above chemical formula 1 may be synthesized using starting materials, intermediate materials, and the like known in the art and by synthetic methods known in the art.

In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above chemical formula 1. In addition, in this specification, by introducing various substituents into the core structure of the structure shown above, HOMO and LUMO energy levels of the compound can also be adjusted.

In addition, the present specification provides an organic light emitting device including the above-mentioned compound.

The organic light emitting device according to the present specification is characterized by comprising: an anode, a cathode, and 1 or more organic layers provided between the anode and the cathode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.

The organic light emitting device of the present specification can be manufactured by a general method and material for manufacturing an organic light emitting device, except that the organic layer is formed by using the compound of chemical formula 1.

The compound may be used not only in the vacuum vapor deposition method but also in the solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.

The organic layer of the organic light-emitting device of the present specification 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 1 or more of a hole transporting layer, a hole injecting layer, an electron blocking layer, a hole transporting and injecting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, and an electron transporting and injecting layer as an organic layer. However, the structure of the organic light emitting device of the present specification is not limited thereto, and may include a smaller or larger number of organic layers.

In an embodiment of the present specification, the organic layer may include a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include a compound represented by chemical formula 1.

In one embodiment of the present specification, the organic layer may include a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include a compound represented by chemical formula 1.

In an embodiment of the present specification, the organic layer may include an electron injection layer, an electron transport and injection layer, or a hole blocking layer, and the electron injection layer, the electron transport and injection layer, or the hole blocking layer may include a compound represented by chemical formula 1.

In an embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron transport and injection layer, and the electron injection layer, the electron transport layer, or the electron transport and injection layer may include a compound represented by chemical formula 1.

In one embodiment of the present specification, the organic layer includes an electron modulation layer, and the electron modulation layer may include a compound represented by chemical formula 1.

In one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes a compound represented by chemical formula 1.

In the organic light emitting device of the present specification, the organic layer is an electron transporting and injecting layer including the compound represented by chemical formula 1.

In one embodiment of the present specification, the chemical formula 1 is includedThe thickness of the organic layer of the compound is

To->

Preferably +.>

To->

More preferably +.>

To->

In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1.

In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1 as a main body.

In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1 as a dopant.

In another embodiment, the organic layer may contain other organic compounds, metals, or metal compounds in addition to the compound represented by chemical formula 1.

In an organic light emitting device according to an embodiment of the present specification, the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant. At this time, the dopant in the light emitting layer includes 1 to 50 parts by weight with respect to 100 parts by weight of the host.

As another example, the organic layer includes a light-emitting layer including the compound represented by the chemical formula 1 as a host, and may further include another host.

In one embodiment of the present specification, the dopant includes an arylamine compound, a boron and nitrogen-containing heterocyclic compound, an Ir complex, or the like.

The organic light emitting device of the present specification may further include 1 or more organic layers among a hole transporting layer, a hole injecting layer, an electron blocking layer, an electron transporting and injecting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, and a hole transporting and injecting layer.

In an embodiment of the present specification, the organic light emitting device includes: an anode, a cathode, and at least 2 organic layers disposed between the anode and the cathode, wherein at least one of the at least 2 organic layers contains a compound represented by the chemical formula 1.

In one embodiment of the present specification, the organic layer of 2 or more layers may be two or more selected from the group consisting of a light-emitting layer, a hole-transporting layer, a hole-injecting layer, a hole-transporting and injecting layer, and an electron blocking layer.

In one embodiment of the present specification, the 2 or more organic layers may be two or more selected from the group consisting of a light-emitting layer, an electron transporting layer, an electron injecting layer, an electron transporting and injecting layer, an electron adjusting layer, and a hole blocking layer.

In one embodiment of the present specification, the organic layer includes 2 or more electron transport layers, and at least one of the 2 or more electron transport layers includes a compound represented by chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by chemical formula 1 may be contained in 1 layer of the 2 or more electron transport layers, or may be contained in each of the 2 or more electron transport layers.

In addition, in an embodiment of the present specification, when the compound is included in each of the 2 or more electron transport layers, materials other than the compound represented by the chemical formula 1 may be the same as or different from each other.

When the organic layer containing the compound represented by the above chemical formula 1 is an electron transporting layer, an electron injecting layer, or an electron transporting and injecting layer, the electron transporting layer, the electron injecting layer, or the electron transporting and injecting layer may further contain an n-type dopant or an organometallic compound. The n-type dopant or the organometallic compound may use materials known in the art, for example, a metal or a metal complex may be used.

For example, the n-type dopant or the organometallic compound may be LiQ, and is not limited thereto. The electron transporting layer, the electron injecting layer, or the electron transporting and injecting layer including the compound represented by the above chemical formula 1 may further include LiQ (Lithium Quinolate, lithium quinolinolate).

According to one example, the compound represented by chemical formula 1 above and the n-type dopant or organometallic compound above may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4. According to one example, the compound represented by chemical formula 1 above and the n-type dopant or the organometallic compound described above may be included in a weight ratio of 1:1.

In one embodiment of the present specification, the organic layer includes 2 or more hole transport layers, and at least one of the 2 or more hole transport layers includes a compound represented by chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by chemical formula 1 may be contained in 1 layer of the above-described 2 or more hole transport layers, or may be contained in each of the 2 or more hole transport layers.

In addition, in an embodiment of the present specification, when the compound represented by the above chemical formula 1 is included in each of the 2 or more hole transport layers, materials other than the compound represented by the above chemical formula 1 may be the same or different from each other.

In one embodiment of the present specification, the organic layer may include a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazole group, or a benzocarbazole group, in addition to the organic layer including the compound represented by the chemical formula 1.

In one embodiment of the present specification, the organic light-emitting device may have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device having a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.

In the organic light emitting device of the present invention, the organic layer may include an electron blocking layer, and the electron blocking layer may use materials known in the art.

For example, the above-described organic light emitting device may have a laminated 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/light emitting 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 blocking layer/light emitting layer/electron transport layer/cathode

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

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

(13) Anode/hole injection layer/hole transport layer/electron blocking 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/first hole transport layer/second hole transport layer/light emitting layer/electron transport and injection layer/cathode

(19) Anode/hole injection layer/first hole transport layer/second hole transport layer/light emitting layer/hole blocking layer/electron transport and injection layer/cathode

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

The structure of the organic light emitting device of the present specification may have the structure shown in fig. 1 to 3, but is not limited thereto.

Fig. 1 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 5, and a cathode 9 are stacked in this order. In the structure shown above, the above-described compound may be contained in the above-described light-emitting layer 5.

Fig. 2 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 9 are stacked in this order. In the structure shown above, the above-mentioned compound may be contained in the above-mentioned hole injection layer 3, hole transport layer 4, light-emitting layer 5, electron transport layer 6, or electron injection layer 7.

Fig. 3 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4-1, a second hole transport layer 4-2, a light-emitting layer 5, an electron transport and injection layer 8, and a cathode 9 are stacked in this order. In the structure shown above, the above-mentioned compound may be contained in the above-mentioned hole injection layer 3, the first hole transport layer 4-1, the second hole transport layer 4-2, the light emitting layer 5, or the electron transport and injection layer 8.

In an embodiment of the present disclosure, the electron transporting and injecting layer and the light emitting layer may be disposed adjacent to each other.

In an embodiment of the present disclosure, the electron transport layer and the light emitting layer may be disposed adjacent to each other.

In an embodiment of the present disclosure, the hole blocking layer and the light emitting layer may be disposed adjacent to each other.

In an embodiment of the present disclosure, the hole blocking layer and the electron transporting layer may be disposed adjacent to each other.

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that 1 or more of the organic layers include the above-described compound, i.e., the compound represented by 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 material or different materials.

For example, the organic light emitting device according to the present specification may be manufactured as follows: PVD (physical vapor deposition) such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation) is used to vapor deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer is formed on the anode, and then a substance that can function as a cathode is vapor deposited on the organic layer to manufacture the anode. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

The organic layer may further include one or more of a hole transporting layer, a hole injecting layer, an electron blocking layer, an electron transporting and injecting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, and a hole transporting and injecting layer.

The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, or the like, but is not limited thereto, and may have a single-layer structure. The organic layer may be formed into a smaller number of layers by a solvent process (solvent process) other than vapor deposition, such as spin coating, dip coating, knife coating, screen printing, ink jet printing, or thermal transfer printing, using various polymer materials.

The anode is an electrode for injecting holes, and is preferably a substance having a large work function as an anode substance in order to allow holes to be smoothly injected 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, indium Zinc Oxide); znO of Al or SnO ₂ A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.

The cathode is an electrode for injecting electrons, and is preferably a substance having a small work function as a cathode substance in order to facilitate injection of 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 LiO ₂ And/or Al, but is not limited thereto.

The hole injection layer is a layer that functions to smooth injection of holes from the anode to the light-emitting layer, and the hole injection substance is a substance that can well receive holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers. The thickness of the hole injection layer may be 1 to 150nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the degradation of the hole injection characteristic can be prevented, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the increase of the driving voltage for improving the movement of holes can be prevented.

The hole transport layer can function to smooth the transport of holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and a substance having a large mobility to the holes is suitable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.

A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.

An electron blocking layer may be disposed between the hole transport layer and the light emitting layer. The above-mentioned compounds or materials known in the art may be used in the above-mentioned electron blocking layer.

The light-emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. As a specific example, there is 8-hydroxy-quinoline aluminum complex (Alq ₃ ) The method comprises the steps of carrying out a first treatment on the surface of the CarbodyAn azole compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (E

Azole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

Examples of the host material of the light-emitting layer include an aromatic condensed ring derivative and a heterocyclic compound. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds

Pyrimidine derivatives, etc., but are not limited thereto.

When the light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent substance such as PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonide), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium, bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) irium), tris (1-phenylquinoline) iridium), ptOEP (octaethylporphyrin platinum, platinum octaethylporphyrin), or Alq may be used ₃ Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum, etc., but not limited thereto. When the light emitting layer emits green light, ir (ppy) can be used as a light emitting dopant ₃ Phosphorescent substances such as (factris (2-phenylpyridine) iridium, planar tris (2-phenylpyridine) iridium), or Alq ₃ Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum), but are not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, (4, 6-F ₂ ppy) ₂ Irpic or other phosphorescent substance, or spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DS B), distyrylarylene (DSA), PFO polymer, PPV polymerFluorescent substances such as molecules, but not limited thereto.

A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.

The electron transport layer can play a role in enabling electron transport to be smooth. The electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high mobility of electrons. As specific examples, there are the above-mentioned compounds or Al complexes of 8-hydroxyquinoline containing Alq ₃ But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The thickness of the electron transport layer may be 1 to 50nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the degradation of the electron transport property can be prevented, and when it is 50nm or less, there is an advantage that the increase of the driving voltage for improving the movement of electrons can be prevented when the thickness of the electron transport layer is too thick.

The electron injection layer can perform a function of smoothly injecting electrons. As the electron injecting substance, the following compounds are preferable: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,

Azole,/->

Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.

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

The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed generally under the same conditions as those of the hole injection layer. Specifically, there are

The diazole derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.

The organic light emitting device according to the present specification may be included in a variety of electronic devices. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, or the like, but is not limited thereto.

Modes for carrying out the invention

In the following, examples will be given to explain the present specification in detail. However, the embodiments according to the present specification may be modified into various forms, and the scope of the present application is not to be construed as limited to the embodiments described in detail below. The embodiments of the present application are provided to more fully explain the present description to those skilled in the art.

< production example 1: synthesis of Compound 1

Bromine-2-chloronaphthalene (bromoo-2-chloronapthalene) (7.25 g,30 mmol) and the above-mentioned compound 1-1 (14.76 g,33 mmol) were charged into tetrahydrofuran (300 mL). K put into 2M ₂ CO ₃ (200 mL) and tetrakis (triphenylphosphine) palladium (0) (0.3 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized 2 times from toluene to produce the above-mentioned compound 1-2.

The above-mentioned compounds 1-2 (95.1 g,197.3 mmol) and 4,4', 5',5'-octamethyl-2,2' -bis (1, 3, 2-dioxapentaborane) (4, 4',4', 5'-octamethyl-2,2' -bi (1, 3, 2-dioxabiline)) (55.1 g,217.0 mmol) was added to 1, 4-dioxido

Alkane (1000 mL). Potassium acetate (Potassium acetate) (58.0 g) and Pd (dppf) Cl were charged ₂ ([ 1,1' -bis (diphenylphosphine) ferrocene)]Palladium (II) dichloride (1, 1' -Bis (diphenylphosphino) ferrocene)]dichloropalladium (II)), 4.3 g), and then stirred and refluxed for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized 2 times from ethyl acetate to prepare the above-mentioned compounds 1 to 3.

The above-mentioned compounds 1-3 (17.21 g,30 mmol) and 2-chloronaphtho [2,1-d]

Azole (2-chloronahtho [2, 1-d)]Oxazoles) (6.72 g,33 mmol) were added to tetrahydrofuran (300 mL). K put into 2M ₂ CO ₃ (200 mL), palladium acetate (Palladium acetate) (0.14 g), and s-phos (2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (2-dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl), 0.50 g) of the ligand (ligand) were stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized 2 times from toluene to produce the above compound 1.

(3.9 g, yield 21%, MS: [ M+H)] ⁺ ＝615)。

< production example 2: synthesis of Compound 2

The above-mentioned compound 2 was produced by the same method as the production method of the above-mentioned production example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝539

< manufacturing example 3: synthesis of Compound 3

/>

The above-mentioned compound 3 was produced by the same method as the production method of the above-mentioned production example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝539

< production example 4: synthesis of Compound 4

The above-mentioned compound 4 was produced by the same method as the production method of the above-mentioned production example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝539

< production example 5: synthesis of Compound 5-

The above-mentioned compound 5 was produced by the same method as the production method of the above-mentioned production example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝539

< production example 6: synthesis of Compound 6

The above-mentioned compound 6 was produced by the same method as the production method of the above-mentioned production example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝643

< production example 7: synthesis of Compound 7

The above-mentioned compound 7 was produced by the same method as the production method of the above-mentioned production example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝643

< production example 8: synthesis of Compound 8

The above-mentioned compound 8 was produced by the same method as the production method of the above-mentioned production example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝831

< production example 9: synthesis of Compound 9-

The above-mentioned compound 9 was produced by the same method as the production method of the above-mentioned production example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝795

< manufacturing example 10: synthesis of Compound 10

The above-mentioned compound 10 was produced by the same method as the production method of production example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝631

< production example 11: synthesis of Compound 11

The above-mentioned compound 11 was produced by the same method as the production method of the above-mentioned production example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝743

< manufacturing example 12: synthesis of Compound 12 ]

The above-mentioned compound 12 was produced by the same method as the production method of production example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝539

< manufacturing example 13: synthesis of Compound 13

The above-mentioned compound 13 was produced by the same method as the production method of production example 1, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝591

< production example 14: synthesis of Compound 14-

4'-bromo-5' -chloro-1,1':2',1 '-terphenyl (4' -bromo-5'-chloro-1,1':2', 1' -terphenyl) (10.31 g,30 mmol) andthe above compound 14-1 (13.97 g,33 mmol) was added to tetrahydrofuran (300 mL). K put into 2M ₂ CO ₃ (200 mL) and tetrakis (triphenylphosphine) palladium (0) (0.3 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized 2 times from toluene to produce the above-mentioned compound 14-2.

The above compound 14-2 (16.80 g,30 mmol) and the above compound 14-3 (12.25 g,33 mmol) were put into tetrahydrofuran (300 mL). K put into 2M ₂ CO ₃ (200 mL), palladium acetate (0.14 g) and s-phos (2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl, 0.50 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resultant solid was filtered and recrystallized 2 times from toluene to produce the above-mentioned compound 14.

(6.92 g, yield 30%, MS: [ M+H)] ⁺ ＝769)。

< production example 15: synthesis of Compound 15

The above-mentioned compound 15 was produced by the same method as the production method of production example 14, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝717

< manufacturing example 16: synthesis of Compound 16

9-bromo-10-chlorophenanthrene (9-bromoo-10-chlorophenynthrene) (8.75 g,30 mmol) and the above compound 16-1 (24.5 g,66 mmol) were added to tetrahydrofuran (300 mL). K put into 2M ₂ CO ₃ (200 mL), palladium acetate (0.14 g) and s-phos (2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl, 0.50 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resultant solid was filtered and recrystallized 2 times from toluene to produce the above-mentioned compound 16.

(14.76 g, yield 74%, MS: [ M+H)] ⁺ ＝665)。

< production example 17: synthesis of Compound 17

The above-mentioned compound 17 was produced by the same method as the production method of production example 16, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝565

< manufacturing example 18: synthesis of Compound 18-

The above-mentioned compound 18 was produced by the same method as the production method of production example 16, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝717

< production example 19: synthesis of Compound 19

The above-mentioned compound 19 was produced by the same method as the production method of production example 16, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝665

< manufacturing example 20: synthesis of Compound 20

The above-mentioned compound 20 was produced by the same method as the production method of production example 16, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝521

< production example 21: synthesis of Compound 21

The above-mentioned compound 21 was produced by the same method as the production method of production example 16, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝597

< manufacturing example 22: synthesis of Compound 22

The above-mentioned compound 22 was produced by the same method as the production method of production example 16, except that each starting material was used as in the above-mentioned reaction formula.

MS:[M+H] ⁺ ＝565

Examples (example)

< examples 1 to 1>

ITO (indium tin oxide) to

The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.

In preparation for thisThe following compound HI-A was used as the substrate on the ITO transparent electrode

And performing thermal vacuum evaporation to form a hole injection layer. Vacuum evaporating the hole injection layer sequentially>

The following compounds HAT and +.>

And (c) the following compound HT-a, thereby forming a first hole transport layer and a second hole transport layer.

Then, on the second hole transport layer, the film thickness is set to

The following compound BH and compound BD were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer.

Vacuum vapor deposition is performed on the light-emitting layer to obtain a mixture of the compound 1 and the following compound LiQ at a weight ratio of 1:1

Form electron transport and injection layers. On the electron transport and injection layer, lithium fluoride (LiF) is added in sequence +.>

Is made of aluminum +.>

And the thickness of the metal layer is evaporated to form a cathode.

In the above process, the vapor deposition rate of the organic matter is maintained

Second to->

Lithium fluoride maintenance of cathode per second

Vapor deposition rate per second, aluminum maintenance->

Vapor deposition rate per second, vacuum degree at vapor deposition was maintained at 1X10 ^-7 To 5X10 ^-5 The support, thereby manufacturing the organic light emitting device.

< examples 1-2 to 1-22>

An organic light-emitting device was manufactured in the same manner as in example 1-1 above, except that the compounds 2 to 22 described in table 1 below were used instead of the compound 1 of example 1-1.

< comparative examples 1-1 to 1-12>

An organic light-emitting device was manufactured in the same manner as in example 1-1, except that the compounds ET-1 to ET-12 described in table 1 below were used instead of the compound 1 of example 1-1. The structures of the compounds ET-1 to ET-12 of Table 1 below are shown below.

Experimental example

The organic light-emitting devices fabricated in examples 1-1 to 1-22 and comparative examples 1-1 to 1-12 described above were subjected to a temperature of 10mA/cm ² The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm ² The time (T90) at which the initial luminance was 90% was measured at the current density of (a). It is subjected toThe results are shown in Table 1 below.

TABLE 1

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As described in table 1 above, it was confirmed that in the case of the organic light emitting device using the compound of chemical formula 1 according to the present invention, excellent characteristics in terms of driving voltage, efficiency and/or lifetime were exhibited.

Specifically, the compound of the present invention is characterized in that two five-membered rings ("" five-membered rings "") substituted or condensed with an aryl group to form a naphthalene ring

Oxazole or thiazole) has at least 2 linking groups between them. It was confirmed that in the case of using the device of the present invention, the device comprising the compound of the present invention was used >

The voltage, efficiency and lifetime characteristics are improved compared with those of the case of the azole or benzothiazole, or the case of the compound of the comparative example in which the number of linking groups is 1.

In addition, it was confirmed that voltage, efficiency and life characteristics were improved as compared with the case of using a comparative example compound in which the five-membered ring was not substituted or condensed, or the linking group was not arylene.

Claims

1. An organic light emitting device comprising: an anode, a cathode, and 1 or more organic layers disposed between the anode and the cathode, wherein 1 or more of the organic layers contains a compound represented by the following chemical formula 1:

chemical formula 1

In the chemical formula 1 described above, a compound having the formula,

m and n are each integers from 0 to 3,

m+n is 1 or more.

2. The organic light-emitting device according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3:

Chemical formula 1-1

Chemical formula 1-2

Chemical formulas 1-3

In the chemical formulas 1-1 to 1-3, the definitions of X1, X2, ar, L1, L2, m, and n are the same as those in the chemical formula 1.

3. The organic light-emitting device according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-3:

chemical formula 2-1

Chemical formula 2-2

Chemical formula 2-3

In the chemical formulas 2-1 to 2-3, R1 to R4, ar, L1, L2, m and n are as defined in the chemical formula 1.

4. An organic light-emitting device according to claim 1 wherein Ar, L1 and L2 are the same or different from each other, each independently being a monocyclic to tricyclic or hexacyclic arylene group.

5. The organic light-emitting device according to claim 1, wherein Ar, L1, and L2 are the same or different from each other, each independently being phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, or spirobifluorenylene.

6. The organic light-emitting device according to claim 1, wherein the Ar, L1, and L2 are the same or different from each other, each independently represented by any one of the following structures:

in the structure, a broken line indicates a bonding position.

7. The organic light-emitting device according to claim 1, wherein the chemical formula 1 is represented by any one of the following compounds:

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8. The organic light-emitting device of claim 1, wherein the organic layer comprises an electron transport layer, an electron injection layer, or an electron transport and injection layer, the electron transport layer, the electron injection layer, or the electron transport and injection layer comprising the compound.

9. The organic light emitting device of claim 8, wherein the electron transport layer, the electron injection layer, or the electron transport and injection layer further comprises an n-type dopant.

10. The organic light emitting device of claim 9, wherein the compound and the n-type dopant are included in a weight ratio of 2:8 to 8:2.

11. The organic light-emitting device of claim 1, wherein the organic layer comprises a hole blocking layer comprising the compound.

12. The organic light-emitting device according to claim 1, wherein the organic layer further comprises 1 or more of a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer.