KR20230117044A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device using the same.

Description

Novel compound and organic light emitting device using the same

The present invention relates to a novel 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 has a wide viewing angle, excellent contrast, and a fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

An organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, 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.

The development of new materials for organic materials used in the organic light emitting device as described above is continuously required.

Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a compound represented by Formula 1 below:

[Formula 1]

In Formula 1,

L ₁ and L ₂ are each independently a single bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing one or more heteroatoms of N, O and S,

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; A substituted or unsubstituted C _3-60 aliphatic ring group; Or a substituted or unsubstituted C _2-60 heterocyclic group containing one or more heteroatoms of N, O and S;

However, Ar ₁ and Ar ₂ are not substituted or unsubstituted fluorenyl,

One of R ₁ to R ₅ is unsubstituted or deuterium-substituted phenanthryl, the other is a substituent represented by Formula 2 below, and the others are each independently hydrogen or deuterium,

[Formula 2]

In Formula 2,

L ₃ is a single bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing one or more heteroatoms of N, O and S,

Ar ₃ is substituted or unsubstituted biphenylyl; Substituted or unsubstituted naphthyl; A substituted or unsubstituted phenanthryl; Substituted or unsubstituted dibenzofuranyl; Or a substituted or unsubstituted dibenzothiophenyl,

However, when R ₂ is unsubstituted phenanthryl and R ₄ is a substituent represented by Formula 2, Ar ₃ is substituted biphenylyl, substituted naphthyl, substituted phenanthryl, substituted or unsubstituted di benzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

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

The compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics of an organic light emitting device.

1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron injection and transport layer 5 and a cathode 6.
2 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron blocking layer 8, a light emitting layer 4, a hole blocking layer 9, an electron injection and transport layer ( 5) and an example of an organic light emitting element composed of a cathode 6 is shown.

Hereinafter, in order to aid understanding of the present invention, it will be described in more detail.

(Definition of Terms)

는 다른 치환기에 연결되는 결합을 의미하고, "D"는 중수소를 의미한다.In this specification, and

means a bond connected to another substituent, and "D" means deuterium.

In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; cyano group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; Alkyl thioxy group; Arylthioxy group; an alkyl sulfoxy group; aryl sulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; Aralkenyl group; Alkyl aryl group; Alkylamine group; Aralkylamine group; heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing at least one of N, O and S atoms, or substituted or unsubstituted with a substituent in which two or more substituents from among the above-exemplified substituents are connected. it means. For example, "a substituent in which two or more substituents are linked" may be a biphenylyl group. That is, the biphenylyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected. As an example, the term “substituted or unsubstituted” means “unsubstituted or selected from the group consisting of deuterium, halogen, cyano, C _1-10 alkyl, C _1-10 alkoxy and C _6-20 aryl. substituted with one or more substituents"; or "unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, phenyl and naphthyl". Also, in the present specification, the term "substituted with one or more substituents" may be understood as "substituted with one to the maximum number of substitutable hydrogens." Alternatively, in the present specification, the term “substituted with one or more substituents” may be understood as “substituted with 1 to 5 substituents” or “substituted with 1 or 2 substituents”.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with an aryl group having 6 to 25 carbon atoms or a straight-chain, branched-chain or cyclic chain alkyl group having 1 to 25 carbon atoms in the ester group. Specifically, it may be a substituent of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.

In the present specification, a substituted or unsubstituted silyl group means -Si(Z ₁ )(Z ₂ )(Z ₃ ), where Z ₁ , Z ₂ and Z ₃ are each independently hydrogen, deuterium, substituted or unsubstituted substituted C _1-60 alkyl, substituted or unsubstituted C _1-60 haloalkyl, substituted or unsubstituted C _2-60 alkenyl, substituted or unsubstituted C _2-60 haloalkenyl, or substituted or unsubstituted may be C _6-60 aryl. According to an exemplary embodiment, Z ₁ , Z ₂ and Z ₃ are each independently hydrogen, deuterium, substituted or unsubstituted C _1-10 alkyl, substituted or unsubstituted C _1-10 haloalkyl, substituted or unsubstituted C _1-10 haloalkyl, or substituted or unsubstituted C _6-20 aryl. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. Not limited.

In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.

In this specification, examples of the halogen group include fluoro, chloro, bromo, or iodo.

In the present specification, the alkyl group may be straight-chain or branched-chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another embodiment, specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5 -methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4- trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, etc., but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. 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, a stilbenyl group, a styrenyl group, and the like, but are not limited thereto.

In the present specification, the aliphatic group (Alicyclic group) refers to a monovalent substituent derived from a saturated or unsaturated hydrocarbon ring compound containing only carbon as a ring-forming atom and having no aromaticity, and includes both monocyclic or condensed polycyclic compounds. understood to be inclusive. According to one embodiment, the carbon number of the aliphatic ring group is 3 to 60. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. Examples of such aliphatic groups include monocyclic groups such as cycloalkyl groups, bridged hydrocarbon groups, spiro hydrocarbon groups, substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds, and the like. can be heard

Specifically, examples of the cycloalkyl group include 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, and the like, but are not limited thereto.

In addition, examples of the bridged hydrocarbon group include bicyclo[1.1.0]butyl, bicyclo[2.2.1]heptyl, bicyclo[4.2.0]octa-1,3,5-trienyl, adamantyl, decalinyl, etc., but is not limited thereto.

In addition, examples of the spiro ring hydrocarbon group include spiro[3.4]octyl and spiro[5.5]undecanyl, but are not limited thereto.

In addition, the substituent derived from the hydrogenated derivative of the aromatic hydrocarbon compound refers to a substituent derived from a compound in which hydrogen is added to some of the unsaturated bonds of the monocyclic or polycyclic aromatic hydrocarbon compound, and examples of such a substituent include 1 H -indenyl , 2 H -indenyl, 4 H -indenyl, 2,3-dihydro-1 H -indenyl, 1,4-dihydronaphthalenyl, 1,2,3,4-tetrahydronaphthalenyl, 6,7,8,9-tetrahydro-5 H -benzo [7] annulenyl (6,7,8,9-tetrahydro-5 H -benzo [7] annulenyl), 6,7-dihydro-5 H - Benzocycloheptenyl, etc., but is not limited thereto.

In the present specification, an aryl group is understood to mean a substituent derived from a monocyclic or condensed polycyclic compound having aromaticity while containing only carbon as a ring-forming atom, and the number of carbon atoms is not particularly limited, but preferably has 6 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenylyl group, a terphenylyl group, etc. as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, a heterocyclic group refers to a monovalent substituent derived from a monocyclic or condensed polycyclic compound further including one or more heteroatoms selected from O, N, Si, and S in addition to carbon as a ring-forming atom. As such, it is understood to encompass both substituents having aromaticity and substituents not having aromaticity. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 60 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of such a heterocyclic group include a heteroaryl group, a substituent derived from a hydrogenated derivative of a heteroaromatic compound, and the like.

Specifically, the heteroaryl group refers to a substituent derived from a monocyclic or condensed polycyclic compound further including at least one heteroatom selected from N, O, and S in addition to carbon as a ring-forming atom, and refers to a substituent having aromaticity. do. According to one embodiment, the number of carbon atoms of the heteroaryl group is 2 to 60 carbon atoms. According to another embodiment, the heteroaryl group has 2 to 30 carbon atoms. According to another embodiment, the heteroaryl group has 2 to 20 carbon atoms. Examples of the heteroaryl group include a thiophenyl group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridinyl group, a bipyridinyl group, a pyrimidinyl group, and a triazinyl group. group, acridinyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, isoquinolinyl group, indole diary, carbazolyl group, benzoxazolyl group, benzoimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, dibenzofuranyl group, phenanthrolinyl group, isooxa A zolyl group, a thiadiazolyl group, and a phenothiazinyl group, but are not limited thereto.

In addition, the substituent derived from the hydrogenated derivative of the heteroaromatic compound refers to a substituent derived from a compound in which hydrogen is added to some of the unsaturated bonds of the monocyclic or polycyclic heteroaromatic compound, and examples of such substituents include 1,3-di Hydroisobenzofuranyl (1,3-dihydroisobenzofuranyl), 2,3-dihydrobenzofuranyl (2,3-dihydrobenzofuranyl), 1,3-dihydrobenzo[ c ]thiophenyl (1,3-dihydrobenzo[ c ]thiophenyl), 2,3-dihydro[ b ]thiophenyl (2,3-dihydro[ b ]thiophenyl), and the like, but are not limited thereto.

In the present specification, an aralkyl group, an aralkenyl group, an alkylaryl group, an arylamine group, and an aryl group among arylsilyl groups are the same as the examples of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the examples of the above-mentioned alkyl group. In the present specification, the description of the above-described heteroaryl may be applied to the heteroaryl among heteroarylamines. In the present specification, the alkenyl group among the aralkenyl groups is the same as the examples of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of heteroaryl described above may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied, except that the hydrocarbon ring is formed by combining two substituents. In the present specification, the heterocyclic group is not a monovalent group, and the description of the above-described heteroaryl may be applied, except that it is formed by combining two substituents.

In the present specification, “deuterated or substituted with deuterium” means that at least one of substitutable hydrogens in a compound, a divalent linking group, or a monovalent substituent is substituted with deuterium.

Also, “unsubstituted or substituted with deuterium” or “substituted or unsubstituted with deuterium” means “unsubstituted or substituted with one to the maximum number of deuterium hydrogen atoms”. For example, the term "unsubstituted or deuterium-substituted phenanthryl" means "unsubstituted or deuterium-substituted phenanthryl", considering that the maximum number of deuterium-substituted hydrogens in the phenanthryl structure is 9, "unsubstituted or deuterium-substituted phenanthryl" It can be understood in the sense of "substituted phenanthryl".

In addition, the meaning of "deuterated structure" means a compound of any structure in which at least one hydrogen is substituted with deuterium, a divalent linking group, or a monovalent substituent. As an example, a deuterated structure of phenyl may be understood to refer to monovalent substituents of all structures in which at least one substitutable hydrogen in a phenyl group is substituted with a deuterium as follows.

In addition, the “deuterium substitution rate” or “degree of deuteration” of a compound is the number of deuterium atoms substituted for the total number of hydrogen atoms that may exist in the compound (the sum of the number of hydrogen atoms that can be substituted with deuterium atoms and the number of deuterium atoms that are substituted in the compound). means that the ratio is calculated as a percentage. Therefore, when the "deuterium substitution rate" or "degree of deuteration" of a compound is referred to as "K%", it means that K% of hydrogen substitutable with deuterium in the compound is substituted with deuterium.

At this time, the "deuterium substitution rate" or "deuteration degree" is MALDI-TOF MS (Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometer), nuclear magnetic resonance spectroscopy ( ¹ H NMR), TLC / MS (Thin -Layer Chromatography/Mass Spectrometry) or GC/MS (Gas Chromatography/Mass Spectrometry) can be used to measure according to a commonly known method. More specifically, when using MALDI-TOF MS, the "deuterium substitution rate" or "degree of deuteration" is obtained by calculating the number of deuterium substituted in the compound through MALDI-TOF MS analysis, and then replacing the total number of hydrogens that may exist in the compound. It can be obtained by calculating the ratio of the number of deuterium atoms as a percentage.

(compound)

Meanwhile, the present invention provides a compound represented by Formula 1 above.

Specifically, the compound represented by Formula 1 has a structure in which a specific substituent (biphenylyl, naphthyl, phenanthryl, dibenzofuranyl, or dibenzothiophenyl) is substituted together with a phenanthryl group and an amino group on a benzene ring. have In particular, the compound represented by Formula 1 does not have substituted or unsubstituted fluorenyl such as fluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl as a substituent of an amino group. there is The compound represented by Formula 1 having such a structure can effectively block electron movement to the hole transport layer compared to compounds having a different structure, so it can be used as a material for the electron blocking layer, and also contributes to the stabilization of excitons and at the same time gives a red color. It has excellent energy transfer ability to the dopant and can be used as a host material.

Accordingly, an organic light emitting device employing the compound may exhibit a lower driving voltage than an organic light emitting device employing a compound having a substituent different from that of the present application, and may simultaneously improve efficiency and lifetime characteristics.

In addition, R ₁ is unsubstituted or phenanthryl substituted with deuterium, one of R ₂ , R ₃ , R ₄ and R ₅ is a substituent represented by Formula 2, and the others are each independently hydrogen or deuterium;

R ₂ is unsubstituted or phenanthryl substituted with deuterium, one of R ₁ , R ₃ , R ₄ and R ₅ is a substituent represented by Formula 2, and the others are each independently hydrogen or deuterium; or

R ₃ is unsubstituted or deuterium-substituted phenanthryl, one of R ₁ , R ₂ , R ₄ and R ₅ is a substituent represented by Formula 2, and the others may each independently be hydrogen or deuterium.

More specifically, R ₁ is unsubstituted or deuterium-substituted phenanthryl, R ₂ is a substituent represented by Formula 2, R ₃ , R ₄ and R ₅ are each independently hydrogen or deuterium;

R ₁ is unsubstituted or deuterium-substituted phenanthryl, R ₃ is a substituent represented by Formula 2, R ₂ , R ₄ and R ₅ are each independently hydrogen or deuterium;

R ₁ is unsubstituted or deuterium-substituted phenanthryl, R ₄ is a substituent represented by Formula 2, R ₂ , R ₃ and R ₅ are each independently hydrogen or deuterium;

R ₁ is unsubstituted or deuterium-substituted phenanthryl, R ₅ is a substituent represented by Formula 2, R ₂ , R ₃ and R ₄ are each independently hydrogen or deuterium;

R ₂ is unsubstituted or deuterium-substituted phenanthryl, R ₁ is a substituent represented by Formula 2, R ₃ , R ₄ and R ₅ are each independently hydrogen or deuterium;

R ₂ is unsubstituted or deuterium-substituted phenanthryl, R ₃ is a substituent represented by Formula 2, R ₁ , R ₄ and R ₅ are each independently hydrogen or deuterium;

R ₂ is unsubstituted or deuterium-substituted phenanthryl, R ₄ is a substituent represented by Formula 2, R ₁ , R ₃ and R ₅ are each independently hydrogen or deuterium;

R ₂ is unsubstituted or deuterium-substituted phenanthryl, R ₅ is a substituent represented by Formula 2, R ₁ , R ₃ and R ₄ are each independently hydrogen or deuterium;

R ₃ is unsubstituted or deuterium-substituted phenanthryl, R ₁ is a substituent represented by Formula 2, R ₂ , R ₄ and R ₅ are each independently hydrogen or deuterium;

R ₃ is unsubstituted or deuterium-substituted phenanthryl, R ₂ is a substituent represented by Formula 2, R ₁ , R ₄ and R ₅ are each independently hydrogen or deuterium;

R ₃ is unsubstituted or deuterium-substituted phenanthryl, R ₄ is a substituent represented by Formula 2, R ₁ , R ₂ and R ₅ are each independently hydrogen or deuterium; or

R ₃ is unsubstituted or deuterium-substituted phenanthryl, R ₅ is a substituent represented by Formula 2, and R ₁ , R ₂ and R ₄ may each independently represent hydrogen or deuterium.

Preferably,

R ₁ is unsubstituted or deuterium-substituted phenanthryl, R ₃ is a substituent represented by Formula 2, R ₂ , R ₄ and R ₅ are each independently hydrogen or deuterium;

R ₁ is unsubstituted or deuterium-substituted phenanthryl, R ₄ is a substituent represented by Formula 2, R ₂ , R ₃ and R ₅ are each independently hydrogen or deuterium;

R ₂ is unsubstituted or deuterium-substituted phenanthryl, R ₃ is a substituent represented by Formula 2, R ₁ , R ₄ and R ₅ are each independently hydrogen or deuterium;

R ₂ is unsubstituted or deuterium-substituted phenanthryl, R ₄ is a substituent represented by Formula 2, R ₁ , R ₃ and R ₅ are each independently hydrogen or deuterium;

R ₃ is unsubstituted or deuterium-substituted phenanthryl, R ₄ is a substituent represented by Formula 2, R ₁ , R ₂ and R ₅ are each independently hydrogen or deuterium; or

R ₃ is unsubstituted or deuterium-substituted phenanthryl, R ₅ is a substituent represented by Formula 2, and R ₁ , R ₂ and R ₄ are each independently hydrogen or deuterium.

In one embodiment, L ₁ and L ₂ are each independently a single bond; A substituted or unsubstituted C _6-20 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing one or more heteroatoms selected from N, O and S.

In other embodiments, L ₁ and L ₂ are each independently a single bond; C _6-20 arylene unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, phenyl and naphthyl; Or it may be C _2-20 heteroarylene containing one heteroatom of O and S unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, phenyl and naphthyl.

Specifically, L ₁ and L ₂ may each independently represent a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenyldiyl, or substituted or unsubstituted naphthylene.

More specifically, L ₁ and L ₂ are each independently a single bond, phenylene, naphthylphenylene, biphenyldiyl, naphthylene, or phenylnaphthylene;

The phenylene, naphthylphenylene, biphenyldiyl, naphthylene and phenylnaphthylene may be unsubstituted or substituted with deuterium.

For example, L ₁ and L ₂ may each independently be a single bond, or any one selected from the group consisting of or a deuterated structure thereof:

.

.

Preferably, at least one of L ₁ and L ₂ may be a single bond.

In this case, L ₁ and L ₂ may be the same as each other. or L ₁ and L ₂ may be different.

In one embodiment, Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-20 aryl; A substituted or unsubstituted C _3-20 aliphatic ring group; Or a substituted or unsubstituted C _2-60 heterocyclic group containing at least one heteroatom selected from N, O, and S.

In another embodiment, Ar ₁ and Ar ₂ are each independently C _6-20 aryl which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C _1-4 alkyl, phenyl and naphthyl. (but not fluorenyl); C _3-20 aliphatic ring unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C _1-4 alkyl, phenyl and naphthyl; Or a C _2-20 heterocycle containing one or more heteroatoms of O and S that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C _1-4 alkyl, phenyl and naphthyl. it can be

Specifically, Ar ₁ and Ar ₂ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, dihydroindenyl, tetrahydronaphthyl, tetrahydrobenzo[7]anulenyl, adamantyl , dibenzofuranyl, or dibenzothiophenyl;

Ar ₁ and Ar ₂ may be substituted or unsubstituted.

More specifically, Ar ₁ and Ar ₂ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, 2,3-dihydro-1H-indenyl, 1,2,3,4-tetra hydronaphthyl, 6,7,8,9-tetrahydro-5H-benzo[7]anulenyl, adamantyl, dibenzofuranyl, or dibenzothiophenyl;

Ar ₁ and Ar ₂ may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C _1-4 alkyl, phenyl, and naphthyl.

For example, Ar ₁ and Ar ₂ may each independently be any one selected from the group consisting of, or a deuterated structure thereof, but is not limited thereto:

.

.

Here, Ar ₁ and Ar ₂ may be different. Alternatively, Ar ₁ and Ar ₂ may be identical to each other.

In one embodiment, L ₁ -Ar ₁ and L ₂ -Ar ₂ may be identical to each other.

In other embodiments, L ₁ -Ar ₁ and L ₂ -Ar ₂ can be different.

In addition, one of R ₁ to R ₅ may be any one substituent selected from the group consisting of a1 to a5 below:

In the above formulas a1 to a5,

D means deuterium,

n is an integer from 0 to 9;

Preferably, one of R ₁ to R ₅ is any one substituent selected from the group consisting of a2, a3 and a5.

In one embodiment, L ₃ is a single bond; A substituted or unsubstituted C _6-20 arylene; Or a substituted or unsubstituted C _2-20 heteroarylene containing one heteroatom of O and S.

In other embodiments, L ₃ is a single bond; It may be C _6-20 arylene unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, phenyl and naphthyl.

For example, L ₃ can be a single bond or substituted or unsubstituted phenylene.

More specifically, for example, L ₃ may be a single bond or unsubstituted or deuterium-substituted phenylene.

In addition, Ar ₃ is substituted or unsubstituted biphenylyl; Substituted or unsubstituted naphthyl; A substituted or unsubstituted phenanthryl; Substituted or unsubstituted dibenzofuranyl; Or a substituted or unsubstituted dibenzothiophenyl,

However, when R ₂ is unsubstituted phenanthryl and R ₄ is a substituent represented by Formula 2, Ar ₃ is substituted biphenylyl, substituted naphthyl, substituted phenanthryl, substituted or unsubstituted di benzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

Here, substituents of biphenylyl, naphthyl, phenanthryl, dibenzofuranyl, and substituted dibenzothiophenyl are selected from the group consisting of deuterium, halogen, cyano, C _1-10 alkyl and C _6-20 aryl. One or more substituents may be selected.

Further, Ar ₃ is biphenylyl, naphthyl, phenanthryl, dibenzofuranyl, or substituted dibenzothiophenyl;

Ar ₃ is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C _1-4 alkyl, and C _6-20 aryl;

However, when R ₂ is unsubstituted phenanthryl and R ₄ is a substituent represented by Formula 2 above, Ar ₃ is

biphenylyl substituted with one or more substituents selected from the group consisting of deuterium, C _1-4 alkyl, and C _6-20 aryl;

naphthyl substituted with one or more substituents selected from the group consisting of deuterium, C _1-4 alkyl, and C _6-20 aryl;

phenanthryl substituted with one or more substituents selected from the group consisting of deuterium, C _1-4 alkyl, and C _6-20 aryl;

dibenzofuranyl unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C _1-4 alkyl, and C _6-20 aryl; or

It may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C _1-4 alkyl, and C _6-20 aryl.

More specifically, Ar ₃ is biphenylyl, naphthyl, phenanthryl, dibenzofuranyl, or dibenzothiophenyl;

Ar ₃ is unsubstituted or substituted with one or more deuterium, one phenyl, one biphenylyl, or one naphthyl;

However, when R ₂ is unsubstituted phenanthryl and R ₄ is a substituent represented by Formula 2 above, Ar ₃ is

biphenylyl substituted with 1 to 9 deuterium, 1 phenyl, 1 biphenylyl, or 1 naphthyl;

naphthyl substituted with 1 to 7 deuterium, 1 phenyl, 1 biphenylyl, or 1 naphthyl;

phenanthryl substituted with 1 to 9 deuterium, 1 phenyl, 1 biphenylyl, or 1 naphthyl;

dibenzofuranyl unsubstituted or substituted with 1 to 7 deuterium, 1 phenyl, 1 biphenylyl, or 1 naphthyl; or

dibenzothiophenyl which is unsubstituted or substituted with 1 to 7 deuterium, 1 phenyl, 1 biphenylyl, or 1 naphthyl.

For example, Ar ₃ may be any one selected from the group consisting of;

From above,

Q is deuterium, phenyl, biphenylyl, or naphthyl;

m1 is an integer from 0 to 7;

m2 is an integer from 0 to 4;

m3 is an integer from 0 to 5;

m4 is an integer from 0 to 9;

However, when R ₂ is unsubstituted phenanthryl and R ₄ is a substituent represented by Formula 2 above, Ar ₃ may be any one selected from the group consisting of:

From above,

Q is deuterium, phenyl, biphenylyl, or naphthyl;

m1 is an integer from 0 to 7;

m5 is an integer from 1 to 7;

m6 is an integer from 0 to 4;

m7 is an integer from 0 to 5,

m6+m7 is an integer from 1 to 9;

m8 is an integer from 1 to 9;

In one embodiment, when Q is deuterium,

m1 is an integer from 0 to 7;

m2 is an integer from 0 to 4;

m3 is an integer from 0 to 5;

m4 is an integer from 0 to 9;

When Q is deuterium, phenyl, biphenylyl, or naphthyl,

m1, m2, m3 and m4 may each independently be 0 or 1.

However, when R ₂ is unsubstituted phenanthryl, R ₄ is a substituent represented by Formula 2, and Q is deuterium,

m1 is an integer from 0 to 7;

m5 is an integer from 1 to 7;

m6 is an integer from 0 to 4;

m7 is an integer from 0 to 5,

m6+m7 is an integer from 1 to 9;

m8 is an integer from 1 to 9;

When Q is deuterium, phenyl, biphenylyl, or naphthyl,

m1, m5, m6, m7, m8 are each independently 0 or 1,

m6+m7 can be 1 or 2.

In addition, the compound may be represented by any one of Formulas 1-1 to 1-6:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-1 to 1-6,

p is an integer from 0 to 3;

A is a substituent represented by any one of the following formulas a1 to a5,

In the above formulas a1 to a5,

n is an integer from 0 to 9;

L ₁ to L ₃ and Ar ₁ to Ar ₃ are as defined in Formula 1 above;

However, in Formula 1-3, Ar ₃ is substituted biphenylyl; substituted naphthyl, substituted phenanthryl; Substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiophenyl.

In addition, the compound may contain no deuterium or one or more deuterium atoms.

When the compound contains deuterium, the deuterium substitution rate of the compound may be 1% to 100%. Specifically, the deuterium substitution rate of the compound is 5% or more, 10% or more, 20% or more, 30% or more, 40% or more, 50% or more, 60% or more, 70% or more, 75% or more, 80% or more, Alternatively, it may be 90% or more and 100% or less.

For example, the compound may contain no deuterium or 1 to 50 deuterium atoms. More specifically, the compound does not contain deuterium, or at least 1, at least 2, at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, or at least 9 More than 50, 40 or less, 30 or less, 28 or less, 26 or less, 24 or less, 22 or less, 20 or less, 18 or less, 16 or less, 14 or less, 13 or less , 12 or less, 11 or less, or 10 or less deuterium.

On the other hand, representative examples of the compound represented by Formula 1 are as follows:

.

In addition, the compound represented by Formula 1 can be prepared by, for example, a preparation method as shown in Reaction Scheme 1 below:

[Scheme 1]

In Scheme 1, X is halogen, preferably bromo or chloro, and descriptions of the remaining substituents are as defined above.

Specifically, the compound represented by Formula 1 may be prepared by an amine substitution reaction of reactants A1 and A2. At this time, the amine substitution reaction is preferably performed under a palladium catalyst and a base, and a reactor for the reaction may be changed to a reactor known in the art. This manufacturing method may be more specific in Preparation Examples to be described later.

(organic light emitting device)

Meanwhile, the present invention provides an organic light emitting device including the compound represented by Formula 1 above. In one example, the present invention provides a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1. .

Here, the organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer or an electron blocking layer.

Specifically, the organic material layer of the organic light emitting device of the present invention 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, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer as organic material layers. However, the structure of the organic light emitting device is not limited thereto and may include fewer organic layers.

In one embodiment, the organic material layer may include a light emitting layer, and in this case, the organic material layer including the compound may be a light emitting layer.

In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection and transport layer, wherein the organic material layer including the compound may be a light emitting layer or a hole transport layer.

In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron injection and transport layer, wherein the organic material layer containing the compound may be a light emitting layer or an electron blocking layer.

In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, and an electron injection and transport layer, wherein the organic material layer containing the compound may be a light emitting layer or an electron blocking layer. there is.

In addition, the organic light emitting device according to the present invention has a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate, wherein the first electrode is an anode and the second electrode is a cathode. may be minor. In addition, the organic light emitting device according to the present invention has an inverted type organic layer in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate, wherein the first electrode is a cathode and the second electrode is an anode. It may be a light emitting device. For example, the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .

1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron injection and transport layer 5 and a cathode 6. In this structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer.

2 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron blocking layer 8, a light emitting layer 4, a hole blocking layer 9, an electron injection and transport layer ( 5) and an example of an organic light emitting element composed of a cathode 6 is shown. In such a structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer or the electron blocking layer.

The organic light emitting device according to the present invention may be manufactured with materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by Chemical Formula 1. Also, 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 according to the present invention 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, depositing a metal or a metal oxide having conductivity or an alloy thereof 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, it can be prepared by 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 to these.

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

As the anode material, a material having a high work function is generally preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ :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 easily inject electrons into the organic material layer. Specific examples of the anode material include 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 hole injection layer is a layer for injecting holes from the electrode, and the hole injection material has the ability to transport holes and has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and generated in the light emitting layer A compound that prevents migration of excitons to the electron injecting layer or electron injecting material and has excellent thin film formation ability is preferred. 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, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic matter, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light emitting layer, and has high hole mobility. material is suitable. As the hole transport material, a compound represented by Formula 1, an arylamine-based organic material, a conductive polymer, or a block copolymer having both conjugated and non-conjugated parts may be used, but is not limited thereto.

The electron blocking layer is formed on the hole transport layer, and is preferably provided in contact with the light emitting layer to control hole mobility and prevent excessive movement of electrons to increase the probability of hole-electron coupling, thereby increasing the efficiency of the organic light emitting device. means a layer that serves to improve The electron blocking layer includes an electron blocking material, and examples of the electron blocking material include a compound represented by Chemical Formula 1 or an arylamine-based organic material, but is not limited thereto.

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.

The light emitting layer may include a host material and a dopant material. As such a host material, the compound represented by Chemical Formula 1 may be used. In addition, the host material may further include a condensed aromatic ring derivative or a heterocyclic compound other than the compound represented by Formula 1 above. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

On the other hand, when the organic material layer containing the compound is a light emitting layer. In other words, when the light emitting layer includes the compound represented by Formula 1 as a host material, the light emitting layer may further include a compound represented by Formula 3 below:

[Formula 3]

In Formula 3,

R ₁₁ to R ₁₄ are each independently hydrogen; heavy hydrogen; cyano; halogen; or substituted or unsubstituted C _1-60 alkyl, or two adjacent R ₁₁ to R ₁₄ bond to each other to form a substituted or unsubstituted benzene ring fused with the adjacent ring;

One of R ₁₅ to R ₁₈ is a substituted or unsubstituted C _6-60 aryl; or a substituted or unsubstituted C _2-60 heterocyclic group containing one or more heteroatoms of N, O, and S, and the others are each independently hydrogen; heavy hydrogen; cyano; halogen; or a substituted or unsubstituted C _1-60 alkyl;

L ₁₁ is a single bond; or a substituted or unsubstituted C _6-60 arylene;

Ar ₁₁ and Ar ₁₂ are each independently a substituted or unsubstituted C _6-60 aryl; A substituted or unsubstituted C _3-60 aliphatic ring group; or a substituted or unsubstituted C _2-60 heterocyclic group containing at least one heteroatom selected from N, O and S.

Specifically, two adjacent R ₁₁ to R ₁₄ combine with each other to form a benzene ring unsubstituted or substituted with deuterium fused with the adjacent ring, and the others may be hydrogen or deuterium.

In addition, one of R ₁₅ to R ₁₈ is a substituted or unsubstituted C _6-20 aryl; or a substituted or unsubstituted C _2-20 heteroaryl containing one or more heteroatoms selected from N, O and S, and the others are each independently hydrogen; heavy hydrogen; cyano; halogen; Or it may be a substituted or unsubstituted C _1-10 alkyl.

For example, one of R ₁₅ to R ₁₈ is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, and the others may each independently be hydrogen or deuterium.

In one embodiment, R ₁₅ is substituted or unsubstituted C _6-20 aryl; or a substituted or unsubstituted C _2-20 heteroaryl containing at least one heteroatom selected from N, O and S, and R ₁₆ , R ₁₇ and R ₁₈ are each independently hydrogen; heavy hydrogen; cyano; halogen; or C _1-10 alkyl.

For example, R ₁₅ is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. And, R ₁₆ , R ₁₇ and R ₁₈ may each independently be hydrogen or deuterium.

In other embodiments, R ₁₆ is substituted or unsubstituted C _6-20 aryl; or a substituted or unsubstituted C _2-20 heteroaryl containing at least one heteroatom selected from N, O and S, and R ₁₅ , R ₁₇ and R ₁₈ are each independently hydrogen; heavy hydrogen; cyano; halogen; or C _1-10 alkyl.

For example, R ₁₆ is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. And, R ₁₅ , R ₁₇ and R ₁₈ may each independently be hydrogen or deuterium.

In another embodiment, R ₁₇ is substituted or unsubstituted C _6-20 aryl; or a substituted or unsubstituted C _2-20 heteroaryl containing at least one heteroatom selected from N, O and S, and R ₁₅ , R ₁₆ and R ₁₈ are each independently hydrogen; heavy hydrogen; cyano; halogen; or C _1-10 alkyl.

For example, R ₁₇ is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. And, R ₁₅ , R ₁₆ and R ₁₈ may each independently be hydrogen or deuterium.

In another embodiment, R ₁₈ is substituted or unsubstituted C _6-20 aryl; or a substituted or unsubstituted C _2-20 heteroaryl containing at least one heteroatom selected from N, O and S, and R ₁₅ , R ₁₆ and R ₁₇ are each independently hydrogen; heavy hydrogen; cyano; halogen; or C _1-10 alkyl.

For example, R ₁₈ is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. And, R ₁₅ , R ₁₆ and R ₁₇ may each independently be hydrogen or deuterium.

In one embodiment, L ₁₁ is a single bond; Or it may be a substituted or unsubstituted C _6-20 arylene.

For example, L ₁₁ may be a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenyldiyl, or substituted or unsubstituted naphthylene.

In one embodiment, Ar ₁₁ and Ar ₁₂ are each independently substituted or unsubstituted C _6-20 aryl; Or a substituted or unsubstituted C _2-20 heteroaryl containing one or more heteroatoms selected from N, O and S.

For example, Ar ₁₁ and Ar ₁₂ are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenylyl, substituted or unsubstituted naphthyl, substituted or unsubstituted substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

In one embodiment, the compound represented by Chemical Formula 3 may be represented by any one of the following Chemical Formulas 3-1 to 3-4:

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

In Chemical Formulas 3-1 to 3-4,

each R' is independently deuterium, halogen, or cyano;

r is an integer from 0 to 4;

s is an integer from 0 to 6;

R ₁₅ to R ₁₈ , L ₁₁ , Ar ₁₁ and Ar ₁₂ are as defined in Formula 3 above.

Meanwhile, the compound represented by Formula 3 may be any one selected from the group consisting of the following compounds:

.

In addition, the compound represented by Chemical Formula 3 can be prepared by, for example, a preparation method as shown in Scheme 2 below:

[Scheme 2]

In Scheme 1, X' is halogen, preferably bromo or chloro, and descriptions of the remaining substituents are as defined above.

Specifically, the compound represented by Chemical Formula 3 may be prepared by an amine substitution reaction of reactants B1 and B2. At this time, the amine substitution reaction is preferably performed under a palladium catalyst and a base, and a reactor for the reaction may be changed to a reactor known in the art. This manufacturing method may be more specific in Preparation Examples to be described later.

In addition, the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 3 in the light emitting layer may be included in a weight ratio of 1:99 to 99:1. At this time, in terms of effectively balancing the charge between the host by properly maintaining the ratio of holes and electrons in the light emitting layer, the compound represented by Formula 1 and the compound represented by Formula 3 in the light emitting layer are 30:70 to 70: It is more preferable that it is included in a weight ratio of 30, a weight ratio of 40:60 to 60:40, or a weight ratio of 50:50.

Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periplanthene, etc. having an arylamino group, and styrylamine compounds include substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, wherein one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are 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.

More specifically, the following compounds may be used as the dopant material, but are not limited thereto:

.

.

The hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to improve the efficiency of the organic light emitting device by controlling electron mobility and preventing excessive movement of holes to increase the probability of hole-electron coupling layers that play a role. The hole blocking layer includes a hole blocking material, and examples of the hole blocking material include azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; A compound having an electron withdrawing group such as a phosphine oxide derivative may be used, but is not limited thereto.

The electron injection and transport layer is a layer that simultaneously serves as an electron transport layer and an electron injection layer for injecting electrons from an electrode and transporting the received electrons to the light emitting layer, and is formed on the light emitting layer or the hole blocking layer. As such an electron injecting and transporting material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Examples of specific electron injection and transport materials include Al complexes of 8-hydroxyquinoline; Complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes; triazine derivatives, etc., but are not limited thereto. Or fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds , or may be used together with nitrogen-containing 5-membered ring derivatives, etc., but is not limited thereto.

The electron injection and transport layer may also be formed as a separate layer such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the light emitting layer or the hole blocking layer, and the above-described electron injection and transport material may be used as an electron transport material included in the electron transport layer. In addition, the electron injection layer is formed on the electron transport layer, and examples of electron injection materials included in the electron injection layer include LiF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, Thiophyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like can be used.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, 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)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. It is not limited to this.

The organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided light emitting device, and in particular, may be a bottom emission device requiring relatively high light emitting efficiency.

In addition, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

Preparation of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

Synthesis Example 1: Preparation of Compound 1

In a nitrogen atmosphere, sub1 (15 g, 36.2 mmol), amine1 (12.2 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of Compound 1. (Yield 53%, MS: [M+H] ⁺ = 700)

Synthesis Example 2: Preparation of Compound 2

In a nitrogen atmosphere, sub1 (15 g, 36.2 mmol), amine2 (17 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.2 g of Compound 2. (Yield 51%, MS: [M+H] ⁺ = 826)

Synthesis Example 3: Preparation of Compound 3

In a nitrogen atmosphere, sub1 (15 g, 36.2 mmol), amine3 (17 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.9 g of Compound 3. (Yield 60%, MS: [M+H] ⁺ = 826)

Synthesis Example 4: Preparation of Compound 4

In a nitrogen atmosphere, sub1 (15 g, 36.2 mmol), amine4 (14.1 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.5 g of Compound 4. (Yield 50%, MS: [M+H] ⁺ = 750)

Synthesis Example 5: Preparation of Compound 5

In a nitrogen atmosphere, sub1 (15 g, 36.2 mmol), amine5 (16 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.7 g of Compound 5. (Yield 51%, MS: [M+H] ⁺ = 800)

Synthesis Example 6: Preparation of Compound 6

In a nitrogen atmosphere, sub1 (15 g, 36.2 mmol), amine6 (13.9 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.7 g of Compound 6. (Yield 66%, MS: [M+H] ⁺ = 744)

Synthesis Example 7: Preparation of Compound 7

In a nitrogen atmosphere, sub1 (15 g, 36.2 mmol), amine7 (17.3 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.3 g of Compound 7. (Yield 64%, MS: [M+H] ⁺ = 834)

Synthesis Example 8: Preparation of Compound 8

In a nitrogen atmosphere, sub1 (15 g, 36.2 mmol), amine8 (19.5 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.1 g of Compound 8. (Yield 53%, MS: [M+H] ⁺ = 892)

Synthesis Example 9: Preparation of Compound 9

In a nitrogen atmosphere, sub2 (15 g, 36.2 mmol), amine9 (14.1 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.1 g of Compound 9. (Yield 63%, MS: [M+H] ⁺ = 750)

Synthesis Example 10: Preparation of Compound 10

In a nitrogen atmosphere, sub2 (15 g, 36.2 mmol), amine10 (14.1 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.8 g of Compound 10. (Yield 51%, MS: [M+H] ⁺ = 750)

Synthesis Example 11: Preparation of Compound 11

In a nitrogen atmosphere, sub2 (15 g, 36.2 mmol), amine6 (13.9 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.4 g of Compound 11. (Yield 61%, MS: [M+H] ⁺ = 744)

Synthesis Example 12: Preparation of Compound 12

In a nitrogen atmosphere, sub2 (15 g, 36.2 mmol), amine11 (12.7 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of Compound 12. (Yield 52%, MS: [M+H] ⁺ = 714)

Synthesis Example 13: Preparation of Compound 13

In a nitrogen atmosphere, sub2 (15 g, 36.2 mmol), amine12 (18.9 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.8 g of Compound 13. (Yield 53%, MS: [M+H] ⁺ = 876)

Synthesis Example 14: Preparation of compound 14

In a nitrogen atmosphere, sub2 (15 g, 36.2 mmol), amine13 (14.1 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.8 g of Compound 14. (Yield 62%, MS: [M+H] ⁺ = 750)

Synthesis Example 15: Preparation of Compound 15

In a nitrogen atmosphere, sub2 (15 g, 36.2 mmol), amine14 (14.1 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.2 g of Compound 15. (Yield 56%, MS: [M+H] ⁺ = 750)

Synthesis Example 16: Preparation of Compound 16

In a nitrogen atmosphere, sub3 (15 g, 33 mmol), amine15 (12.9 g, 34.6 mmol), and sodium tert-butoxide (4.8 g, 49.5 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13 g of Compound 16. (Yield 50%, MS: [M+H] ⁺ = 790)

Synthesis Example 17: Preparation of Compound 17

In a nitrogen atmosphere, sub4 (15 g, 33 mmol), amine16 (12 g, 34.6 mmol), and sodium tert-butoxide (4.8 g, 49.5 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.6 g of Compound 17. (Yield 70%, MS: [M+H] ⁺ = 764)

Synthesis Example 18: Preparation of Compound 18

In a nitrogen atmosphere, sub5 (15 g, 31.8 mmol), amine17 (14.1 g, 33.4 mmol), and sodium tert-butoxide (4.6 g, 47.8 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.9 g of Compound 18. (Yield 62%, MS: [M+H] ⁺ = 856)

Synthesis Example 19: Preparation of Compound 19

In a nitrogen atmosphere, sub6 (15 g, 31.8 mmol), amine18 (13.3 g, 33.4 mmol), and sodium tert-butoxide (4.6 g, 47.8 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.1 g of Compound 19. (Yield 61%, MS: [M+H] ⁺ = 832)

Synthesis Example 20: Preparation of Compound 20

In a nitrogen atmosphere, sub6 (15 g, 31.8 mmol), amine19 (12.4 g, 33.4 mmol), and sodium tert-butoxide (4.6 g, 47.8 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.2 g of Compound 20. (Yield 67%, MS: [M+H] ⁺ = 806)

Synthesis Example 21: Preparation of compound 21

In a nitrogen atmosphere, sub7 (15 g, 36.2 mmol), amine1 (12.2 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of Compound 21. (Yield 53%, MS: [M+H] ⁺ = 700)

Synthesis Example 22: Preparation of Compound 22

In a nitrogen atmosphere, sub7 (15 g, 36.2 mmol), amine20 (15 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.8 g of Compound 22. (Yield 60%, MS: [M+H] ⁺ = 774)

Synthesis Example 23: Preparation of compound 23

In a nitrogen atmosphere, sub7 (15 g, 36.2 mmol), amine21 (17.3 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.4 g of Compound 23. (Yield 51%, MS: [M+H] ⁺ = 834)

Synthesis Example 24: Preparation of Compound 24

In a nitrogen atmosphere, sub7 (15 g, 36.2 mmol), amine22 (13.5 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.1 g of Compound 24. (Yield 53%, MS: [M+H] ⁺ = 734)

Synthesis Example 25: Preparation of Compound 25

In a nitrogen atmosphere, sub8 (15 g, 36.2 mmol), amine23 (20 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.2 g of Compound 25. (Yield 62%, MS: [M+H] ⁺ = 904)

Synthesis Example 26: Preparation of compound 26

In a nitrogen atmosphere, sub9 (15 g, 32.3 mmol), amine24 (9.4 g, 33.9 mmol), and sodium tert-butoxide (4.7 g, 48.4 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.5 g of Compound 26. (Yield 55%, MS: [M+H] ⁺ = 706)

Synthesis Example 27: Preparation of compound 27

In a nitrogen atmosphere, sub10 (15 g, 32.3 mmol), amine1 (10.9 g, 33.9 mmol), and sodium tert-butoxide (4.7 g, 48.4 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.8 g of Compound 27. (Yield 57%, MS: [M+H] ⁺ = 750)

Synthesis Example 28: Preparation of Compound 28

In a nitrogen atmosphere, sub11 (15 g, 32.3 mmol), amine25 (13.5 g, 33.9 mmol), and sodium tert-butoxide (4.7 g, 48.4 mmol) were added to 300 mL of Xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.3 g of Compound 28. (Yield 65%, MS: [M+H] ⁺ = 826)

Synthesis Example 29: Preparation of Compound 29

In a nitrogen atmosphere, sub9 (15 g, 32.3 mmol), amine1 (10.9 g, 33.9 mmol), and sodium tert-butoxide (4.7 g, 48.4 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.7 g of Compound 29. (Yield 69%, MS: [M+H] ⁺ = 750)

Synthesis Example 30: Preparation of compound 30

In a nitrogen atmosphere, sub12 (15 g, 32.3 mmol), amine1 (10.9 g, 33.9 mmol), and sodium tert-butoxide (4.7 g, 48.4 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.9 g of Compound 30. (Yield 70%, MS: [M+H] ⁺ = 750)

Synthesis Example 31: Preparation of Compound 31

In a nitrogen atmosphere, sub13 (15 g, 32.3 mmol), amine26 (11.3 g, 33.9 mmol), and sodium tert-butoxide (4.7 g, 48.4 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16 g of Compound 31. (Yield 65%, MS: [M+H] ⁺ = 762)

Synthesis Example 32: Preparation of compound 32

In a nitrogen atmosphere, sub13 (15 g, 32.3 mmol), amine1 (10.9 g, 33.9 mmol), and sodium tert-butoxide (4.7 g, 48.4 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.7 g of Compound 32. (Yield 61%, MS: [M+H] ⁺ = 750)

Synthesis Example 33: Preparation of Compound 33

In a nitrogen atmosphere, sub11 (15 g, 32.3 mmol), amine27 (12.6 g, 33.9 mmol), and sodium tert-butoxide (4.7 g, 48.4 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17 g of Compound 33. (Yield 66%, MS: [M+H] ⁺ = 800)

Synthesis Example 34: Preparation of Compound 34

In a nitrogen atmosphere, sub14 (15 g, 32.3 mmol), amine28 (13.5 g, 33.9 mmol), and sodium tert-butoxide (4.7 g, 48.4 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.7 g of Compound 34. (Yield 59%, MS: [M+H] ⁺ = 826)

Synthesis Example 35: Preparation of Compound 35

In a nitrogen atmosphere, sub15 (15 g, 32.3 mmol), amine29 (13.5 g, 33.9 mmol), and sodium tert-butoxide (4.7 g, 48.4 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.6 g of Compound 35. (Yield 70%, MS: [M+H] ⁺ = 826)

Synthesis Example 36: Preparation of compound 36

In a nitrogen atmosphere, sub16 (15 g, 32.3 mmol), amine1 (10.9 g, 33.9 mmol), and sodium tert-butoxide (4.7 g, 48.4 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.4 g of Compound 36. (Yield 68%, MS: [M+H] ⁺ = 750)

Synthesis Example 37: Preparation of Compound 37

In a nitrogen atmosphere, sub17 (15 g, 36.2 mmol), amine30 (15.1 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.2 g of Compound 37. (Yield 65%, MS: [M+H] ⁺ = 776)

Synthesis Example 38: Preparation of compound 38

In a nitrogen atmosphere, sub17 (15 g, 36.2 mmol), amine1 (12.2 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of Compound 38. (Yield 57%, MS: [M+H] ⁺ = 700)

Synthesis Example 39: Preparation of compound 39

In a nitrogen atmosphere, sub18 (15 g, 36.2 mmol), amine31 (17 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.6 g of Compound 39. (Yield 59%, MS: [M+H] ⁺ = 826)

synthesis example 40: preparation of compound 40

In a nitrogen atmosphere, sub19 (15 g, 34 mmol), amine32 (11.5 g, 35.7 mmol), and sodium tert-butoxide (4.9 g, 51 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.8 g of Compound 40. (Yield 52%, MS: [M+H] ⁺ = 726)

Synthesis Example 41: Preparation of compound 41

In a nitrogen atmosphere, sub20 (15 g, 36.2 mmol), amine33 (15.1 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.1 g of Compound 41. (Yield 61%, MS: [M+H] ⁺ = 776)

Synthesis Example 42: Preparation of Compound 42

In a nitrogen atmosphere, sub21 (15 g, 36.2 mmol), amine34 (16 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.9 g of Compound 42. (Yield 69%, MS: [M+H] ⁺ = 800)

Synthesis Example 43: Preparation of Compound 43

In a nitrogen atmosphere, sub22 (15 g, 32.3 mmol), amine35 (10.9 g, 33.9 mmol), and sodium tert-butoxide (4.7 g, 48.4 mmol) were added to 300 mL of Xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.3 g of Compound 43. (Yield 59%, MS: [M+H] ⁺ = 750)

Synthesis Example 44: Preparation of Compound 44

In a nitrogen atmosphere, sub23 (15 g, 36.2 mmol), amine36 (15.1 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.1 g of Compound 44. (Yield 68%, MS: [M+H] ⁺ = 776)

Synthesis Example 45: Preparation of Compound 45

In a nitrogen atmosphere, sub24 (15 g, 36.2 mmol), amine37 (16 g, 38 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 300 mL of xylene and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.6 g of Compound 45. (Yield 61%, MS: [M+H] ⁺ = 800)

Synthesis Example 46: Preparation of Compound 46

In a nitrogen atmosphere, sub25 (15 g, 32.3 mmol), amine38 (13.5 g, 33.9 mmol), and sodium tert-butoxide (4.7 g, 48.4 mmol) were added to 300 mL of Xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of Compound 46. (Yield 54%, MS: [M+H] ⁺ = 826)

Synthesis Example 47: Preparation of compound 47

In a nitrogen atmosphere, sub26 (15 g, 32.3 mmol), amine39 (12.6 g, 33.9 mmol), and sodium tert-butoxide (4.7 g, 48.4 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. When the reaction was completed after 5 hours, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.2 g of Compound 47. (Yield 63%, MS: [M+H] ⁺ = 800)

Example 1

A glass substrate coated with ITO (indium tin oxide) to a thickness of 1,000 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum deposition machine.

The following compound HI-1 was formed to a thickness of 1150 Å as a hole injection layer on the prepared ITO transparent electrode, but the following compound A-1 was p-doped at a concentration of 1.5%. A hole transport layer having a thickness of 800 Å was formed by vacuum depositing the following HT-1 compound on the hole injection layer. Then, the compound 1 prepared in Synthesis Example 1 was vacuum deposited to form a film thickness of 150 Å on the hole transport layer to form an electron blocking layer.

Subsequently, the following RH-1 compound as a host and the following Dp-7 compound as a dopant were vacuum-deposited on the electron blocking layer in a weight ratio of 98:2 to form a red light emitting layer having a thickness of 400 Å.

A hole blocking layer was formed on the light emitting layer by vacuum depositing the HB-1 compound to a film thickness of 30 Å. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 Å.

A negative electrode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å / sec, the deposition rate of lithium fluoride on the cathode was 0.3 Å / sec, and the deposition rate of aluminum was 2 Å / sec, and the vacuum degree during deposition was 2 × 10 ^-7 ~ 5ⅹ10 ^-6 torr was maintained.

Examples 2 to 47

An organic light emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in the organic light emitting device of Example 1.

Examples 48 to 60

In the organic light-emitting device of Example 1, the following compound EB-1 was used instead of Compound 1 as an electron blocking layer, RH-1 was used as a first host instead of single host RH-1 as a host, and the compounds listed in Table 2 were used as a second host. Thus, an organic light emitting device was manufactured in the same manner as in Example 1, except that the first host and the second host were used in a weight ratio of 1:1.

The structures of Compounds 1 to 47 used in Examples 1 to 60 are summarized as follows.

Comparative Examples 1 to 6

An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in the organic light emitting device of Example 1. At this time, the structures of comparative compounds C-1 to C-6 are as follows.

Comparative Examples 7 to 12

In the organic light emitting device of Example 1, the EB-1 compound was used instead of Compound 1 as an electron blocking layer, RH-1 was used as a first host instead of a single host RH-1 as a host, and the compounds listed in Table 2 were used as a second host. Thus, an organic light emitting device was manufactured in the same manner as in Example 1, except that the first host and the second host were used in a weight ratio of 1:1.

Experimental Example 1: Evaluation of device characteristics

When current was applied to the organic light emitting devices prepared in Examples 1 to 60 and Comparative Examples 1 to 12, voltage and efficiency were measured (15 mA/cm ² ), and the results are shown in Table 1 and Table 1 below. 2. Here, the lifetime T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

division electron blocking layer Driving voltage (V) Efficiency (cd/A) Lifetime T95(hr) luminescent color Example 1 compound 1 3.39 22.70 212 Red Example 2 compound 2 3.38 22.92 224 Red Example 3 compound 3 3.39 22.92 228 Red Example 4 compound 4 3.41 23.02 212 Red Example 5 compound 5 3.34 22.62 213 Red Example 6 compound 6 3.34 23.07 224 Red Example 7 compound 7 3.34 22.79 225 Red Example 8 compound 8 3.34 23.01 231 Red Example 9 compound 9 3.42 23.44 142 Red Example 10 compound 10 3.40 23.35 141 Red Example 11 compound 11 3.42 23.78 145 Red Example 12 compound 12 3.34 23.88 126 Red Example 13 compound 13 3.34 23.86 137 Red Example 14 compound 14 3.39 23.69 129 Red Example 15 compound 15 3.33 24.10 128 Red Example 16 compound 16 3.66 22.33 145 Red Example 17 compound 17 3.67 21.44 125 Red Example 18 compound 18 3.66 22.05 130 Red Example 19 compound 19 3.65 21.80 125 Red Example 20 compound 20 3.64 21.54 138 Red Example 21 compound 21 3.61 22.96 169 Red Example 22 compound 22 3.53 22.78 162 Red Example 23 compound 23 3.62 23.01 175 Red Example 24 compound 24 3.61 23.08 175 Red Example 25 compound 25 3.60 22.65 171 Red Example 26 compound 26 3.54 23.05 151 Red Example 27 compound 27 3.42 23.44 194 Red Example 28 compound 28 3.37 23.84 197 Red Example 29 compound 29 3.34 23.36 206 Red Example 30 compound 30 3.39 23.39 204 Red Example 31 compound 31 3.38 24.03 183 Red Example 32 compound 32 3.38 23.50 191 Red Example 33 compound 33 3.38 23.81 227 Red Example 34 compound 34 3.40 23.64 229 Red Example 35 compound 35 3.33 23.60 230 Red Example 36 compound 36 3.40 23.82 215 Red Example 37 compound 37 3.41 23.49 187 Red Example 38 compound 38 3.33 23.65 192 Red Example 39 compound 39 3.37 23.46 193 Red Example 40 compound 40 3.57 22.66 170 Red Example 41 compound 41 3.58 22.66 158 Red Example 42 compound 42 3.53 22.67 152 Red Example 43 compound 43 3.41 23.54 206 Red Example 44 compound 44 3.35 22.62 217 Red Example 45 compound 45 3.39 23.48 204 Red Example 46 compound 46 3.40 23.44 232 Red Example 47 compound 47 3.34 23.82 220 Red Comparative Example 1 C-1 3.82 19.59 109 Red Comparative Example 2 C-2 3.85 19.46 117 Red Comparative Example 3 C-3 4.03 17.72 90 Red Comparative Example 4 C-4 4.06 17.79 87 Red Comparative Example 5 C-5 3.82 18.02 97 Red Comparative Example 6 C-6 3.84 18.23 112 Red

division first host 2nd host Driving voltage (V) Efficiency (cd/A) Lifetime T95(hr) luminescent color Example 48 RH-1 compound 1 3.33 25.93 293 Red Example 49 compound 3 3.50 26.24 298 Red Example 50 compound 14 3.44 26.80 274 Red Example 51 compound 21 3.49 26.52 291 Red Example 52 compound 22 3.45 25.25 280 Red Example 53 compound 28 3.49 26.57 276 Red Example 54 compound 29 3.51 25.10 295 Red Example 55 compound 30 3.47 25.14 298 Red Example 56 compound 34 3.44 25.64 293 Red Example 57 compound 37 3.37 26.09 286 Red Example 58 compound 43 3.38 25.08 281 Red Example 59 compound 44 3.37 26.17 274 Red Example 60 compound 46 3.35 26.95 287 Red Comparative Example 7 C-1 3.80 20.83 179 Red Comparative Example 8 C-2 3.81 20.78 187 Red Comparative Example 9 C-3 3.98 18.95 124 Red Comparative Example 10 C-4 4.08 19.04 131 Red Comparative Example 11 C-5 3.83 19.31 143 Red Comparative Example 12 C-6 3.88 19.67 152 Red

As shown in Tables 1 and 2, the organic light emitting device of the example using the compound represented by Formula 1 as a host material of the electron blocking layer or the light emitting layer is the organic light emitting device of the comparative example using a compound having a structure different from this. It can be seen that compared to the reduced driving voltage and improved efficiency and lifespan characteristics. Through this, the compound represented by Formula 1 can not only effectively block the movement of electrons to the hole transport layer, but also can balance the charge between the hosts well, contribute to the stabilization of excitons, and at the same time, energy transfer ability to the red dopant You can check this excellence.

1: substrate 2: anode
3: hole transport layer 4: light emitting layer
5: electron injection and transport layer 6: cathode
7: hole injection layer 8: electron blocking layer
9: hole blocking layer

Claims (18)

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

In Formula 1,
L ₁ and L ₂ are each independently a single bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing one or more heteroatoms of N, O and S,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; A substituted or unsubstituted C _3-60 aliphatic ring group; Or a substituted or unsubstituted C _2-60 heterocyclic group containing one or more heteroatoms of N, O and S;
However, Ar ₁ and Ar ₂ are not substituted or unsubstituted fluorenyl,
One of R ₁ to R ₅ is unsubstituted or deuterium-substituted phenanthryl, the other is a substituent represented by Formula 2 below, and the others are each independently hydrogen or deuterium,
[Formula 2]

In Formula 2,
L ₃ is a single bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing one or more heteroatoms of N, O and S,
Ar ₃ is substituted or unsubstituted biphenylyl; Substituted or unsubstituted naphthyl; A substituted or unsubstituted phenanthryl; Substituted or unsubstituted dibenzofuranyl; Or a substituted or unsubstituted dibenzothiophenyl,
However, when R ₂ is unsubstituted phenanthryl and R ₄ is a substituent represented by Formula 2, Ar ₃ is substituted biphenylyl, substituted naphthyl, substituted phenanthryl, substituted or unsubstituted di benzofuranyl, or substituted or unsubstituted dibenzothiophenyl.
According to claim 1,
R ₁ is unsubstituted or phenanthryl substituted with deuterium, one of R ₂ , R ₃ , R ₄ and R ₅ is a substituent represented by Formula 2, and the others are each independently hydrogen or deuterium;
R ₂ is unsubstituted or phenanthryl substituted with deuterium, one of R ₁ , R ₃ , R ₄ and R ₅ is a substituent represented by Formula 2, and the others are each independently hydrogen or deuterium; or
R ₃ is unsubstituted or phenanthryl substituted with deuterium, one of R ₁ , R ₂ , R ₄ and R ₅ is a substituent represented by Formula 2, and the others are each independently hydrogen or deuterium;
compound.
According to claim 1,
L ₁ and L ₂ are each independently a single bond, phenylene, naphthylphenylene, biphenyldiyl, naphthylene, or phenylnaphthylene;
The phenylene, naphthylphenylene, biphenyldiyl, naphthylene and phenylnaphthylene are unsubstituted or substituted with deuterium,
compound.
According to claim 1,
Ar ₁ and Ar ₂ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, 2,3-dihydro-1H-indenyl, 1,2,3,4-tetrahydronaphthyl, 6,7,8,9-tetrahydro-5H-benzo[7]anulenyl, adamantyl, dibenzofuranyl, or dibenzothiophenyl;
Wherein Ar ₁ and Ar ₂ are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C _1-4 alkyl, phenyl and naphthyl;
compound.
According to claim 1,
One of R ₁ to R ₅ is a substituent represented by any one of the following formulas a1 to a5,
compound:

In the above formulas a1 to a5,
n is an integer from 0 to 9;
According to claim 1,
L ₃ is a single bond or unsubstituted or deuterium substituted phenylene.
compound.
According to claim 1,
Ar ₃ is any one selected from the group consisting of

From above,
Q is deuterium, phenyl, biphenylyl, or naphthyl;
m1 is an integer from 0 to 7;
m2 is an integer from 0 to 4;
m3 is an integer from 0 to 5;
m4 is an integer from 0 to 9;
However, when R ₂ is unsubstituted phenanthryl and R ₄ is a substituent represented by Formula 2 above, Ar ₃ is any one selected from the group consisting of
compound:

From above,
Q is deuterium, phenyl, biphenylyl, or naphthyl;
m1 is an integer from 0 to 7;
m5 is an integer from 1 to 7;
m6 is an integer from 0 to 4;
m7 is an integer from 0 to 5,
m6+m7 is an integer from 1 to 9;
m8 is an integer from 1 to 9;
According to claim 1,
The compound is represented by any one of Formulas 1-1 to 1-6,
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-1 to 1-6,
p is an integer from 0 to 3;
A is a substituent represented by any one of the following formulas a1 to a5,

In the above formulas a1 to a5,
n is an integer from 0 to 9;
L ₁ to L ₃ and Ar ₁ to Ar ₃ are as defined in claim 1,
However, in Formula 1-3, Ar ₃ is substituted biphenylyl; substituted naphthyl, substituted phenanthryl; Substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiophenyl.
According to claim 1,
The compound is any one selected from the group consisting of the following compounds,
compound:

.
a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound according to any one of claims 1 to 9. That is, an organic light emitting element.
According to claim 10,
The organic material layer containing the compound is a light emitting layer or an electron blocking layer,
organic light emitting device.
According to claim 11,
When the organic material layer containing the compound is a light emitting layer, the light emitting layer further comprises a compound represented by Formula 3 below.
Organic Light-Emitting Elements:
[Formula 3]

In Formula 3,
R ₁₁ to R ₁₄ are each independently hydrogen; heavy hydrogen; cyano; halogen; or substituted or unsubstituted C _1-60 alkyl, or two adjacent R ₁₁ to R ₁₄ bond to each other to form a substituted or unsubstituted benzene ring fused with the adjacent ring;
One of R ₁₅ to R ₁₈ is a substituted or unsubstituted C _6-60 aryl; or a substituted or unsubstituted C _2-60 heterocyclic group containing one or more heteroatoms of N, O, and S, and the others are each independently hydrogen; heavy hydrogen; cyano; halogen; or a substituted or unsubstituted C _1-60 alkyl;
L ₁₁ is a single bond; or a substituted or unsubstituted C _6-60 arylene;
Ar ₁₁ and Ar ₁₂ are each independently a substituted or unsubstituted C _6-60 aryl; A substituted or unsubstituted C _3-60 aliphatic ring group; or a substituted or unsubstituted C _2-60 heterocyclic group containing at least one heteroatom selected from N, O and S.
According to claim 12,
Two neighboring R ₁₁ to R ₁₄ combine with each other to form a benzene ring unsubstituted or substituted with deuterium fused with the adjacent ring, and the others are hydrogen or deuterium,
organic light emitting device.
According to claim 12,
One of R ₁₅ to R ₁₈ is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothio phenyl, and the others are each independently hydrogen or deuterium,
organic light emitting device.
According to claim 12,
L ₁₁ is a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenyldiyl, or substituted or unsubstituted naphthylene;
organic light emitting device.
According to claim 12,
Ar ₁₁ and Ar ₁₂ are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenylyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, A substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl,
organic light emitting device.
According to claim 12,
The compound represented by Formula 3 is represented by any one of Formulas 3-1 to 3-4,
Organic Light-Emitting Elements:
[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

In Chemical Formulas 3-1 to 3-4,
each R' is independently deuterium, halogen, or cyano;
r is an integer from 0 to 4;
s is an integer from 0 to 6;
R ₁₅ to R ₁₈ , L ₁₁ , Ar ₁₁ and Ar ₁₂ are as defined in claim 12.
According to claim 12,
The compound represented by Formula 3 is any one selected from the group consisting of the following compounds,
Organic Light-Emitting Elements:

.