KR102542198B1 - Compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification provides a compound represented by Formula 1 and an organic light emitting device including the same.

Description

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0145641 filed with the Korean Intellectual Property Office on November 14, 2019, the entire contents of which are incorporated herein.

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.

Development of new materials for the organic light emitting device as described above has been continuously demanded.

Publication of Patent Publication 10-2015-0011347

In the present specification, a compound and an organic light emitting device including the same are provided.

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

[Formula 1]

In Formula 1,

R is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to adjacent groups to form a substituted or unsubstituted ring;

R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; or a substituted or unsubstituted heterocyclic group, or bonded to adjacent groups to form a substituted or unsubstituted ring;

At least one of R1 to R11 and R14 to R16 is represented by the following formula (2),

[Formula 2]

In Formula 2,

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

Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

At least one of Ar1 and Ar2 is a substituted or unsubstituted fluorenyl group,

When any one of R1 to R8 is represented by Formula 2, R4 or R5 is combined with R to form a substituted or unsubstituted ring,

* means a position binding to R1 to R11 and R14 to R16.

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

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

1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 7, and a cathode 9 are sequentially stacked.
2 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 7, an electron injection and transport layer 8 and a cathode 9 An example of this sequentially stacked organic light emitting element is shown.
3 is an organic light emitting layer in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 7, an electron injection and transport layer 8, and a cathode 9 are sequentially stacked. An example of a device is shown.
4 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting auxiliary layer 6, a light emitting layer 7, an electron injection and transport layer 8, and a cathode 9 An example of this sequentially stacked organic light emitting element is shown.

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

In the present specification, when a certain component is said to "include", it means that it may further include other components without excluding other components unless otherwise stated.

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

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

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification,

Means a site to be bonded to another substituent or binding part.

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

In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; nitrile group; nitro group; hydroxy group; amino group; silyl group; boron group; alkoxy group; aryloxy group; an alkyl group; cycloalkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or is substituted with a substituent in which two or more substituents from among the above exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; nitrile group; an alkyl group; cycloalkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or is substituted with a substituent in which two or more substituents from among the above exemplified substituents are connected, or does not have any substituents.

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

In the present specification, examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

In the present specification, the silyl group may be represented by a chemical formula of -SiY _a Y _b Y _c , wherein Y _a , Y _b and Y _c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto. don't

In the present specification, the boron group may be represented by the chemical formula -BY _d Y _e , wherein Y _d and Y _e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.

In the present specification, the oxygen of the ether group may be preferably substituted with a straight-chain, branched-chain or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 60 carbon atoms. Specifically, the ether group is represented by -R _ether0 -OR _ether1 , and R _ether0 and R _ether1 may be an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, or an aryl group having 6 to 60 carbon atoms, but is limited thereto It doesn't work.

In the present specification, the alkyl group may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, etc., but is not limited thereto.

In the present specification, a haloalkyl group means an alkyl group substituted with a halogen group.

In the present specification, the description of the above-described alkyl group may be applied except that the arylalkyl group is substituted with an aryl group.

In the present specification, the alkoxy group may be straight chain, branched chain or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto.

Alkyl groups, alkoxy groups, and substituents containing other alkyl moieties described herein include both straight-chain and branched forms.

In the present specification, a haloalkoxy group means an alkoxy group substituted with a halogen group.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.

In the present specification, the amine group is -NH ₂ , and the amine group may be substituted with the aforementioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the carbon number of the amine group is 1 to 20. According to one embodiment, the carbon number of the amine group is 1 to 10. Specific examples of the substituted amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, diphenylamine group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, A ditolylamine group, a phenyltolylamine group, a diphenylamine group, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, etc. as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto no.

(9,9-디메틸플루오레닐기),

(9-메틸-9-페닐플루오레닐기),

(9,9-디페닐플루오레닐기),

,

,

등일 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

(9,9-dimethylfluorenyl group),

(9-methyl-9-phenylfluorenyl group),

(9,9-diphenylfluorenyl group),

,

,

and the like, but is not limited thereto.

In the present specification, the aryl group in the aryloxy group may be applied to the above description of the aryl group.

In the present specification, the heterocyclic group includes one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include a pyridinyl group, a pyrrolyl group, a pyrimidinyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a carbazolyl group, and a dibenzothio group. Phenyl group, imidazole group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group , pyranyl group, thiopyranyl group, pyrazinyl group, oxazinyl group, thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, quinolinyl group, isoquinolinyl group, quinolyl group, quinazolinyl group, quinox Salinyl group, naphthyridinyl group, acridinyl group, xanthenyl group, phenanthridinyl group, diazanaphthalenyl group, triazanedenyl group, indolyl group, indolinyl group, indolizinyl group, phthalazinyl group, pyrido Pyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazole group, phenazinyl group, imidazopyridine group, phenoxazinyl group, phenanthridinyl group, A phenanthrolinyl group, a phenothiazinyl group, an imidazopyridinyl group, an imidazophenanthridinyl group. A benzoimidazoquinazolinyl group or a benzimidazophenanthridinyl group, but is not limited thereto.

In the present specification, the sulfonyl group is -SO ₂ R ⁰ , the sulfoxyl group is -SOR ⁰ , the sulfonamide group is -SO ₂ NR ⁰ , the sulfonate group is -SO ₃ R ⁰ , and each R ⁰ is independently A straight-chain or branched-chain alkyl group having 1 to 60 carbon atoms; an aryl group having 6 to 40 carbon atoms; or a heteroaryl group having 2 to 40 carbon atoms. In an exemplary embodiment, R ⁰ is each independently a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 18 carbon atoms; or a heteroaryl group having 2 to 20 carbon atoms.

In the present specification, the heterocyclic group described above may be applied except that the heteroaryl group is aromatic.

In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, "ring" refers to a hydrocarbon ring; or a heterocyclic ring.

The hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for the divalent group.

In the present specification, the meaning of forming a ring by bonding with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; A substituted or unsubstituted aromatic heterocycle; or to form a condensed ring thereof. The hydrocarbon ring means a ring composed of only carbon and hydrogen atoms. The heterocycle refers to a ring containing one or more selected from N, O, P, S, Si, and Se. In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle and aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, an aliphatic hydrocarbon ring is a non-aromatic ring and refers to a ring composed of only carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc. Not limited to this.

In the present specification, an aromatic hydrocarbon ring means an aromatic ring composed of only carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, Benzofluorene, spirofluorene and the like, but are not limited thereto. In the present specification, an aromatic hydrocarbon ring may be interpreted as the same meaning as an aryl group.

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

In the present specification, an aromatic heterocycle means an aromatic ring containing one or more of heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , phenanthridine, diazanaphthalene, driazainden, indole, indolizine, benzothiazole, benzooxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

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

The present specification provides a compound represented by Formula 1 below. When the compound represented by Chemical Formula 1 is used in the organic layer of the organic light emitting device, the efficiency of the organic light emitting device is improved, and the organic light emitting device has a low driving voltage and excellent lifespan characteristics.

Chemical Formula 1 according to the present invention is characterized in that an amine group containing a fluorene group is bonded to a spiroacridine fluorene structure through an ortho-phenylene group (Formula 2). As shown in Formula 1, when the amine group has a phenylene group connected to the ortho position, compared to compounds having a phenylene group connected to the para position or meta position, the HOMO energy level is relatively shallow, so that holes are easily transferred from the adjacent layer toward the anode. Therefore, it shows the effect of reducing the voltage when driving the device. In addition, since the triplet energy is highest in the case of having a phenylene group connected to the ortho position, electrons passing through the light emitting layer can be effectively blocked.

In addition, when a fluorenyl group is included in the amine group, the hole mobility is faster than when a general aryl group, for example, a biphenyl group, etc. is connected, and the HOMO energy level is easily controlled depending on the binding position of the fluorenyl group. , it is effective in matching the energy difference with the adjacent layer.

Hereinafter, Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

R is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to adjacent groups to form a substituted or unsubstituted ring;

R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; or a substituted or unsubstituted heterocyclic group, or bonded to adjacent groups to form a substituted or unsubstituted ring;

At least one of R1 to R11 and R14 to R16 is represented by the following formula (2),

[Formula 2]

In Formula 2,

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

Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

At least one of Ar1 and Ar2 is a substituted or unsubstituted fluorenyl group,

When any one of R1 to R8 is represented by Formula 2, R4 or R5 is combined with R to form a substituted or unsubstituted ring,

* means a position binding to R1 to R11 and R14 to R16.

According to an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or bonded to an adjacent group to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or bonded to an adjacent group to form a substituted or unsubstituted ring having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or bonded to an adjacent group to form a substituted or unsubstituted ring having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or a direct bond with R4 or R5; or a ring containing O, S, N, P, C=O, C or Si. At this time, the ring is substituted or unsubstituted with one or more substituents selected from the group consisting of hydrogen, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an arylamine group, a heterocyclic group, a nitrile group, an amide group, and an ester group, and the substituent may form a condensed ring to form a spiro structure.

According to an exemplary embodiment of the present specification, R is a substituted or unsubstituted phenyl group, or bonded to an adjacent group to form a ring.

According to an exemplary embodiment of the present specification, R is a substituted or unsubstituted phenyl group, or bonded to an adjacent group to form a carbazole ring.

According to an exemplary embodiment of the present specification, R is a phenyl group, or combines with R4 or R5 to form a carbazole ring.

According to an exemplary embodiment of the present specification, R is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or directly bonded with R4 or R5 to form a ring having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and R is directly bonded to R4 or R5 to form a ring having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R is a substituted or unsubstituted phenyl group, and forms a direct bond with R4 or R5.

According to an exemplary embodiment of the present specification, R is a phenyl group and forms a direct bond with R4 or R5.

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

According to an exemplary embodiment of the present specification, R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or bonded to an adjacent group to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or bonded to an adjacent group to form a substituted or unsubstituted ring having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of R1 to R11 and R14 to R16 is represented by Formula 2, the others are the same as or different from each other, and each independently hydrogen; or deuterium, or bonded to adjacent groups to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, at least one of R1 to R11 and R14 to R16 is represented by Formula 2, the others are the same as or different from each other, and each independently hydrogen; or deuterium, or bonded to adjacent groups to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of R1 to R11 and R14 to R16 is represented by Formula 2, the others are the same as or different from each other, and each independently hydrogen; or deuterium, and R4 and R5 may be directly bonded with R to form a substituted or unsubstituted carbazole ring.

According to an exemplary embodiment of the present specification, at least one of R1 to R11 and R14 to R16 is represented by Formula 2, the others are the same as or different from each other, and each independently hydrogen; or deuterium, and R4 and R5 may be directly bonded with R to form a carbazole ring.

According to an exemplary embodiment of the present specification, at least one of R1 to R11 and R14 to R16 is represented by Formula 2, the others are hydrogen, and R4 and R5 are directly bonded to R to form a carbazole ring.

According to an exemplary embodiment of the present specification, at least one of R1 to R3, R5 to R11, and R14 to R16 is represented by Formula 2, the others are hydrogen, and R4 may combine with R to form a carbazole ring. there is.

According to an exemplary embodiment of the present specification, R4 is combined with R to form a carbazole ring.

According to an exemplary embodiment of the present specification, R5 is combined with R to form a carbazole ring.

According to an exemplary embodiment of the present specification, at least one of R1 to R11 and R14 to R16 is represented by Formula 2, and the remainder not represented by Formula 2 is hydrogen.

According to an exemplary embodiment of the present specification, R12 and R13 are hydrogen; or deuterium.

According to an exemplary embodiment of the present specification, R12 and R13 are hydrogen.

According to an exemplary embodiment of the present specification, at least one of R1 to R11 and R14 to R16 is represented by Formula 2 below.

[Formula 2]

In Formula 2,

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

Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

At least one of Ar1 and Ar2 is a substituted or unsubstituted fluorenyl group,

When any one of R1 to R8 is represented by Formula 2, R4 or R5 is combined with R to form a substituted or unsubstituted ring,

* means a position binding to R1 to R11 and R14 to R16.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms.

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

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

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or an arylene group.

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

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; phenylene group; or a biphenylene group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or a phenylene group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; ortho-phenylene group; meta-phenylene group; or a para-phenylene group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a phenylene group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond or one of the following structural formulas.

In the above structural formula, the dotted line means the binding position.

According to an exemplary embodiment of the present specification, L1 is a direct bond; or a phenylene group.

According to an exemplary embodiment of the present specification, L1 is a direct bond; or a para-phenylene group.

According to an exemplary embodiment of the present specification, L2 is a direct bond; or a phenylene group.

According to an exemplary embodiment of the present specification, L2 is a direct bond; or a para-phenylene group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group unsubstituted or substituted with an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with an alkyl group or an aryl group; A biphenyl group unsubstituted or substituted with an alkyl group or an aryl group; A terphenyl group unsubstituted or substituted with an alkyl group or an aryl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; biphenyl group; terphenyl group; naphthyl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; biphenyl group; terphenyl group; naphthyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; biphenyl group; or a dimethylfluorenyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently represented by any one of the following structural formulas.

In the above structural formula, the dotted line means the binding position.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted fluorenyl group.

According to an exemplary embodiment of the present specification, Ar1 is a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, Ar1 is a fluorenyl group unsubstituted or substituted with an alkyl group.

According to an exemplary embodiment of the present specification, Ar1 is a dimethylfluorenyl group.

According to an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted fluorenyl group.

According to an exemplary embodiment of the present specification, Ar2 is a phenyl group; biphenyl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, Ar2 is a phenyl group; biphenyl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group.

According to an exemplary embodiment of the present specification, Ar2 is a phenyl group; biphenyl group; or a dimethylfluorenyl group.

According to an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a substituted or unsubstituted fluorenyl group.

According to an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a fluorenyl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a fluorenyl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a dimethylfluorenyl group.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted fluorenyl group, and Ar2 is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted fluorenyl group, and Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted fluorenyl group, Ar2 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted fluorenyl group.

According to an exemplary embodiment of the present specification, Ar1 is a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group, and Ar2 is a phenyl group; biphenyl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, Ar1 is a fluorenyl group unsubstituted or substituted with an alkyl group, and Ar2 is a phenyl group; biphenyl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group.

According to an exemplary embodiment of the present specification, Ar1 is a dimethylfluorenyl group, Ar2 is a phenyl group; biphenyl group; or a dimethylfluorenyl group.

According to an exemplary embodiment of the present specification, Ar1 is a dimethylfluorenyl group, and Ar2 is a phenyl group.

According to an exemplary embodiment of the present specification, Ar1 is a dimethylfluorenyl group, and Ar2 is a biphenyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are dimethylfluorenyl groups.

According to an exemplary embodiment of the present specification, when any one of R1 to R8 is represented by Formula 2, R4 or R5 bonds directly with R to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, when any one of R1 to R8 is represented by Formula 2, R4 or R5 bonds directly with R to form a carbazole ring.

According to an exemplary embodiment of the present specification, when any one of R1 to R3 and R5 to R8 is represented by Formula 2, R4 bonds directly with R to form a carbazole ring.

According to an exemplary embodiment of the present specification, when any one of R1 to R4 and R6 to R8 is represented by Formula 2, R5 bonds directly with R to form a carbazole ring.

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

[Formula 2-1]

In Formula 2-1, the definitions of L1, L2 and Ar2 are the same as those in Formula 2,

Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group. According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each Independently, a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted methyl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are methyl groups.

According to an exemplary embodiment of the present specification, Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1-1 to 2-1-4.

[Formula 2-1-1]

[Formula 2-1-2]

[Formula 2-1-3]

[Formula 2-1-4]

In Formulas 2-1-1 to 2-1-4, the definitions of L1, L2 and Ar2 to Ar4 are the same as those in Formula 2.

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

[Formula 1-1]

In Formula 1-1,

G1 to G3 and G5 to G16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; or a substituted or unsubstituted heterocyclic group, or bonded to adjacent groups to form a substituted or unsubstituted ring;

At least one of G1 to G3, G5 to G11, and G14 to G16 is represented by Formula 2 above.

In one embodiment of the present specification, at least one of G1 to G3, G5 to G11, and G14 to G16 is represented by Formula 2, the others are the same as or different from each other, and each independently hydrogen; or deuterium.

In one embodiment of the present specification, at least one of G1 to G3, G5 to G11, and G14 to G16 is represented by Formula 2, and the others are hydrogen.

In one embodiment of the present specification, any one of G1 to G3, G5 to G11, and G14 to G16 is represented by Formula 2, and the others are hydrogen.

In one embodiment of the present specification, at least one of G1 to G3 and G5 to G8 is represented by Formula 2 above.

In one embodiment of the present specification, at least one of G1 to G3 is represented by Formula 2 above.

In one embodiment of the present specification, at least one of G5 to G8 is represented by Formula 2 above.

In one embodiment of the present specification, G5 is represented by Formula 2 above.

In one embodiment of the present specification, G6 is represented by Formula 2 above.

In one embodiment of the present specification, G7 is represented by Formula 2 above.

In one embodiment of the present specification, G8 is represented by Formula 2 above.

In one embodiment of the present specification, at least one of G9 to G11 and G14 to G16 is represented by Formula 2 above.

In one embodiment of the present specification, G14 is represented by Formula 2 above.

In one embodiment of the present specification, G15 is represented by Formula 2 above.

In one embodiment of the present specification, G16 is represented by Formula 2 above.

In one embodiment of the present specification, the above definitions of R1 to R16 may be applied to the definitions of G1 to G16.

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

[Formula 1-2]

In Formula 1-2,

Y1 to Y16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; or a substituted or unsubstituted heterocyclic group, or bonded to adjacent groups to form a substituted or unsubstituted ring;

At least one of Y9 to Y11 and Y14 to Y16 is represented by Formula 2 above.

In one embodiment of the present specification, Y1 to Y8, Y12 and Y13 are the same as or different from each other, and each independently hydrogen; or deuterium.

In one embodiment of the present specification, Y1 to Y8, Y12 and Y13 are hydrogen.

In one embodiment of the present specification, at least one of Y9 to Y11 and Y14 to Y16 is represented by Formula 2, the others are the same as or different from each other, and each independently hydrogen; or deuterium.

In one embodiment of the present specification, at least one of Y9 to Y11 and Y14 to Y16 is represented by Formula 2, and the others are hydrogen.

In one embodiment of the present specification, any one of Y9 to Y11 and Y14 to Y16 is represented by Formula 2, and the others are hydrogen.

In one embodiment of the present specification, Y9 is represented by Formula 2 above.

In one embodiment of the present specification, Y10 is represented by Formula 2 above.

In one embodiment of the present specification, Y11 is represented by Formula 2 above.

In one embodiment of the present specification, Y14 is represented by Formula 2 above.

In one embodiment of the present specification, Y15 is represented by Formula 2 above.

In one embodiment of the present specification, Y16 is represented by Formula 2 above.

In one embodiment of the present specification, the definitions of R1 to R16 described above may be applied to the definitions of Y1 to Y16.

According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of Formulas 3-1 to 3-7 below.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

[Formula 3-5]

[Formula 3-6]

[Formula 3-7]

In Chemical Formulas 3-1 to 3-7, definitions of R1 to R3 and R5 to R16 are the same as those in Chemical Formula 1, and definitions of L1, L2, Ar1 and Ar2 are the same as those in Chemical Formula 2.

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

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

In Formulas 4-1 to 4-3, definitions of R1 to R16 are the same as those in Formula 1, and definitions of L1, L2, Ar1 and Ar2 are the same as those in Formula 2.

According to an exemplary embodiment of the present specification, Formula 1 may be represented by any one of the following structural formulas.

The compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification may have a core structure prepared as in Preparation Examples to be described later. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.

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

In addition, the present specification provides an organic light emitting device including the aforementioned compound.

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

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

In this specification, when a part is said to "include" a certain component, it means that it may further include other components without excluding other components unless otherwise stated.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic light emitting device of the present specification, the organic light emitting device 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 as organic material layers. there is. However, the structure of the organic light emitting diode is not limited thereto and may include a smaller number of organic material layers.

In one embodiment of the present specification, the organic material layer may include a light emitting layer, and the light emitting layer may include the compound represented by Chemical Formula 1.

In one embodiment of the present specification, the light emitting layer may further include a phosphorescent material or a delayed fluorescent compound. The delayed fluorescent compound is a light-emitting organic compound having a gap (ΔEst) between the lowest triplet state T1 and the first excited singlet state S1 of 0.2 eV or less.

When the gap (ΔEst) between the first excited singlet state S1 and the lowest triplet state T1 of the delayed fluorescent compound satisfies the above range, the exciton generated in the triplet moves to the singlet by reverse system transition (RISC) As the rate and speed of the organic light emitting device increase, the time for which excitons stay in the triplet is reduced, thereby increasing the efficiency and lifespan of the organic light emitting device.

In one embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, or a light emitting auxiliary layer, and the organic material layer includes a hole injection layer, a hole transport layer, a hole injection and transport layer, The electron blocking layer or the light emitting auxiliary layer includes the compound represented by Formula 1 above.

In one embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer comprises the compound represented by Formula 1 include

In one embodiment of the present specification, the organic material layer includes a hole injection layer, and the hole injection layer includes the compound represented by Chemical Formula 1.

In one embodiment of the present specification, the organic material layer includes a hole transport layer, and the hole transport layer includes the compound represented by Chemical Formula 1.

In one embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound represented by Chemical Formula 1.

In one embodiment of the present specification, the organic material layer includes a light emitting auxiliary layer, and the light emitting auxiliary layer includes the compound represented by Chemical Formula 1.

In the organic light emitting device of the present specification, the organic material layer may include a hole transport layer and a hole injection layer, and each of the hole transport layer and the hole injection layer may include the compound represented by Formula 1.

In one embodiment of the present specification, the organic material layer is a hole injection layer, and the hole injection layer includes the compound represented by Chemical Formula 1.

In one embodiment of the present specification, the organic material layer is a hole transport layer, and the hole transport layer includes the compound represented by Chemical Formula 1.

In one embodiment of the present specification, the organic material layer is an electron blocking layer, and the electron blocking layer includes the compound represented by Chemical Formula 1.

In one embodiment of the present specification, the organic material layer is a light emitting auxiliary layer, and the light emitting auxiliary layer includes the compound represented by Chemical Formula 1.

In one embodiment of the present specification, the thickness of the organic material layer including the compound represented by Formula 1 may be 5 Å to 600 Å, 50 Å to 500 Å, or 100 Å to 500 Å.

In another exemplary embodiment, the thickness of the organic material layer including the compound represented by Formula 1 may be 50 Å to 2000 Å, 100 Å to 1500 Å, or 200 Å to 1200 Å.

In another exemplary embodiment, the organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 1 described above.

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

In one embodiment of the present specification, the organic light emitting device includes a first electrode; a second electrode; a light emitting layer provided between the first electrode and the second electrode; and two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers is represented by Chemical Formula 1. Contains a compound.

In one embodiment of the present specification, the organic light emitting device includes a first electrode; a second electrode; a light emitting layer provided between the first electrode and the second electrode; and two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, wherein at least two of the two or more organic material layers include the compound represented by Formula 1 .

In one embodiment of the present specification, the two or more organic material layers may be at least two selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a hole transport and hole injection layer, and an electron blocking layer.

In one embodiment of the present specification, the two or more organic material layers are two or more selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and electron injection layer, an electron control layer, and a hole blocking layer. can

In one embodiment of the present specification, the organic material layer includes one or more hole injection layers and one or more hole transport layers, and at least one of the one or more hole injection layers and the one or more hole transport layers is represented by Formula 1 above. contains a compound that is Specifically, in one embodiment of the present specification, the compound represented by Chemical Formula 1 may be included in one layer of one or more hole injection layers and one or more hole transport layers, and one or more hole injection layers and one or more hole injection layers. It may be included in each transport layer.

In another exemplary embodiment, the organic material layer including the compound represented by Chemical Formula 1 may include an additional organic compound. For example, the organic layer containing the formula (1) is 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylidene]cyclopropylidene]-cyanomethyl]-2,3 ,5,6-tetrafluorobenzonitrile may be further included. According to one example, the compound represented by Formula 1 and the organic compound may be included in a weight ratio of 100:0.1 to 100:30, for example, 100:1 to 100:10.

In one embodiment of the present specification, the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes the compound represented by Chemical Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of the two or more hole transport layers.

In addition, in one embodiment of the present specification, when the compound is included in each of the two or more hole transport layers, materials other than the compound represented by Formula 1 may be the same as or different from each other.

In one embodiment of the present specification, the organic material layer further includes a hole injection layer or a hole transport layer containing a compound containing an arylamine group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic material layer containing the compound represented by Formula 1 can include

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

According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

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

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

For example, the structure of an organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 4 . 1 to 4 illustrate organic light emitting diodes, but are not limited thereto.

1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 7, and a cathode 9 are sequentially stacked. In such a structure, the compound may be included in the light emitting layer 7 .

2 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 7, an electron injection and transport layer 8 and a cathode 9 The structure of this sequentially stacked organic light emitting element is illustrated. In this structure, the compound may be included in at least one of the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light emitting layer 7, and the electron injection and transport layer 8.

In FIG. 3 , a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 7, an electron injection and transport layer 8, and a cathode 9 are sequentially stacked. The structure of the element is illustrated. In this structure, the compound may be included in one or more of the hole injection layer 3 , the hole transport layer 4 , the light emitting layer 7 , and the electron injection and transport layer 8 .

4 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting auxiliary layer 6, a light emitting layer 7, an electron injection and transport layer 8, and a cathode 9 The structure of this sequentially stacked organic light emitting element is illustrated. In this structure, the compound may be included in one or more of the hole injection layer 3, the hole transport layer 4, the light emitting auxiliary layer 6, the light emitting layer 7, and the electron injection and transport layer 8.

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

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

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. After forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

In addition to this method, an organic light emitting device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. However, the manufacturing method is not limited thereto.

As the first electrode material, a material having a high work function is generally preferable so that holes can be smoothly injected into the organic material layer. For example, metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : A combination of a metal and an oxide such as Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The second electrode material is preferably a material having a small work function so as to facilitate electron injection into the organic material layer. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

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

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

In the present specification, when an additional light emitting layer is provided, the light emitting material of the light emitting layer is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively. Materials with good quantum efficiency for For example, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene; and rubrene, but are not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode. The hole injecting material preferably has a hole-transporting ability to have a hole-injecting effect in the first electrode and an excellent hole-injecting effect in the light-emitting layer or the light-emitting material. In addition, a material having excellent ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material is preferable. Also, a material having excellent thin film forming ability is preferred. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the first electrode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, and arylamine-based organic materials; carbazole-based organic matter; Nitrile-based organic matter; hexanitrile hexaazatriphenylene-based organic materials; quinacridone-based organic substances; perylene-based organic materials; polythiophene-based conductive polymers such as anthraquinone and polyaniline, or mixtures of two or more of the above examples, but are not limited thereto. In addition, the compound represented by the above formula (1) may be used.

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 transporting holes from the first electrode or the hole injection layer to the light emitting layer, and a material having high hole mobility is preferable. Specific examples include, but are not limited to, arylamine-based organic materials, carbazole-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions. In addition, the compound represented by the above formula (1) may be used.

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

The electron injection layer is a layer for injecting electrons from an electrode. As the electron injecting material, it is preferable to have an excellent ability to transport electrons and have an excellent electron injecting effect from the second electrode or into the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. Derivatives thereof, metal complex compounds and nitrogen-containing 5-membered ring derivatives, mixtures of two or more of the above examples, etc. are not limited thereto.

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

The electron blocking layer is a layer capable of improving lifespan and efficiency of a device by preventing holes injected from the hole injection layer from passing through the light emitting layer and entering the electron injection layer. Known materials can be used without limitation, and can be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and a layer that simultaneously injects and transports holes.

The hole blocking layer is a layer that blocks holes from reaching the second electrode, and may be generally formed under the same conditions as the hole injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, pyridine, pyrimidine or triazine derivatives, but not limited thereto.

The electron control layer is a layer that controls the movement of electrons to the light emitting layer, and materials known in the art may be used.

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

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

The compound according to the present specification may act on a principle similar to that applied to an organic light emitting device in an organic light emitting device including an organic phosphorescent device, an organic solar cell, an organic photoreceptor, and an organic transistor. For example, the organic solar cell may have a structure including a cathode, an anode, and a photoactive layer provided between the cathode and anode, and the photoactive layer may include the compound.

Hereinafter, examples and comparative examples will be described in detail to describe the present specification in detail. However, the Examples and Comparative Examples according to the present specification may be modified in many different forms, and the scope of the present specification is not construed as being limited to the Examples and Comparative Examples detailed below. Examples and comparative examples in the present specification are provided to more completely explain the present specification to those skilled in the art.

<Synthesis example>

[Synthesis Example 1] Synthesis of Compound 1

The above 12'-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol), (2-((9,9-dimethyl-9H-fluoren-2-yl )(phenyl)amino)phenyl)boronic acid 8.37g (20.64mmol) and tetrakis(triphenylphosphine)palladium 2mol% were added to 80ml of tetrahydrofuran, and potassium carbonate 8.56g (61.92mmol) was added to 40ml of water. was dissolved and mixed. After stirring at 80 ° C. for 12 hours, the reaction was terminated and cooled to room temperature to separate water and an organic layer. After receiving only the organic layer, anhydrous magnesium sulfate was added thereto, stirred, filtered through a silica pad, and the solution was concentrated under reduced pressure. After column purification, compound 1 was obtained in 11.37 g (yield: 72%).

MS: [M+H]+= 765

[Synthesis Example 2] Synthesis of Compound 2

The 12'-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2-([1,1'-biphenyl] -4-yl (9 Except for using 9.94 g (20.64 mmol) of ,9-dimethyl-9H-fluoren-3-yl) amino) phenyl) boronic acid, the reaction and purification were performed in the same manner as in the synthesis of Compound 1 to obtain 12.15 g of Compound 2 (yield: 70 %) was obtained.

MS: [M+H]+= 842

[Synthesis Example 3] Synthesis of Compound 3

상기 11'-bromospiro[fluorene-9,8'-indolo[3,2,1-de]acridine] 10.0g (20.64mmol) 및 (2-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino) phenyl)boronic acid 9.94g(20.64mmol)을 이용한 것 외에는 상기 화합물 1의 합성과 동일한 방법으로 반응하고 정제하여 화합물 3을 13.02g (수율 75%) 수득하였다.

10.0g (20.64mmol) of the 11'-bromospiro[fluorene-9,8'-indolo[3,2,1-de]acridine] and (2-([1,1'-biphenyl]-4-yl(9 Except for using 9.94 g (20.64 mmol) of ,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid, the reaction and purification were performed in the same manner as in the synthesis of Compound 1 to obtain 13.02 g of Compound 3 (yield: 75 %) was obtained.

MS: [M+H]+= 842

[Synthesis Example 4] Synthesis of Compound 4

The 11'-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2-([1,1'-biphenyl] -3-yl (9 Except for using 9.94 g (20.64 mmol) of ,9-dimethyl-9H-fluoren-4-yl) amino) phenyl) boronic acid, the reaction and purification were performed in the same manner as in the synthesis of Compound 1 to obtain 13.02 g of Compound 4 (yield: 75 %) was obtained.

MS: [M+H]+= 842

[Synthesis Example 5] Synthesis of Compound 5

The 10'-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2-([1,1'-biphenyl] -2-yl (9 ,9-dimethyl-9H-fluoren-1-yl) amino) phenyl) boronic acid 9.94 g (20.64 mmol) was reacted and purified in the same manner as in the synthesis of Compound 1 to obtain 11.80 g of Compound 5 (yield: 68 %) was obtained.

MS: [M+H]+= 842

[Synthesis Example 6] Synthesis of Compound 6

The 10'-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2-([1,1'-biphenyl] -4-yl (9 Except for using 9.94 g (20.64 mmol) of ,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid, the reaction and purification were performed in the same manner as in the synthesis of Compound 1 to obtain 12.85 g of Compound 6 (yield: 74 %) was obtained.

MS: [M+H]+= 842

[Synthesis Example 7] Synthesis of Compound 7

10.0 g (20.64 mmol) of the 9'-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] and (2-((4-(9,9-dimethyl-9H-fluoren- 2-yl) phenyl) (phenyl) amino) phenyl) boronic acid 9.94 g (20.64 mmol) was reacted and purified in the same manner as in the synthesis of Compound 1 to obtain 11.46 g (yield 66%) of Compound 7. .

MS: [M+H]+= 842

[Synthesis Example 8] Synthesis of Compound 8

The above 9'-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2-((9,9-dimethyl-9H-fluoren-4-yl Except for using 8.37 g (20.64 mmol) of )(phenyl)amino)phenyl)boronic acid, 11.20 g (yield 71%) of Compound 8 was obtained by reacting and purifying in the same manner as in the synthesis of Compound 1.

MS: [M+H]+= 765

[Synthesis Example 9] Synthesis of Compound 9

10.0 g (20.64 mmol) of the 1-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] and (2-([1,1'-biphenyl] -2-yl (9, Except for using 9-dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 9.94g (20.64mmol), the reaction and purification were performed in the same manner as in the synthesis of Compound 1 to obtain 9.37g of Compound 9 (yield: 59%). ) was obtained.

MS: [M+H]+= 842

[Synthesis Example 10] Synthesis of Compound 10

The above 1-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0g (20.64mmol) and (2-((4-(9,9-dimethyl-9H-fluoren-2 -yl) phenyl) (phenyl) amino) phenyl) boronic acid 9.94 g (20.64 mmol) was reacted and purified in the same manner as in the synthesis of Compound 1 to obtain 9.15 g (58% yield) of Compound 10.

MS: [M+H]+= 765

[Synthesis Example 11] Synthesis of Compound 11

상기 2-bromospiro[fluorene-9,8'-indolo[3,2,1-de]acridine] 10.0g (20.64mmol) 및 (2-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 9.94g(20.64mmol)을 이용한 것 외에는 상기 화합물 1의 합성과 동일한 방법으로 반응하고 정제하여 화합물 11을 12.50g (수율 72%) 수득하였다.

The 2-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2-([1,1'-biphenyl] -4-yl (9, 9-dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 9.94g (20.64mmol) was reacted and purified in the same manner as in the synthesis of Compound 1 above to obtain 12.50g of Compound 11 (yield: 72%) ) was obtained.

MS: [M+H]+= 842

[Synthesis Example 12] Synthesis of Compound 12

The above 2-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0g (20.64mmol) and (2-((4-(9,9-dimethyl-9H-fluoren-2 -yl) phenyl) (phenyl) amino) phenyl) boronic acid 9.94 g (20.64 mmol) was reacted and purified in the same manner as in the synthesis of Compound 1 to obtain 12.67 g (73% yield) of Compound 12.

MS: [M+H]+= 842

[Synthesis Example 13] Synthesis of Compound 13

The 3-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0g (20.64mmol) and (2-([1,1'-biphenyl] -3-yl (9, 9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid 9.94 g (20.64 mmol) was reacted and purified in the same manner as in the synthesis of compound 1 above to obtain 12.15 g of compound 13 (yield: 70%) ) was obtained.

MS: [M+H]+= 842

[Synthesis Example 14] Synthesis of Compound 14

The 3-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2-([1,1'-biphenyl] -4-yl (9, 9-dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 9.94g (20.64mmol) was reacted and purified in the same manner as in the synthesis of Compound 1 above to obtain 12.32g of Compound 14 (70% yield) ) was obtained.

MS: [M+H]+= 842

[Synthesis Example 15] Synthesis of Compound 15

The above 1'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene] 10.0g (20.56mmol) and (2-((9,9-dimethyl-9H-fluoren-3-yl)( Except for using 8.33 g (20.56 mmol) of phenyl) amino) phenyl) boronic acid, 8.67 g of Compound 15 (yield: 55%) was obtained by reacting and purifying in the same manner as in the synthesis of Compound 1.

MS: [M+H]+= 767

[Synthesis Example 16] Synthesis of Compound 16

10.0 g (20.56 mmol) of the above 1'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene] and (2-([1,1'-biphenyl]-4-yl(9,9 -dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 9.90g (20.56mmol) was reacted and purified in the same manner as in the synthesis of Compound 1 to obtain 9.01g of Compound 16 (51% yield) obtained.

MS: [M+H]+= 844

[Synthesis Example 17] Synthesis of Compound 17

The above 2'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene] 10.0g (20.56mmol) and (2-([1,1'-biphenyl] -4-yl(9,9 -dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 9.90g (20.56mmol) was reacted and purified in the same manner as in the synthesis of Compound 1 to obtain 12.30g of Compound 17 (71% yield) obtained.

MS: [M+H]+= 844

[Synthesis Example 18] Synthesis of Compound 18

The above 2'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene] 10.0g (20.56mmol) and (2-((9,9-dimethyl-9H-fluoren-2-yl)( Except for using 9.90 g (20.56 mmol) of phenyl) amino) phenyl) boronic acid, 11.67 g (74% yield) of Compound 18 was obtained by reacting and purifying in the same manner as in the synthesis of Compound 1.

MS: [M+H]+= 767

[Synthesis Example 19] Synthesis of Compound 19

The above 3'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene] 10.0g (20.56mmol) and (2-([1,1'-biphenyl] -4-yl(9,9 -dimethyl-9H-fluoren-2-yl)amino)phenyl)boronic acid 9.90g (20.56mmol) was reacted and purified in the same manner as in the synthesis of Compound 1 to obtain 12.13g of Compound 19 (70% yield) obtained.

MS: [M+H]+= 844

[Synthesis Example 20] Synthesis of Compound 20

10.0 g (20.56 mmol) of the 3'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene] and (2-((4-(9,9-dimethyl-9H-fluoren-1- 11.78 g (yield: 68%) of compound 20 was obtained by reacting and purifying in the same manner as in the synthesis of compound 1, except that 9.90 g (20.56 mmol) of yl) phenyl) (phenyl) amino) phenyl) boronic acid was used.

MS: [M+H]+= 844

[Synthesis Example 21] Synthesis of Compound 21

The 12'-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2- (bis (9,9-dimethyl-9H-fluoren-2- Except for using 10.76 g (20.64 mmol) of yl) amino) phenyl) boronic acid, 10.73 g (59% yield) of Compound 21 was obtained by reacting and purifying in the same manner as in the synthesis of Compound 1.

MS: [M+H]+= 882

[Synthesis Example 22] Synthesis of Compound 22

The 11'-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2- (bis (9,9-dimethyl-9H-fluoren-2- Except for using 10.76 g (20.64 mmol) of yl) amino) phenyl) boronic acid, the reaction and purification were performed in the same manner as in the synthesis of Compound 1 to obtain 11.05 g (yield: 61%) of Compound 22.

MS: [M+H]+= 882

[Synthesis Example 23] Synthesis of Compound 23

The 10'-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2- (bis (9,9-dimethyl-9H-fluoren-2- Except for using 10.76 g (20.64 mmol) of yl) amino) phenyl) boronic acid, 11.42 g (yield 63%) of Compound 23 was obtained by reacting and purifying in the same manner as in the synthesis of Compound 1.

MS: [M+H]+= 882

[Synthesis Example 24] Synthesis of Compound 24

The 9'-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2- (bis (9,9-dimethyl-9H-fluoren-3- Except for using 10.76 g (20.64 mmol) of yl) amino) phenyl) boronic acid, 9.42 g of Compound 24 (yield: 52%) was obtained by reacting and purifying in the same manner as in the synthesis of Compound 1.

MS: [M+H]+= 882

[Synthesis Example 25] Synthesis of Compound 25

The above 10'-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2-((9,9-dimethyl-9H-fluoren-2-yl )(9,9-dimethyl-9H-fluoren-3-yl)amino)phenyl)boronic acid 10.76g (20.64mmol) was reacted and purified in the same manner as in the synthesis of Compound 1 above to obtain 11.23g of Compound 25 (Yield 62%) was obtained.

MS: [M+H]+= 882

[Synthesis Example 26] Synthesis of Compound 26

The above 9'-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2-((9,9-dimethyl-9H-fluoren-3-yl )(9,9-dimethyl-9H-fluoren-4-yl)amino)phenyl)boronic acid 10.76g (20.64mmol) was reacted and purified in the same manner as in the synthesis of Compound 1, except that 9.06g of Compound 26 was obtained. (Yield 50%) was obtained.

MS: [M+H]+= 882

[Synthesis Example 27] Synthesis of Compound 27

10.0 g (20.64 mmol) of the above 1-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] and (2-((9,9-dimethyl-9H-fluoren-2-yl) (9,9-dimethyl-9H-fluoren-4-yl)amino)phenyl)boronic acid 10.76g (20.64mmol) was reacted and purified in the same manner as in the synthesis of Compound 1 above to obtain Compound 27 with 10.33g ( Yield 57%) was obtained.

MS: [M+H]+= 882

[Synthesis Example 28] Synthesis of Compound 28

The 2-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2- (bis (9,9-dimethyl-9H-fluoren-2-yl) Except for using 10.76 g (20.64 mmol) of ) amino) phenyl) boronic acid, 11.23 g (yield 62%) of Compound 28 was obtained by reacting and purifying in the same manner as in the synthesis of Compound 1.

MS: [M+H]+= 882

[Synthesis Example 29] Synthesis of Compound 29

The above 3-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2- (bis (9,9-dimethyl-9H-fluoren-3-yl) Except for using 10.76 g (20.64 mmol) of ) amino) phenyl) boronic acid, 11.60 g (yield 64%) of Compound 29 was obtained by reacting and purifying in the same manner as in the synthesis of Compound 1.

MS: [M+H]+= 882

[Synthesis Example 30] Synthesis of Compound 30

The above 1'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene] 10.0g (20.56mmol) and (2-((9,9-dimethyl-9H-fluoren-1-yl)( Except for using 10.72 g (20.56 mmol) of 9,9-dimethyl-9H-fluoren-3-yl) amino) phenyl) boronic acid, the reaction and purification were performed in the same manner as in the synthesis of Compound 1 to obtain 9.24 g (yield) of Compound 30. 51%) was obtained.

MS: [M+H]+= 884

[Synthesis Example 31] Synthesis of Compound 31

2'-bromo-10-phenyl-10H-spiro [acridine-9,9'-fluorene] 10.0g (20.56mmol) and (2-(bis(9,9-dimethyl-9H-fluoren-2-yl) Except for using 10.72 g (20.56 mmol) of amino) phenyl) boronic acid, 11.99 g (yield 66%) of Compound 31 was obtained by reacting and purifying in the same manner as in the synthesis of Compound 1.

MS: [M+H]+= 884

[Synthesis Example 32] Synthesis of Compound 32

The above 3'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene] 10.0g (20.56mmol) and (2-(bis(9,9-dimethyl-9H-fluoren-2-yl) Except for using 10.72 g (20.56 mmol) of amino) phenyl) boronic acid, 11.44 g (yield 63%) of Compound 32 was obtained by reacting and purifying in the same manner as in the synthesis of Compound 1.

MS: [M+H]+= 884

[Synthesis Example 33] Synthesis of Compound 33

The above 10'-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2-((9,9-dimethyl-9H-fluoren-2-yl ) (phenyl) amino) phenyl) boronic acid 8.37 g (20.64 mmol) was reacted and purified in the same manner as in the synthesis of Compound 1 to obtain 10.41 g (yield: 64%) of Compound 33.

MS: [M+H]+= 765

[Synthesis Example 34] Synthesis of Compound 34

The 2-bromospiro [fluorene-9,8'-indolo [3,2,1-de] acridine] 10.0 g (20.64 mmol) and (2-((9,9-dimethyl-9H-fluoren-2-yl) Except for using 8.37 g (20.64 mmol) of (phenyl) amino) phenyl) boronic acid, 11.04 g (70% yield) of Compound 34 was obtained by reacting and purifying in the same manner as in the synthesis of Compound 1 above.

MS: [M+H]+= 765

<Experimental example>

<Experimental Example 1-1>

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

Compound 1 prepared according to Synthesis Example 1 and the compound of Chemical Formula HI-A were vacuum deposited at a weight ratio of 100:3 on the prepared ITO transparent electrode to form a hole injection layer with a thickness of 100 Å.

Compound 1 prepared according to Synthesis Example 1, which is a material for transporting holes, was vacuum deposited to a thickness of 1100 Å to form a hole transport layer on the hole injection layer.

Subsequently, an electron blocking layer was formed by vacuum depositing EB 1 (TCTA) to a film thickness of 50 Å on the hole transport layer.

Subsequently, a light emitting layer was formed by vacuum depositing the following BH and BD at a weight ratio of 25:1 to a film thickness of 200 Å on the electron blocking layer.

On the light emitting layer, the compound ET 1 and lithium quinolate (LiQ) were vacuum deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 250 Å.

A negative electrode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 2,000 Å on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, the deposition rate of lithium fluoride on the negative electrode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum level during deposition was 2 × 10 ^- Maintaining ⁷ to 5 ⅹ 10 ^-6 torr, an organic light emitting device was manufactured.

<Experimental Examples 1-2 to 1-34>

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

<Comparative Examples 1-1 and 1-2>

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Comparative Example Compounds HT 1 and HT 2 were used instead of Compound 1 in Experimental Example 1-1.

division compound Voltage
(V@750nit) efficiency
(cd/A@750nit) color coordinates
(x,y) Experimental Example 1-1 compound 1 3.55 7.75 (0.139, 0.051) Experimental Example 1-2 compound 2 3.52 7.78 (0.138, 0.050) Experimental Example 1-3 compound 3 3.30 7.96 (0.138, 0.052) Experimental Example 1-4 compound 4 3.31 7.94 (0.137, 0.051) Experimental Example 1-5 compound 5 3.55 7.75 (0.139, 0.053) Experimental Example 1-6 compound 6 3.52 7.78 (0.138, 0.051) Experimental Example 1-7 compound 7 3.30 7.96 (0.139, 0.051) Experimental Example 1-8 compound 8 3.31 7.94 (0.138, 0.050) Experimental Example 1-9 compound 9 3.55 7.75 (0.138, 0.052) Experimental Example 1-10 compound 10 3.52 7.78 (0.137, 0.051) Experimental Example 1-11 compound 11 3.30 7.96 (0.139, 0.053) Experimental Example 1-12 compound 12 3.31 7.94 (0.138, 0.051) Experimental Example 1-13 compound 13 3.55 7.75 (0.139, 0.051) Experimental Example 1-14 compound 14 3.52 7.78 (0.138, 0.050) Experimental Example 1-15 compound 15 3.30 7.96 (0.138, 0.052) Experimental Example 1-16 compound 16 3.31 7.94 (0.137, 0.051) Experimental Example 1-17 compound 17 3.55 7.75 (0.139, 0.053) Experimental Example 1-18 compound 18 3.52 7.78 (0.138, 0.051) Experimental Example 1-19 compound 19 3.30 7.96 (0.139, 0.051) Experimental Example 1-20 compound 20 3.31 7.94 (0.138, 0.050) Experimental Example 1-21 compound 21 3.55 7.75 (0.138, 0.052) Experimental Example 1-22 compound 22 3.52 7.78 (0.137, 0.051) Experimental Example 1-23 compound 23 3.30 7.96 (0.139, 0.053) Experimental Example 1-24 compound 24 3.31 7.94 (0.138, 0.051) Experimental Example 1-25 compound 25 3.55 7.75 (0.139, 0.051) Experimental Example 1-26 compound 26 3.52 7.78 (0.138, 0.050) Experimental Example 1-27 compound 27 3.30 7.96 (0.138, 0.052) Experimental Example 1-28 compound 28 3.31 7.94 (0.137, 0.051) Experimental Example 1-29 compound 29 3.55 7.75 (0.139, 0.053) Experimental Example 1-30 compound 30 3.52 7.78 (0.139, 0.051) Experimental Example 1-31 compound 31 3.30 7.96 (0.138, 0.050) Experimental Example 1-32 compound 32 3.31 7.94 (0.138, 0.052) Experimental Example 1-33 compound 33 3.55 7.75 (0.137, 0.051) Experimental Example 1-34 compound 34 3.52 7.78 (0.139, 0.051) Comparative Example 1-1 HT 1 4.30 6.96 (0.138, 0.050) Comparative Example 1-2 HT 2 4.31 6.94 (0.137, 0.052)

From the results of Table 1, Experimental Examples 1-1 to 1-34 using the compound represented by Formula 1 according to the present invention in the hole injection layer and / or hole transport layer are compared to Comparative Examples 1-1 to 1-2. Overall, the driving voltage and efficiency characteristics showed excellent results. Specifically, Experimental Examples 1-1 to 1-34 did not contain a fluorene group, or Comparative Example 1- Compared to 1 and 1-2, the voltage was reduced by about 24% at most, and the efficiency was increased by about 15% at most.

Therefore, when the compound represented by Chemical Formula 1 according to the present invention is used in an organic light emitting device, it can be confirmed that it exhibits excellent characteristics in terms of driving voltage and efficiency.

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

Claims (13)

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

In Formula 1-1,
At least one of G1 to G3 and G5 to G8 is represented by Formula 2 below, the others are the same as or different from each other, and each independently hydrogen; or deuterium;
G9 to G16 are the same as or different from each other, and each independently hydrogen; or deuterium;
[Formula 2]

In Formula 2,
L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or an arylene group having 6 to 30 carbon atoms,
Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms,
At least one of Ar1 and Ar2 is a fluorenyl group unsubstituted or substituted with an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms,
* means a position binding to G1 to G3 and G5 to G8. The compound according to claim 1, wherein Chemical Formula 2 is represented by the following Chemical Formula 2-1:
[Formula 2-1]

In Formula 2-1, the definitions of L1, L2 and Ar2 are the same as those in Formula 2,
Ar3 and Ar4 are the same as or different from each other, and are each independently an alkyl group having 1 to 30 carbon atoms; or an aryl group having 6 to 30 carbon atoms. delete delete The compound according to claim 1, wherein Chemical Formula 1-1 is represented by any one of the following Chemical Formulas 3-1 to 3-4:
[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

In Formulas 3-1 to 3-4, R1 to R3 and R5 to R16 are the same as or different from each other, and each independently hydrogen; or deuterium, and the definitions of L1, L2, Ar1 and Ar2 are as defined in Formula 2. delete The method according to claim 1, wherein L1 and L2 are the same as or different from each other, each independently a direct bond; Or a compound that is a phenylene group. The method according to claim 1, wherein the Ar1 is a fluorenyl group substituted with a methyl group or a phenyl group, the Ar2 is a phenyl group; biphenyl group; naphthyl group; Or a compound that is a fluorenyl group substituted with a methyl group or a phenyl group. The compound according to claim 1, wherein Ar1 and Ar2 are dimethylfluorenyl groups. The compound according to claim 1, wherein Chemical Formula 1-1 is represented by any one of the following structural formulas:

. a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers is the compound according to any one of claims 1, 2, 5, and 7 to 10. An organic light emitting device comprising a. The method of claim 11,
The organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, wherein the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound. The method of claim 11,
The organic material layer includes a light emitting auxiliary layer, wherein the light emitting auxiliary layer includes the compound.

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