KR20220062468A - Compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification relates to a compound represented by chemical formula 1 and an organic light emitting device including the same. The compound according to an exemplary embodiment of the present specification can be used as a material of an organic material layer of the organic light emitting device, and by using the same, it is possible to improve efficiency, lower driving voltage, and/or improve lifespan characteristics of the organic light emitting device.

Description

Compound and organic light emitting device comprising the same

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2019-0019011 filed with the Korean Intellectual Property Office on February 19, 2019, the entire contents of which are incorporated herein by reference.

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up. The development of new materials for the organic light emitting device as described above is continuously required.

Korean Patent Publication No. 10-2016-0087331

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

The present invention provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

X ₁ to X ₃ are each N or CR ₂₁ , at least one is N,

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

R ₁ and R ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R and R ₂₁ are each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r is an integer of 1 to 4, and when r is 2 or more, R is the same or different,

R ₃ to R ₁₀ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group containing O or S, or combined with an adjacent substituent to form a substituted or unsubstituted ring,

When all of R ₃ to R ₁₀ are hydrogen, at least one of R ₁ and R ₂ is not unsubstituted phenyl.

In addition, the first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. do.

The compound according to an exemplary embodiment of the present specification may be used as a material of an organic material layer of an organic light emitting device, and by using it, it is possible to improve efficiency, low driving voltage and/or lifespan characteristics in an organic light emitting device.

1 to 3 illustrate an organic light emitting device according to an exemplary embodiment of the present specification.

Hereinafter, the present specification will be described in more detail.

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

In the compound represented by Formula 1, the nitrogen-containing heterocyclic ring serving as an electron acceptor in the same benzene ring of dibenzofuran is located at the 1st position of dibenzofuran, and the unit serving as an electron donor is the nitrogen-containing heterocyclic ring and the para position is substituted for Since the electron donor unit and the electron acceptor unit exist simultaneously in the same molecule, it is advantageous for both hole and electron transport. Since it is higher than the meta position, the stability of the material is high, so that when used as a material for the organic material layer of an organic light emitting device, the effect of high efficiency and long life can be obtained.

In the present specification, when a part "includes" a certain component, this means that other components may be further included, rather than excluding other components, unless otherwise stated.

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

는 치환기가 결합되는 위치를 의미한다.In this specification,

denotes a position at which a substituent is bonded.

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

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents. For example, the "substituent to which two or more substituents are connected" may be an aryl group substituted with an aryl group, an aryl group substituted with a heterocyclic group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, and the like.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferable that it has 1-10 carbon atoms. Specific examples include a methyl group; ethyl group; Profile group; n-propyl group; isopropyl group; butyl group; n-butyl group; isobutyl group; tert-butyl group; sec-butyl group; 1-methylbutyl group; 1-ethylbutyl group; pentyl group; n-pentyl group; isopentyl group; neopentyl group; tert-pentyl group; hexyl group; n-hexyl group; 1-methylpentyl group; 2-methylpentyl group; 4-methyl-2-pentyl group; 3,3-dimethylbutyl group; 2-ethylbutyl group; heptyl group; n-heptyl group; 1-methylhexyl group; cyclopentylmethyl group; cyclohexylmethyl group; octyl group; n-octyl group; tert-octyl group; 1-methylheptyl group; 2-ethylhexyl group; 2-propylpentyl group; n-nonyl group; 2,2-dimethylheptyl group; 1-ethylpropyl group; 1,1-dimethylpropyl group; isohexyl group; 2-methylpentyl group; 4-methylhexyl group; 5-methylhexyl group, and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms. Specifically, a cyclopropyl group; cyclobutyl group; cyclopentyl group; 3-methylcyclopentyl group; 2,3-dimethylcyclopentyl group; cyclohexyl group; 3-methylcyclohexyl group; 4-methylcyclohexyl group; 2,3-dimethylcyclohexyl group; 3,4,5-trimethylcyclohexyl group; 4-tert-butylcyclohexyl group; cycloheptyl group; There is a cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiR ₁₀₁ R ₁₀₂ R ₁₀₃ , wherein R ₁₀₁ , R ₁₀₂ and R ₁₀₃ are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically a trimethylsilyl group; triethylsilyl group; t-butyldimethylsilyl group; vinyl dimethyl silyl group; propyldimethylsilyl group; triphenylsilyl group; diphenylsilyl group; There is a phenylsilyl group, but is not limited thereto.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferable that it has 1 to 10 carbon atoms. Specifically, a methoxy group; ethoxy group; n-propoxy group; isopropoxy group; i-propyloxy group; n-butoxy group; isobutoxy group; tert-butoxy group; sec-butoxy group; n-pentyloxy group; neopentyloxy group; isopentyloxy group; n-hexyloxy group; 3,3-dimethylbutyloxy group; 2-ethylbutyloxy group; n-octyloxy group; n-nonyloxy group; n-decyloxy group; benzyloxy group; It may be a p-methylbenzyloxy group, but is not limited thereto.

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

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms. The aryl group may be monocyclic or polycyclic. When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. More specifically, it is preferable that it has 6 to 20 carbon atoms. Specifically, the monocyclic aryl group includes a phenyl group; biphenyl group; It may be a terphenyl group, and the like, but is not limited thereto. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms, and more specifically, it is preferable that it has 10 to 20 carbon atoms. Specifically, the polycyclic aryl group includes a naphthyl group; anthracenyl group; phenanthryl group; triphenyl group; pyrenyl group; phenalenyl group; perylenyl group; chrysenyl group; It may be a fluorenyl group, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

,

,

및

등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

and

and the like, but is not limited thereto.

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

In the present specification, the heterocyclic group is a heterocyclic group including at least one of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably has 1 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 1 to 30 carbon atoms. Examples of the heterocyclic group include a pyridyl group, a pyrrole group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, Triazole group, oxadiazole group, thiadiazole group, dithiazole group, tetrazole group, pyranyl group, thiopyranyl group, pyrazinyl group, oxazinyl group, thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, qui Nolinyl group, isoquinolinyl group, quinolyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, acridyl group, xanthenyl group, phenanthridinyl group, diazanaphthalenyl group, triazaindenyl group, indole group , indolinyl group, indolizinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group , benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl group, carbazole group, benzocarbazole group, dibenzocarbazole group, indolocarbazole group, indenocarbazole group, phenazinyl group, imidazopyridine group, phenoxazinyl group , a phenanthridine group, a phenanthroline group, a phenothiazine group, an imidazopyridine group, an imidazophenanthridine group, and the like, but are not limited thereto.

In the present specification, the number of atoms constituting the ring of the heterocyclic group is 3 to 25. In another exemplary embodiment, the number of atoms constituting the ring of the heterocyclic group is 5 to 17.

In the present specification, the heteroaryl group is aromatic, and the description of the above-described heterocyclic group may be applied.

In the present specification, the arylene group and the heteroarylene group are divalent groups, and the descriptions of the aryl group and the heteroaryl group may be applied, respectively, except that they are monovalent groups.

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

In the present specification, the meaning of adjacent groups bonding to each other to form a substituted or unsubstituted ring means that adjacent groups are bonded to each other as described above to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. means, and may form a monocyclic or polycyclic ring, and may be in an aliphatic, aromatic or condensed form thereof, but is not limited thereto.

In the present specification, the meaning of forming a substituted or unsubstituted ring by bonding with an adjacent group means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with an adjacent group; a substituted or unsubstituted aromatic hydrocarbon ring; substituted or unsubstituted aliphatic heterocycle; substituted or unsubstituted aromatic heterocycle; Or it means that they form a combined form.

In the present specification, the aliphatic hydrocarbon ring is a non-aromatic ring and refers to a ring consisting only of carbon and hydrogen atoms.

In the present specification, examples of the aromatic hydrocarbon ring include, but are not limited to, a phenyl group, a naphthyl group, an anthracenyl group, and the like.

In the present specification, the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms.

In the present specification, the aromatic heterocycle refers to an aromatic ring including one or more heteroatoms.

In the exemplary embodiment of the present specification, each of X ₁ to X ₃ is independently N or CR ₂₁ , and at least one is N.

In the exemplary embodiment of the present specification, X ₁ and X ₃ are N.

In an exemplary embodiment of the present specification, X ₂ is N.

In an exemplary embodiment of the present specification, X ₂ is CR ₂₁ .

In an exemplary embodiment of the present specification, X ₁ to X ₃ are N.

In an exemplary embodiment of the present specification, R and R ₂₁ are each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, R and R ₂₁ are each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted alkyl group.

In an exemplary embodiment of the present specification, R and R ₂₁ are each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, R and R ₂₁ are hydrogen.

* In an exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, R ₁ and R ₂ are the same as each other, and a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, R ₁ and R ₂ are the same as each other, and a substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present specification, R ₁ and R ₂ are the same as each other, and a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, R ₁ and R ₂ are the same as each other, and a phenyl group; biphenyl group; dibenzofuran group; or a dibenzothiophene group.

In an exemplary embodiment of the present specification, R ₁ and R ₂ are different and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, R ₁ and R ₂ are different and each independently a substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present specification, one of R ₁ and R ₂ is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted biphenyl group.

In an exemplary embodiment of the present specification, one of R ₁ and R ₂ is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted dibenzofuran group.

In an exemplary embodiment of the present specification, one of R ₁ and R ₂ is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted dibenzothiophene group.

In one embodiment of the present specification, L is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, L is a direct bond; a substituted or unsubstituted C6 to C30 arylene group; Or a substituted or unsubstituted C2 to C30 heteroarylene group.

In one embodiment of the present specification, L is a direct bond; or a substituted or unsubstituted C6 to C30 arylene group.

In one embodiment of the present specification, L is a direct bond; or a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, L is a direct bond; or a phenylene group.

In one embodiment of the present specification, L is a direct bond.

In an exemplary embodiment of the present specification, L is a phenylene group.

In an exemplary embodiment of the present specification, L is a substituted or unsubstituted arylene group; Or in the case of a substituted or unsubstituted heteroarylene group, the substituent is bonded to the para (para) position.

In an exemplary embodiment of the present specification, L is a substituted or unsubstituted arylene group; Or, in the case of a substituted or unsubstituted heteroarylene group, the substituent is bonded to the meta position. When the substituent is bonded to the ortho position, the steric hindrance is severe and the stability of the material is deteriorated.

In an exemplary embodiment of the present specification, R ₃ To R ₁₀ Are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group containing O or S, or combine with an adjacent group to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R ₃ To R ₁₀ Are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, R ₃ To R ₁₀ Are the same as or different from each other, and each independently combine with an adjacent group to form a substituted or unsubstituted dimethylindene group; a substituted or unsubstituted benzofuran group; Or a substituted or unsubstituted benzothiophene group is formed.

In the exemplary embodiment of the present specification, when all of R3 to R10 are hydrogen, at least one of R1 and R2 is not unsubstituted phenyl.

In the exemplary embodiment of the present specification, when R3 to R10 are all hydrogen, at least one of R1 and R2 is a substituted or unsubstituted C8 to C60 aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, when R3 to R10 are all hydrogen, at least one of R1 and R2 is a substituted or unsubstituted C8 to C60 aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, when all of R3 to R10 are hydrogen, at least one of R1 and R2 is a substituted or unsubstituted C8 to C40 aryl group; Or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

In the exemplary embodiment of the present specification, when all of R3 to R10 are hydrogen, at least one of R1 and R2 is a substituted or unsubstituted C8 to C30 aryl group; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In the exemplary embodiment of the present specification, when all of R3 to R10 are hydrogen, at least one of R1 and R2 is a biphenyl group; dibenzofuran group; or a dibenzothiophene group.

In the exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

X ₁ to X ₃ , R ₁ , R ₂ , R and r have the same definitions as in Formula 1,

X ₄ is O; S; or CR ₂₂ R ₂₃ ,

R ₁₁ , R ₁₄ and R ₁₅ are each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group containing O or S,

R ₁₂ and R ₁₃ are each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group containing O or S,

R ₂₂ and R ₂₃ are each independently a substituted or unsubstituted alkyl group,

r11, r12, r13 and r15 are each independently an integer of 1 to 4,

r14 is an integer from 1 to 6,

When r11 to r15 are each independently 2 or more, the substituents in parentheses are the same as or different from each other,

In Formula 1-1, when R ₁₁ is hydrogen, at least one of R ₁ and R ₂ is not unsubstituted phenyl.

In an exemplary embodiment of the present specification, R ₁₁ , R ₁₄ and R ₁₅ are each independently hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, R ₁₁ , R ₁₄ and R ₁₅ are each independently hydrogen; heavy hydrogen; phenyl group; dibenzofuran group; or a dibenzothiophene group.

In an exemplary embodiment of the present specification, R ₁₂ and R ₁₃ are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, R ₁₂ and R ₁₃ are each independently a phenyl group; dibenzofuran group; or a dibenzothiophene group.

In an exemplary embodiment of the present specification, X ₄ is O.

In an exemplary embodiment of the present specification, X ₄ is S.

In an exemplary embodiment of the present specification, X ₄ is CR ₂₂ R ₂₃ .

In an exemplary embodiment of the present specification, R ₂₂ and R ₂₃ are a methyl group.

In the exemplary embodiment of the present specification, Chemical Formula 1-1 may be represented by any one of the following Chemical Formulas 1-1-1 to 1-1-3.

[Formula 1-1-1]

[Formula 1-1-2]

[Formula 1-1-3]

In Formulas 1-1-1 to 1-1-3, the definitions of X ₁ to X ₃ , R ₁ , R ₂ , R and r are the same as those in Formula 1, and the definition of R ₁₁ is in Formula 1 Same as definition in -1.

In the exemplary embodiment of the present specification, Chemical Formula 1-2 may be represented by the following Chemical Formula 1-2-1 or 1-2-2, but is not limited thereto.

[Formula 1-2-1]

[Formula 1-2-2]

In Formulas 1-2-1 and 1-2-2, the definitions of X ₁ to X ₃ , R ₁ , R ₂ , R and r are the same as those in Formula 1, and the definitions of R ₁₂ and R ₁₃ is the same as the definition in Formula 1-2.

In an exemplary embodiment of the present specification, Chemical Formula 1-3 may be represented by any one of Chemical Formulas 1-3-1 to 1-3-6 below.

[Formula 1-3-1]

[Formula 1-3-2]

[Formula 1-3-3]

[Formula 1-3-4]

[Formula 1-3-5]

[Formula 1-3-6]

In Formulas 1-3-1 to 1-3-6, the definitions of X ₁ to X ₃ , R ₁ , R ₂ , R and r are the same as those in Formula 1, and X ₄ , R ₁₄ , R The definitions of ₁₅ , r14 and r15 are the same as those in Formula 1-3.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is selected from the following compounds.

In one embodiment of the present specification, the 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.

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

In an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 above.

In an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes a host, and the host is a compound represented by Formula 1 above.

In an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes the compound represented by Formula 1, and the emission layer including the compound represented by Formula 1 has green or red color. For example, it has an emission wavelength within the range of 450 nm to 700 nm. Specifically, when it is green, it has an emission wavelength in a region of 450 nm to 600 nm, and when it is red, it has an emission wavelength in a region of 600 nm to 700 nm.

In an exemplary embodiment of the present specification, the organic material layer may include a light emitting layer, and the light emitting layer may further include a compound represented by the following Chemical Formula 2.

[Formula 2]

In Formula 2,

R _a and R _b are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R _c and R _d are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; amino group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a heteroaryl group having 2 to 60 carbon atoms including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,

m and n are each independently an integer of 0 to 7,

When m and n are each 2 or more, the substituents in parentheses are the same as or different from each other.

In an exemplary embodiment of the present specification, R _a and R _b are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

In an exemplary embodiment of the present specification, R _a and R _b are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present specification, R _a and R _b are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group.

In an exemplary embodiment of the present specification, R _a and R _b are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, R _a and R _b are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group and a naphthyl group; biphenyl group; terphenyl group; a naphthyl group unsubstituted or substituted with a phenyl group; a fluorenyl group unsubstituted or substituted with an alkyl group; dibenzofuran group; or a dibenzothiophene group.

In an exemplary embodiment of the present specification, the compound represented by Formula 2 may be any one selected from the following compounds.

In an exemplary embodiment of the present specification, the content ratio (weight ratio) of the compound represented by Formula 1 to the compound represented by Formula 2 is 10:90 to 90:10, 30:70 to 70:30, 30:70 to 50:50.

In an exemplary embodiment of the present specification, the light emitting layer may include a dopant together with the compound represented by Formula 1 above.

In the exemplary embodiment of the present specification, the dopant may be a fluorescent or phosphorescent dopant.

In the exemplary embodiment of the present specification, the dopant may be a phosphorescent dopant.

In an exemplary embodiment of the present specification, the light emitting layer may include a metal complex as a phosphorescent dopant together with the compound represented by Formula 1 above.

In another exemplary embodiment, the emission layer may include an iridium-based (Ir) dopant as a phosphorescent dopant together with the compound represented by Formula 1 above.

The iridium-based (Ir) dopant is as follows, but is not limited thereto.

When the emission layer includes a dopant, the dopant may be included in an amount of 0.01 to 30 parts by weight and 0.01 to 20 parts by weight based on 100 parts by weight of the host.

In the exemplary embodiment of the present specification, the organic material layer includes two or more light emitting layers, and at least one of the two or more light emitting layers includes the compound represented by Formula 1 above. The light emitting layer including the compound represented by Formula 1 may have a green color, and the light emitting layer not including the compound represented by Formula 1 may include a blue, red, or green light emitting compound known in the art.

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

In one embodiment of the present specification, the second electrode is a negative electrode or a positive electrode.

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

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

For example, the structure of an organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3 . 1 to 3 illustrate an organic light emitting device, but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which a first electrode 102 , a light emitting layer 106 , and a second electrode 110 are sequentially stacked on a substrate 101 . The compound represented by Formula 1 is included in the light emitting layer.

2 shows the structure of an organic light emitting device in which a first electrode 102, a hole injection layer 103, a hole transport layer 104, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101. is exemplified. According to an exemplary embodiment of the present invention, the compound represented by Formula 1 is included in at least one of the organic material layers. According to another exemplary embodiment, the compound represented by Formula 1 is included in at least one of the hole injection layer, the hole transport layer, and the light emitting layer.

3 shows a first electrode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer ( 108), the electron injection layer 109, and the second electrode 110 are sequentially stacked in the structure of the organic light emitting device is illustrated. According to an exemplary embodiment of the present invention, the compound represented by Formula 1 is included in at least one of the organic material layers. According to another exemplary embodiment, the compound represented by Formula 1 is included in one or more layers of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

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

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

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form the anode. It can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then 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 Formula 1 may be formed into 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 refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Laid-Open No. 2003/012890). However, the manufacturing method is not limited thereto.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : a combination of a metal such as Sb and an oxide; 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 to facilitate electron injection into the organic material layer. metals or alloys thereof such as, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; LiF/Al or a multi-layered material such as LiO ₂ /Al, but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.

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

In the present specification, when the compound represented by Formula 1 is included in an organic material layer other than the light emitting layer, the light emitting material of the light emitting layer receives and combines holes and electrons from the hole transport layer and the electron transport layer, respectively, to emit light in the visible ray region. As the material, a material having good quantum efficiency for fluorescence or phosphorescence is preferable. In addition, when an additional light emitting layer is provided separately from the light emitting layer including the compound represented by Formula 1, the light emitting material of the additional light emitting layer is preferably the above-mentioned material.

Examples of the light-emitting material include 8-hydroxyquinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene; and rubrene, but is not limited thereto.

The hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injecting material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injecting effect for the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in the ability to form a thin film is preferable. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material, metal porphyrin (porphyrin), oligothiophene, arylamine-based organic material; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic substances; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer, and a material having high hole mobility is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transport material is a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; complexes comprising Alq3; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material, as used in accordance with the prior art. In particular, suitable cathode materials are conventional materials having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer is followed.

The electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injecting material is excellent in the ability to transport electrons and has an electron receiving effect from the cathode and an excellent electron injecting effect with respect to the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof; metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

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

The electron blocking layer is a layer capable of improving the lifetime and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer. A known material can be used without limitation, and may be formed between the light emitting layer and the hole injection layer or between the light emitting layer and the layer that simultaneously injects and transports holes. The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but is not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a back emission type, or a double side emission type depending on the material used.

The organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described compound.

A method of preparing the compound of Formula 1 and manufacturing an organic light emitting device using the same will be described in detail in Examples below. 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] Synthesis of compound 1

Step 1) Synthesis of compound 1-1

In a nitrogen atmosphere, 1-bromo-4-chlorodibenzo[b,d]furan (15.0g, 53.3mmol) and bis(pinacolato)diboron (14.9g, 58.6mmol) were mixed with 1,4-dioxane 300ml It was refluxed and stirred. After that, potassium acetate (7.8 g, 79.9 mmol) was added, and after sufficient stirring, bis (dibenzylideneacetone) palladium (0) (0.9 g, 1.6 mmol) and tricyclohexyl phosphine (0.9 g, 3.2 mmol) were added. was put in. After reacting for 10 hours, cooling to room temperature, and separating the organic layer using chloroform and water, the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.4 g of compound 1-1. (Yield 71%, MS[M+H] ⁺ = 330)

Step 2) Synthesis of compound 1-2

Compound 1-1 (15.0 g, 45.6 mmol) and Intermediate A (13.4 g, 50.2 mmol) were placed in 300 ml of THF (tetrahydrofuran) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, and after stirring sufficiently, tetrakis (triphenylphosphine) palladium (0) (1.6 g, 1.4 mmol) was added. After the reaction for 8 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.8 g of compound 1-2. (yield 80%, MS[M+H] ⁺ = 435)

Step 3) Synthesis of compound 1

Compound 1-2 (15.0 g, 34.6 mmol) and Intermediate a (9.3 g, 38 mmol) were added to 300 ml of toluene in a nitrogen atmosphere, and the mixture was stirred and refluxed. Thereafter, sodium tert-butoxide (5.0 g, 51.9 mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.5 g, 1.0 mmol) were added. After the reaction for 7 hours, it was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. After the concentrated compound was purified by silica gel column chromatography, 8.2 g of compound 1 was prepared through sublimation purification. (Yield 37%, MS[M+H] ⁺ = 642)

[Synthesis Example 2] Synthesis of compound 2

In Synthesis Example 1, compound 2 was prepared in the same manner as in the preparation method of compound 1, except that the intermediate a was changed to the intermediate b and used. (MS[M+H] ⁺ = 732)

[Synthesis Example 3] Synthesis of compound 3

In Synthesis Example 1, compound 3 was prepared in the same manner as in the preparation method of compound 1, except that the intermediate a was changed to the intermediate c and used. (MS[M+H] ⁺ = 656)

[Synthesis Example 4] Synthesis of compound 4

In Synthesis Example 1, compound 4 was prepared in the same manner as in the preparation method of compound 1, except that the intermediate a was changed to the intermediate d and used. (MS[M+H] ⁺ = 682)

[Synthesis Example 5] Synthesis of compound 5

In Synthesis Example 1, compound 5 was prepared in the same manner as in the preparation method of compound 1, except that the intermediate a was changed to the intermediate e and used. (MS[M+H] ⁺ = 748)

[Synthesis Example 6] Synthesis of compound 6

In Synthesis Example 1, compound 6 was prepared in the same manner as in the preparation method of compound 1, except that the intermediate A was changed to the intermediate B and the intermediate a was changed to the intermediate f. (MS[M+H] ⁺ = 642)

[Synthesis Example 7] Synthesis of compound 7

In Synthesis Example 1, compound 7 was prepared in the same manner as in the preparation method of compound 1, except that Intermediate A was changed to Intermediate C and Intermediate a was changed to Intermediate f. (MS[M+H] ⁺ = 656)

[Experimental example]

Experimental Example 1-1

A glass substrate coated with ITO (Indium Tin Oxide) to a thickness of 1,400 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, the following HT-A and 5 parts by weight of PD as a hole injection layer were thermally vacuum-deposited to a thickness of 100 Å, and then only the HT-A material was deposited to a thickness of 1150 Å to form a hole transport layer. The following HT-B was thermally vacuum-deposited to a thickness of 450 Å as an electron blocking layer thereon. Subsequently, compound 1 (host) and GD (dopant) of 15 parts by weight (based on 100 parts by weight of host) were vacuum-deposited to a thickness of 400 Å as a light emitting layer. Then, as a hole blocking layer, the following ET-A was vacuum-deposited to a thickness of 50 Å. Then, as the electron transport layer, ET-B and Liq were thermally vacuum-deposited at a ratio of 2:1 to a thickness of 250 Å, and then, as an electron injection layer, LiF and magnesium were vacuum-deposited to a thickness of 30 Å at a ratio of 1:1. On the electron injection layer, magnesium and silver were deposited in a ratio of 1:4 to a thickness of 160 Å to form a cathode, thereby manufacturing an organic light emitting diode.

Experimental Examples 1-2 to 1-7

Organic light emitting devices of Experimental Examples 1-2 to 1-7 were respectively manufactured in the same manner as in Experimental Example 1-1, except that the host material was changed as shown in Table 1 below.

Comparative Experimental Examples 1-1 to 1-6

An organic light emitting diode was manufactured in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1. In Table 1, compounds GH-A, GH-B, GH-C, GH-D, GH-E and GH-F are as follows, respectively.

Experimental Examples 2-1 to 2-4

An organic light emitting diode was manufactured in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1. In Table 1 below, the ratio of each compound means a weight ratio, and the compound PGH is as follows.

Comparative Experimental Examples 2-1 to 2-3

An organic light emitting diode was manufactured in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1. In Table 1, the ratio of each compound means a weight ratio, and the compounds GH-A, GH-B, GH-D and PGH are as described above.

After heat treatment by storing the organic light emitting diodes prepared in Experimental Examples and Comparative Experimental Examples in an oven at 100° C. for 30 minutes, By applying a current, voltage, efficiency, and lifetime (T95) were measured, and the results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying a current density of 10 mA/cm ² , and T95 is the time until the initial luminance decreases to 95% at a current density of 20 mA/cm ² .

host
matter @ 10mA/cm ² @ 20mA/cm ² Voltage
(V) efficiency
(cd/A) life span
(T95, hr) Experimental Example 1-1 compound 1 4.83 46.6 115 Experimental Example 1-2 compound 2 4.84 45.4 110 Experimental Example 1-3 compound 3 4.88 46.2 100 Experimental Example 1-4 compound 4 4.76 47.5 108 Experimental Example 1-5 compound 5 4.81 47.0 113 Experimental Example 1-6 compound 6 4.79 45.9 105 Experimental Example 1-7 compound 7 4.73 46.2 107 Comparative Experimental Example 1-1 GH-A 5.22 45.8 80 Comparative Experimental Example 1-2 GH-B 5.23 38.1 75 Comparative Experimental Example 1-3 GH-C 5.71 22.0 10 Comparative Experimental Example 1-4 GH-D 5.91 40.1 45 Comparative Experimental Example 1-5 GH-E 6.23 35.3 5 Comparative Experimental Example 1-6 GH-F 5.88 29.0 30 Experimental Example 2-1 PGH: Compound 1
(60:40) 4.38 52.7 130 Experimental Example 2-2 PGH: compound 3
(60:40) 4.27 52.3 128 Experimental Example 2-3 PGH: Compound 4
(60:40) 4.29 53.0 125 Experimental Example 2-4 PGH: Compound 5
(60:40) 4.31 53.6 135 Comparative Experimental Example 2-1 PGH:GH-A
(60:40) 4.52 48.0 90 Comparative Experimental Example 2-2 PGH:GH-C
(60:40) 4.91 43.2 65 Comparative Experimental Example 2-3 PGH:GH-D
(60:40) 5.31 49.5 50

In the compound represented by Formula 1, a nitrogen-containing heterocycle serving as an electron acceptor to the same benzene ring of dibenzofuran is positioned at the 1st position of dibenzofuran, and the compound including a carbazole structure is para of the nitrogen-containing heterocycle. replaced in position. Since the electron donor unit and the electron acceptor unit exist simultaneously in the same molecule, it is advantageous for both hole and electron transport. As shown in 1, it has a structure suitable for use as a host material for the light emitting layer.

In addition, in the case of RH-A or RH-B, where the carbazole has no substituents and the triazine has two unsubstituted phenyls, the molecular arrangement is changed when heat treatment is performed on the thin film due to the low glass transition temperature, so the characteristics of the device are improved. A decrease appears, and in the case of GH-C having an ortho position, the binding force with dibenzofuran is weakened due to the interaction between the two substituents, resulting in deterioration of lifespan characteristics.

In the case of GH-E, in which an electron acceptor unit is substituted, because LUMO (Lowest Unoccupied Molecular Orbital) orbital does not exist at position 2 of dibenzofuran, electrons do not spread to dibenzofuran and the conjugation is broken, which is disadvantageous for electron transport. Do. In addition, when a unit having too low triplet energy, such as pyrene, is substituted, such as GH-D, it is difficult to transfer energy to a dopant due to low triplet energy, resulting in low efficiency.

When the compound of Formula 1 is mixed with the compound of Formula 2 such as PGH and applied, hole injection into the light emitting layer is smoothed and the voltage is lowered, and an exciplex is formed between the two molecules, so Experimental Examples 2-1 to 2 As can be seen from -4, the effect of lower voltage, high efficiency, and longer life is shown. When compared with the results of Comparative Experimental Examples 2-1 to 2-3, it can be seen that this effect is more pronounced in Chemical Formula 1.

101: substrate
102: first electrode
103: hole injection layer
104: hole transport layer
105: electron blocking layer
106: light emitting layer
107: hole blocking layer
108: electron transport layer
109: electron injection layer
110: second electrode

Claims (12)

A compound represented by the following formula (1):
[Formula 1]

In Formula 1,
X ₁ to X ₃ are each N or CR ₂₁ , at least one is N,
L is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R ₁ and R ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R and R ₂₁ are each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r is an integer of 1 to 4, and when r is 2 or more, R is the same or different,
R ₃ to R ₁₀ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group containing O or S, or combined with an adjacent substituent to form a substituted or unsubstituted ring,
When all of R ₃ to R ₁₀ are hydrogen, at least one of R ₁ and R ₂ is not unsubstituted phenyl. The method according to claim 1,
X ₁ and X ₃ are N, and X ₂ is N or CR ₂₁ The compound. The method according to claim 1,
L is a direct bond; Or a compound that is a substituted or unsubstituted phenylene group. The method according to claim 1,
wherein R ₁ and R ₂ are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted dibenzothiophene group; Or a compound that is a substituted or unsubstituted dibenzofuran group. The method according to claim 1,
Formula 1 is a compound represented by any one of the following Formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,
X ₁ to X ₃ , R ₁ , R ₂ , R and r have the same definitions as in Formula 1,
X ₄ is O; S; or CR ₂₂ R ₂₃ ,
R ₁₁ , R ₁₄ and R ₁₅ are each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group containing O or S,
R ₁₂ and R ₁₃ are each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group containing O or S,
R ₂₂ and R ₂₃ are each independently a substituted or unsubstituted alkyl group,
r11, r12, r13 and r15 are each independently an integer of 1 to 4,
r14 is an integer from 1 to 6,
When r11 to r15 are each independently 2 or more, the substituents in parentheses are the same as or different from each other,
In Formula 1-1, when R ₁₁ is hydrogen, at least one of R ₁ and R ₂ is not unsubstituted phenyl. The method according to claim 1,
The compound represented by Formula 1 is any one selected from the following compounds:

. a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 6 light emitting element. 8. The method of claim 7,
The organic material layer includes an emission layer, and the emission layer includes the compound. 8. The method of claim 7,
The organic material layer includes an emission layer, the emission layer includes a host material, and the host material includes the compound. 9. The method of claim 8,
The light emitting layer is an organic light emitting device further comprising a compound represented by the following formula 2:
[Formula 2]

In Formula 2,
R _a and R _b are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R _c and R _d are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; amino group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a heteroaryl group having 2 to 60 carbon atoms including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
m and n are each independently an integer of 0 to 7,
When m and n are each 2 or more, the substituents in parentheses are the same as or different from each other. 11. The method of claim 10,
Formula 2 is an organic light emitting device represented by any one of the following compounds:

. 8. The method of claim 7,
The organic material layer further comprises one or two or more layers 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.

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