KR20230105124A - 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 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.

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; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

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

Ar2 is the following formula A,

[Formula A]

In the formula A,

Any one of Ar3 and G1 to G8 is a site bonded to L2 of Formula 1, the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L3 is a direct bond; Or a substituted or unsubstituted arylene group.

In addition, an exemplary embodiment of the present specification includes a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layers includes the aforementioned compound.

A compound according to an exemplary embodiment of the present specification is used in an organic material layer of an organic light emitting device to lower a driving voltage of the organic light emitting device and improve light efficiency. In addition, the lifespan characteristics of the device can be improved by the thermal stability of the compound.

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 the compound of Formula 1 above.

Since Chemical Formula 1 according to an exemplary embodiment of the present specification includes phenothiazine 5,5-dioxide at position 10 of anthracene and includes an aryl group or a heteroaryl group at position 9 of anthracene, transfer of electrons and electrons It has structural properties such as improved viscosity and improved molecular stability. Accordingly, an organic light emitting device including the organic light emitting diode is excellent in terms of driving voltage, efficiency, and lifetime.

Throughout the present specification, the term "combination thereof" included in the expression of the Markush form means one or more mixtures or combinations selected from the group consisting of the components described in the expression of the Markush form, and the components It means including one or more selected from the group consisting of.

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; cyano group; an alkyl group; cycloalkyl group; alkoxy group; aryloxy group; Alkyl thioxy group; Arylthioxy group; alkenyl group; haloalkyl group; haloalkoxy group; arylalkyl 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 a heterocyclic group, is substituted with a substituent 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, bicyclo [2.2.1]heptyl group, bicyclo[2.2.1]octyl group, norbornyl group, etc., but are 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 haloalkoxy group means that at least one halogen group is substituted for the hydrogen of the alkoxy group in the definition of the alkoxy 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 arylalkyl group means that the alkyl group is substituted with an aryl group, and examples of the aryl group and the alkyl group described above may be applied to the aryl group and the alkyl group of the arylalkyl group.

In the present specification, the aryloxy group means that in the definition of the alkoxy group, it is substituted with an aryl group instead of the alkyl group of the alkoxy group, and the aryloxy group includes a phenoxy group, p-toryloxy group, m-toryloxy group, 3,5- Dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4 -Methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenane A triloxy group, a 9-phenanthryloxy group, and the like, but are not limited thereto.

In the present specification, the alkyl group of the alkyl thioxy group is the same as the example of the above-mentioned alkyl group. Specifically, the alkylthioxy group includes a methylthioxy group, an ethylthioxy group, a tert-butylthioxy group, a hexylthioxy group, an octylthioxy group, and the like, but is not limited thereto.

In the present specification, the aryl group in the arylthioxy group is the same as the example of the above-mentioned aryl group. Specifically, the arylthioxy group includes, but is not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group, and the like.

In the present specification, the heterocyclic 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, An aromatic heterocyclic group or an aliphatic heterocyclic group is included. The aromatic heterocyclic group may be represented by a heteroaryl group. The number of carbon atoms of the heterocyclic group is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. Examples of the heterocyclic 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, phenoxathiine group, phenoxazine group, phenothiazine group, decahydrobenzocarbazole group, hexahydrocarbazole group, dihydrobenzoazacillin group, dihydroindenocarbazole group, spirofluorene xanthene group, spirofluorene thioxanthene group, tetrahydronaphthothiophene group, tetrahydronaphthofuran group, tetrahydrobenzothiophene group, and tetrahydrobenzofuran group, etc. There is, but is not limited to this.

In the present specification, the silyl group is an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group; It may be 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 the alkyl group and the aryl group of the alkylarylsilyl group may be the alkyl group and the aryl group An example of may be applied, and examples of the heterocyclic group may be applied to the heteroaryl group of the heteroarylsilyl group.

In the present specification, the boron group may be -BY ₁₀₀ Y ₁₀₁ , wherein Y ₁₀₀ and Y 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 heterocyclic group having 2 to 30 carbon atoms. The boron group specifically includes, but is not limited to, a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, and a diphenyl boron group.

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, 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 heterocyclic 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 heterocyclic 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 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 heterocyclic groups.

In the present specification, the alkyl group of the N-alkylarylamine group, the alkylthioxy group, and the N-alkylheteroarylamine group is the same as the above-mentioned alkyl group. Specifically, the alkylthioxy group includes a methylthioxy group, an ethylthioxy group, a tert-butylthioxy group, a hexylthioxy group, an octylthioxy group, and the like, but is not limited thereto.

In the present specification, the aryl group in the aryloxy group, arylthioxy group, N-arylalkylamine group, and N-arylheteroarylamine group is the same as the aryl group described above. Specifically, the aryloxy group includes a phenoxy group, p-tolyloxy group, m-toryloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, etc., and arylthioxy group includes phenylthioxy group, 2- methylphenylthioxy group, 4-tert-butylphenylthioxy group, etc., but are not limited thereto.

In the present specification, the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from examples of the cycloalkyl group, the aryl group, and combinations thereof The hydrocarbon ring group is a phenyl group, a cyclohexyl group, an adamantyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.1]octyl group, a tetrahydronaphthalene group, a tetrahydroanthracene group, 1,2, 3,4-tetrahydro-1,4-methanonaphthalene group, 1,2,3,4-tetrahydro-1,4-ethanonaphthalene group, spirocyclopentane fluorene group, spiroadamantane fluorene group , and spirocyclohexanefluorene groups, but are not limited thereto.

In the present specification, the meaning of “adjacent” in “forming a ring by bonding with adjacent groups” is the same as described above, and the “ring” refers to a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring.

In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, except for the non-monovalent cycloalkyl group, aryl group, and combinations thereof It may be selected from examples, and the hydrocarbon ring may be benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2, 3,4-tetrahydro-1,4-methanonaphthalene, 1,2,3,4-tetrahydro-1,4-ethanonaphthalene, spirocyclopentanefluorene, spiroadamantanefluorene, and spirocyclo hexane fluorene and the like, but is not limited thereto.

In the present specification, the heterocycle 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 heterocyclic ring may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocyclic ring may be selected from examples of heteroaryl groups among the heterocyclic groups, except for non-monovalent ones. there is.

In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , thiocaine, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran, but are not limited thereto.

In the present specification, examples of the aliphatic or aromatic and aliphatic condensed heterocycles include tetrahydrobenzonaphthothiophene and tetrahydrobenzonaphthofuran, but are not limited thereto.

In the present specification, the arylene group means that the aryl group has 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.

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.

Hereinafter, the compound of Formula 1 will be described in detail.

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; or a substituted or unsubstituted polycyclic heteroaryl group having 10 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the substituted or unsubstituted heteroaryl group of Ar1 is represented by Formula B below.

[Formula B]

In the formula B,

X1 is O or S;

Any one of G101 to G109 is a site bonded to L1 in Formula 1, the others 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 cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring;

m is 0 or 1;

When m is 0, g109 is an integer from 1 to 4,

When m is 1, g109 is 1 or 2;

When the g109 is 2 or 2 or more, the 2 or 2 or more G109s are the same as or different from each other.

According to an exemplary embodiment of the present specification, Formula B is any one of the following Formulas B-1 to B-4.

[Formula B-1]

[Formula B-2]

[Formula B-3]

[Formula B-4]

In the formulas B-1 and B-2,

Any one of G101 to G104 and G110 to G113 is a site bound to L1 in Formula 1, the others 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 cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring;

In the formulas B-3 and B-4,

Any one of G101 to G109 is a site bound to L1 in Formula 1, the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring;

g'109 is 1 or 2;

When g'109 is 2, the two G109s are the same as or different from each other.

According to an exemplary embodiment of the present specification, Formula B-3 is selected from any one of the following structures.

In the above structure,

Any one of G101 to G109 is a site bound to L1 in Formula 1, the others 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 cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring;

g'109 is 1 or 2;

When g'109 is 2, the two G109s are the same as or different from each other.

According to an exemplary embodiment of the present specification, Formula B-4 is selected from any one of the following structures.

In the above structure,

Any one of G101 to G109 is a site bound to L1 in Formula 1, the others 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 cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or bonded to adjacent groups to form a substituted or unsubstituted ring;

g'109 is 1 or 2;

When g'109 is 2, the two G109s are the same as or different from each other.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-5.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Formulas 1-1 to 1-5,

The definitions of R1 to R8, L1, L2 and Ar1 are the same as defined in Formula 1 above,

The definition of L3 is the same as defined in Formula A above,

G'1 to G'8 and Ar'3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently hydrogen; or deuterium, wherein L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, and Ar1 is a substituted or unsubstituted with at least one of deuterium, a linear or branched chain alkyl group having 1 to 30 carbon atoms, and combinations thereof a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a polycyclic heteroaryl group having 10 to 30 carbon atoms substituted or unsubstituted with one or more of combinations thereof, wherein L3 is a direct bond; Or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, substituted or unsubstituted with deuterium, and any one of Ar3 and G1 to G8 is a site bonded to L2 of Formula 1, and the others are the same as or different from each other, hydrogen each independently; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently hydrogen; or deuterium.

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

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

According to an exemplary embodiment of the present specification, the L1 and L2 are the same as or different from each other, and are each independently 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 and L2 are the same as or different from each other, and are each independently 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 and L2 are the same as or different from each other, and are each independently a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, the L1 and L2 are the same as or different from each other, and are each independently a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, the L1 and L2 are the same as or different from each other, and are each independently a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen; Or a naphthylene group unsubstituted or substituted with deuterium.

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; or a substituted or unsubstituted polycyclic heteroaryl group having 10 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; or a substituted or unsubstituted polycyclic heteroaryl group having 10 to 20 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 unsubstituted or substituted with one or more of deuterium, a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, and a combination thereof. ; or a heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a polycyclic heteroaryl group having 10 to 30 carbon atoms substituted or unsubstituted with at least one of combinations thereof.

According to an exemplary embodiment of the present specification, Ar1 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms unsubstituted or substituted with one or more of deuterium, a linear or branched chain alkyl group having 1 to 20 carbon atoms, and a combination thereof. ; or a heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a polycyclic heteroaryl group having 10 to 20 carbon atoms substituted or unsubstituted with one or more of combinations thereof.

According to an exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; A terphenyl group unsubstituted or substituted with heavy hydrogen; A naphthyl group unsubstituted or substituted with heavy hydrogen; A phenanthrene group unsubstituted or substituted with heavy hydrogen; A fluorene group unsubstituted or substituted with at least one of heavy hydrogen, a methyl group, and combinations thereof; A dibenzofuran group unsubstituted or substituted with at least one of heavy hydrogen, a phenyl group, and combinations thereof; a dibenzothiophene group unsubstituted or substituted with at least one of heavy hydrogen, a phenyl group, and combinations thereof; A benzonaphthofuran group unsubstituted or substituted with heavy hydrogen; Or a benzonaphthothiophene group unsubstituted or substituted with deuterium.

According to one embodiment of the present specification, the L3 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, the L3 is a direct bond; Or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to one embodiment of the present specification, the L3 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen.

According to one embodiment of the present specification, the L3 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen.

According to one embodiment of the present specification, the L3 is a direct bond; Or a phenylene group unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, any one of Ar3 and G1 to G8 is a site bound to L2 of Formula 1, the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; 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, any one of Ar3 and G1 to G8 is a site bound to L2 of Formula 1, the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, any one of Ar3 and G1 to G8 is a site bound to L2 of Formula 1, the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, any one of Ar3 and G1 to G8 is a site bound to L2 of Formula 1, the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, any one of Ar3 and G1 to G8 is a site bonded to L2 of Formula 1, the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with heavy hydrogen; A biphenyl group unsubstituted or substituted with heavy hydrogen; Or a naphthyl group unsubstituted or substituted with deuterium.

According to a practical condition of the present specification, when Ar3 is not bonded to L2 of Formula 1, Ar3 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to a practical condition of the present specification, when Ar3 is not bonded to L2 of Formula 1, Ar3 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to a practical condition of the present specification, when Ar3 is not bonded to L2 of Formula 1, Ar3 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium.

According to a practical condition of the present specification, when Ar3 is not bonded to L2 of Formula 1, Ar3 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium.

According to one practical condition of the present specification, when Ar3 is not bonded to L2 of Formula 1, Ar3 is a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; Or a naphthyl group unsubstituted or substituted with deuterium.

According to one practical condition of the present specification, the remaining groups not bonded to L2 of Formula 1 among the G1 to G8 are the same as or different from each other, and each independently hydrogen; or deuterium.

According to one practical condition of the present specification, the remaining groups not bonded to L2 of Formula 1 among the G1 to G8 are hydrogen.

According to one practical condition of the present specification, the remaining groups not bonded to L2 of Formula 1 among the G1 to G8 are deuterium.

According to an exemplary embodiment of the present specification, Ar'3 and G'1 to G'8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; 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, Ar'3 and G'1 to G'8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar'3 and G'1 to G'8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, Ar'3 and G'1 to G'8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, Ar'3 and G'1 to G'8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with heavy hydrogen; A biphenyl group unsubstituted or substituted with heavy hydrogen; Or a naphthyl group unsubstituted or substituted with deuterium.

According to one practical condition of the present specification, Ar'3 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one practical condition of the present specification, Ar'3 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to one practical condition of the present specification, Ar'3 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium.

According to one practical condition of the present specification, Ar'3 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium.

According to one practical condition of the present specification, Ar'3 is a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; Or a naphthyl group unsubstituted or substituted with deuterium.

According to one practical condition of the present specification, the G'1 to G'8 are the same as or different from each other, and each independently hydrogen; or deuterium.

According to one practical condition of the present specification, G'1 to G'8 are hydrogen.

According to one practical condition of the present specification, the G'1 to G'8 are deuterium.

According to an exemplary embodiment of the present specification, in Formulas B-1 and B-2, any one of G101 to G104 and G110 to G113 is a site bound to L1 of Formula 1, and the others are the same as or different from each other, , each independently hydrogen; heavy hydrogen; 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, in Formulas B-1 and B-2, any one of G101 to G104 and G110 to G113 is a site bound to L1 of Formula 1, and the others are the same as or different from each other, , each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in Formulas B-1 and B-2, any one of G101 to G104 and G110 to G113 is a site bound to L1 of Formula 1, and the others are the same as or different from each other, , each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, in Formulas B-1 and B-2, any one of G101 to G104 and G110 to G113 is a site bound to L1 of Formula 1, and the others are the same as or different from each other, , each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, in Formulas B-3 and B-4, any one of G101 to G109 is a site bound to L1 of Formula 1, and the others are the same as or different from each other, and each independently hydrogen; or deuterium.

According to an exemplary embodiment of the present specification, in Chemical Formulas B-3 and B-4, one of G101 to G109 is a site bonded to L1 of Chemical Formula 1, and the others are hydrogen.

According to an exemplary embodiment of the present specification, in Chemical Formulas B-3 and B-4, any one of G101 to G109 is a site bonded to L1 of Chemical Formula 1, and the others are deuterium.

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 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 a fluorescent dopant.

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

According to one embodiment of the present specification, the non-pyrene-based compound includes a boron-based compound.

According to an exemplary embodiment of the present specification, the light emitting layer further includes at least one host different from the compound of Formula 1.

A host different from the compound of Formula 1 may be used without limitation as long as it is an anthracene-based host used in the art if it is different from Formula 1, but is not limited thereto.

According to one embodiment of the present specification, the light emitting layer includes a host and a dopant.

According to one embodiment of the present specification, the light emitting layer includes a host and a dopant, and the host includes the compound represented by Formula 1.

According to one embodiment of the present specification, the dopant is a blue dopant.

According to one embodiment of the present specification, the organic light emitting device is a blue organic light emitting device.

According to an exemplary embodiment of the present specification, the light emitting layer includes two or more kinds of mixed hosts, and at least one of the two or more kinds of mixed hosts includes the compound represented by Formula 1.

According to an exemplary embodiment of the present specification, the light emitting layer includes two or more types of mixed hosts, at least one of the two or more types of mixed hosts includes the compound represented by Formula 1, and the rest includes Formula 1 and It includes different anthracene-based compounds.

If at least one of the two or more mixed hosts includes the compound represented by Formula 1, and the others are different from Formula 1, any anthracene-based host used in the art may be used without limitation, and is limited to this. it is not going to be

An organic light emitting device using two or more types of mixed hosts according to an exemplary embodiment of the present specification is intended to improve the performance of the device by mixing the advantages of each host. For example, when two types of hosts are mixed, high efficiency And by mixing one host having a low voltage effect and one host having a long lifespan effect, an organic light emitting device having effects of high efficiency, low voltage and long lifespan may be manufactured.

According to one embodiment of the present specification, the organic light emitting device has a maximum emission wavelength (λ _max ) of an emission spectrum of 400 nm to 470 nm.

According to one embodiment of the present specification, the light emitting layer includes a host and a dopant, and the dopant is a fluorescent dopant.

According to one embodiment of the present specification, the light emitting layer includes a host and a dopant, and the dopant includes at least one selected from a pyrene-based compound and a non-pyrene-based compound.

The pyrene-based compounds and non-pyrene-based compounds may be used without limitation as long as they are compounds used in the art, but are not limited thereto.

According to one embodiment of the present specification, the non-pyrene-based compound includes a boron-based compound.

According to an exemplary embodiment of the present specification, the light emitting layer includes a host and a dopant, the host includes a compound represented by Formula 1, and the dopant includes at least one selected from a pyrene-based compound and a non-pyrene-based compound. includes

According to one embodiment of the present specification, the light emitting layer includes a host and a dopant, and the light emitting layer includes a host:dopant in a weight ratio of 0.1:99.9 to 20:80.

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 a cathode, one or more organic material layers, and an anode 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 diode, but are not limited thereto.

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

2 shows a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 8, a hole blocking layer 9 on a substrate 1, electron injection and The structure of the organic light emitting device in which the transport layer 10 and the second electrode 3 are sequentially stacked is illustrated. The compound is included in the light emitting layer (8).

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 of Formula 1 according to an exemplary embodiment of the present specification, the host material may include 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.

According to an exemplary embodiment of the present specification, the dopant is represented by Chemical Formula D-1, but is not limited thereto.

[Formula D-1]

In the above formula D-1,

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 alkylsilyl 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 straight-chain or branched-chain alkylsilyl 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 straight-chain or branched-chain alkylsilyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine 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; 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 or a straight-chain or branched-chain alkylsilyl 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; methyl group; tert-butyl group; a diphenylamine group unsubstituted or substituted with a methyl group or a tert-butyl group; trimethylsilyl group; a phenyl group unsubstituted or substituted with a methyl group, a tert-butyl group, or a trimethylsilyl group; or a biphenyl group.

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

According to an exemplary embodiment of the present specification, Chemical Formula D-1 may be prepared as shown in Reaction Scheme 1 below, but is not limited thereto.

[Scheme 1]

In Scheme 1,

The definitions of T1 to T5 and t3 to t5 are the same as defined in Formula D-1 above.

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.

According to an exemplary embodiment of the present specification, the hole injection layer includes a compound represented by Chemical Formula HI-1, but is not limited thereto.

[Formula HI-1]

In the above formula HI-1,

R315 to R317 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof, or bonded to adjacent groups to form a substituted or unsubstituted ring,

r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 are the same as or different from each other;

r316 is an integer of 1 to 5, and when r316 is 2 or more, 2 or more of R316 are the same as or different from each other.

According to an exemplary embodiment of the present specification, R317 is a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, R317 is a carbazole group; phenyl group; biphenyl group; triphenylene group; terphenyl group; And any one selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group, or combines with an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.

According to an exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently a phenyl group; or a biphenyl group, or bonded to an adjacent group to form an indene substituted with a methyl group.

According to an exemplary embodiment of the present specification, Formula HI-1 is represented by any one of the following compounds.

According to an exemplary embodiment of the present specification, the hole injection layer includes a compound represented by Formula HI-2, but is not limited thereto.

[Formula HI-2]

In the above formula HI-2,

R401 to R403 are the same as or the same as each other, and are each independently a halogen group;

r401 to r403 are 4.

According to an exemplary embodiment of the present specification, R401 to R403 are F.

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

According to an exemplary embodiment of the present specification, the hole injection layer includes Chemical Formulas HI-1 and HI-2.

According to an exemplary embodiment of the present specification, the hole injection layer includes Chemical Formulas HI-1 and HI-2 in a weight ratio of 1:99 to 99:1.

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.

According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by Formula HT-1, but is not limited thereto.

[Formula HT-1]

In the above formula HT-1,

L501 and L502 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R501 and Ar501 to Ar504 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, L501 and L502 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L501 and L502 are phenylene groups.

According to an exemplary embodiment of the present specification, R501 and Ar501 to Ar504 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.

According to an exemplary embodiment of the present specification, R501 and Ar501 to Ar504 are the same as or different from each other, and each independently a phenyl group; or a naphthyl group.

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

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, fluorenylidene 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.

According to one embodiment of the present specification, the electron injection and transport layer is a layer that transports electrons to the light emitting layer. The electron injection and transport layer may use the materials exemplified in the electron transport layer and the electron injection layer, but are not limited thereto.

According to an exemplary embodiment of the present specification, the electron injection and transport layer includes a compound represented by Formula ET-1, but is not limited thereto.

[Formula ET-1]

In the above formula ET-1,

At least one of Z11 to Z13 is N and the others are CH,

At least one of Z21 to Z23 is N and the others are CH,

L601 and L602 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar601 to Ar604 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, L601 and L602 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L601 and L602 are phenylene groups.

According to an exemplary embodiment of the present specification, Ar601 to Ar604 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.

According to an exemplary embodiment of the present specification, Ar601 to Ar604 are phenyl groups.

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

According to one embodiment of the present specification, the electron injection and transport layer may further include a metal complex compound. The metal complex compound is as described above.

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.

Examples of Chemical Formula HI-I may be applied as the material of the electron blocking layer, but are not limited thereto.

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.

According to an exemplary embodiment of the present specification, the hole blocking layer includes a compound represented by Chemical Formula HB-1, but is not limited thereto.

[Formula HB-1]

In the above formula HB-1,

At least one of Z31 to Z33 is N, the others are CH,

L603 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R601, R602, Ar605 and Ar606 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or bonded to adjacent groups to form a ring.

According to an exemplary embodiment of the present specification, the L603 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 L603 is a direct bond; or a biphenylylene group.

According to an exemplary embodiment of the present specification, R601 and R602 are the same as or different from each other, and each independently a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R601 and R602 are methyl groups.

According to an exemplary embodiment of the present specification, R601 and R602 are phenyl groups.

According to an exemplary embodiment of the present specification, R601 and R602 combine with each other to form an aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, R601 and R602 combine with each other to form a fluorene ring.

According to an exemplary embodiment of the present specification, Ar605 and Ar606 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.

According to an exemplary embodiment of the present specification, Ar605 and Ar606 are the same as or different from each other, and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar605 and Ar606 are biphenyl groups.

According to an exemplary embodiment of the present specification, Ar605 and Ar606 are phenyl groups.

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

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.

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

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.

<Preparation Example 1> Synthesis of Compound 1

1-(10-bromoantracen-9-yl)naphtho[2,3-b]benzofuran (4.50 g, 9.51 mmol) and compound a-1 (4.94 g, 11.42 mmol) were added to a 500 mL round bottom flask under a nitrogen atmosphere. After completely dissolving in 240 mL of tetrahydrofuran, 2M aqueous solution of potassium carbonate (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.55 g, 0.48 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 310 mL of toluene to prepare Compound 1 (4.12 g, yield: 62%).

MS[M+H] ⁺ = 700

<Preparation Example 2> Synthesis of Compound 2

Compound 7-(10-bromoantracen-9-yl)naphtho[1,2-b]benzofuran (4.50 g, 9.51 mmol), and compound a-2 (4.94 g, 11.42 mmol) were added to a 500 mL round bottom flask under a nitrogen atmosphere. After completely dissolving in 240 mL of tetrahydrofuran, 2M aqueous solution of potassium carbonate (120 mL) was added, tetrakis-(triphenylphosphine)palladium (0.55 g, 0.48 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 290 mL of toluene to prepare Compound 2 (4.36 g, yield: 65%).

MS[M+H] ⁺ = 700

<Preparation Example 3> Synthesis of Compound 3

Compound 2-(10-bromoantracen-9-yl)dibenzo[b,d]furan (4.50 g, 10.64 mmol), and compound a-3 (5.53. g, 12.77 mmol) were added to a 500 mL round bottom flask under a nitrogen atmosphere. After completely dissolving in 240 mL of tetrahydrofuran, 2M aqueous solution of potassium carbonate (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.61 g, 0.53 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 mL of toluene to prepare compound 3 (4.61 g, yield: 67%).

MS[M+H] ⁺ = 650

<Preparation Example 4> Synthesis of Compound 4

Compound 3-(10-bromoantracen-9-yl)dibenzo[b,d]furan (4.50 g, 10.64 mmol), and compound a-4 (5.53 g, 12.77 mmol) were added to a 500 mL round bottom flask in a nitrogen atmosphere. After completely dissolving in 240 mL of hydrofuran, a 2M aqueous solution of potassium carbonate (120 mL) was added, tetrakis-(triphenylphosphine)palladium (0.61 g, 0.53 mmol) was added, followed by heating and stirring for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 mL of toluene to prepare Compound 4 (4.38 g, yield: 63%).

MS[M+H] ⁺ = 650

<Preparation Example 5> Synthesis of Compound 5

Compound 1-(10-bromoantracen-9-yl)dibenzo[b,d]furan (4.50 g, 10.64 mmol), and compound a-5 (6.17 g, 12.77 mmol) were added to a 500 mL round bottom flask in a nitrogen atmosphere. After completely dissolving in 240 mL of hydrofuran, 2M aqueous solution of potassium carbonate (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.61 g, 0.53 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 mL of toluene to prepare Compound 5 (4.11 g, yield: 55%).

MS[M+H] ⁺ = 700

<Preparation Example 6> Synthesis of Compound 6

Compound 4-(10-bromoantracen-9-yl)dibenzo[b,d]furan (4.50 g, 10.64 mmol), and compound a-6 (6.17 g, 12.77 mmol) were added in a 500 mL round bottom flask under a nitrogen atmosphere. After completely dissolving in 240 mL of hydrofuran, 2M aqueous solution of potassium carbonate (120 mL) was added, tetrakis-(triphenylphosphine)palladium (0.61 g, 0.53 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 mL of toluene to prepare Compound 6 (3.88 g, yield: 52%).

MS[M+H] ⁺ = 700

<Preparation Example 7> Synthesis of Compound 7

10-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)naphtho[2,1-b]benzofuran (4.50 g , 9.36 mmol), and compound a-7 (5.71 g, 11.32 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis- (triphenylphosphine) palladium ( 0.54 g, 0.47 mmol) was added thereto and heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 mL of toluene to prepare compound 7 (4.98 g, yield: 68%).

MS[M+H] ⁺ = 784

<Preparation Example 8> Synthesis of Compound 8

Compound 2-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)naphtho[2,3-b]benzofuran (4.50 g, 9.36 mmol) and compound a-8 (5.71 g, 11.23 mmol) were completely dissolved in 240 mL of tetrahydrofuran, 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.54 g, 0.47 mmol) was added and heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 mL of toluene to prepare Compound 8 (5.13 g, yield: 70%).

MS[M+H] ⁺ = 784

<Preparation Example 9> Synthesis of Compound 9

Compound 9-bromo-10-(phenyl-d5)anthracene-1,2,3,4,5,6,7,8-d8 (4.50 g, 13.01 mmol), and compound in a 500 mL round bottom flask under a nitrogen atmosphere. After completely dissolving a-9 (7.94 g, 15.61 mmol) in 240 mL of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.75 g, 0.65 mmol) was added. After adding, the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 mL of toluene to prepare Compound 9 (5.26 g, yield: 62%).

MS[M+H] ⁺ = 649

<Preparation Example 10> Synthesis of Compound 10

9-bromo-10-(naphthalen-1-yl-d7)anthracene-1,2,3,4,5,6,7,8-d8 (4.50 g, 11.31 mmol) in a 500 mL round bottom flask under a nitrogen atmosphere. After completely dissolving , and compound a-10 (6.91 g, 13.57 mmol) in 240 mL of tetrahydrofuran, 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis- (triphenylphosphine) palladium (0.65 g, 0.57 mmol) was added and heated and stirred for 7 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 320 mL of toluene to prepare Compound 10 (5.59 g, yield: 71%).

MS[M+H] ⁺ = 701

<Preparation Example 11> Synthesis of Compound 11

Compound 9-bromo-10-(phenyl-d5)anthracene-1,2,3,4,5,6,7,8-d8 (4.50 g, 13.01 mmol), and compound in a 500 mL round bottom flask under a nitrogen atmosphere. After completely dissolving a-11 (6.95 g, 15.61 mmol) in 240 mL of tetrahydrofuran, 2M aqueous solution of potassium carbonate (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.75 g, 0.65 mmol) was added. After adding, the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 mL of toluene to prepare Compound 11 (4.87 g, yield: 64%).

MS[M+H] ⁺ = 585

<Preparation Example 12> Synthesis of Compound 12

Compound 9-([1,1'-biphenyl]-4-yl-d9)-10-bromoanthracene-1,2,3,4,5,6,7,8-d8 in a 500 mL round bottom flask under a nitrogen atmosphere. (4.50 g, 10.56 mmol) and compound a-12 (5.64 g, 12.68 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and 2M potassium carbonate aqueous solution (120 mL) was added thereto, and tetrakis-(triphenylphosphine) ) After adding palladium (0.61 g, 0.53 mmol), the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 mL of toluene to prepare Compound 12 (4.46 g, yield: 63%).

MS[M+H] ⁺ = 665

<Preparation Example 13> Synthesis of Compound 13

After completely dissolving compound 9-bromo-10-phenylanthracene (4.50 g, 13.51 mmol) and compound a-13 (7.02 g, 16.22 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere, 2M potassium carbonate Aqueous solution (120 mL) was added, and after adding tetrakis-(triphenylphosphine)palladium (0.78 g, 0.68 mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 mL of toluene to prepare Compound 13 (4.22 g, yield: 56%).

MS[M+H] ⁺ = 560

<Preparation Example 14> Synthesis of Compound 14

After completely dissolving compound 9-bromo-10-phenylanthracene (4.50 g, 13.51 mmol) and compound a-14 (7.02 g, 16.22 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere, 2M potassium carbonate Aqueous solution (120 mL) was added, and after adding tetrakis-(triphenylphosphine)palladium (0.78 g, 0.68 mmol), the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 mL of toluene to prepare Compound 14 (3.97 g, yield: 52%).

MS[M+H] ⁺ = 560

Fabrication of organic light emitting device

Example 1-1

A glass substrate coated with ITO (indium tin oxide) to a thickness of 1,000 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the 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 such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum deposition machine.

A hole injection layer was formed by thermally vacuum-depositing the following compound HI1 and the following compound HI2 to a thickness of 100 Å in a ratio of 98:2 (molar ratio) on the ITO transparent electrode prepared as described above. A hole transport layer was formed by vacuum depositing a compound (1150 Å) represented by Chemical Formula HT1 on the hole injection layer. Subsequently, an electron blocking layer was formed by vacuum depositing a compound of EB1 to a film thickness of 50 Å on the hole transport layer. Subsequently, Compound 1 synthesized in Preparation Example 1 and the compound represented by the following Chemical Formula BD were vacuum deposited on the electron blocking layer to a film thickness of 200 Å at a weight ratio of 25:1 to form a light emitting layer. A hole blocking layer was formed on the light emitting layer by vacuum depositing a compound of HB1 to a film thickness of 50 Å. Subsequently, a compound represented by Chemical Formula ET1 and a compound represented by Chemical Formula LiQ were vacuum deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 310 Å. A negative electrode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7Å / sec, the deposition rate of lithium fluoride on the cathode was 0.3Å / sec, and the deposition rate of aluminum was 2Å / sec, and the vacuum level during deposition was 2ⅹ10 ^-7 ~ Maintaining 5x10 ^-6 torr, an organic light emitting device was manufactured.

Examples 1-2 to 1-14

An organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compounds shown in Table 1 were used instead of the compounds of Preparation Example 1.

Comparative Examples 1-1 to 1-3

An organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compounds shown in Table 1 were used instead of the compounds of Preparation Example 1. The compounds of BH1 to BH3 used in Table 1 are as follows.

Experimental Example 1

When current was applied to the organic light emitting devices prepared in Examples 1-1 to 1-14 and Comparative Examples 1-1 to 1-3, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. showed up T95 means the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(light emitting layer) Voltage
(V@10mA
/cm ² ) efficiency
(cd/A@10mA
/cm ² ) color coordinates
(x,y) T95
(hr) Example 1-1 compound 1 4.31 6.53 (0.147, 0.045) 230 Example 1-2 compound 2 4.33 6.51 (0.146, 0.046) 230 Examples 1-3 compound 3 4.37 6.53 (0.145, 0.045) 235 Example 1-4 compound 4 4.39 6.56 (0.146, 0.047) 240 Example 1-5 compound 5 4.35 6.58 (0.147, 0.045) 245 Example 1-6 compound 6 4.31 6.57 (0.146, 0.06) 245 Examples 1-7 compound 7 4.33 6.59 (0.145, 0.045) 260 Examples 1-8 compound 8 4.31 6.54 (0.147, 0.047) 270 Examples 1-9 compound 9 4.37 6.45 (0.146, 0.046) 285 Examples 1-10 compound 10 4.39 6.51 (0.147, 0.046) 280 Example 1-11 compound 11 4.34 6.52 (0.147, 0.046) 305 Examples 1-12 compound 12 4.35 6.50 (0.147, 0.046) 315 Examples 1-13 compound 13 4.35 6.54 (0.146, 0.047) 225 Examples 1-14 compound 14 4.36 6.52 (0.145, 0.045) 220 Comparative Example 1-1 BH1 4.95 5.69 (0.146, 0.045) 75 Comparative Example 1-2 BH2 4.83 5.78 (0.146, 0.047) 80 Comparative Example 1-3 BH3 4.77 6.05 (0.145, 0.046) 135

As shown in Table 1, the organic light emitting device using the compound of the present specification as a light emitting layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.

The organic light emitting devices of Examples 1-1 to 1-14 using the compound of the present specification have lower voltage and higher efficiency than the organic light emitting devices of Comparative Examples 1-1 to 1-3 prepared using materials of BH1, BH2, and BH3. and long life characteristics.

Although the preferred embodiment (light emitting layer) of the present invention has been described above, the present invention is not limited thereto, and it is possible to carry out various modifications within the scope of the claims and detailed description of the invention, and this is also the scope of the invention. belong to the category

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

Claims (12)

A compound of Formula 1:
[Formula 1]

In Formula 1,
R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar2 is the following formula A,
[Formula A]

In the formula A,
Any one of Ar3 and G1 to G8 is a site bonded to L2 of Formula 1, the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L3 is a direct bond; Or a substituted or unsubstituted arylene group. The method according to claim 1, wherein Ar1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a compound that is a substituted or unsubstituted polycyclic heteroaryl group having 10 to 30 carbon atoms. The compound according to claim 1, wherein the substituted or unsubstituted heteroaryl group of Ar1 is of Formula B below:
[Formula B]

In the formula B,
X1 is O or S;
Any one of G101 to G109 is a site bonded to L1 in Formula 1, the others 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 cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring;
m is 0 or 1;
When m is 0, g109 is an integer from 1 to 4,
When m is 1, g109 is 1 or 2;
When g109 is 2 or 2 or more, the 2 or 2 or more G109s are the same as or different from each other. The compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-5:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Formulas 1-1 to 1-5,
The definitions of R1 to R8, L1, L2 and Ar1 are the same as defined in Formula 1 above,
The definition of L3 is the same as defined in Formula A above,
G'1 to G'8 and Ar'3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. The method according to claim 1, wherein R1 to R8 are the same as or different from each other, and each independently hydrogen; or deuterium;
Wherein L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium,
Ar1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, unsubstituted or substituted with one or more of heavy hydrogen, a linear or branched chain alkyl group having 1 to 30 carbon atoms, and a combination thereof; Or a heavy hydrogen, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a polycyclic heteroaryl group having 10 to 30 carbon atoms unsubstituted or substituted with one or more of combinations thereof,
L3 is a direct bond; Or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium,
Any one of Ar3 and G1 to G8 is a site bonded to L2 of Formula 1, the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a compound that is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium. The compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:

. a first electrode; a second 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 according to any one of claims 1 to 6. light emitting element. The organic light emitting device of claim 7, 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 8 , wherein the light emitting layer includes a dopant, and the dopant includes a fluorescent dopant. The organic light emitting device of claim 9, wherein the fluorescent dopant includes at least one selected from a pyrene-based compound and a non-pyrene-based compound. The organic light emitting device of claim 10, wherein the non-pyrene-based compound includes a boron-based compound. The organic light emitting device of claim 8, wherein the light emitting layer further includes at least one host different from the compound.

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