TW202030307A - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1, and an organic light emitting device comprising the same.

Description

Heterocyclic compound and organic light emitting device including the same

This application claims the priority and rights of the Korean patent application No. 10-2018-0140966 filed in the Korean Intellectual Property Office on November 15, 2018. The entire content of the Korean patent application is incorporated into this case for reference .

This specification relates to a heterocyclic compound and an organic light-emitting device including it.

An electroluminescent device is a self-emissive display device and has the advantages of wide viewing angle, high response speed and excellent contrast.

The organic light emitting device has a structure in which an organic thin film is provided between two electrodes. When a voltage is applied to an organic light emitting device having such a structure, the electrons and holes injected from the two electrodes are combined and paired in the organic thin film, and light is emitted as the electrons and holes are annihilated. If necessary, the organic thin film may be formed as a single layer or multiple layers.

If necessary, the material of the organic thin film may have a light-emitting function. For example, as the material of the organic thin film, a compound capable of forming a light-emitting layer by itself may be used, or a compound capable of serving as a host or dopant of a host-dopant-based light-emitting layer may also be used. In addition, compounds capable of performing the functions of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, etc., can also be used as the material of the organic thin film.

In order to improve the effectiveness, lifespan, or efficiency of organic light-emitting devices, it is always necessary to develop an organic thin film material. [Prior Art Literature] [Patent Literature]

U.S. Patent No. 4,356,429

[technical problem]

The present disclosure relates to providing a heterocyclic compound and an organic light emitting device including the heterocyclic compound. [Technical solutions]

One embodiment of the present application provides a heterocyclic compound represented by the following Chemical Formula 1. [Chemical formula 1]

In Chemical Formula 1, X ₁ to X ₃ are the same or different from each other, and are each independently CRa; or N, at least one of X ₁ to X ₃ is N, and Ra is selected from the group consisting of: hydrogen; A substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; -SiRR'R''; and -P(=O)RR', L ₁ to L ₄ are the same or different from each other, and are each independent Ground is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroaryl group, Z ₁ to Z ₄ are the same or different from each other, and are each independently selected from the group consisting of hydrogen; Deuterium; halogen; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; -CN; -SiRR'R''; and -P(=O)RR', m, n, p and q are integers from 1 to 5, and when m, n, p, and q are each 2 or greater than 2, the substituents in the parentheses are the same or different from each other, and R, R'and R" are the same or different from each other , And each independently is hydrogen; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

Another embodiment of the application provides an organic light-emitting device, the organic light-emitting device comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed on the Between the first electrode and the second electrode, wherein one or more of the organic material layers includes a heterocyclic compound represented by Chemical Formula 1. [Advantageous effect]

The compound described in this specification can be used as a material for an organic material layer of an organic light-emitting device. The compound can function as a hole injection material, a hole transport material, a luminescent material, an electron transport material, an electron injection material, a charge generation material, and the like. Specifically, the compound can be used as a charge generation layer material or an electron transport layer material of an organic light-emitting device.

When the compound represented by Chemical Formula 1 is used in the organic material layer, the device driving voltage can be reduced, the light efficiency can be improved, and the device lifetime properties can be improved by the thermal stability of the compound.

In the following, this application will be explained in detail.

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

In this specification, halogen may be fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples thereof may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tertiary butyl, second butyl, 1-methyl-butyl , 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4- Methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl Base, n-octyl, third octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl- Propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but not limited to these.

In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples thereof may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl Alkenyl, 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)ethylene Group-1-yl, distyryl, styryl, etc., but not limited to these.

In the present specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

In this specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1-20. Specific examples thereof may include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tertiary butoxy Group, second butoxy group, n-pentoxy group, neopentyloxy group, isopentoxy group, n-hexoxy group, 3,3-dimethylbutoxy group, 2-ethylbutoxy group, n-octyloxy group , N-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but not limited to this.

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted with other substituents. In this context, polycyclic refers to a group in which a cycloalkyl group is directly connected to or fused with another cyclic group. In this context, other cyclic groups may be cycloalkyl groups, but may also be different types of cyclic groups, such as heterocycloalkyl groups, aryl groups, and heteroaryl groups. The number of carbon groups of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methyl Cyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tertiarybutylcyclohexyl, cycloheptyl, cyclooctyl, etc., but not limited to these.

In the present specification, the heterocycloalkyl group includes O, S, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with other substituents. In this context, polycyclic refers to a group in which a heterocycloalkyl group is directly connected to or fused with another cyclic group. In this context, other cyclic groups can be heterocycloalkyl groups, but can also be different types of cyclic groups, such as cycloalkyl groups, aryl groups, and heteroaryl groups. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

In the present specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted with other substituents. In this context, polycyclic refers to a group in which the aryl group is directly connected to or fused with other cyclic groups. In this context, other cyclic groups can be aryl groups, but can also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl, and heteroaryl. Aryl groups include spirocyclic groups. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group may include phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, phenanthryl, perylene, fluorenanthryl, triphenylene, phenalenyl group, pyrenyl , Fused tetraphenyl (tetracenyl group), fused pentaphenyl, fluorenyl, indenyl, naphthyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, its fused Ring etc., but not limited to this.

In this specification, the phosphine oxide group is represented by -P(=O)R ₁₀₃ R ₁₀₄ , and R ₁₀₃ and R ₁₀₄ are the same as or different from each other, and may each independently be a substituent formed by at least one of the following: Hydrogen; Deuterium; Halogen; Alkyl; Alkenyl; Alkoxy; Cycloalkyl; Aryl; and Heterocyclic Group. Specific examples of the phosphine oxide group may include a diphenyl phosphine oxide group, a dinaphthyl phosphine oxide group, etc., but are not limited thereto.

In this specification, the silyl group is a substituent containing Si, and the Si atom is directly connected as a radical, and is represented by -SiR ₁₀₄ R ₁₀₅ R ₁₀₆ . R ₁₀₄ to R ₁₀₆ are the same or different from each other, and may each independently be a substituent formed by at least one of the following: hydrogen; deuterium; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; aryl基; and heterocyclic group. Specific examples of the silyl group may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl , Diphenylsilyl, phenylsilyl, etc., but not limited to this.

In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

、

、

、

、

、

等，然而，所述結構並非僅限於此。When the fluorenyl group is substituted, it can include

,

,

,

,

,

Etc. However, the structure is not limited to this.

In this specification, the heteroaryl group contains O, S, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with other substituents. In this context, polycyclic refers to a group in which a heteroaryl group is directly connected to or fused with other cyclic groups. In this context, other cyclic groups may be heteroaryl groups, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl, and aryl. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of heteroaryl groups may include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, Triazolyl, furazanyl group, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl group, diazinyl, oxazinyl, Thiazinyl, dioxynyl group, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl, qninozolinyl, naphthalene Ridinyl, acridinyl, phenanthridinyl, imidazopyridinyl, naphthazine, triazaindenyl, indolyl, indolazinyl, benzothiazolyl, benzoxazolyl, benzo Imidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenazinyl, silafluorene ( dibenzosilole), spirobi (dibenzosilole), dihydrophenazine, phenoxazinyl, phenanthridyl group, imidazopyridyl, thienyl, indole [2,3-a]carb Azolyl, indole[2,3-b]carbazolyl, indolinyl, 10,11-dihydro-dibenzo[b,f]azayl, 9,10-dihydroacridinyl , Phenazinyl, phenothiazinyl group, phthalazinyl, naphthylidinyl group, phenantholinyl, benzo[c][1,2,5]thiadiazolyl, 5,10 -Dihydrobenzo[b,e][1,4]azasilinyl (5,10-dihydrobenzo[b,e][1,4]azasilinyl), pyrazole[1,5-c ]Quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazole[1,2-e]indolinyl, 5,11-dihydroindeno[ 1,2-b]carbazolyl group (5,11-dihydroindeno[1,2-b]carbazolyl group), etc., but not limited to this.

In this specification, the amine group can be selected from the group consisting of: monoalkylamino group; monoarylamino group; monoheteroarylamino group; -NH ₂ ; dialkylamino group; diarylamino group ; Diheteroarylamino; Alkylarylamino; Alkylheteroarylamino; And arylheteroarylamino, and although not particularly limited thereto, the number of carbon atoms is preferably 1 To 30. Specific examples of the amino group may include methylamino, dimethylamino, ethylamino, diethylamino, anilino, naphthylamino, benzidine, dibenzylamino, anthrylamino, 9-methyl -Anthrylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenyl group Phenylamino, biphenylfluorenylamino, phenyltriphenyleneamino, biphenyltriphenyleneamino, etc., but not limited to these.

In this specification, an aryl group refers to an aryl group having two bonding sites, that is, a divalent group. Except for the divalent ones, the descriptions of aryl groups provided above can be applied here. In addition, the heteroaryl group refers to a heteroaryl group having two bonding sites, that is, a divalent group. Except for the divalent ones, the descriptions of heteroaryl groups provided above can be applied here.

In this specification, the "adjacent" group may refer to a substituent directly connected to the atom substituted by the corresponding substituent, the substituent positioned closest to the corresponding substituent in space, or the substitution of the atom substituted by the corresponding substituent Another substituent of. For example, two substituents substituted for the ortho position in the benzene ring and two substituents substituted for the same carbon in the aliphatic ring can be interpreted as groups "adjacent" to each other.

In the present specification, the term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is changed to another substituent, and the substitution position is not limited as long as it is the position where the hydrogen atom is substituted (ie, the substituent The position where substitution may be performed) is sufficient, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

In this specification, "substituted or unsubstituted" refers to substitution with one or more substituents selected from the group consisting of: C1 to C60 linear or branched alkyl; C2 to C60 linear or Branched alkenyl; C2 to C60 linear or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aromatic C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R''; -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamines are either unsubstituted, or substituted by a substituent connected to two or more substituents selected from the above-mentioned substituents, or unsubstituted, and

R, R', R'' are the same or different from each other, and are each independently hydrogen; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl base.

An example of the present application provides a heterocyclic compound represented by Chemical Formula 1.

In an embodiment of the present application, X ₁ to X ₃ are the same or different from each other, and may each independently be CRa; or N.

In an embodiment of the present application, at least one of X ₁ to X ₃ may be N.

In an embodiment of the present application, X ₁ and X ₂ may be N, and X3 may be CRa.

In an embodiment of the present application, X ₁ and X ₃ may be N, and X ₂ may be CRa.

In an embodiment of the present application, X ₁ to X ₃ may be N.

[化學式3]

[化學式4]

In an embodiment of the present application, Chemical Formula 1 may be represented by any of the following Chemical Formula 2 to Chemical Formula 4. [Chemical formula 2]

[Chemical formula 3]

[Chemical formula 4]

In Chemical Formula 2 to Chemical Formula 4,

L ₁ to L ₄ , Z ₁ to Z ₄ , m, n, p, and q have the same definitions as in Chemical Formula 1,

X ₂ and X ₃ are CRa, and

Ra has the same definition as in Chemical Formula 1.

Specifically, compared with Chemical Formula 3, Chemical Formula 2 has a higher electron mobility because the degree of separation of electron distribution between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) is greater than that of Chemical Formula 3. Therefore, in terms of driving and efficiency, more superior properties can be obtained, and compared with Chemical Formula 2, Chemical Formula 3 is superior in terms of lifetime due to the wider electron distribution.

In an embodiment of the present application, Ra can be selected from the group consisting of: hydrogen; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; -SiRR'R''; And -P(=O)RR'.

In another embodiment, Ra can be selected from the group consisting of: hydrogen; substituted or unsubstituted aryl; and substituted or unsubstituted heteroaryl.

In another embodiment, Ra can be selected from the group consisting of hydrogen; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl.

In another embodiment, Ra can be selected from the group consisting of: hydrogen; substituted or unsubstituted C6 to C40 aryl; and substituted or unsubstituted C2 to C40 heteroaryl.

In another embodiment, Ra can be selected from the group consisting of hydrogen; C6 to C40 aryl; and C2 to C40 heteroaryl.

In another embodiment, Ra may be hydrogen.

In another embodiment, Ra may be phenyl.

In an embodiment of the present application, L ₁ to L ₄ are the same as or different from each other, and may each independently be a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroaryl group.

In another embodiment, L ₁ to L ₄ are the same or different from each other, and can each independently be a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 hetero Aryl.

In another embodiment, L ₁ to L ₄ are the same or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl; or a substituted or unsubstituted C2 to C40 hetero Aryl.

In another embodiment, L ₁ to L ₄ are the same or different from each other, and may each independently be a C6 to C40 arylene group; or a C2 to C40 heteroaryl group.

In another embodiment, L ₁ to L ₄ are the same or different from each other, and may each independently be a C6 to C20 arylene group; or a C2 to C20 heteroaryl group.

In another embodiment, L ₁ to L ₄ are the same or different from each other, and may each independently be phenylene; biphenylene; biterphenylene; phenanthrenyl; naphthylene; divalent carbazolyl ; Divalent dibenzofuranyl; divalent dibenzothienyl; divalent quinazolinyl; or divalent pyridyl.

In an embodiment of the present application, Z ₁ to Z ₄ are the same or different from each other, and can be each independently selected from the group consisting of: hydrogen; deuterium; halogen; substituted or unsubstituted aryl; Substituted or unsubstituted heteroaryl; -CN; -SiRR'R''; and -P(=O)RR'.

In another embodiment, Z ₁ to Z ₄ are the same or different from each other, and can each be independently selected from the group consisting of hydrogen; deuterium; halogen; substituted or unsubstituted C6 to C60 aryl; Substituted or unsubstituted C2 to C60 heteroaryl; -CN; -SiRR'R''; and -P(=O)RR'.

In another embodiment, Z ₁ to Z ₄ are the same or different from each other, and can be each independently selected from the group consisting of: hydrogen; deuterium; halogen; substituted or unsubstituted C6 to C40 aryl; Substituted or unsubstituted C2 to C40 heteroaryl; -CN; -SiRR'R''; and -P(=O)RR'.

In another embodiment, Z ₁ to Z ₄ are the same or different from each other, and can be each independently selected from the group consisting of: hydrogen; substituted or unsubstituted C6 to C40 aryl; substituted or unsubstituted Substituted C2 to C40 heteroaryl; -CN; and -P(=0)RR'.

In another embodiment, Z ₁ to Z ₄ are the same or different from each other, and can be each independently selected from the group consisting of: hydrogen; C6 to C40 aryl; unsubstituted or substituted with C6 to C40 aryl C2 to C40 heteroaryl; -CN; and -P(=0)RR'.

In another embodiment, Z ₁ to Z ₄ are the same or different from each other, and may each independently be hydrogen; phenyl; triphenylene; dibenzofuranyl; carbazolyl; dibenzothienyl; quinoline Group; pyridyl; quinazolinyl unsubstituted or substituted with phenyl; -CN; or -P(=0)RR'.

In an embodiment of the present application, when Z ₁ to Z ₄ are carbazolyl and 1,3-bis(9H-carbazol-9-yl)benzyl, high T ₁ and hole transmission ability are obtained . With high T ₁ , the excitons generated in the light-emitting layer can be constrained, and the terphenylene and dibenzofuranyl groups can also polarize the molecules themselves by enhancing the hole transport ability, and therefore, can particularly improve the device Drive, efficiency and longevity.

In addition, there is no electron distribution in the phosphine group, which prevents the electrons from spreading widely. When electrons are injected due to the influence of the electron withdrawing group, the aryl group substituted by the cyano group can improve the device efficiency by stabilizing the molecule.

In one embodiment of the present application, R, R', and R" are the same or different from each other, and may each independently be hydrogen; substituted or unsubstituted alkyl; substituted or unsubstituted aryl ; Or substituted or unsubstituted heteroaryl.

In another embodiment, R, R′ and R″ are the same or different from each other, and may each independently be a substituted or unsubstituted C1 to C60 alkyl; or a substituted or unsubstituted C6 to C60 Aryl.

In another embodiment, R, R′ and R″ are the same or different from each other, and may each independently be a substituted or unsubstituted C1 to C40 alkyl group; or a substituted or unsubstituted C6 to C40 group Aryl.

In another embodiment, R, R′, and R″ are the same or different from each other, and may each independently be a C1 to C40 alkyl group; or a C6 to C40 aryl group.

In another embodiment, R, R′ and R″ are the same or different from each other, and may each independently be a methyl group; or a phenyl group.

In another embodiment, R, R'and R" can be phenyl.

[化學式6]

[化學式7]

In an embodiment of the present application, Chemical Formula 1 may be represented by any of the following Chemical Formula 5 to Chemical Formula 7. [Chemical formula 5]

[Chemical formula 6]

[Chemical formula 7]

In Chemical Formula 5 to Chemical Formula 7,

L ₃ , L ₄ , Z ₁ to Z ₄ , m, n, p, q, and X ₁ to X ₃ have the same definitions as in Chemical Formula 1,

L ₂₂ is a substituted or unsubstituted polycyclic arylene group; or a substituted or unsubstituted heteroaryl group,

L ₃₁ and L ₃₂ are the same or different from each other, and are each independently a substituted or unsubstituted polycyclic arylene group, and

Z ₂₂ , Z ₃₁ and Z ₃₂ are the same or different from each other, and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; substituted or unsubstituted aryl; substituted or unsubstituted hetero Aryl; -CN; -SiRR'R''; and -P(=O)RR'.

In an embodiment of the present application, L ₂₂ is a substituted or unsubstituted polycyclic arylene group; or a substituted or unsubstituted heteroaryl group.

In another embodiment, L ₂₂ is a substituted or unsubstituted C10 to C60 polycyclic arylene group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In another embodiment, L ₂₂ is a substituted or unsubstituted C10 to C40 polycyclic arylene group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

In another embodiment, L ₂₂ is a C10 to C40 polycyclic arylene group; or a C2 to C40 heteroaryl group.

In another embodiment, L ₂₂ may be naphthyl; phenanthryl; terphenylene; divalent dibenzofuranyl; divalent carbazolyl; divalent dibenzothienyl; or divalent pyridine base.

In an embodiment of the present application, L ₃₁ and L ₃₂ are the same or different from each other, and may each independently be a substituted or unsubstituted polycyclic arylene group.

In another embodiment, L ₃₁ and L ₃₂ are the same or different from each other, and may each independently be a substituted or unsubstituted C10 to C60 polycyclic arylene group.

In another embodiment, L ₃₁ and L ₃₂ are the same or different from each other, and may each independently be a substituted or unsubstituted C10 to C40 polycyclic arylene group.

In another embodiment, L ₃₁ and L ₃₂ are the same or different from each other, and may each independently be a C10 to C40 polycyclic arylene group.

In another embodiment, L ₃₁ and L ₃₂ are the same or different from each other, and may each independently be naphthyl; or phenanthryl.

In an embodiment of the present application, Z ₂₂ , Z ₃₁ and Z ₃₂ are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; substituted or unsubstituted aromatic Group; substituted or unsubstituted heteroaryl; -CN; -SiRR'R''; and -P(=O)RR'.

In another embodiment, Z ₂₂ , Z ₃₁ and Z ₃₂ are the same or different from each other, and are each independently selected from the group consisting of hydrogen; substituted or unsubstituted C6 to C60 aryl; and substituted Or unsubstituted C2 to C60 heteroaryl.

In another embodiment, Z ₂₂ , Z ₃₁ and Z ₃₂ are the same or different from each other, and each is independently selected from the group consisting of hydrogen; and substituted or unsubstituted C2 to C60 heteroaryl.

In another embodiment, Z ₂₂ , Z ₃₁ and Z ₃₂ are the same or different from each other, and each is independently selected from the group consisting of hydrogen; and C2 to C40 heteroaryl.

In another embodiment, Z ₂₂ , Z ₃₁ and Z ₃₂ are the same or different from each other, and may each independently be hydrogen; pyridyl; or carbazolyl.

[化學式5-2]

[化學式5-3]

[化學式5-4]

In an embodiment of the present application, Chemical Formula 5 may be represented by any of the following Chemical Formula 5-1 to Chemical Formula 5-4. [Chemical formula 5-1]

[Chemical formula 5-2]

[Chemical formula 5-3]

[Chemical formula 5-4]

In Chemical Formula 5-1 to Chemical Formula 5-4,

L ₃ , L ₄ , Z ₁ to Z ₄ , p, q, and X ₁ to X ₃ have the same definitions as in Chemical Formula 5.

[化學式6-2]

[化學式6-3]

In an embodiment of the present application, Chemical Formula 6 may be represented by any one of the following Chemical Formula 6-1 to Chemical Formula 6-3. [Chemical formula 6-1]

[Chemical formula 6-2]

[Chemical formula 6-3]

In Chemical Formula 6-1 to Chemical Formula 6-3, Z ₁ , Z ₂₂ , L ₂₂ , L ₃ , L ₄ , Z ₃ , Z ₄ , n, p, q, and X ₁ to X ₃ have the same values as in Chemical Formula 6 The same definition.

In the heterocyclic compound provided in one embodiment of the present application, Chemical Formula 1 is represented by any one of the following compounds.

In addition, by introducing various substituents into the structure of Chemical Formula 1, a compound having the unique properties of the introduced substituent can be synthesized. For example, by introducing into the core structure substituents commonly used as hole injection layer materials, hole transport layer materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials for the manufacture of organic light-emitting devices, synthesis Materials that meet the requirements of each organic material layer.

In addition, by introducing various substituents into the structure of Chemical Formula 1, the energy band gap can be finely controlled, and at the same time, the properties at the interface between organic materials can be enhanced, and material applications can become diverse化.

In addition, an embodiment of the present application provides an organic light emitting device, which includes: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed on Between the first electrode and the second electrode, wherein one or more of the organic material layers include a heterocyclic compound according to Chemical Formula 1.

The specific details of the heterocyclic compound represented by Chemical Formula 1 are the same as the description provided above.

In an embodiment of the present application, the first electrode may be an anode, and the second electrode may be a cathode.

In another embodiment, the first electrode may be a cathode, and the second electrode may be an anode.

In one embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the blue organic light emitting device. For example, the heterocyclic compound according to Chemical Formula 1 may be included in the electron transport layer of the blue organic light emitting device.

In one embodiment of the present application, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the green organic light emitting device. For example, the heterocyclic compound according to Chemical Formula 1 may be included in the electron transport layer of the green organic light-emitting device.

In one embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the red organic light emitting device. For example, the heterocyclic compound according to Chemical Formula 1 may be included in the electron transport layer of the red organic light-emitting device.

In addition to using the above heterocyclic compound to form one or more organic material layers, ordinary organic light-emitting device manufacturing methods and materials can be used to manufacture the organic light-emitting device of the present disclosure.

When manufacturing an organic light-emitting device, the heterocyclic compound can be formed into an organic material layer by a solution coating method and a vacuum deposition method. In this article, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, etc., but is not limited to this.

The organic material layer of the organic light-emitting device of the present disclosure may be formed as a single-layer structure, or may also be formed as a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device according to an embodiment of the present disclosure may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited to this, and may include a smaller number of organic material layers.

In the organic light emitting device of the present disclosure, the organic material layer may include a light emitting layer, and the light emitting layer may include a heterocyclic compound.

In another organic light emitting device, the organic material layer includes a light emitting layer, the light emitting layer includes a host material, and the host material may include a heterocyclic compound.

As another example, the organic material layer including the heterocyclic compound includes the heterocyclic compound represented by Chemical Formula 1 as a host, and may be used with an iridium-based dopant.

In the organic light-emitting device of the present disclosure, the organic material layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer may include a heterocyclic compound.

In the organic light-emitting device of the present disclosure, the organic material layer includes an electron transport layer, and the electron transport layer may include a heterocyclic compound.

In another organic light-emitting device, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include a heterocyclic compound.

The organic light-emitting device of the present disclosure may further include one, two or selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. More layers.

1 to 3 show the stacking sequence of electrodes and organic material layers of an organic light-emitting device according to an embodiment of the present application. However, the scope of this application is not limited to these drawings, and the structure of organic light-emitting devices known in the art can also be used in this application.

FIG. 1 shows an organic light emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are continuously stacked on a substrate 100. However, the structure is not limited to this structure, and as shown in FIG. 2, an organic light-emitting device in which a cathode, an organic material layer, and an anode are continuously laminated on a substrate can also be obtained.

Fig. 3 shows a case where the organic material layer is a multilayer. The organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited to this laminated structure, and may not include other layers other than the light-emitting layer when necessary, and may further include other necessary functional layers.

If necessary, the organic material layer including the compound of Chemical Formula 1 may further include other materials.

In the organic light-emitting device according to an embodiment of the present application, materials other than the compound of Chemical Formula 1 are shown below, however, these materials are only for illustrative purposes and not used to limit the scope of the present application, and It can be replaced by materials known in the art.

As the anode material, a material having a relatively large work function can be used, and a transparent conductive oxide, metal, conductive polymer, etc. can be used. Specific examples of anode materials 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 ( 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] (poly[3,4-(ethylene-1,2-dioxy)thiophene], PEDOT), polypyrrole and polyaniline, but not limited to this.

As the cathode material, a material having a relatively small work function can be used, and a metal, metal oxide, conductive polymer, etc. can be used. Specific examples of cathode materials include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gamma, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials, such as LiF/A1 or LiO ₂ /A1 etc., but not limited to this.

As the hole injection material, a known hole injection material can be used, and for example, a phthalocyanine compound, such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429; or a starburst-type ) Amine derivatives, such as tris(4-hydrazino-9-ylphenyl)amine (TCTA), 4,4',4 described in the literature [Advanced Materials, 6, P.677 (1994)] ''-Tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) or 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl] Benzene (m-MTDAPB), polyaniline/dodecylbenzenesulfonic acid as a conductive polymer with solubility, poly(3,4-ethylenedioxythiophene)/poly(4-styrene sulfonate) , Polyaniline/camphorsulfonic acid or polyaniline/poly(4-styrene-sulfonate), etc.

As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular or high molecular materials can also be used.

As electron transport materials, the following metal complexes can be used: oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives Derivatives, tetracyanoanthraquinone dimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and its derivatives, etc., and also High molecular materials and low molecular materials can be used.

As an example of an electron injection material, LiF is usually used in this technology, however, this application is not limited to this.

As the light-emitting material, a red, green or blue light-emitting material may be used, and if necessary, two or more light-emitting materials may be mixed and used. In this context, two or more luminescent materials can be used by being deposited as individual supply sources or by being premixed and deposited as one supply source. In addition, fluorescent materials can also be used as luminescent materials, however, phosphorescent materials can also be used. As the light-emitting material, a material that emits light by combining electrons and holes injected from the anode and the cathode, respectively, can be used alone, however, a material having a host material and a dopant material that participate in light-emitting together can also be used.

When mixing the luminescent material host, the host of the same series can be mixed, or the host of different series can be mixed. For example, any two or more of the n-type host material or the p-type host material can be selected and used as the host material of the light-emitting layer.

The organic light emitting device according to an embodiment of the present application may be a top emission type, a bottom emission type or a double emission type depending on the material used.

The heterocyclic compound according to an embodiment of the present application can also be used in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, etc., according to similar principles used in organic light-emitting devices.

Hereinafter, the specification will be explained in more detail with reference to examples, however, these examples are only for illustrative purposes, and the scope of the application is not limited to this.

＜ Preparation example ＞

< Preparation Example 1> Preparation of compound 2

Preparation compound 2-1

After dissolving 2,4-dichloro-6-phenyl-1,3,5-triazine (30 g, 132.71 millimoles) and phenylboronic acid (16.18 grams, 132.71 millimoles) in tetrahydrofuran (tetrahydrofuran, THF) (300 ml) and H ₂ O (60 ml), and (N ₂ conditions) Pd(PPh ₃ ) ₄ (7.67 g, 6.64 millimoles) and K ₂ CO ₃ (45.85 g, 331.77 millimoles), and the result was stirred for 24 hours under reflux. After the reaction was completed, methylene chloride (MC) was introduced to dissolve the reaction solution, and then the result was extracted with distilled water. The organic layer was dried with anhydrous MgSO ₄ , and after removing the solvent with a rotary evaporator, it was purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain compound 2-1 (16 g , 45%).

Preparation compound 2-2

After dissolving compound 2-1 (16 g, 59.91 millimoles) and zinc cyanide (14.07 g, 119.82 millimoles) in dimethylformamide (DMF) (160 ml), add them (N ₂ conditions) Pd(PPh ₃ ) ₄ (3.46 g, 3.00 mmol) was introduced, and the result was stirred for 16 hours under reflux. After the reaction was completed, the result was cooled to room temperature, and then the obtained solid was filtered and washed with distilled water. The obtained solid was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 2-2 (14 g, 90%).

Preparation compound 2-3

After dissolving compound 2-2 (14 g, 54.20 mmol) in benzene (300 mL), potassium tert-butoxide (18.3 g, 186.46 mmol) and acetonitrile (6.68 g, 162.61) were added to it. Millimoles), and the results were stirred at 20°C. When the reaction was complete, ether and 2% NaHCO _{3 were added to it} . Thereafter, the results were concentrated, and the resulting compound was recrystallized to obtain compound 2-3 (11 g, 67%).

Preparation compound 2-4

After adding compound 2-3 (11 g, 36.75 mmol) and N,N-dimethylbenzamide (6.03 g, 40.42 mmol) to POCl ₃ (110 mL), the result was refluxed . When the reaction is completed, the reaction material is introduced into ice water, and then ammonium hydroxide is added thereto. The results were extracted with chloroform and distilled water. The organic layer was dried and concentrated with MgSO ₄ , and the resulting compound was recrystallized to obtain compound 2-4 (10 g, 64%).

Preparation compound 2

After dissolving compound 2-4 (10 g, 23.70 mmol) and [1,1'-biphenyl]-4-ylboronic acid (5.16 g, 26.07 mmol) in toluene (Tol) (100 mL) , EtOH (20 ml) and H ₂ O (20 ml), and (N ₂ conditions) Pd(PPh ₃ ) ₄ (1.37 g, 1.19 mmol) and K ₂ CO ₃ (8.19 g, 59.26 millimoles), and the result was stirred for 16 hours under reflux. After the reaction was completed, the result was cooled to room temperature, and the generated solid was filtered, and then washed with ethyl acetate (EA) and MeOH. After that, all the solids were dissolved in excess dichloromethane, and then silica gel filtration was performed to obtain compound 2 (9 g, 70%).

In addition to using intermediate A in Table 1 below instead of 2,4-dichloro-6-phenyl-1,3,5-triazine, using intermediate B in Table 1 below instead of phenylboronic acid, using the intermediate in Table 1 below Substance C was used instead of N,N-dimethylbenzamide, and the intermediate D of Table 1 below was used instead of [1,1'-biphenyl]-4-ylboronic acid. The same as Preparation Example 1 The target compound was synthesized by the method.

74% 10

72% 18

81% 24

67% 34

64% 37

69% 51

70% 55

68% 60

82% 63

77% 64

62% 73

66% 74

66% 86

70% 91

59% 99

62% 103

64% 106

64% 111

71% 126

73% 132

77% 142

75% 148

65% 149

78% 152

69% 155

67% 165

70% 167

81% 180

79% 183

64% 184

65% 198

76% 200

77% 201

65% 219

72% 222

64% 225

65% 233

66% 240

70% 244

81% 246

79% 255

64% 260

65% 264

76% 271

77% 272

65% 276

72% 290

64% 293

65% 338

66% 348

70% 355

59% 373

62% 380

64% 384

64% 399

71% 403

73% 415

77% 425

65% 430

72% 440

64% 454

65% 459

66% 479

70% 511

59% 512

62% 518

64% 550

59% 561

62% 564

64% 574

64% 582

71% 598

73% 604

77% 606

65% 608

72% 645

64% 650

65% 654

66% 681

70% 685

81% 690

79% 694

64% 708

65% 709

76% 751

77% 763

65% 768

72% 818

64% 835

65% 844

66% 871

70% 872

81% 890

79% [Table 1] Compound Intermediate A Intermediate B Intermediate C Intermediate D Target compound Yield 8

74% 10

72% 18

81% twenty four

67% 34

64% 37

69% 51

70% 55

68% 60

82% 63

77% 64

62% 73

66% 74

66% 86

70% 91

59% 99

62% 103

64% 106

64% 111

71% 126

73% 132

77% 142

75% 148

65% 149

78% 152

69% 155

67% 165

70% 167

81% 180

79% 183

64% 184

65% 198

76% 200

77% 201

65% 219

72% 222

64% 225

65% 233

66% 240

70% 244

81% 246

79% 255

64% 260

65% 264

76% 271

77% 272

65% 276

72% 290

64% 293

65% 338

66% 348

70% 355

59% 373

62% 380

64% 384

64% 399

71% 403

73% 415

77% 425

65% 430

72% 440

64% 454

65% 459

66% 479

70% 511

59% 512

62% 518

64% 550

59% 561

62% 564

64% 574

64% 582

71% 598

73% 604

77% 606

65% 608

72% 645

64% 650

65% 654

66% 681

70% 685

81% 690

79% 694

64% 708

65% 709

76% 751

77% 763

65% 768

72% 818

64% 835

65% 844

66% 871

70% 872

81% 890

79%

< Preparation Example 2> Synthesis of compound 902

Preparation compound 902

In a 250 ml round bottom flask, magnesium (0.92 g, 37.81 mmol) and I ₂ (0.2 g) were introduced into THF (50 ml) under nitrogen, and the result was refluxed for 2 hours. The result was cooled to room temperature, and 2-chloro-4,6-diphenylpyrimidine (8.53 g, 31.99 mmol) dissolved in THF (50 mL) was slowly added dropwise. After the dropping, the result was refluxed for 2 hours and cooled to room temperature. In another 500 ml round-bottomed flask, place 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (10 g , 29.09 millimoles) was dissolved in THF (50 ml), and the reaction solution was cooled to 0°C. The reaction solution prepared above was slowly dropped therein while keeping the temperature at 0°C. After the reaction, the reaction was terminated with 4 mol/liter (M) hydrochloric acid aqueous solution, and the result was extracted. The organic layer was concentrated in vacuo, and then recrystallized with toluene to obtain compound 902 (9 g, 57%).

Compounds other than the compounds described in Preparation Example 1, Preparation Example 2, and Table 1 were also prepared in the same manner as the method described in the above Preparation Example.

Table 2 and Table 3 below show the 1H nuclear magnetic resonance (NMR) data and field desorption mass spectrometry (FD-MS) data of the synthesized compounds, and the synthesis of the target compound was identified by the following data.

[Table 2] Numbering ¹ H NMR (CDCl ₃ , 300 Mz) 2 8.41-8.30(9H, m), 7.85(2H, d), 7.75(2H, d), 7.50-7.41(12H, m) 8 8.41-8.30(9H, m), 8.08-7.98(3H, m), 7.54-7.50(11H, m), 7.39-7.25(4H, m) 10 8.41-8.30(9H, m), 7.98(1H, d), 7.82(1H, d), 7.69(1H, d), 7.57-7.50(11H, m), 7.39-7.25(4H, m) 18 9.27(1H, s), 8.79(1H, d), 8.41-8.30(10H, m), 8.15(1H, d), 7.70-7.64(4H, m), 7.52-7.50(10H, m) twenty four 8.41-8.35(7H, m), 7.97-7.96(4H, d), 7.77(4H, d), 7.51-7.50(15H, m) 34 8.41-8.35(5H, m), 7.96-7.94(4H, m), 7.75-7.73(5H, m), 7.61(1H, d), 7.50-7.41(12H, m), 7.25(2H, d) 37 8.41-8.35(5H, m), 8.08(1H, d), 7.98-7.96(3H, m), 7.75-7.74(3H, m), 7.54-7.31(15H, m) 51 8.97(1H, d), 8.41-8.35(5H, m), 8.15-8.10(2H, m), 8.00-7.96(3H, m), 7.75(2H, d), 7.59-7.41(11H, m), 7.25(2H, d) 55 8.41-8.35(5H, m), 7.96-7.95(4H, d), 7.82-7.75(4H, m), 7.50-7.41(9H, m), 7.25(2H, d) 60 8.55(2H, d), 8.41-8.35(5H, m), 8.19-8.17(4H, d), 7.96-7.94(4H, d), 7.75(2H, d), 7.58-7.35(16H, m), 7.25-7.16(6H, m) 63 8.41(1H, s), 8.30(2H, d), 7.96(6H, d), 7.85(2H, d), 7.75(8H, d), 7.49-7.41(12H, m), 7.25(6H, d) 64 8.41-8.35(3H, m), 7.96-7.94(6H, m), 7.75-7.73(7H, m), 7.61(1H, d), 7.50-7.41(12H, m), 7.25(4H, d) 73 8.55(1H, d), 8.41-8.35(3H, m), 8.21-8.19(2H, m), 7.96-7.94(5H, m), 7.80-7.35(19H, m), 7.25-7.16(6H, m) ) 74 8.55(1H, d), 8.41-8.35(3H, m), 7.96-7.92(6H, m), 7.75-7.70(5H, m), 7.56-7.41(11H, m), 7.25(4H, d) 86 8.87(1H, d), 8.55(1H, d), 8.41-8.30(5H, m), 8.05(1H, d), 7.96(5H, d), 7.75(4H, d), 7.64(1H, t) , 7.50-7.41(10H, m), 7.25(6H, d) 91 8.41-8.35(6H, m), 7.94(3H, m), 7.75-7.73(3H, m), 7.61-7.41(13H, m) 99 8.41-8.35(6H, m), 7.98-7.94(2H, m), 7.82-7.69(5H, m), 7.61-7.31(14H, m) 103 8.55(1H, d), 8.41-8.35(6H, m), 8.21-8.19(2H, d), 7.94(2H, d), 7.80-7.35(19H, m), 7.20(2H, q) 106 9.08(1H, d), 8.84(1H, d), 8.41-8.35(6H, m), 8.17(1H, d), 8.05(1H, s), 7.94-7.90(2H, m), 7.75-7.61( 8H, m), 7.50-7.41(9H, m) 111 8.97(1H, d), 8.41-8.35(6H, m), 8.25(1H, d), 8.15-8.10(2H, m), 8.00-7.94(2H, m), 7.75-7.73(3H, m), 7.61-7.41(12H, m) 126 8.41-8.38(3H, m), 7.96-7.94(6H, d), 7.75-7.73(11H, m), 7.61(3H, d), 7.49-7.41(12H, m), 7.25(2H, d) 132 8.55(1H, d), 8.41-8.35(5H, m), 8.19(1H, d), 7.94-7.91(7H, m), 7.75-7.73(6H, m), 7.61-7.35(15H, m), 7.20-7.16(2H, q) 142 9.09(1H, s), 8.49-8.38(5H, m), 8.16-7.94(9H, m), 7.75-7.73(6H, m), 7.61-7.41(12H, m) 148 9.24(1H, s), 8.70(1H, d), 8.59(1H, s), 8.42-8.35(5H, m), 7.94(2H, s), 7.75-7.73(6H, m), 7.61-7.41( 12H, m) 149 9.18-9.14(4H, m), 8.59-8.55(3H, m), 8.38-8.35(4H, m), 7.94(2H, s), 7.75-7.73(8H, m), 7.61(2H, d), 7.50-7.41(9H, m), 7.23(2H, t) 152 8.41-8.30(6H, m), 7.96-7.94(3H, m), 7.85(2H, d), 7.75-7.73(7H, m), 7.61(1H, d), 7.50-7.41(12H, m), 7.25(2H, d) 155 8.41-8.38(3H, m), 7.96-7.94(6H, m), 7.75-7.73(11H, m), 7.61(3H, d), 7.49-7.41(12H, m), 7.25(2H, d) 165 8.55(1H, d), 8.45-8.30(8H, m), 7.96-7.93(4H, m), 7.75-7.70(6H, m), 7.61-7.41(12H, m), 7.25(4H, d) 167 9.08(2H, d), 8.84(2H, d), 8.41-8.38(2H, m), 8.17(2H, d), 8.05(2H, s), 7.96-7.90(5H, m), 7.75-7.62( 14H, m), 7.49-7.41(6H, m), 7.25(2H, d) 180 8.55(2H, d), 8.41-8.35(4H, m), 8.19-8.17(4H, d), 7.96-7.94(5H, m), 7.75-7.73(5H, m), 7.61-7.35(17H, m) ), 7.25-7.16(6H, m) 183 8.41-8.30(5H, m), 8.08(1H, d), 7.98-7.96(3H, m), 7.88-7.85(3H, m), 7.75(4H, d), 7.54-7.25(15H, m) 184 8.41-8.35(5H, m), 8.08(1H, d), 7.98-7.88(4H, m), 7.75-7.73(3H, m), 7.61-7.31(14H, m) 198 9.27(1H, s), 8.79(1H, d), 8.41-8.30(8H, m), 8.15(1H, d), 8.08(1H, d), 7.98(1H, d), 7.88(1H, d) , 7.70-7.64(4H, tt), 7.54-7.50(9H, m), 7.39-7.31(2H, m) 200 8.46(1H, s), 8.41-8.35(5H, m), 8.08-7.98(6H, m), 7.88(1H, d), 7.61-7.50(10H, m), 7.39-7.31(2H, tt) 201 8.97(1H, d), 8.41-8.35(5H, m), 8.25(1H, d), 8.15-7.98(5H, m), 7.88(1H, d), 7.59-7.50(10H, m), 7.39- 7.31(2H, tt) 219 8.41-8.35(5H, m), 8.08-7.96(6H, m), 7.82(1H, d), 7.69(1H, d), 7.57-7.50(10H, m), 7.39-7.25(6H, m) 222 8.55(1H, d), 8.41-8.35(5H, m), 8.19(1H, d), 8.08-7.91(10H, m), 7.58-7.50(10H, m), 7.39-7.16(7H, m) 225 8.55(1H, d), 8.45-8.30(9H, m), 8.08-7.93(6H, m), 7.70(1H, t), 7.56-7.49(10H, m), 7.39-7.25(6H, m) 233 8.41-8.30(11H, m), 8.13-7.96(6H, m), 7.84-7.83(2H, m), 7.58-7.50(12H, m), 7.39-7.25(4H, m) 240 8.55(2H, d), 8.41-8.35(5H, m), 8.19-8.17(4H, d), 8.08-7.94(7H, m), 7.60-7.50(13H, m), 7.39-7.16(10H, m) ) 244 8.41-8.35(5H, m), 7.98-7.94(3H, m), 7.82-7.69(5H, m), 7.61-7.39(14H, m) 246 8.41-8.36(3H, m), 7.96-7.94(5H, m), 7.82-7.69(7H, m), 7.61-7.25(16H, m) 255 8.55(1H, d), 8.45-8.30(9H, m), 7.98-7.93(2H, dd), 7.82(1H, d), 7.70-7.69(2H, m), 7.57-7.49(10H, m), 7.39-7.25(4H, m) 260 8.46-8.35(6H, m), 8.06-7.98(5H, m), 7.82(1H, d), 7.69-7.50(11H, m), 7.39-7.31(2H, tt) 264 8.41-8.35(5H, m), 7.98-7.96(5H, m), 7.82-7.69(6H, m), 7.57-7.50(14H, m), 7.39-7.31(2H, m) 271 8.41-8.35(5H, m), 7.98-7.94(5H, m), 7.82(1H, d), 7.69(1H, d), 7.57-7.49(11H, m), 7.39-7.25(4H, m) 272 8.41-8.30(7H, m), 7.98-7.96(3H, m), 7.85-7.69(6H, m), 7.57-7.25(15H, m) 276 8.41-8.36(3H, m), 7.98-7.94(7H, m), 7.82-7.69(7H, m), 7.61-7.25(18H, m) 290 8.46-8.35(6H, m), 8.06-7.96(7H, m), 7.82(1H, d), 7.69-7.50(11H, m), 7.39-7.25(4H, m) 293 8.41-8.30(11H, m), 8.13(1H, d), 7.98-7.96(3H, m), 7.84-7.82(3H, m), 7.69(1H, d), 7.58-7.50(12H, m), 7.39-7.25(4H, m) 338 8.55(1H, d), 8.41-8.30(7H, m), 8.15(1H, d), 8.08-7.91(8H, m), 7.58-7.50(10H, m), 7.39-7.16(7H, m) 348 9.27(1H, s), 8.79(1H, d), 8.55(1H, d), 8.41-8.30(8H, m), 8.19-8.15(2H, dd), 7.94-7.91(5H, m), 7.70- 7.50(13H, m), 7.35(1H, t), 7.20-7.16(2H, tt) 355 8.55(1H, d), 8.41-8.35(5H, m), 8.19(1H, d), 7.95-7.91(7H, m), 7.82(2H, d), 7.58-7.50(8H, m), 7.35( 1H, t), 7.20-7.16(2H, m) 373 8.55(2H, d), 8.41-8.35(5H, m), 8.24-8.19(5H, m), 7.94(2H, d), 7.80(1H, d), 7.68-7.50(14H, m), 7.35( 2H, d), 7.20-7.16(4H, tt) 380 8.55(1H, d), 8.46-8.35(6H, m), 8.24-8.19(3H, m), 8.06-7.94(5H, m), 7.68-7.50(12H, m), 7.35(1H, t), 7.20-7.16(2H, tt) 384 8.55(1H, d), 8.41-8.35(5H, m), 8.21-8.19(3H, m), 7.97-7.94(5H, m), 7.77(4H, m), 7.68(1H, m), 7.60- 7.50(15H, m), 7.35(1H, t), 7.20-7.16(2H, tt) 399 8.55(1H, d), 8.45-8.35(6H, m), 7.98-7.92(3H, m), 7.82(1H, d), 7.70-7.69(2H, m), 7.57-7.49(10H, m), 7.39-7.31(2H, tt) 403 8.55(2H, d), 8.45-8.35(6H, m), 8.21-8.19(2H, m), 7.94-7.92(3H, m), 7.80(1H, d), 7.70-7.49(13H, m), 7.35(1H, t), 7.20-7.16(2H, tt) 415 8.55(1H, d), 8.45-8.35(6H, m), 7.95-7.92(4H, m), 7.82(2H, d), 7.70(1H, t), 7.56-7.49(8H, m) 425 8.55(1H, d), 8.45-8.32(6H, m), 7.96-7.93(6H, m), 7.75-7.70(7H, m), 7.61-7.41(13H, m), 7.25(2H, d) 430 8.55(1H, d), 8.45-8.30(9H, m), 7.98-7.93(4H, m), 7.82(1H, d), 7.70-7.69(2H, m), 7.57-7.49(10H, m), 7.39-7.25(6H, m) 440 8.55(1H, d), 8.46-8.32(8H, m), 8.06-7.93(7H, m), 7.70-7.49(11H, m), 7.25(2H, d) 454 9.08(1H, d), 8.84(1H, d), 8.41-8.35(5H, m), 8.17(1H, d), 8.05(1H, s), 7.94-7.90(3H, m), 7.75-7.61( 8H, m), 7.50-7.41(9H, m) 459 9.08(1H, d), 8.84(1H, d), 8.41-8.35(5H, m), 8.17(1H, d), 8.05(1H, s), 7.98(1H, d), 7.90(1H, d) , 7.82(1H, d), 7.70-7.50(13H, m), 7.39-7.31(2H, tt) 479 9.18-9.08(5H, m), 8.84(1H, d), 8.59-8.55(3H, m), 8.36-8.35(4H, m), 8.17(1H, d), 8.05(1H, s), 7.90( 1H, d), 7.74-7.62(6H, m), 7.50(6H, m), 7.23(2H, t) 511 9.27(1H, s), 8.79(1H, d), 8.41-8.30(8H, m), 8.15(1H, d), 7.94(2H, d), 7.70-7.49(14H, m) 512 9.27(1H, s), 8.79(1H, d), 8.41-8.30(10H, m), 8.15(1H, d), 7.85(2H, d), 7.75-7.64(6H, m), 7.52-7.41( 10H, m) 518 9.27(1H, s), 8.79(1H, d), 8.41-8.30(10H, m), 8.15-7.98(4H, m), 7.70-7.64(4H, m), 7.54-7.50(9H, m), 7.39-7.25(4H, m) 550 9.27(1H, s), 8.79(1H, d), 8.41-8.30(12H, m), 7.98-7.94(2H, m), 7.82(1H, d), 7.73-7.50(16H, m), 7.39- 7.25(4H, m) 561 9.27(1H, s), 8.97(1H, d), 8.79(1H, d), 8.41-8.25(11H, m), 8.15-8.10(2H, m), 7.96-7.94(1H, m), 7.73- 7.50(15H, m) 564 9.27(1H, s), 8.79(1H, d), 8.38-8.33(10H, m), 7.97-7.94(5H, m), 7.77-7.61(10H, m), 7.52-7.50(13H, m) 574 9.09(1H, s), 8.49(1H, d), 8.41-8.35(5H, m), 8.16(1H, d), 8.08(1H, d), 8.00-7.94(3H, m), 7.75-7.73( 3H, m), 7.61-7.41(12H, m) 582 9.09(1H, s), 8.55-8.49(2H, dd), 8.41-8.35(5H, m), 8.19-8.16(2H, m), 8.08(1H, d), 8.00-7.91(6H, m), 7.61-7.50(10H, m), 7.35(1H, t), 7.20-7.16(2H, tt) 598 9.24(1H, s), 9.09(1H, s), 8.70(1H, d), 8.59(1H, s), 8.49-8.35(6H, m), 8.16(1H, d), 8.08(1H, d) , 8.00(1H, d), 7.61-7.50(9H, m) 604 8.97(1H, d), 8.41-8.35(5H, m), 8.25(1H, d), 8.15-8.10(2H, m), 8.00-7.94(3H, m), 7.75-7.73(3H, m), 7.59-7.41(12H, m) 606 8.97(1H, d), 8.41-8.36(3H, m), 8.25(1H, d), 8.15-8.10(2H, m), 8.00-7.94(5H, m), 7.75-7.73(5H, m), 7.61-7.41(12H, m), 7.25(2H, d) 608 8.97(1H, d), 8.41-8.25(8H, m), 8.15-7.98(6H, m), 7.59-7.50(10H, m), 7.39-7.25(4H, m) 645 9.09(2H, s), 8.55-8.30(10H, m), 8.16-7.93(7H, m), 7.70-7.49(10H, m), 7.25(2H, d) 650 9.09(2H, s), 8.49-8.35(6H, m), 8.16-7.98(10H, m), 7.61-7.50(9H, m) 654 9.09(2H, s), 8.49(2H, d), 8.41-8.35(3H, m), 8.16-7.96(10H, m), 7.77(4H, m), 7.61-7.50(13H, m) 681 8.97(1H, d), 8.41-8.25(10H, m), 8.15-8.10(3H, m), 8.00-7.96(3H, m), 7.84-7.83(2H, m), 7.59-7.50(12H, m) ) 685 8.41-8.30(9H, m), 8.13(1H, d), 7.96-7.95(4H, m), 7.84-7.82(4H, m), 7.58-7.50(10H, m) 690 8.55(2H, d), 8.41-8.30(9H, m), 8.19-8.13(5H, m), 7.96-7.94(4H, m), 7.84-7.83(2H, m), 7.60-7.50(15H, m) ), 7.35(2H, m), 7.20-7.16(4H, tt) 694 8.41-8.35(5H, m), 7.97-7.94(6H, m), 7.77-7.73(7H, m), 7.61(1H, d), 7.51-7.41(15H, m) 708 9.27(1H, s), 8.79(1H, d), 8.41-8.30(8H, m), 8.15(1H, d), 7.97-7.96(4H, s), 7.77-7.64(8H, m), 7.52- 7.50(13H, m) 709 9.27(1H, s), 8.79(1H, d), 8.41-8.30(9H, m), 7.97-7.94(6H, m), 7.77-7.61(10H, m), 7.52-7.50(13H, m) 751 8.87(1H, d), 8.55(1H, d), 8.41-8.35(5H, m), 8.05(1H, d), 7.96-7.94(5H, m), 7.64-7.49(11H, m), 7.25( 2H, d) 763 8.87(1H, d), 8.55(2H, d), 8.41-8.35(5H, m), 8.21-8.19(2H, m), 8.05(1H, d), 7.96-7.94(4H, m), 7.80( 1H, d), 7.68-7.49(12H, m), 7.35(1H, t), 7.25-7.16(4H, m) 768 9.27(1H, s), 8.87(1H, d), 8.79(1H, d), 8.55(1H, d), 8.41-8.30(8H, m), 8.15(1H, d), 8.05(1H, t) , 7.96(3H, d), 7.70-7.64(5H, m), 7.52-7.49(8H, m), 7.25(2H, d) 818 9.24(1H, s), 8.70(1H, d), 8.42-8.30(8H, m), 8.08-7.98(3H, m), 7.57-7.50(9H, m), 7.39-7.25(4H, m) 835 9.24(1H, s), 8.70(1H, d), 8.42-8.35(6H, m), 7.95(2H, d), 7.82(2H, d), 7.57-7.50(7H, m) 844 9.18-9.14(4H, m), 8.55(2H, d), 8.41-8.35(5H, m), 7.94(2H, m), 7.75-7.73(5H, m), 7.61(1H, d), 7.50- 7.41(9H, m), 7.23(2H, t) 871 8.55(2H, d), 8.41-8.35(5H, m), 8.19-8.17(4H, m), 7.94(4H, d), 7.60-7.49(14H, m), 7.35(2H, t), 7.20- 7.16(4H, tt) 872 8.55(2H, d), 8.41-8.30(7H, m), 8.19-8.17(4H, m), 7.94(2H, d), 7.85(2H, d), 7.75(2H, d), 7.68-7.35( 16H, m), 7.20-7.16(4H, tt) 890 8.55(2H, d), 8.46(1H, s), 8.41-8.35(5H, m), 8.19-8.17(4H, m), 8.06-7.94(6H, m), 7.61-7.50(13H, m), 7.35(2H, t), 7.20-7.16(4H, tt) 902 8.59(1H, s), 8.28-8.24(3H, m), 7.79(4H, d), 7.70(1H, s), 7.57-7.41(16H, m)

[table 3] Compound FD-MS Compound FD-MS 2 m/z=539.63 (C37H25N5=539.21) 8 m/z=629.71 (C43H27N5O=629.22) 10 m/z=629.71 (C43H27N5O=629.22) 18 m/z=613.71 (C43H27N5=613.23) twenty four m/z=663.70 (C43H30N5OP=663.22) 34 m/z=615.72 (C43H29N5=615.24) 51 m/z=589.69 (C41H27N5=589.23) 55 m/z=564.64 (C38H24N6=564.21) 60 m/z=870.01 (C61H39N7=869.33) 63 m/z=767.92 (C55H37N5=767.30) 64 m/z=691.82 (C49H33N5=691.27) 73 m/z=780.91 (C55H36N6=780.30) 74 m/z=721.87 (C49H31N5S=721.23) 86 m/z=742.87 (C52H34N6=742.28) 91 m/z=539.63 (C37H25N5=539.21) 99 m/z=629.71 (C43H27N5O=629.22) 103 m/z=704.82 (C49H32N6=704.27) 106 m/z=639.75 (C45H29N5=639.24) 111 m/z=589.69 (C41H27N5=589.23) 126 m/z=767.92 (C55H37N5=767.30) 132 m/z=780.91 (C55H36N6=780.30) 142 m/z=715.84 (C51H33N5=715.27) 148 m/z=616.71 (C42H28N6=616.24) 149 m/z=770.88 (C52H34N8=770.29) 152 m/z=691.82 (C49H33N5=691.27) 155 m/z=767.92 (C55H37N5=767.30) 165 m/z=797.96 (C55H35N5S=797.26) 167 m/z=815.96 (C59H37N5=815.30) 180 m/z=946.11 (657H43N7=945.36) 183 m/z=705.80 (C49H31N5O=705.25) 184 m/z=629.71 (C43H27N5O=629.22) 198 m/z=703.79 (C49H29N5O=703.24) 200 m/z=603.67 (C41H25N5O=603.21) 201 m/z=603.67 (C41H25N5O=603.21) 219 m/z=719.79 (C49H29N5O2=719.23) 222 m/z=794.90 (C55H34N6O=794.28) 225 m/z= 811.95 (C55H33N5OS=811.24) 233 m/z=833.93 (C57H35N7O=833.29) 240 m/z=960.09 (C67H41N7O=959.34) 244 m/z=629.71 (C43H27N5O=629.22) 246 m/z=705.80 (C49H31N5O=705.25) 255 m/z=735.85 (C49H29N5OS=735.21) 260 m/z=603.67 (C41H25N5O=603.21) 264 m/z=753.78 (C49H32N5O2P=753.23) 271 m/z=629.71 (C43H27N5O=629.22) 272 m/z=705.80 (C49H31N5O=705.25) 276 m/z=781.90 (C55H35N5O=781.28) 290 m/z=679.77 (C47H29N5O=679.24) 293 m/z=833.93 (C57H35N7O=833.29) 338 m/z=794.90 (C55H34N6O=794.28) 348 m/z=778.90 (C55H34N6=778.28) 355 m/z=653.73 (C44H27N7=653.23) 373 m/z=793.91 (C55H35N7=793.30) 380 m/z=678.78 (C47H30N6=678.25) 384 m/z=828.90 (C55H37N6OP=828.28) 399 m/z=659.76 (C43H25N5OS=659.18) 403 m/z=734.87 (C49H30N6S=734.23) 415 m/z=594.69 (C38H22N6S=594.16) 425 m/z=797.96 (C55H35N5S=797.26) 430 m/z= 811.95 (C55H33N5OS=811.24) 440 m/z= 685.83 (C47H29N5S=695.21) 454 m/z=639.75 (C45H29N5=639.24) 459 m/z=653.73 (C44H27N7=653.23) 479 m/z=718.81 (C48H30N8=718.26) 511 m/z=613.71 (C43H27N5=613.23) 512 m/z=689.80 (C49H31N5=689.26) 518 m/z=779.88 (C55H33N5O=779.27) 550 m/z=855.98 (C61H37N5O=855.30) 561 m/z=739.86 (C53H33N5=739.27) 564 m/z=889.98 (C61H40N5OP=889.30) 574 m/z=589.69 (C41H27N5=589.23) 582 m/z=678.78 (C47H30N6=678.25) 598 m/z=514.58 (C34H22N6=514.19) 604 m/z=589.69 (C41H27N5=589.23) 606 m/z=665.78 (C47H31N5=665.26) 608 m/z=679.77 (C47H29N5O=679.24) 645 m/z=745.89 (C51H31N5S=745.23) 650 m/z=613.71 (C43H27N5=613.23) 654 m/z=763.82 (C51H34N5OP=763.25) 681 m/z=717.82 (C49H31N7=717.26) 685 m/z=692.77 (C46H28N8=692.24) 690 m/z=998.14 (C69H43N9=997.36) 694 m/z=739.80 (C49H34N5OP=739.25) 708 m/z=813.88 (C55H36N5OP=813.27) 709 m/z=889.98 (C61H40N5OP=889.30) 751 m/z=590.67 (C40H26N6=590.22) 763 m/z=755.87 (C52H33N7=755.28) 768 m/z=740.85 (C52H32N6=740.27) 818 m/z=630.70 (C42H26N6O=630.22) 835 m/z=489.53 (C31H19N7=489.17) 844 m/z=694.78 (C46H30N8=694.26) 871 m/z=793.91 (C55H35N7=793.30) 872 m/z=870.01 (C61H39N7=869,33) 890 m/z=843.97 (C59H37N7=843.31) 902 m/z=539.63 (C37H25N5=539.21)

< Experimental example 1> -Manufacturing organic light-emitting device

A transparent indium tin oxide (ITO) electrode obtained from glass for organic light-emitting diodes (manufactured by Samsung-Corning Co, Ltd.) with trichloroethylene, acetone, ethanol and distilled water The film was continuously subjected to ultrasonic cleaning for 5 minutes each, and the transparent ITO electrode film was stored in isopropanol and used.

Next, the ITO substrate was installed in the substrate folder of the vacuum deposition equipment, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamine Base) triphenylamine (2-TNATA) is introduced into the unit in the vacuum deposition equipment.

Subsequently, the chamber was evacuated until the vacuum degree therein reached 10 ^-6 Torr, and then 2-TNATA was evaporated by applying current to the cell to deposit a hole injection layer with a thickness of 600 angstroms on the ITO substrate.

The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was introduced to another unit of the vacuum deposition equipment, and by adding The cell was evaporated by applying current to deposit a hole transport layer with a thickness of 300 angstroms on the hole injection layer.

After forming the hole injection layer and the hole transport layer as described above, a blue light-emitting material having the following structure is deposited thereon as a light-emitting layer. Specifically, in the side unit of the vacuum deposition equipment, H1 (blue emitting host material) is vacuum deposited to a thickness of 200 angstroms, and 5% of D1 (blue emitting dopant material) is vacuum deposited on the host material. ).

Subsequently, the compound of Table 4 below was deposited to a thickness of 300 angstroms as an electron transport layer.

As the electron injection layer, lithium fluoride (LiF) was deposited to a thickness of 10 angstroms, and an aluminum cathode was used up to a thickness of 1,000 angstroms, and thus an organic light emitting diode was manufactured.

At the same time, for each material to be used in the manufacture of organic light-emitting diodes, all organic compounds required for the manufacture of organic light-emitting diodes are purified by vacuum sublimation at 10 ^-6 Torr to 10 ^-8 Torr.

2 ) Driving voltage and luminous efficiency of organic light-emitting devices

For the organic light-emitting device manufactured as above, the electroluminescent (EL) properties were measured using M7000 manufactured by Maxines Co., Ltd., and using the measurement results, the life span manufactured by Maxines Co., Ltd. was used. The measurement system (M6000) measured T95 with a standard brightness of 700 cd/m². The measurement results of the driving voltage, luminous efficiency, external quantum efficiency, and color coordinate (CIE) of the white organic light-emitting device manufactured according to the present disclosure are shown in Table 4 below.

[Table 4] Compound Drive voltage (V) Luminous efficiency (cd/A) CIE (x, y) Life (T95) Example 1 2 4.38 6.80 (0.134, 0.101) 37 Example 2 8 5.44 6.44 (0.134, 0.102) 32 Example 3 10 4.42 6.78 (0.134, 0.101) 36 Example 4 18 5.38 6.20 (0.134, 0.103) 35 Example 5 twenty four 5.60 6.12 (0.134, 0.102) 34 Example 6 34 5.45 6.01 (0.134, 0.101) 33 Example 7 37 5.44 6.22 (0.134, 0.102) 30 Example 8 51 5.46 6.18 (0.134, 0.101) 29 Example 9 55 5.40 6.13 (0.134, 0.101) 31 Example 10 60 4.40 6.92 (0.134, 0.100) 35 Example 11 63 5.37 6.35 (0.134, 0.101) 32 Example 12 64 5.38 6.41 (0.134, 0.100) 30 Example 13 73 4.81 6.93 (0.134, 0.100) 30 Example 14 74 5.48 6.21 (0.134, 0.100) 32 Example 15 86 5.47 6.28 (0.134, 0.100) 33 Example 16 91 5.45 6.98 (0.134, 0.100) 34 Example 17 99 4.92 5.98 (0.134, 0.102) 31 Example 18 103 5.12 6.20 (0.134, 0.101) 32 Example 19 106 4.89 6.87 (0.134, 0.102) 30 Example 20 111 5.12 6.88 (0.134, 0.100) 34 Example 21 126 5.21 7.00 (0.134, 0.103) 37 Example 22 132 4.38 6.66 (0.134, 0.100) 36 Example 23 142 5.40 6.36 (0.134, 0.102) 32 Example 24 148 5.42 6.26 (0.134, 0.101) 48 Example 25 149 5.39 6.19 (0.134, 0.100) 31 Example 26 152 5.55 6.27 (0.134, 0.102) 31 Example 27 155 4.98 6.20 (0.134, 0.103) 30 Example 28 165 5.41 6.19 (0.134, 0.100) 32 Example 29 167 5.22 6.28 (0.134, 0.103) 36 Example 30 180 5.19 6.41 (0.134, 0.102) 33 Example 31 183 5.43 6.17 (0.134, 0.100) 30 Example 32 184 4.94 6.85 (0.134, 0.099) 31 Example 33 198 5.92 6.87 (0.134, 0.102) 34 Example 34 200 4.98 7.03 (0.134, 0.100) 35 Example 35 201 5.00 6.21 (0.134, 0.103) 32 Example 36 219 4.93 6.35 (0.134, 0.101) 35 Example 37 222 4.74 6.92 (0.134, 0.104) 36 Example 38 225 5.03 6.27 (0.134, 0.100) 35 Example 39 233 5.11 6.22 (0.134, 0.103) 36 Example 40 240 5.38 6.20 (0.134, 0.102) 32 Example 41 244 5.60 6.12 (0.134, 0.101) 35 Example 42 246 5.45 6.01 (0.134, 0.102) 31 Example 43 255 5.44 6.22 (0.134, 0.100) 30 Example 44 260 5.46 6.18 (0.134, 0.103) 33 Example 45 264 5.40 6.13 (0.134, 0.100) 52 Example 46 271 5.19 6.11 (0.134, 0.100) 35 Example 47 272 5.21 6.31 (0.134, 0.103) 32 Example 48 276 5.19 6.41 (0.134, 0.102) 33 Example 49 290 5.43 6.17 (0.134, 0.100) 31 Example 50 293 4.94 6.85 (0.134, 0.099) 40 Example 51 338 4.51 6.87 (0.134, 0.102) 38 Example 52 348 4.45 7.03 (0.134, 0.100) 35 Example 53 355 5.00 6.21 (0.134, 0.103) 32 Example 54 373 4.46 7.03 (0.134, 0.101) 34 Example 55 380 4.50 6.92 (0.134, 0.104) 36 Example 56 384 4.52 6.44 (0.134, 0.100) 44 Example 57 399 5.11 6.22 (0.134, 0.103) 36 Example 58 403 5.46 6.18 (0.134, 0.103) 33 Example 59 415 5.40 6.13 (0.134, 0.100) 37 Example 60 425 5.19 6.11 (0.134, 0.100) 35 Example 61 430 5.21 6.31 (0.134, 0.103) 32 Example 62 440 5.19 6.41 (0.134, 0.102) 33 Example 63 454 5.43 6.17 (0.134, 0.100) 31 Example 64 459 5.12 6.20 (0.134, 0.101) 37 Example 65 479 4.87 6.87 (0.134, 0.102) 32 Example 66 511 5.39 6.88 (0.134, 0.100) 34 Example 67 512 4.47 7.00 (0.134, 0.103) 35 Example 68 518 5.34 6.31 (0.134, 0.100) 33 Example 69 550 5.40 6.36 (0.134, 0.102) 32 Example 70 561 5.42 6.26 (0.134, 0.101) 32 Example 71 564 5.39 6.19 (0.134, 0.100) 52 Example 72 574 5.55 6.27 (0.134, 0.102) 31 Example 73 582 4.98 6.20 (0.134, 0.103) 30 Example 74 598 5.41 6.19 (0.134, 0.100) 32 Example 75 604 4.62 6.52 (0.134, 0.103) 36 Example 76 606 5.43 6.17 (0.134, 0.100) 31 Example 77 608 5.12 6.20 (0.134, 0.101) 37 Example 78 645 4.87 6.87 (0.134, 0.102) 32 Example 79 650 5.50 6.32 (0.134, 0.101) 33 Example 80 654 5.44 6.44 (0.134, 0.102) 47 Example 81 681 5.34 6.38 (0.134, 0.101) 31 Example 82 685 5.38 6.20 (0.134, 0.103) 35 Example 83 690 5.60 6.12 (0.134, 0.102) 34 Example 84 694 5.45 6.01 (0.134, 0.101) 33 Example 85 708 5.44 6.22 (0.134, 0.102) 30 Example 86 709 5.46 6.18 (0.134, 0.101) 41 Example 87 751 5.40 6.13 (0.134, 0.101) 31 Example 88 763 5.44 6.30 (0.134, 0.100) 32 Example 89 768 5.37 6.35 (0.134, 0.101) 32 Example 90 818 5.38 6.41 (0.134, 0.100) 30 Example 91 835 4.81 6.93 (0.134, 0.100) 30 Example 92 844 5.48 6.21 (0.134, 0.100) 31 Example 93 871 5.47 6.28 (0.134, 0.100) 33 Example 94 872 4.45 6.98 (0.134, 0.100) 36 Example 95 890 4.52 6.63 (0.134, 0.102) 31 Example 96 902 5.49 6.11 (0.134, 0.100) 32 Comparative example 1-1 E1 5.56 5.91 (0.134, 0.100) 28 Comparative example 1-2 BBQB 5.50 6.10 (0.134, 0.101) 30 Comparative example 1-3 TBQB 5.51 6.15 (0.134, 0.102) 29 Comparative example 1-4 E2 5.43 5.50 (0.133, 0.106) 25 Comparative example 1-5 E3 5.52 6.08 (0.133, 0.101) 13 Comparative example 1-6 E4 5.52 5.99 (0.132, 0.102) 29

As can be seen from the results in Table 4, compared to Comparative Example 1-1, the organic light-emitting device using the electron transport layer material of the disclosed blue organic light-emitting device has a lower driving voltage and significantly improved luminous efficiency and lifetime. Specifically, it has been identified that compounds 2, 10, 60, 132, 373, 384, 512, 604, and 872 are significantly superior in driving, efficiency, and life span.

This result is believed to be due to the fact that when the disclosed compound with appropriate length, strength and flatness is used as the electron transport layer, the compound in an excited state is prepared by receiving electrons under specific conditions, and specifically In other words, when the hetero-skeleton site of a compound is formed in an excited state, the excitation energy moves to a stable state before the excited hetero-skeleton site undergoes other reactions, and the relatively stable compound can effectively transmit The electron does not decompose or destroy the compound. For reference, those compounds that are stable when excited are considered to be aryl or acene compounds or polycyclic hetero compounds. Therefore, it is believed that the compound of the present disclosure obtains excellent results in all aspects of driving, efficiency, and life, thereby enhancing electron transport properties or improving stability.

100: substrate 200: anode 300: organic material layer 301: hole injection layer 302: hole transmission layer 303: light-emitting layer 304: hole barrier 305: electron transport layer 306: electron injection layer 400: Cathode

1 to 3 are diagrams each schematically showing a laminated structure of an organic light emitting device according to an embodiment of the present application.

100: substrate

200: anode

300: organic material layer

400: Cathode

Claims (13)

A heterocyclic compound represented by the following chemical formula 1: [Chemical formula 1]

Wherein, in the chemical formula 1, X ₁ to X ₃ are the same or different from each other, and are each independently CRa or N; at least one of X ₁ to X ₃ is N; Ra is selected from the group consisting of: hydrogen; A substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; -SiRR'R''; and -P(=O)RR'; L ₁ to L ₄ are the same or different from each other, and each Are independently substituted or unsubstituted arylene or substituted or unsubstituted heteroaryl; Z ₁ to Z ₄ are the same or different from each other, and are each independently selected from the group consisting of hydrogen; Deuterium; halogen; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; -CN; -SiRR'R''; and -P(=O)RR'; m, n, p and q are integers from 1 to 5, and when m, n, p, and q are each 2 or greater than 2, the substituents in the parentheses are the same or different from each other; and R, R'and R" are the same or different from each other , And each independently is hydrogen; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl. The heterocyclic compound according to claim 1, wherein the substituted or unsubstituted refers to substitution with one or more substituents selected from the group consisting of: C1 to C60 linear or branched alkyl ; C2 to C60 linear or branched alkenyl; C2 to C60 linear or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R''; -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or Polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine, either unsubstituted or substituted by a substituent connected to two or more substituents selected from the above-mentioned substituents, or Unsubstituted; and R, R′, and R″ have the same definitions as in Chemical Formula 1. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 4: [Chemical Formula 2]

[Chemical formula 3]

[Chemical formula 4]

In Chemical Formula 2 to Chemical Formula 4, L ₁ to L ₄ , Z ₁ to Z ₄ , m, n, p, and q have the same definitions as in Chemical Formula 1; X ₂ and X ₃ are CRa; and Ra has the same meaning as in The same definition in Chemical Formula 1. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formula 5 to Chemical Formula 7: [Chemical Formula 5]

[Chemical formula 6]

[Chemical formula 7]

In Chemical Formula 5 to Chemical Formula 7, L ₃ , L ₄ , Z ₁ to Z ₄ , m, n, p, q, and X ₁ to X ₃ have the same definitions as in Chemical Formula 1; L ₂₂ is substituted or unsubstituted A substituted polycyclic arylene group; or a substituted or unsubstituted heteroaryl group; L ₃₁ and L ₃₂ are the same or different from each other, and are each independently a substituted or unsubstituted polycyclic arylene group; And Z ₂₂ , Z ₃₁ and Z ₃₂ are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen group; substituted or unsubstituted aryl group; substituted or unsubstituted Heteroaryl; -CN; -SiRR'R''; and -P(=O)RR'. The heterocyclic compound according to claim 1, wherein L ₁ to L ₄ are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 To C60 extend heteroaryl. The heterocyclic compound according to claim 1, wherein Z ₁ to Z ₄ are the same as or different from each other, and are each independently selected from the group consisting of: hydrogen; substituted or unsubstituted C6 to C40 aryl; Substituted or unsubstituted C2 to C40 heteroaryl; -CN; and -P(=0)RR'. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds:

. An organic light emitting device, including: First electrode The second electrode is arranged opposite to the first electrode; and One or more organic material layers arranged between the first electrode and the second electrode, Wherein, one or more of the one or more organic material layers includes the heterocyclic compound according to any one of Claims 1 to 7. The organic light-emitting device according to claim 8, wherein the one or more organic material layers include a light-emitting layer, and the light-emitting layer includes the heterocyclic compound. The organic light-emitting device according to claim 8, wherein the one or more organic material layers include an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer includes the heterocyclic compound. The organic light-emitting device according to claim 8, wherein the one or more organic material layers include an electron transport layer, and the electron transport layer includes the heterocyclic compound. The organic light-emitting device according to claim 8, wherein the one or more organic material layers include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the heterocyclic compound . The organic light-emitting device according to claim 8, further comprising one selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer One, two or more layers.

Images