KR102551490B1 - Compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification relates to a compound of Formula 1 and an organic light emitting device including the same.

Description

Compound and an organic light emitting device including the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.

Development of new materials for the organic light emitting device as described above has been continuously demanded.

Korean Patent Publication No. 2000-0051826

The present specification provides a compound and an organic light emitting device including the same.

An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar2 is a group represented by the following formula (2),

[Formula 2]

In Formula 2,

X1 is O or S;

Any one of G1 to G8 is a site bonded to Ar2 of Formula 1, and the remaining groups of G1 to G8 not bonded to Ar2 of Formula 1, Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

q1 is 1 or 2;

q2 is 1 or 2;

When q1 is 2, the two Q1s are the same as or different from each other,

When q2 is 2, the two Q2s are the same as or different from each other.

In addition, the present specification is a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one organic material layer includes the compound.

The compounds described in this specification can be used as a material for an organic material layer of an organic light emitting device. A compound according to another exemplary embodiment may improve efficiency, low driving voltage, and/or lifetime characteristics of an organic light emitting device.

1 and 2 illustrate an example of an organic light emitting device according to an exemplary embodiment of the present specification.

Hereinafter, this specification will be described in more detail.

An exemplary embodiment of the present specification provides a compound represented by Formula 1 above.

Formula 1 according to an exemplary embodiment of the present specification is a compound in which Formula 2, which is a five-ring ring containing O or S as a substituent, is directly bonded to an anthracene core, and has excellent structural characteristics in electron and hole transport. Therefore, an organic light emitting device including the organic light emitting diode is excellent in driving voltage, efficiency, and lifespan.

Examples of substituents in the present specification are described below, but are not limited thereto.

는 연결되는 부위를 의미한다.In this specification,

indicates the connecting part.

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

In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; hydroxy group; cyano group; nitro group; an alkyl group; cycloalkyl group; alkoxy group; alkenyl group; haloalkyl group; silyl group; boron group; amine group; aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of heteroaryl groups, is substituted with substituents in which two or more substituents among the above exemplified substituents are connected, or does not have any substituents.

또는

의 치환기가 될 수 있다. 또한, 3개의 치환기가 연결되는 것은 (치환기 1)-(치환기 2)-(치환기 3)이 연속하여 연결되는 것뿐만 아니라, (치환기 1)에 (치환기 2) 및 (치환기 3)이 연결되는 것도 포함한다. 예컨대, 페닐기, 나프틸기 및 이소프로필기가 연결되어,

,

또는

의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 정의가 동일하게 적용된다.In the present specification, two or more substituents are linked means that the hydrogen of any one substituent is linked to another substituent. For example, when two substituents are connected, a phenyl group and a naphthyl group are connected.

or

can be a substituent of In addition, the three substituents are connected not only by connecting (substituent 1)-(substituent 2)-(substituent 3) in succession, but also by connecting (substituent 2) and (substituent 3) to (substituent 1). include For example, a phenyl group, a naphthyl group and an isopropyl group are connected,

,

or

can be a substituent of The above definition is equally applied to the case where 4 or more substituents are connected.

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

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl group, etc. , but is not limited thereto.

In the present specification, the alkoxy group may be straight chain, branched chain or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It is not limited.

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 include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited thereto.

In the present specification, the haloalkyl group means that at least one halogen group is substituted for the hydrogen of the alkyl group in the definition of the alkyl group.

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

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and 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. It is preferable that it is 10-30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, and the like, but is not limited thereto.

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

,

,

,

,

,

,

및

등이 있으나, 이에 한정되지 않는다.When the fluorene group is substituted,

,

,

,

,

,

,

and

etc., but is not limited thereto.

As used herein, "adjacent" refers to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. can For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, the heteroaryl group includes at least one atom or heteroatom other than carbon, and specifically, the heteroatom may include at least one atom selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, and an acridine group. , pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group (phenoxathiine), phenoxazine group (phenoxazine), phenothiazine group (phenothiazine group), dihydroindenocarbazole group, spirofluorene xanthene group and spirofluorene Thioxanthene group and the like, but is not limited thereto.

In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, and the like. Examples of the above-described alkyl group may be applied to the alkyl group of the alkylsilyl group, examples of the above-described aryl group may be applied to the aryl group of the arylsilyl group, and examples of the heteroaryl group of the heteroarylsilyl group may be applied.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. The boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.

In the present specification, the amine group is selected from the group consisting of -NH ₂ , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group. It may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group. , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthreate Nyl fluorenyl amine group, N-biphenyl fluorenyl amine group and the like, but are not limited thereto.

In the present specification, the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group. The alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl group. The aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and heteroaryl group described above.

In the present specification, the N-alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the above-mentioned alkyl group and heteroaryl group.

In the present specification, examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group or a substituted or unsubstituted dialkylamine group. The alkyl group in the alkylamine group may be a straight-chain or branched-chain alkyl group. The alkylamine group including two or more alkyl groups may include a straight-chain alkyl group, a branched-chain alkyl group, or a straight-chain alkyl group and a branched-chain alkyl group at the same time. For example, the alkyl group in the alkylamine group may be selected from examples of the aforementioned alkyl groups.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group or a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from examples of the above-described heteroaryl groups.

In the present specification, an arylene group means an aryl group having two bonding sites, that is, a divalent group. The description of the aryl group described above can be applied except that each is a divalent group.

In the present specification, a heteroarylene group means a heteroaryl group having two binding sites, that is, a divalent group. The above description of the heteroaryl group may be applied except that each is a divalent group.

Unless defined otherwise herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein may be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patent applications, patents and other references mentioned herein are hereby incorporated by reference in their entirety, and in case of conflict, the present specification, including definitions, will control unless a specific passage is stated. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.

According to an exemplary embodiment of the present specification, Formula 2 is represented by any one of Formulas 2-1 to 2-6 below.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

In Formulas 2-1 to 2-6,

The definitions of X1, G1 to G8, Q1, Q2, q1 and q2 are the same as defined in Formula 2 above.

According to an exemplary embodiment of the present specification, Formula 1 is represented by Formula 1-1 below.

[Formula 1-1]

In Formula 1-1,

The definitions of L1, Ar1, R1 to R8 are the same as defined in Formula 1 above,

The definitions of X1, Q1, Q2, q1 and q2 are the same as defined in Formula 2 above,

G101 to G105 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

g105 is an integer from 1 to 3;

When g105 is 2 or more, the two or more G105s are the same as or different from each other.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 1-2 to 1-10.

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

[Formula 1-10]

In Formulas 1-2 to 1-10,

The definitions of L1, Ar1, R1 to R8 are the same as defined in Formula 1 above,

The definitions of X1, Q1, Q2, q1 and q2 are the same as defined in Formula 2 above,

G101 to G105 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

g105 is an integer from 1 to 3;

When g105 is 2 or more, the two or more G105s are the same as or different from each other.

According to an exemplary embodiment of the present specification, X1 is O.

According to one embodiment of the present specification, X1 is S.

According to an exemplary embodiment of the present specification, Formula 2 is represented by any one of Formulas 2-7 to 2-12 below.

[Formula 2-7]

[Formula 2-8]

[Formula 2-9]

[Formula 2-10]

[Formula 2-11]

[Formula 2-12]

In Chemical Formulas 2-7 to 2-12,

The definitions of G1 to G8, Q1, Q2, q1 and q2 are the same as defined in Chemical Formula 2 above.

According to an exemplary embodiment of the present specification, Formula 2 is represented by any one of Formulas 2-13 to 2-18 below.

[Formula 2-13]

[Formula 2-14]

[Formula 2-15]

[Formula 2-16]

[Formula 2-17]

[Formula 2-18]

In Formulas 2-13 to 2-18,

The definitions of G1 to G8, Q1, Q2, q1 and q2 are the same as defined in Chemical Formula 2 above.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-11 to 1-19.

[Formula 1-11]

[Formula 1-12]

[Formula 1-13]

[Formula 1-14]

[Formula 1-15]

[Formula 1-16]

[Formula 1-17]

[Formula 1-18]

[Formula 1-19]

In Formulas 1-11 to 1-19,

The definitions of L1, Ar1, R1 to R8 are the same as defined in Formula 1 above,

The definitions of Q1, Q2, q1 and q2 are the same as defined in Formula 2 above,

G101 to G105 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

g105 is an integer from 1 to 3;

When g105 is 2 or more, the two or more G105s are the same as or different from each other.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 1-20 to 1-28.

[Formula 1-20]

[Formula 1-21]

[Formula 1-22]

[Formula 1-23]

[Formula 1-24]

[Formula 1-25]

[Formula 1-26]

[Formula 1-27]

[Formula 1-28]

In Formulas 1-20 to 1-28,

The definitions of L1, Ar1, R1 to R8 are the same as defined in Formula 1 above,

The definitions of Q1, Q2, q1 and q2 are the same as defined in Formula 2 above,

G101 to G105 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

g105 is an integer from 1 to 3;

When g105 is 2 or more, the two or more G105s are the same as or different from each other.

According to an exemplary embodiment of the present specification, R1 to R8 are hydrogen.

According to an exemplary embodiment of the present specification, G1 is a site binding to Ar2 of Formula 1.

According to an exemplary embodiment of the present specification, G2 is a site binding to Ar2 of Formula 1.

According to an exemplary embodiment of the present specification, G3 is a site binding to Ar2 of Formula 1.

According to an exemplary embodiment of the present specification, G4 is a site binding to Ar2 of Formula 1.

According to an exemplary embodiment of the present specification, G5 is a site binding to Ar2 of Formula 1.

According to an exemplary embodiment of the present specification, G6 is a site binding to Ar2 of Formula 1.

According to an exemplary embodiment of the present specification, G7 is a site binding to Ar2 of Formula 1.

According to an exemplary embodiment of the present specification, G8 is a site binding to Ar2 of Formula 1.

According to an exemplary embodiment of the present specification, the remaining groups, Q1 and Q2, not bonded to Ar2 of Formula 1 among G1 to G8 are hydrogen.

According to an exemplary embodiment of the present specification, G101 to G105 are hydrogen.

According to an exemplary embodiment of the present specification, the L1 is a direct bond; Or a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present specification, the L1 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the L1 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, the L1 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, the L1 is a direct bond; or an arylene group.

According to an exemplary embodiment of the present specification, the L1 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the L1 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, the L1 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, the L1 is a direct bond; or a phenylene group.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 is a monocyclic or polycyclic aryl group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 is a phenyl group; biphenyl group; or a naphthyl group.

According to an exemplary embodiment of the present specification, Formula 1 is any one selected from the following compounds.

The present specification provides an organic light emitting device including the aforementioned compound.

In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

In this specification, when a part is said to "include" a certain component, it means that it may further include other components without excluding other components unless otherwise stated.

In the present specification, the 'layer' means compatible with 'film' mainly used in the art, and means a coating covering a target area. The size of the 'layer' is not limited, and each 'layer' may have the same size or different sizes. According to an exemplary embodiment, the size of a 'layer' may be the same as the size of an entire device, may correspond to the size of a specific functional region, or may be as small as a single sub-pixel.

In this specification, the meaning that a specific material A is included in the B layer means that i) one or more types of material A are included in one layer B, and ii) the layer B is composed of one or more layers, and the material A is a multi-layer B All of the layers included in one or more layers are included.

In the present specification, the meaning that a specific material A is included in the C layer or the D layer means that i) included in one or more of the one or more C layers, ii) included in one or more of the one or more D layers, or iii ) means all of those included in one or more C layers and one or more D layers, respectively.

The present specification is a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1. do.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light emitting device is not limited thereto and may include fewer organic layers.

According to one embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer includes the compound.

According to one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.

According to one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound as a host of the light emitting layer.

According to one embodiment of the present specification, the light emitting layer includes a dopant, and the dopant includes at least one selected from the group consisting of a fluorescent dopant, a phosphorescent dopant, and a thermally delayed fluorescence dopant.

According to an exemplary embodiment of the present specification, the fluorescent dopant includes at least one selected from the group consisting of arylamine-based compounds and boron-based compounds.

According to an exemplary embodiment of the present specification, the fluorescent dopant is an arylamine-based compound.

According to one embodiment of the present specification, the fluorescent dopant is a boron-based compound.

According to one embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes a host and a dopant, the host includes the compound, and the dopant includes the fluorescent dopant, the phosphorescent dopant, and a thermal delay and at least one selected from the group consisting of fluorescent dopants.

According to an exemplary embodiment of the present specification, the arylamine-based compound is represented by Formula D-1 below.

[Formula D-1]

In the above formula D-1,

L101 and L102 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar101 to Ar104 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, L101 and L102 are a direct bond.

According to an exemplary embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and each independently represents a monocyclic or polycyclic aryl having 6 to 30 carbon atoms unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms. energy; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and each independently represents a phenyl group substituted with a methyl group; or a dibenzofuran group.

According to an exemplary embodiment of the present specification, Formula D-1 is represented by the following compound.

According to an exemplary embodiment of the present specification, the boron-based compound is represented by Formula D-2 below.

[Formula D-2]

In the above formula D-2,

T1 to T5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted aryl group,

t3 and t4 are each an integer from 1 to 4,

t5 is an integer from 1 to 3;

When t3 is 2 or more, the two or more T3s are the same as or different from each other,

When t4 is 2 or more, the two or more T4s are the same as or different from each other,

When t5 is 2 or more, the two or more T5s are the same as or different from each other.

According to an exemplary embodiment of the present specification, the T1 to T5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the T1 to T5 are the same as or different from each other, and each independently hydrogen; a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the T1 to T5 are the same as or different from each other, and each independently hydrogen; tert-butyl group; diphenylamine group; or a phenyl group unsubstituted or substituted with a tert-butyl group.

According to an exemplary embodiment of the present specification, Formula D-2 is represented by the following compound.

According to an exemplary embodiment of the present specification, the phosphorescent dopant and the thermally delayed fluorescent dopant use one known in the art, but are not limited thereto.

According to one embodiment of the present specification, the light emitting layer includes a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, it includes a weight ratio of 99:1 to 50:50, more specifically, a weight ratio of 99:1 to 95:5.

According to an exemplary embodiment of the present specification, the organic light emitting device includes one layer or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer. contains more

According to one embodiment of the present specification, the organic light emitting device may include a first electrode; a second electrode provided to face the first electrode; a light emitting layer provided between the first electrode and the second electrode; and two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode.

According to an exemplary embodiment of the present specification, two or more organic material layers between the light emitting layer and the first electrode or between the light emitting layer and the second electrode include a light emitting layer, a hole transport layer, a hole injection layer, a hole injection and transport layer, and an electron blocking layer. , a hole blocking layer, an electron injection layer, an electron transport layer, and two or more may be selected from the group consisting of an electron injection and transport layer.

According to one embodiment of the present specification, two or more hole transport layers are included between the light emitting layer and the first electrode. The two or more hole transport layers may include the same or different materials.

According to one embodiment of the present specification, the first electrode is an anode or a cathode.

According to one embodiment of the present specification, the second electrode is a cathode or an anode.

According to one embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

According to one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of an inverted type in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

For example, the structure of an organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2 . 1 and 2 illustrate the organic light emitting device, but are not limited thereto.

1 illustrates a structure of an organic light emitting device in which a first electrode 2, a light emitting layer 4, and a second electrode 3 are sequentially stacked on a substrate 1. The compound of Formula 1 is included in the light emitting layer.

2, a first electrode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, a light emitting layer 4, an electron transport layer 8, and an electron transport layer 8 are formed on a substrate 1. The structure of the organic light emitting device in which the injection layer 9 and the second electrode 3 are sequentially stacked is exemplified. The compound of Formula 1 is included in the light emitting layer.

The organic light emitting device of the present specification may be manufactured with materials and methods known in the art, except that the light emitting layer includes the compound, that is, the compound represented by Formula 1 above.

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

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. After forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.

In addition, the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

In addition to this method, an organic light emitting device may be fabricated by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. However, the manufacturing method is not limited thereto.

As the first electrode material, a material having a high work function is generally preferable so that holes can be smoothly injected into the organic material layer. For example, metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : A combination of a metal and an oxide such as Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The second electrode material is preferably a material having a small work function so as to facilitate electron injection into the organic material layer. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. In the case of including an additional light emitting layer in addition to the light emitting layer including the compound represented by Formula 1 according to an exemplary embodiment of the present specification, the host material includes a condensed and/or non-condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, aromatic amine derivatives include pyrene, anthracene, chrysene, and periplanthene having an arylamine group as condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted for a substituted or unsubstituted arylamine, and one or two or more are selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. The substituent is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but is not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

The hole injection layer is a layer that receives holes from an electrode. It is preferable that the hole injection material has the ability to transport holes and has a hole receiving effect from the anode and an excellent hole injection effect with respect to the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material is desirable. Also, a material having excellent thin film forming ability is preferred. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, and arylamine-based organic materials; hexanitrile hexaazatriphenylene-based organic materials; quinacridone-based organic substances; perylene-based organic materials; Examples include polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transporting them to the light emitting layer, and a material having high hole mobility is preferable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transport material is a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is preferable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material, as used according to the prior art. In particular, a suitable cathode material is a conventional material having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium and samarium, etc., followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that receives electrons from an electrode. As the electron injecting material, it is preferable to have an excellent ability to transport electrons, an electron receiving effect from the second electrode, and an excellent electron injecting effect to the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and bis(8-hydroxyquinolinato)manganese. , tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h ]quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , but is not limited thereto.

The electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer. Known materials can be used without limitation, and may be formed between the light emitting layer and the hole injection layer, between the light emitting layer and the hole transport layer, or between the light emitting layer and a layer that simultaneously injects and transports holes.

The hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but are not limited thereto.

An organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double side emission type depending on materials used.

Hereinafter, examples and comparative examples will be described in detail to describe the present specification in detail. However, the Examples and Comparative Examples according to the present specification may be modified in many different forms, and the scope of the present specification is not construed as being limited to the Examples and Comparative Examples detailed below. Examples and comparative examples in the present specification are provided to more completely explain the present specification to those skilled in the art.

Synthesis Example 1. Synthesis of core-1

<1-a> Preparation of compound 1-a

6-Chloronaphthalen-2-ol (50 g, 279.9 mmol) was added to dichloromethane (250 ml) and completely dissolved. After diisopropylamine (2.8 g, 28.0 mmol) was added, n-bromosuccinimide (54.8 g, 307.9 mmol) was slowly added. After reacting at 40° C. for 3 hours, 1000 ml of water was added dropwise. After stirring at room temperature for 1 hour, the organic layer was extracted with dichloromethane and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and purified using column chromatography to obtain compound 1-a (48.3 g, yield 67%).

MS: [M+H]+ = 258

<1-b> Preparation of compound 1-b

After dissolving the compound 1-a (45 g, 174.8 mmol) and (3-hydroxynaphthalen-2-yl) boronic acid (39.4 g, 209.7 mmol) in tetrahydrofuran (500 ml), Pd (PPh ₃ ) ₄ (10.1 g, 8.74 mmol) and 100 ml of 2M K ₂ CO ₃ aqueous solution were added and refluxed for 18 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and purified using column chromatography to obtain compound 1-b (35.3 g, yield 63%).

MS: [M+H]+ = 321

<1-c> Preparation of compound 1-c

After dissolving the compound 1-b (35 g, 109.1 mmol) in 1,2-dichlorobenzene (500 ml), zeolite (Zeolite HSZ-360) (12.7 g) was added and stirred at 160° C. for 20 hours. The reaction solution was cooled, and the organic layer was extracted with dichloromethane and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and purified using column chromatography to obtain compound 1-c (20.1 g, yield 61%).

MS: [M+H]+ = 303

<1-d> Preparation of compound core-1

Compound 1-c (20 g, 66.0 mmol), bis(pinacolato)diboron (29.2 g, 99.1 mmol), tricyclohexylphosphine (1.1 g, 3.96 mmol), potassium acetate (19.4 g, 198 mmol) ) and Pd(dba) ₂ (1.1 g, 1.98 mmol) in 1,4-dioxane (200 ml) and refluxed for 10 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and purified using column chromatography to obtain compound core-1 (17.7g, yield 68%).

MS: [M+H]+ = 395

Synthesis Example 2. Synthesis of core-2

<2-a> Preparation of compound 2-a

Synthesized and purified in the same manner except for using (2-hydroxynaphthalen-1-yl)boronic acid instead of (3-hydroxynaphthalen-2-yl)boronic acid in 1-b of Synthesis Example 1 Compound 2-a was obtained.

MS: [M+H]+ = 321

<2-b> Preparation of compound 2-b

Compound 2-b was obtained through the same synthesis and purification except for using compound 2-a instead of compound 1-b in 1-c of Synthesis Example 1.

MS: [M+H]+ = 303

<2-c> Preparation of compound core-2

Compound core-2 was obtained through the same synthesis and purification except for using compound 2-b instead of compound 1-c in 1-d of Synthesis Example 1.

MS: [M+H]+ = 395

Synthesis Example 3. Synthesis of core-3

<3-a> Preparation of compound 3-a

After dispersing 6-chloronaphthalen-2-ol (60 g, 335.9 mmol) in 600 ml of dimethylformamide, a solution of n-bromosuccinimide (65.8 g, 369.5 mmol) dissolved in 150 ml of dimethylformamide was slowly added dropwise. did. After reacting at room temperature for 2 hours, 1200 ml of water was added dropwise. After stirring at room temperature for 1 hour, the organic layer was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and purified using column chromatography to obtain compound 3-a (51.9 g, yield 60%).

MS: [M+H]+ = 258

<3-b> Preparation of compound 3-b

Compound 3-b was obtained through the same synthesis and purification except for using compound 3-a instead of compound 1-a in 1-b of Synthesis Example 1.

MS: [M+H]+ = 321

<3-c> Preparation of compound 3-c

Compound 3-c was obtained through the same synthesis and purification except for using compound 3-b instead of compound 1-b in 1-c of Synthesis Example 1.

MS: [M+H]+ = 303

<3-d> Preparation of compound core-3

Compound core-3 was obtained through the same synthesis and purification except for using compound 3-d instead of compound 1-c in 1-d of Synthesis Example 1.

MS: [M+H]+ = 395

Synthesis Example 4. Synthesis of core-4

<4-a> Preparation of compound 4-a

Synthesized and purified in the same manner except for using (2-hydroxynaphthalen-1-yl)boronic acid instead of (3-hydroxynaphthalen-2-yl)boronic acid in 1-b of Synthesis Example 1 Compound 4-a was obtained.

MS: [M+H]+ = 321

<4-b> Preparation of compound 4-b

Compound 4-b was obtained through the same synthesis and purification except for using compound 4-a instead of compound 1-b in 1-c of Synthesis Example 1.

MS: [M+H]+ = 303

<4-c> Preparation of compound core-4

Compound core-4 was obtained through the same synthesis and purification except for using compound 4-b instead of compound 1-c in 1-d of Synthesis Example 1.

MS: [M+H]+ = 395

Synthesis Example 5. Synthesis of BH-1

<5-a> Preparation of compound BH-1

After dissolving 9-bromo-10-phenylanthracene (10.6 g, 31.7 mmol) and compound core-1 (15 g, 38.0 mmol) in tetrahydrofuran (300 ml), Pd(PPh ₃ ) ₄ (1.8 g, 1.58 mmol) and 60 ml of 2M K ₂ CO ₃ aqueous solution were added and refluxed for 5 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and purified using column chromatography to obtain compound BH-1 (11.2 g, yield 68%).

MS: [M+H]+ = 521

Synthesis Example 6. Synthesis of BH-2

<6-a> Preparation of compound BH-2

Compound BH-2 was obtained through the same synthesis and purification except for using 9-bromo-10-(naphthalen-1-yl)anthracene in Synthesis Example 5-a instead of 9-bromo-10-phenylanthracene.

MS: [M+H]+ = 571

Synthesis Example 7. Synthesis of BH-3

<7-a> Preparation of compound BH-3

Compound BH-3 was obtained through the same synthesis and purification except for using 9-bromo-10-(naphthalen-2-yl)anthracene in Synthesis Example 5-a instead of 9-bromo-10-phenylanthracene.

MS: [M+H]+ = 571

Synthesis Example 8. Synthesis of BH-4

<8-a> Preparation of compound BH-4

Compound BH-4 was obtained through the same synthesis and purification except for using compound core-2 instead of compound core-1 in Synthesis Example 5-a.

MS: [M+H]+ = 521

Synthesis Example 9. Synthesis of BH-5

<9-a> Preparation of compound BH-5

Same as in Synthesis Example 5-a except that 9-bromo-10-phenylanthracene was replaced with 9-bromo-10-(naphthalen-1-yl)anthracene and compound core-2 was used instead of compound core-1. Compound BH-5 was obtained through synthesis and purification.

MS: [M+H]+ = 571

Synthesis Example 10. Synthesis of BH-6

<10-a> Preparation of compound BH-6

Same as in Synthesis Example 5-a, except that 9-bromo-10-(naphthalen-2-yl)anthracene was used instead of 9-bromo-10-phenylanthracene, and compound core-2 was used instead of compound core-1. Compound BH-6 was obtained through synthesis and purification.

MS: [M+H]+ = 571

Synthesis Example 11. Synthesis of BH-7

<11-a> Preparation of compound BH-7

Compound BH-7 was obtained through the same synthesis and purification except for using compound core-3 instead of compound core-1 in Synthesis Example 5-a.

MS: [M+H]+ = 521

Synthesis Example 12. Synthesis of BH-8

<12-a> Preparation of compound BH-8

Same as in Synthesis Example 5-a, except that 9-bromo-10-(naphthalen-1-yl)anthracene was used instead of 9-bromo-10-phenylanthracene, and compound core-3 was used instead of compound core-1. Compound BH-8 was obtained through synthesis and purification.

MS: [M+H]+ = 571

Synthesis Example 13. Synthesis of BH-9

<13-a> Preparation of compound BH-9

Same as in Synthesis Example 5-a, except that 9-bromo-10-(naphthalen-2-yl)anthracene was used instead of 9-bromo-10-phenylanthracene, and compound core-3 was used instead of compound core-1. Compound BH-9 was obtained through synthesis and purification.

MS: [M+H]+ = 571

Synthesis Example 14. Synthesis of BH-10

<14-a> Preparation of compound BH-10

Compound BH-10 was obtained through the same synthesis and purification except for using compound core-4 instead of compound core-1 in Synthesis Example 5-a.

MS: [M+H]+ = 521

Synthesis Example 15. Synthesis of BH-11

<15-a> Preparation of compound BH-11

Except for using 9-bromo-10-(naphthalen-1-yl)anthracene instead of 9-bromo-10-phenylanthracene in Synthesis Example 5-a and using compound core-4 instead of compound core-1 Compound BH-11 was obtained through synthesis and purification in the same manner.

MS: [M+H]+ = 571

Synthesis Example 16. Synthesis of BH-12

<16-a> Preparation of compound BH-12

Except for using 9-bromo-10-(naphthalen-2-yl)anthracene instead of 9-bromo-10-phenylanthracene in Synthesis Example 5-a and using compound core-4 instead of compound core-1 Compound BH-12 was obtained through synthesis and purification in the same manner.

MS: [M+H]+ = 571

Manufacturing of organic light emitting devices

Example 1

A glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 150 nm was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product of Fischer Co. was used as a detergent, and distilled water filtered through a second filter of a product of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with solvents of isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using nitrogen plasma, the substrate was transferred to a vacuum evaporator. A hole injection layer was formed by thermally vacuum depositing the HAT-CN compound to a thickness of 5 nm on the ITO transparent electrode thus prepared. Subsequently, HTL1 was thermally vacuum deposited to a thickness of 100 nm to form a first hole transport layer, and then HTL2 was thermally vacuum deposited to a thickness of 10 nm to form a second hole transport layer. Then, the following compound BD1 as a dopant and the compound BH-1 (weight ratio 5:95) as a host were simultaneously vacuum deposited to form a light emitting layer having a thickness of 20 nm. Subsequently, an electron transport layer was formed by vacuum depositing ETL to a thickness of 20 nm. Subsequently, LiF was vacuum deposited to a thickness of 0.5 nm to form an electron injection layer. Then, aluminum was deposited to a thickness of 100 nm to form a cathode to manufacture an organic light emitting device.

In the above process, the deposition rate of the organic material was maintained at 0.04 to 0.09 nm/sec, the deposition rate of lithium fluoride of the electron transport layer was 0.03 nm/sec, and the aluminum of the cathode was 0.2 nm/sec. Maintaining 1×10 ^-7 to 5×10 ^-5 torr, an organic light emitting device was manufactured.

Example 2

An organic light emitting device was manufactured in the same manner as in Example 1 except that BD2 was used instead of BD1 as the dopant of the light emitting layer.

Example 3

An organic light emitting device was manufactured in the same manner as in Example 1 except that BD2 was used instead of BD1 as a dopant of the light emitting layer and the compound BH-2 was used instead of the compound BH-1 as a host.

Example 4

An organic light emitting diode was manufactured in the same manner as in Example 1 except that BD2 was used instead of BD1 as the dopant of the light emitting layer and the compound BH-3 was used instead of the compound BH-1 as a host.

Example 5

An organic light emitting diode was manufactured in the same manner as in Example 1 except that BD2 was used instead of BD1 as a dopant of the light emitting layer and the compound BH-4 was used instead of the compound BH-1 as a host.

Example 6

An organic light emitting diode was manufactured in the same manner as in Example 1 except that BD2 was used instead of BD1 as the dopant of the light emitting layer and the compound BH-5 was used instead of the compound BH-1 as a host.

Example 7

An organic light emitting device was manufactured in the same manner as in Example 1 except that BD2 was used instead of BD1 as the dopant of the light emitting layer and the compound BH-6 was used instead of the compound BH-1 as a host.

Example 8

An organic light emitting device was manufactured in the same manner as in Example 1, except that BD2 was used instead of BD1 as a dopant of the light emitting layer and the compound BH-7 was used instead of the compound BH-1 as a host.

Example 9

An organic light emitting device was manufactured in the same manner as in Example 1 except that BD2 was used instead of BD1 as a dopant of the light emitting layer and the compound BH-8 was used instead of the compound BH-1 as a host.

Example 10

An organic light emitting device was manufactured in the same manner as in Example 1 except that BD2 was used instead of BD1 as a dopant of the light emitting layer and the compound BH-9 was used instead of the compound BH-1 as a host.

Example 11

An organic light emitting device was manufactured in the same manner as in Example 1 except that BD2 was used instead of BD1 as a dopant of the light emitting layer and the compound BH-10 was used instead of the compound BH-1 as a host.

Example 12

An organic light emitting diode was manufactured in the same manner as in Example 1 except that BD2 was used instead of BD1 as the dopant of the light emitting layer and the compound BH-11 was used instead of the compound BH-1 as a host.

Example 13

An organic light emitting device was manufactured in the same manner as in Example 1 except that BD2 was used instead of BD1 as a dopant of the light emitting layer and the compound BH-12 was used instead of the compound BH-1 as a host.

Comparative Example 1

An organic light emitting device was manufactured in the same manner as in Example 1 except that BD2 was used instead of BD1 as a dopant of the light emitting layer and the compound BH-13 was used instead of compound BH-1 as a host.

Comparative Example 2

An organic light emitting device was manufactured in the same manner as in Example 1 except that BD2 was used instead of BD1 as a dopant of the light emitting layer and the compound BH-14 was used instead of the compound BH-1 as a host.

Comparative Example 3

An organic light emitting device was manufactured in the same manner as in Example 1 except that BD2 was used instead of BD1 as a dopant of the light emitting layer and the compound BH-15 was used instead of the compound BH-1 as a host.

When current was applied to the organic light emitting devices prepared in Examples 1 to 13 and Comparative Examples 1 to 3, the voltage and efficiency were measured at 10 mA/cm ² , and the initial luminance was 95% at a current density of 10 mA/cm ² . By measuring the time (T95) to become, the results are shown in Table 1 below.

10 mA/cm ² measured value life span
(hr) Voltage
(V) current efficiency
(Cd/A) color coordinates division host dopant CIE x CIE y Example 1 BH-1 BD1 3.75 5.55 0.137 0.130 221 Example 2 BH-1 BD2 3.54 7.51 0.136 0.115 157 Example 3 BH-2 BD2 3.51 7.72 0.137 0.116 129 Example 4 BH-3 BD2 3.40 7.50 0.136 0.119 163 Example 5 BH-4 BD2 3.50 8.62 0.137 0.114 160 Example 6 BH-5 BD2 3.45 8.85 0.136 0.114 155 Example 7 BH-6 BD2 3.39 8.53 0.136 0.116 162 Example 8 BH-7 BD2 3.51 8.67 0.137 0.111 173 Example 9 BH-8 BD2 3.50 8.79 0.136 0.110 161 Example 10 BH-9 BD2 3.48 8.65 0.136 0.113 177 Example 11 BH-10 BD2 3.53 8.35 0.135 0.112 165 Example 12 BH-11 BD2 3.45 8.37 0.136 0.114 170 Example 13 BH-12 BD2 3.42 8.36 0.136 0.117 169 Comparative Example 1 BH-13 BD2 3.75 7.55 0.137 0.121 143 Comparative Example 2 BH-14 BD2 3.65 8.39 0.136 0.114 150 Comparative Example 3 BH-15 BD2 3.55 8.42 0.136 0.120 137

In Table 1, the compound of Formula 1 according to an exemplary embodiment of the present specification includes a compound in which an anthracene core and a substituent represented by Formula 2 are directly bonded, and thus has excellent electron and hole transport properties. Therefore, Examples 1 to 13 including this in the light emitting layer of the organic light emitting device are Comparative Example 1 including a compound in which the anthracene core and Formula 2 are bonded through a linking group (phenylene group), the anthracene core and the furan ring of Formula 2 Comparative Example 2 including a compound in which the benzene ring condensed on the side is directly connected, and Comparative Example 3 including a compound in which the anthracene core and the benzene ring condensed on the furan ring side of Formula 2 are bonded through a linking group (phenylene group) The driving voltage, efficiency, and/or lifespan of the organic light emitting device were superior to those of the organic light emitting device.

1: substrate
2: first electrode
3: second electrode
4: light emitting layer
5: hole injection layer
6: first hole transport layer
7: second hole transport layer
8: electron transport layer
9: electron injection layer

Claims (13)

A compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
R1 to R8 are the same as or different from each other, and each independently hydrogen; or deuterium;
L1 is a direct bond,
Ar1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms;
Ar2 is a group represented by the following formula 2-2 or 2-4;
[Formula 2-2]

[Formula 2-4]

In Formulas 2-2 and 2-4,
X1 is O,
Any one of G1 to G8 is a site bonded to Ar2 of Formula 1, and the remaining groups of G1 to G8 not bonded to Ar2 of Formula 1, Q1 and Q2 are the same as or different from each other, and each independently hydrogen; or deuterium;
q1 is 1 or 2;
q2 is 1 or 2;
When q1 is 2, the two Q1s are the same as or different from each other,
When q2 is 2, the two Q2s are the same as or different from each other. delete delete The compound according to claim 1, wherein Formula 1 is represented by any one of Formulas 1-3, 1-4 and 1-7:
[Formula 1-3]

[Formula 1-4]

[Formula 1-7]

In Formulas 1-3, 1-4 and 1-7,
The definitions of L1, Ar1, R1 to R8 are the same as defined in Formula 1 above,
The definitions of X1, Q1, Q2, q1 and q2 are the same as those defined in Chemical Formulas 2-2 and 2-4,
G101 to G105 are the same as or different from each other, and each independently hydrogen; or deuterium;
g105 is an integer from 1 to 3;
When g105 is 2 or more, the two or more G105s are the same as or different from each other. delete delete The compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:

a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of any one of claims 1, 4, and 7. device. The organic light emitting device of claim 8, wherein the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer includes the compound. The organic light emitting device of claim 8, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the compound. The organic light emitting device of claim 8, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the compound as a host of the light emitting layer. The organic light emitting device of claim 11, wherein the light emitting layer includes a dopant, and the dopant includes at least one selected from the group consisting of a fluorescent dopant, a phosphorescent dopant, and a thermally delayed fluorescence dopant. The organic light emitting device of claim 12, wherein the fluorescent dopant includes at least one selected from the group consisting of arylamine-based compounds and boron-based compounds.

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