KR20230052811A - Compound, and organic light emitting device comprising same - Google Patents

Abstract

The present specification relates to a compound of a chemical formula 1 and an organic light-emitting device containing the same. The compound can improve efficiency, and alleviate low driving voltage, and/or lifespan characteristics in the organic light-emitting device.

Description

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2021-0134629 filed with the Korean Intellectual Property Office on October 12, 2021, all of which are incorporated herein.

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.

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

[Formula 1]

In Formula 1,

R1 to R8 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group;

L1 to L3 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,

Ar1 is a cycloalkyl group unsubstituted or substituted with heavy hydrogen; an aryl group unsubstituted or substituted with one or more substituents selected from heavy hydrogen, an alkyl group, and an aryl group; a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring substituted with at least one substituent selected from heavy hydrogen, an alkyl group, and an aryl group; Or a heteroaryl group that is unsubstituted or substituted with one or more substituents selected from heavy hydrogen, an alkyl group, and an aryl group, and includes N, O, or S,

R101 and R102 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

l1 to l3, r101 and r102 are integers from 1 to 3, respectively;

When l1 is 2 or more, the two or more L1s are the same as or different from each other,

When l2 is 2 or more, the two or more L2s are the same as or different from each other,

When l3 is 2 or more, the two or more L3s are the same as or different from each other,

When r101 is 2 or more, the two or more R101s are the same as or different from each other,

When the number of r102 is 2 or more, the two or more R102s are the same as or different from each other.

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.

The compounds described in this specification can be used as a material for an organic material layer of an organic light emitting device. The compound according to at least one exemplary embodiment of the present specification may improve efficiency, low driving voltage, and/or lifetime characteristics of an organic light emitting device. In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, luminescence, hole blocking, electron transport, or electron injection materials. In addition, compared to conventional organic light emitting devices, there are effects of low driving voltage, high efficiency, and/or long lifespan.

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.

The present specification provides a compound represented by Formula 1 above.

The compound represented by Formula 1 according to an exemplary embodiment of the present specification is an amine compound containing at least two tetrahydronaphthalenes substituted with an alkyl group, and exhibits high heat resistance compared to the molecular weight by including at least two tetrahydronaphthalenes, and is an organic light emitting device. It is included in the organic material layer to improve efficiency, low driving voltage and life characteristics.

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; alkenyl group; haloalkyl group; silyl group; boron group; amine group; aryl group; condensed ring groups of aromatic hydrocarbon rings and aliphatic hydrocarbon rings; And it means that it is substituted with one or more substituents selected from the group consisting of heteroaryl groups, is substituted with substituents in which two or more substituents among the above exemplified substituents are connected, or does not have any substituents.

또는

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

,

또는

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

or

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

,

or

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

In this specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited thereto.

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

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

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited thereto.

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

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

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.

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

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

,

,

,

,

,

,

및

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

,

,

,

,

,

,

and

etc., but is not limited thereto.

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

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

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

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. The boron group specifically includes, 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 heteroaryl group described above.

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

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

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

In the present specification, the hydrocarbon ring group is an aromatic hydrocarbon ring group; an aliphatic hydrocarbon ring group; Or it may be a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and the description of the aryl group described above is applied to the aromatic hydrocarbon ring group, and the description of the cycloalkyl group described above can be applied to the aliphatic hydrocarbon ring group. In addition, a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring may have a structure in which an aryl group and a cycloalkyl group described above are condensed with each other.

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

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

In an exemplary embodiment of the present specification, a portion where a substituent is not indicated in Formula 1 may mean that hydrogen is substituted.

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

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

According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of Formulas 1-1 to 1-3 below.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

The definitions of R1 to R8, R101, R102, r101, r102, L1 to L3, l1 to l3 and Ar1 are the same as defined in Formula 1 above.

According to an exemplary embodiment of the present specification, Formula 1 is represented by Formula 2 below.

[Formula 2]

In Formula 2,

The definitions of R1 to R8, R101, R102, r101, r102, L1 to L3 and l1 to l3 are the same as defined in Formula 1,

Ar11 is a cycloalkyl group unsubstituted or substituted with heavy hydrogen; an aryl group unsubstituted or substituted with one or more substituents selected from heavy hydrogen, an alkyl group, and an aryl group; or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring substituted with at least one substituent selected from heavy hydrogen, an alkyl group, and an aryl group.

According to an exemplary embodiment of the present specification, Formula 1 is represented by Formula 3 or 4 below.

[Formula 3]

[Formula 4]

In Formulas 3 and 4,

The definitions of R1 to R8, R101, R102, r101, r102, L1 to L3 and l1 to l3 are the same as defined in Formula 1,

X1 is O; S; or NR105;

R103 to R105 are the same as or different from each other, and each independently hydrogen; Or an aryl group,

r103 is an integer from 1 to 8;

r104 is an integer from 1 to 7;

When r103 is 2 or more, the two or more R103s are the same as or different from each other,

When the number of r104 is 2 or more, the two or more R104s are the same as or different from each other.

According to an exemplary embodiment of the present specification, Chemical Formula 4 is represented by the following Chemical Formulas 4-1 to 4-3.

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

In Chemical Formulas 4-1 to 4-3,

The definitions of R1 to R8, R101, R102, r101, r102, L1 to L3 and l1 to l3 are the same as defined in Formula 1,

R103 to R105 are the same as or different from each other, and each independently hydrogen; Or an aryl group,

r103 is an integer from 1 to 8;

r104 is an integer from 1 to 7;

When r103 is 2 or more, the two or more R103s are the same as or different from each other,

When the number of r104 is 2 or more, the two or more R104s are the same as or different from each other.

According to an exemplary embodiment of the present specification, R103 and R104 are hydrogen.

According to an exemplary embodiment of the present specification, R105 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R105 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R105 is a phenyl group.

According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, each independently represent a straight or branched chain alkyl group having 1 to 30 carbon atoms, and L1 to L3 are the same as or different from each other, and each independently direct bonding; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, substituted or unsubstituted with heavy hydrogen, and Ar1 is a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from heavy hydrogen, a linear or branched chain alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted with one or more substituents selected from heavy hydrogen and a straight or branched chain alkyl group having 1 to 30 carbon atoms. energy; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted, and a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms containing N, O, or S, wherein R101 and R102 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 the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently represents a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently represents a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently represents a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently represents a straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms.

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

According to an exemplary embodiment of the present specification, the L1 to L3 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the L1 to L3 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the L1 to L3 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, the L1 to L3 are the same as or different from each other, and are represented by any one of the following structural formulas, but are not limited thereto.

In the above structural formula,

R71 and R81 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and the dotted line indicates the bonding position.

According to an exemplary embodiment of the present specification, the L1 to L3 are the same as or different from each other, and are each independently a direct bond; It is 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 to L3 are the same as or different from each other, and are each independently a direct bond; It is 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 to L3 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; A biphenyl group unsubstituted or substituted with heavy hydrogen; A divalent naphthalene group unsubstituted or substituted with heavy hydrogen; or a divalent terphenylene group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, l1 is 1.

According to an exemplary embodiment of the present specification, l1 is 2.

According to an exemplary embodiment of the present specification, l1 is 3.

According to an exemplary embodiment of the present specification, l2 is 1.

According to an exemplary embodiment of the present specification, l2 is 2.

According to an exemplary embodiment of the present specification, l2 is 3.

According to an exemplary embodiment of the present specification, l3 is 1.

According to an exemplary embodiment of the present specification, l3 is 2.

According to an exemplary embodiment of the present specification, l3 is 3.

In the present specification, in Formula 1, when l1 is 2 or more, two or more L1s are the same as or different from each other, and each L1 means that they are connected in series. For example, when l1 is 3 and L1 is a phenylene group, a naphthylene group, and a phenylene group, respectively, they may be connected as follows, but are not limited thereto, and the order or connection position of each L1 may be different.

In addition, Ar1 in Formula 1, for example, when l1 is 3, means that it is bonded to the third terminal substituent in the exemplified structure, that is, to the phenylene group.

According to an exemplary embodiment of the present specification, Ar1 is represented by any one of the following structural formulas, but is not limited thereto.

In the above structural formula,

R105 is the same as described above, and the dotted line indicates the binding position.

According to an exemplary embodiment of the present specification, Ar1 is a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from heavy hydrogen, a linear or branched chain alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted with one or more substituents selected from heavy hydrogen and a straight or branched chain alkyl group having 1 to 30 carbon atoms. energy; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, which is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and contains N, O, or S.

According to an exemplary embodiment of the present specification, Ar1 is a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 25 carbon atoms unsubstituted or substituted with one or more substituents selected from heavy hydrogen, a linear or branched chain alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 25 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms substituted with at least one substituent selected from heavy hydrogen and a straight or branched chain alkyl group having 1 to 20 carbon atoms. energy; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, which is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 25 carbon atoms, and contains N, O, or S.

According to an exemplary embodiment of the present specification, Ar1 is an adamantyl group; A phenyl group unsubstituted or substituted with one or more substituents selected from heavy hydrogen, a tert-butyl group, and a naphthyl group; A biphenyl group unsubstituted or substituted with heavy hydrogen; A terphenyl group unsubstituted or substituted with heavy hydrogen; A quaterphenyl group unsubstituted or substituted with heavy hydrogen; A naphthyl group unsubstituted or substituted with one or more substituents selected from heavy hydrogen and a phenyl group; A phenanthrene group unsubstituted or substituted with heavy hydrogen; A triphenylene group unsubstituted or substituted with heavy hydrogen; A tetrahydronaphthyl group substituted with at least one substituent selected from heavy hydrogen and a methyl group; Dibenzofuran group; Dibenzothiophene group; or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, Ar1 is a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen, 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; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted with one or more substituents selected from heavy hydrogen and a straight or branched chain alkyl group having 1 to 30 carbon atoms. energy; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, which is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and contains N, O, or S.

According to an exemplary embodiment of the present specification, Ar1 is a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 25 carbon atoms unsubstituted or substituted with heavy hydrogen, a straight chain or branched chain alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 25 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms substituted with at least one substituent selected from heavy hydrogen and a straight or branched chain alkyl group having 1 to 20 carbon atoms. energy; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, which is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 25 carbon atoms, and contains N, O, or S.

According to an exemplary embodiment of the present specification, Ar1 is an adamantyl group; A phenyl group unsubstituted or substituted with heavy hydrogen, a tert-butyl group, or a naphthyl group; A biphenyl group unsubstituted or substituted with heavy hydrogen; A terphenyl group unsubstituted or substituted with heavy hydrogen; A quaterphenyl group unsubstituted or substituted with heavy hydrogen; A naphthyl group unsubstituted or substituted with heavy hydrogen or a phenyl group; A phenanthrene group unsubstituted or substituted with heavy hydrogen; A triphenylene group unsubstituted or substituted with heavy hydrogen; A tetrahydronaphthyl group substituted with at least one substituent selected from heavy hydrogen and a methyl group; Dibenzofuran group; Dibenzothiophene group; or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently hydrogen; or deuterium.

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

.

.

A compound represented by Formula 1 according to an exemplary embodiment of the present specification may have a core structure as shown in Reaction Scheme 1 below. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.

<Scheme 1>

In Reaction Scheme 1, the definition of the substituent is the same as in Formula 1, L is the same as the definition of L1 or L2 in Formula 1, l is the same as the definition of l1 or l2 in Formula 1, R is The definition of R101 or R102 in Formula 1 is the same, r is the same as the definition of r101 or r102 in Formula 1, and X may be a halogen group such as Cl or Br.

In Reaction Scheme 1, a process for synthesizing a compound having a specific substituent bonded to a specific position was exemplified, but by a synthetic method known in the art using starting materials and intermediate materials known in the art, Compounds corresponding to the range can be synthesized.

In the present specification, compounds having various energy band gaps may be synthesized by introducing various substituents into the core structure of the compound represented by Formula 1. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents into the core structure of the above structure.

In addition, 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; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1. do.

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

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

According to one embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.

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

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

According to one embodiment of the present specification, the organic material layer includes a hole blocking layer.

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

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, the two or more organic material layers consist of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer and an electron blocking layer. Two or more may be selected from the group.

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 an exemplary 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 hole injection layer 5, the hole transport layer 6, or the electron blocking layer 7.

The organic light emitting device of the present specification is a material known in the art, except that the hole injection layer, the hole transport layer, the hole injection and transport layer, or the electron blocking layer includes the compound, that is, the compound represented by Formula 1 can be produced in this way.

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 cathode material, an organic material layer, and an anode 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 cathode material, an organic material layer, and an anode material on a substrate. However, the manufacturing method is not limited thereto.

In the present specification, the substrate may be a first electrode or a second electrode.

As the anode material, a material having a high work function is generally preferred 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 cathode 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. The host material includes a 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.

According to an exemplary embodiment of the present specification, the host includes a compound represented by Formula H-1 below, but is not limited thereto.

[Formula H-1]

In the above formula H-1,

L20 and L21 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 divalent heterocyclic group,

Ar20 and Ar21 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R201 is hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r201 is an integer of 1 to 8, and when r201 is 2 or more, two or more R201s are the same as or different from each other.

In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L20 and L21 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; A biphenyl group unsubstituted or substituted with heavy hydrogen; A naphthylene group unsubstituted or substituted with heavy hydrogen; Divalent dibenzofuran group; or a divalent dibenzothiophene group.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to 4-cyclic heterocyclic group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently deuterium or a phenyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with heavy hydrogen or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; terphenyl group; A naphthyl group unsubstituted or substituted with heavy hydrogen; phenanthrene group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; or a naphthobenzothiophene group.

In one embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, R201 is hydrogen; or a phenyl group.

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

Examples of the dopant material include an aromatic amine derivative, a styrylamine 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 material includes, but is not limited to, a compound represented by Formula D-1 below.

[Formula D-1]

In the above formula D-1,

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

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

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

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

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

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

According to an exemplary embodiment of the present specification, Formula D-1 may be the following compound, but is not limited thereto.

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,

At least one of X'1 to X'6 is N and the others are CH,

R309 to R314 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or bonded to adjacent groups to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, X'1 to X'6 are N.

According to an exemplary embodiment of the present specification, R309 to R314 are cyano groups.

According to an exemplary embodiment of the present specification, Chemical Formula HI-1 may be the following compound, but is not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. When the organic light emitting device according to an exemplary embodiment of the present specification includes an additional hole transport layer other than the hole transport layer including Chemical Formula 1, the hole transport material may receive holes from the anode or the hole injection layer and transfer them to the light emitting layer. A material having high hole mobility is preferred. 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 phenyl groups; 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. When the organic light emitting device according to an exemplary embodiment of the present specification includes an additional electron injection layer other than the electron injection layer including Formula 1, the electron injection material has excellent ability to transport electrons, and the second electrode It is desirable to have an excellent electron injection effect with respect to the electron-accepting effect from 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 desirable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

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, Chemical Formula ET-1 may be the following compound, but is not limited thereto.

The electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer. When the organic light emitting device according to an exemplary embodiment of the present specification includes an additional electron blocking layer other than the electron blocking layer including Formula 1, known materials may be used without limitation, and in the description of the hole injection layer Examples of materials may be used, but are not limited thereto. The electron blocking layer may be formed between the light emitting layer and the hole transport layer, between the light emitting layer and the hole injection layer, or between the light emitting layer and a layer that simultaneously injects and transports holes.

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

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 to R603 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,

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,

l603 is an integer from 1 to 3, and when l603 is 2 or more, the two or more L603s are the same as or different from each other;

r601 is an integer from 1 to 4, and when r601 is 2 or more, the two or more R601s are the same as or different from each other;

r602 is an integer from 1 to 4, and when r602 is 2 or more, two or more R602s are the same as or different from each other;

r603 is an integer of 1 to 3, and when r603 is 2 or more, 2 or more R603s are the same as or different from each other.

According to an exemplary embodiment of the present specification, Z31 to Z33 are N.

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; phenylene group; naphthylene group; or a biphenylylene group.

According to an exemplary embodiment of the present specification, L603 is a phenylene group; or a naphthylene group.

According to an exemplary embodiment of the present specification, l603 is 2.

According to an exemplary embodiment of the present specification, R601 to R603 are hydrogen.

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 are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. am.

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

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 phenyl group or a phenyl group unsubstituted or substituted with a naphthyl group; or a biphenyl group.

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, Chemical Formula HB-1 may be the following compound, but is not limited thereto.

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

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.

<Synthesis example>

Synthesis Example 1. Synthesis of Compound 1

9- (4-chlorophenyl) phenanthrene (20.00 g, 69.26 mmol), bis (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl) amine (27.53 g, 70.64 mmol) and toluene (200 ml) was added to sodium tert-butoxide (9.32 g, 96.96 mmol), followed by heating and stirring for 10 minutes. After adding bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (20ml) to the mixture, the mixture was heated and stirred for 1 hour. After completion of the reaction and filtration, layer separation was performed with toluene and water. After solvent removal, the compound 1 (34.00 g, 76.47% yield) was obtained by recrystallization with ethyl acetate. (MS[M+H]+ = 642)

Synthesis Example 2. Synthesis of Compound 2

As starting materials, 9-(4-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol) and 5,5,8,8-tetramethyl- N- (4-(5,5,8,8-tetramethyl-5 , 6,7,8-tetrahydronaphthalen-2-yl) phenyl) -5,6,7,8-tetrahydronaphthalen-2-amine (32.90 g, 70.65 mmol) Except for using Synthesis Example 1 Compound 2 (39.00 g, 78.42% yield) was obtained in the same manner as above. (MS[M+H]+ = 718)

Synthesis Example 3. Synthesis of Compound 3

As starting materials, 9-(4'-chloro-[1,1'-biphenyl]-4-yl)-9 H -carbazole (20.00 g, 56.52 mmol) and 5,5,8,8-tetramethyl- N- (4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl)-5,6,7,8-tetrahydronaphthalen-2- Compound 3 (35.00 g, 79.07% yield) was obtained in the same manner as in Synthesis Example 1, except that amine (26.85 g, 57.65 mmol) was used. (MS[M+H]+ = 783)

Synthesis Example 4. Synthesis of Compound 4

As starting materials, 9-(4'-chloro-[1,1'-biphenyl]-3-yl)-9 H -carbazole (20.00 g, 56.52 mmol) and 5,5,8,8-tetramethyl- N- (4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl)-5,6,7,8-tetrahydronaphthalen-2- Compound 4 (35.00 g, 79.07% yield) was obtained in the same manner as in Synthesis Example 1, except that amine (26.85 g, 57.65 mmol) was used. (MS[M+H]+ = 783)

Synthesis Example 5. Synthesis of Compound 5

As starting materials, 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9 H -carbazole (20.00 g, 56.52 mmol) and 5,5,8,8-tetramethyl- N- (4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl)-5,6,7,8-tetrahydronaphthalen-2- Compound 5 (34.50 g, 77.95% yield) was obtained in the same manner as in Synthesis Example 1, except that amine (26.85 g, 57.65 mmol) was used. (MS[M+H]+ = 783)

Synthesis Example 6. Synthesis of Compound 6

As starting materials, 4-bromo-1,1':4',1"-terphenyl (20.00 g, 64.68 mmol) and bis(4-(5,5,8,8-tetramethyl-5,6,7 Compound 6 (39.50 g, 79.30% yield) was obtained in the same manner as in Synthesis Example 1, except that ,8-tetrahydronaphthalen-2-yl)phenyl)amine (35.75 g, 65.97 mmol) was used. (MS[M+H]+ = 770)

Synthesis Example 7. Synthesis of Compound 7

1-(4'-bromo-[1,1'-biphenyl]-4-yl)naphthalene (20.00 g, 55.67 mmol) and bis(4-(5,5,8,8-tetramethyl) as starting materials -5,6,7,8-tetrahydronaphthalen-2-yl) phenyl) amine (30.77 g, 56.78 mmol) was used, but the compound 7 (36.00 g, 78.84%) was prepared in the same manner as in Synthesis Example 1. yield) was obtained. (MS[M+H]+ = 820)

Synthesis Example 8. Synthesis of Compound 8

2-(4'-bromo-[1,1'-biphenyl]-4-yl)naphthalene (20.00 g, 55.67 mmol) and bis(4-(5,5,8,8-tetramethyl) as starting materials -5,6,7,8-tetrahydronaphthalen-2-yl) phenyl) amine (30.77 g, 56.78 mmol) was used, but the compound 8 (36.00 g, 78.84%) was prepared in the same manner as in Synthesis Example 1. yield) was obtained. (MS[M+H]+ = 820)

Synthesis Example 9. Synthesis of Compound 9

As starting materials, 9-(4-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol) and bis(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2 Compound 9 (43.00 g, 78.15% yield) was obtained in the same manner as in Synthesis Example 1, except that -yl)phenyl)amine (38.28 g, 70.65 mmol) was used. (MS[M+H]+ = 794)

Synthesis Example 10. Synthesis of Compound 10

As starting materials, 6-(4-chlorophenyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (20.00 g, 66.92 mmol) and bis(4-(5,5 ,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl)amine (36.99 g, 68.26 mmol) was used, but the same method as in Synthesis Example 1 was used to prepare the compound. 10 (42.00 g, 78.04 % yield) was obtained. (MS[M+H]+ = 804)

Synthesis Example 11. Synthesis of Compound 11

As starting materials, 4-bromo-1,1':4',1"-terphenyl (20.00 g, 64.68 mmol) and bis(4-(5,5,8,8-tetramethyl-5,6,7 Compound 11 (39.50 g, 79.30% yield) was obtained in the same manner as in Synthesis Example 1, except that ,8-tetrahydronaphthalen-1-yl)phenyl)amine (35.75 g, 65.97 mmol) was used. (MS[M+H]+ = 770)

Synthesis Example 12. Synthesis of Compound 12

1-(4'-bromo-[1,1'-biphenyl]-4-yl)naphthalene (20.00 g, 55.67 mmol) and bis(4-(5,5,8,8-tetramethyl) as starting materials -5,6,7,8-tetrahydronaphthalen-1-yl) phenyl) amine (30.77 g, 56.78 mmol) was used, but the compound 12 (36.50 g, 79.94%) in the same manner as in Synthesis Example 1 yield) was obtained. (MS[M+H]+ = 820)

Synthesis Example 13. Synthesis of Compound 13

2-(4'-bromo-[1,1'-biphenyl]-4-yl)naphthalene (20.00 g, 55.67 mmol) and bis(4-(5,5,8,8-tetramethyl) as starting materials -5,6,7,8-tetrahydronaphthalen-1-yl) phenyl) amine (30.77 g, 56.78 mmol) was prepared in the same manner as in Synthesis Example 1, except that Compound 13 (36.00 g, 78.84% yield) was obtained. (MS[M+H]+ = 820)

Synthesis Example 14. Synthesis of Compound 14

As starting materials, 9-(4-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol) and bis(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-1 Compound 14 (43.00 g, 78.15% yield) was obtained in the same manner as in Synthesis Example 1, except that -yl)phenyl)amine (38.28 g, 70.65 mmol) was used. (MS[M+H]+ = 794)

Synthesis Example 15. Synthesis of Compound 15

As starting materials, 5-(4-chlorophenyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (20.00 g, 66.92 mmol) and bis(4-(5,5 The compound was prepared in the same manner as in Synthesis Example 1, except that ,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-1-yl)phenyl)amine (36.99 g, 68.26 mmol) was used. 15 (42.50 g, 78.97 % yield) was obtained. (MS[M+H]+ = 804)

Synthesis Example 16. Synthesis of Compound 16

As starting materials, 9-(4-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol) and bis(3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2 Compound 16 (42.50 g, 77.27% yield) was obtained in the same manner as in Synthesis Example 1, except that -yl)phenyl)amine (38.28 g, 70.65 mmol) was used. (MS[M+H]+ = 794)

Synthesis Example 17. Synthesis of Compound 17

4-bromo-1,1'-biphenyl (20.00 g, 85.80 mmol) and bis(3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro Compound 17 (57.50 g, 57.50 g, 79.19 % yield) was obtained. (MS[M+H]+ = 846)

Synthesis Example 18. Synthesis of Compound 18

As starting materials, 5-(4-chlorophenyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (20.00 g, 66.92 mmol) and bis(4-(5,5 ,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl)amine (36.99 g, 68.26 mmol) was used, but the same method as in Synthesis Example 1 was used to prepare the compound. 18 (42.50 g, 78.97 % yield) was obtained. (MS[M+H]+ = 804)

Synthesis Example 19. Synthesis of Compound 19

Compound 6 (20.0 g, 25.97 mmol) obtained in Synthesis Example 6 was put in benzene-d6 (200 ml) and completely dissolved, and then trifluoromethanesulfonic acid (1.2 ml, 12.98 mmol) was added and stirred for 25 minutes. After completion of the reaction, dichloromethane was added, and the layers were separated to obtain an organic layer. After drying with anhydrous magnesium sulfate (MgSO4), it was filtered. The filtrate was concentrated under reduced pressure and recrystallized with ethyl acetate to obtain the compound 19 (16.50 g, 79.69%). (MS[M+H]+ = 797)

Synthesis Example 20. Synthesis of Compound 20

Compound 20 (16.50 g, 79.79% yield) was obtained in the same manner as in Synthesis Example 19, except that Compound 9 (20.0 g, 25.18 mmol) obtained in Synthesis Example 9 was used. (MS[M+H]+ = 821)

Synthesis Example 21. Synthesis of Compound 21

Compound 21 (16.50 g, 80.38% yield) was obtained in the same manner as in Synthesis Example 19, except that Compound 18 (20.0 g, 24.87 mmol) obtained in Synthesis Example 18 was used. (MS[M+H]+ = 825)

<Experimental Example and Comparative Experimental Example>

Experimental Example 1-1

A glass substrate coated with ITO (Indium Tin Oxide) to a thickness of 1,400 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 compound represented by Chemical Formula HAT was thermally vacuum deposited to a thickness of 100 Å on the prepared ITO transparent electrode to form a hole injection layer. After vacuum depositing a compound represented by Formula HT1 to a thickness of 1150 Å as a hole transport layer thereon, Compound 1 prepared in Synthesis Example 1 was thermally vacuum deposited to a thickness of 150 Å as an electron blocking layer. Subsequently, as a light emitting layer, a compound represented by Chemical Formula BH and a compound represented by Chemical Formula BD were vacuum deposited to a thickness of 200 Å at a weight ratio of 25:1. Then, as a hole blocking layer, a compound represented by Chemical Formula HB1 was vacuum deposited to a thickness of 50 Å. Subsequently, a compound represented by the following formula ET1 and a compound represented by the following LiQ were thermally vacuum-deposited to a thickness of 310 Å at a weight ratio of 1:1 as a layer capable of simultaneously transporting and injecting electrons. An organic light emitting diode was manufactured by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1000 Å to form a cathode on the electron transport and electron injection layers.

Experimental Examples 1-2 to 1-21 and Comparative Experimental Examples 1-1 to 1-4

Experimental Examples 1-2 to 1-21 and Comparative Experimental Example 1-1 in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1 in Experimental Example 1-1. The organic light emitting device of 1-4 was manufactured.

evaluation example

When a current of 10 mA/cm ² was applied to the organic light emitting device prepared in Experimental Example and Comparative Experimental Example, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. Meanwhile, T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

electron blocking layer Voltage (V @ 10mA/cm ² ) Efficiency (cd/A @ 10mA/cm ² ) color coordinates (x, y) life span
(T95, hr) Experimental Example 1-1 compound 1 3.54 5.94 0.140, 0.043 190 Experimental Example 1-2 compound 2 3.56 5.95 0.140, 0.043 190 Experimental Example 1-3 compound 3 3.55 5.93 0.141, 0.043 180 Experimental Example 1-4 compound 4 3.55 5.92 0.141, 0.043 185 Experimental Example 1-5 compound 5 3.54 5.91 0.140, 0.043 185 Experimental Example 1-6 compound 6 3.55 5.90 0.141, 0.043 180 Experimental Example 1-7 compound 7 3.56 5.91 0.140, 0.043 190 Experimental Example 1-8 compound 8 3.57 5.93 0.140, 0.043 185 Experimental Example 1-9 compound 9 3.54 5.92 0.141, 0.044 180 Experimental Example 1-10 compound 10 3.52 5.92 0.140, 0.044 190 Experimental Example 1-11 compound 11 3.57 5.92 0.140, 0.044 185 Experimental Example 1-12 compound 12 3.56 5.94 0.140, 0.044 190 Experimental Example 1-13 compound 13 3.54 5.91 0.140, 0.044 190 Experimental Example 1-14 compound 14 3.54 5.90 0.140, 0.043 185 Experimental Example 1-15 compound 15 3.52 5.93 0.140, 0.043 190 Experimental Example 1-16 compound 16 3.56 5.93 0.140, 0.043 180 Experimental Example 1-17 compound 17 3.54 5.92 0.141, 0.043 185 Experimental Example 1-18 compound 18 3.53 5.92 0.140, 0.043 180 Experimental Example 1-19 compound 19 3.55 5.90 0.141, 0.043 200 Experimental Example 1-20 compound 20 3.54 5.92 0.141, 0.044 205 Experimental Example 1-21 compound 21 3.53 5.92 0.140, 0.043 205 Comparative Experimental Example 1-1 EB1 4.50 3.81 0.145, 0.049 50 Comparative Experimental Example 1-2 EB2 3.87 4.98 0.145, 0.049 95 Comparative Experimental Example 1-3 EB3 3.95 4.90 0.144, 0.048 100 Comparative Experimental Example 1-4 EB4 4.78 3.67 0.145, 0.050 25

Experimental Examples 2-1 to 2-15, Comparative Experimental Examples 1-1, 2-1, and 2-2 The compound represented by Formula EB1 was used instead of Compound 1 as the electron blocking layer in Experimental Example 1-1, Experimental Example 2-1 to 2-15 and Comparative Experimental Example 2- 1 and 2-2 were fabricated organic light emitting devices.

evaluation example

When a current of 10 mA/cm ² was applied to the organic light emitting device prepared in Experimental Example and Comparative Experimental Example, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 2 below. Meanwhile, T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

hole transport layer Voltage (V @ 10mA/cm ² ) Efficiency (cd/A @ 10mA/cm ² ) color coordinates (x, y) life span
(T95, hr) Experimental example 2-1 compound 3 3.57 5.88 0.140, 0.043 185 Experimental Example 2-2 compound 4 3.58 5.87 0.140, 0.043 190 Experimental Example 2-3 compound 5 3.58 5.86 0.140, 0.043 185 Experimental example 2-4 compound 6 3.57 5.87 0.140, 0.043 180 Experimental Example 2-5 compound 7 3.59 5.86 0.140, 0.044 185 Experimental Example 2-6 compound 8 3.58 5.86 0.140, 0.043 190 Experimental Example 2-7 compound 10 3.55 5.89 0.140, 0.044 185 Experimental example 2-8 compound 11 3.57 5.87 0.140, 0.043 185 Experimental example 2-9 compound 12 3.57 5.88 0.140, 0.044 190 Experimental Example 2-10 compound 13 3.59 5.87 0.140, 0.043 185 Experimental Example 2-11 compound 15 3.55 5.88 0.140, 0.043 180 Experimental Example 2-12 compound 17 3.59 5.87 0.140, 0.043 185 Experimental Example 2-13 compound 18 3.56 5.88 0.140, 0.043 180 Experimental Example 2-14 compound 19 3.57 5.87 0.140, 0.043 205 Experimental example 2-15 compound 21 3.56 5.88 0.140, 0.043 205 Comparative Experimental Example 1-1 HT1 4.50 3.81 0.145, 0.049 50 Comparative Experimental Example 2-1 HT2 3.82 5.10 0.145, 0.049 125 Comparative Experimental Example 2-2 HT3 3.75 5.00 0.145, 0.049 110

As shown in Tables 1 and 2, the compound of Formula 1 according to an exemplary embodiment of the present specification has excellent electron blocking ability or hole transporting ability, and thus an organic light emitting device using the compound as an electron blocking layer or a hole transporting layer has driving voltage, efficiency And it was confirmed that it exhibits a significant effect in terms of lifespan. Specifically, the compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification is an amine compound containing at least two tetrahydronaphthalenes substituted with an alkyl group, and exhibits high heat resistance compared to molecular weight by including at least two tetrahydronaphthalenes.

In Experimental Examples 1-1 to 1-21 and 2-1 to 2-15, which are organic light emitting devices to which the compound of Formula 1 is applied according to an exemplary embodiment of the present specification, Ar1 of Formula 1 of the present specification includes an amine group and Si Comparative Experimental Examples 1-1 to 1-4, 2-1 and 2-2 in which a compound having a heteroaryl group, a compound having an aryl group substituted with a carboxyl group, or a compound having a heteroaryl group including Si is applied to an organic light emitting device Driven, respectively It was confirmed that significant effects were exhibited in terms of voltage, efficiency and lifetime.

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 (9)

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 represents a substituted or unsubstituted alkyl group;
L1 to L3 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,
Ar1 is a cycloalkyl group unsubstituted or substituted with heavy hydrogen; an aryl group unsubstituted or substituted with one or more substituents selected from heavy hydrogen, an alkyl group, and an aryl group; a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring substituted with at least one substituent selected from heavy hydrogen, an alkyl group, and an aryl group; Or a heteroaryl group that is unsubstituted or substituted with one or more substituents selected from heavy hydrogen, an alkyl group, and an aryl group, and includes N, O, or S,
R101 and R102 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
l1 to l3, r101 and r102 are integers from 1 to 3, respectively;
When l1 is 2 or more, the two or more L1s are the same as or different from each other,
When l2 is 2 or more, the two or more L2s are the same as or different from each other,
When l3 is 2 or more, the two or more L3s are the same as or different from each other,
When r101 is 2 or more, the two or more R101s are the same as or different from each other,
When the number of r102 is 2 or more, the two or more R102s are the same as or different from each other. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,
The definitions of R1 to R8, R101, R102, r101, r102, L1 to L3, l1 to l3 and Ar1 are the same as defined in Formula 1 above. The compound according to claim 1, wherein Formula 1 is represented by Formula 2 below:
[Formula 2]

In Formula 2,
The definitions of R1 to R8, R101, R102, r101, r102, L1 to L3 and l1 to l3 are the same as defined in Formula 1,
Ar11 is a cycloalkyl group unsubstituted or substituted with heavy hydrogen; an aryl group unsubstituted or substituted with one or more substituents selected from heavy hydrogen, an alkyl group, and an aryl group; or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring substituted with one or more substituents selected from heavy hydrogen, an alkyl group, and an aryl group. The compound according to claim 1, wherein Formula 1 is represented by Formula 3 or 4 below:
[Formula 3]

[Formula 4]

In Formulas 3 and 4,
The definitions of R1 to R8, R101, R102, r101, r102, L1 to L3 and l1 to l3 are the same as defined in Formula 1,
X1 is O; S; or NR105;
R103 to R105 are the same as or different from each other, and each independently hydrogen; Or an aryl group,
r103 is an integer from 1 to 8;
r104 is an integer from 1 to 7;
When r103 is 2 or more, the two or more R103s are the same as or different from each other,
When the number of r104 is 2 or more, the two or more R104s are the same as or different from each other. The method according to claim 1, wherein R1 to R8 are the same as or different from each other, and each independently represents a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms,
Wherein L1 to L3 are the same as or different from each other, and are each independently a direct bond; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium,
Ar1 is a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from heavy hydrogen, a linear or branched chain alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted with one or more substituents selected from heavy hydrogen and a straight or branched chain alkyl group having 1 to 30 carbon atoms. energy; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, which is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and contains N, O, or S;
R101 and R102 are the same as or different from each other, and each independently hydrogen; Or a deuterium compound. 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 of the organic material layers includes the compound of any one of claims 1 to 6. The organic light emitting device of claim 7, wherein the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound. The organic light emitting device of claim 7 , wherein the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.

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