KR20190114519A - Spiro compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Spiro compound and organic light emitting device including the same {SPIRO COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

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

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy 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. The organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.

There is a continuing need for the development of new materials for such organic light emitting devices.

US Patent Application Publication No. 2004-0251816

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

According to an exemplary embodiment of the present specification to provide a spiro compound represented by the formula (1).

[Formula 1]

In Chemical Formula 1

X1 to X3 are the same as or different from each other, and each independently N or CR,

At least one of X1 to X3 is N,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents are bonded to each other to be substituted or unsubstituted An aliphatic ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocycle,

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

R and R1 to R6 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group, or substituted Or an unsubstituted heteroaryl group,

a is an integer of 0 to 8,

b is an integer of 0 to 7,

When a is a plurality, R5 is the same as or different from each other,

When b is a plurality, R6 is the same as or different from each other.

In addition, the present specification is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two 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 spiro compound.

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

1 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
2 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.

Hereinafter, this specification is demonstrated in detail.

The present specification provides a spiro compound represented by Chemical Formula 1.

In the present specification, when a part "includes" a certain component, this means that it may further include other components, without excluding other components unless specifically stated otherwise.

As used herein, when a member is located "on" another member, this includes not only when one member is in contact with another member but also when another member exists between the two members.

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

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

As used herein, the term "substituted or unsubstituted" is deuterium; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.

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

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

In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto.

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

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

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, penalenyl group, perrylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto. no.

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

,

,

,

,

및

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

,

,

,

,

And

And so on. However, the present invention is not limited thereto.

In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Sleepyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, pe Nanthrolinyl group (phenanthroline), isooxazolyl group, thiadiazolyl group, phenothiazinyl group and dibenzofuranyl group and the like, but is not limited thereto.

In the present specification, the arylene group is the same as the definition of an aryl group except that it is divalent.

In the present specification, the heteroarylene group is the same as the definition of the heteroaryl group, except that it is divalent.

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

[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4, the definitions of X1 to X3, R1 to R6, Ar1, Ar2, L, a, and b are as defined in Chemical Formula 1.

According to an exemplary embodiment of the present specification, R and R1 to R6 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, Substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, the R1 to R6 are the same as or different from each other, each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the R1 to R6 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, the R1 to R6 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the R1 to R4 are the same as or different from each other, and each independently a methyl group, ethyl group, propyl group, isopropyl group, butyl group, terbutyl group, isobutyl group, pentyl group, iso Pentyl, hexyl, isohexyl, heptyl, octyl, nonyl, decyl, phenyl, naphthyl, biphenyl, terphenyl, quarterphenyl, anthracene, phenanthrene, pyrene, triphenylene, Or a fluorene group.

According to an exemplary embodiment of the present specification, the R1 to R4 are the same as or different from each other, and each independently a methyl group or a phenyl group.

According to an exemplary embodiment of the present specification, R5 and R6 are hydrogen.

According to an exemplary embodiment of the present specification, X1 to X3 is N.

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 substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 combine with each other to form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocycle.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are bonded to each other to form a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocycle.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are bonded to each other to form a heterocyclic ring substituted or unsubstituted with an aryl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are bonded to each other to form a heterocycle unsubstituted or substituted with 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 contain a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted N, O, or S It is a C3-C30 heteroaryl 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 substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted polycyclic polyamide having 10 to 30 carbon atoms. Monocyclic heteroaryl group having 3 to 30 carbon atoms containing an aryl group, substituted or unsubstituted N, O, or S, or polycyclic having 3 to 30 carbon atoms containing substituted or unsubstituted N, O, or S Heteroaryl 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 contain an aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted N, O, or S 3 to 30 carbon atoms. Polycyclic heteroaryl group of,

The aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted polycyclic heteroaryl group having 3 to 30 carbon atoms containing N, O, or S is substituted or unsubstituted with deuterium, a halogen group, an alkyl group, an alkyl group or an aryl group. It is unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group unsubstituted or substituted with 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 contain an aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted N, O, or S 3 to 30 carbon atoms. Polycyclic heteroaryl group of,

The aryl group having 6 to 30 carbon atoms or a polycyclic heteroaryl group having 3 to 30 carbon atoms containing substituted or unsubstituted N, O, or S; Halogen group; An alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with 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 a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Pyridine group; Pyrimidine groups; Triazine group; Triphenylene group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or a benzonaphthothiophene group,

The phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Pyridine group; Pyrimidine groups; Triazine group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or the benzonaphthothiophene group is deuterium; Halogen group; An alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with 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 a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Pyridine group; Pyrimidine groups; Triazine group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or a benzonaphthothiophene group,

The phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Pyridine group; Pyrimidine groups; Triazine group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or the benzonaphthothiophene group is deuterium; Phenyl group; Naphthyl group; Phenanthrene group; Triphenylene group; Dimethyl fluorene group; Dibenzofuran group; Dibenzothiophene group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a carbazole group unsubstituted or substituted with a phenyl 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 deuterium, naphthyl group, phenanthrene group, triphenylene group, dimethylfluorene group, dibenzofuran group, dibenzothiophene A phenyl group unsubstituted or substituted with a group and a carbazole group; Biphenyl group; A phenyl group substituted or unsubstituted naphthyl group; Terphenyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; Spirobisfluorene group; Phenanthrene group; Triphenylene group; Pyridine group; Pyrimidine groups; Triazine group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Benzonaphthofuran group; Or a benzonaphthothiophene 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 may be represented by the following substituents.

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 unsubstituted or substituted with a naphthyl group, a phenanthrene group, a dibenzofuran group, or a dibenzothiophene group; Biphenyl group; A phenyl group substituted or unsubstituted naphthyl group; Terphenyl group; A fluorene group unsubstituted or substituted with a methyl group; Phenanthrene group; Triphenylene group; Pyridine group; Pyrimidine groups; Triazine group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group, or combine with each other to form a heterocyclic ring substituted or unsubstituted with 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 a phenyl group unsubstituted or substituted with a naphthyl group, a phenanthrene group, a dibenzofuran group, or a dibenzothiophene group; Biphenyl group; A phenyl group substituted or unsubstituted naphthyl group; Terphenyl group; A fluorene group unsubstituted or substituted with a methyl group; Phenanthrene group; Triphenylene group; Pyridine group; Pyrimidine groups; Triazine group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene 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; Naphthyl group; Phenanthrene group; Pyridine group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present specification, L is 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, L is a direct bond or a monocyclic substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L is a direct bond, or a polycyclic substituted or unsubstituted arylene group having 10 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted bivalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, substituted Or an unsubstituted divalent quarterphenyl group, a substituted or unsubstituted divalent fluorene group, a substituted or unsubstituted divalent anthracene group, a substituted or unsubstituted divalent pyrene group, a substituted or unsubstituted divalent triphenylene group Or a substituted or unsubstituted divalent phenanthrene group.

According to an exemplary embodiment of the present specification, L is a phenylene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a naphthylene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms A substituted or unsubstituted bivalent biphenyl group, a divalent terphenyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a divalent quarterphenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms A divalent fluorene group unsubstituted or substituted with a divalent anthracene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a divalent pyrene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, and having 1 to 10 carbon atoms. Or a divalent phenanthrene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, L is a phenylene group, a naphthylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent quarterphenyl group, a divalent fluorene unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms. Group, a bivalent anthracene group, a bivalent pyrene group, a bivalent triphenylene group, or a bivalent phenanthrene group.

According to an exemplary embodiment of the present specification, L may be represented by the following substituents.

According to an exemplary embodiment of the present specification, L is a direct bond.

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

According to an exemplary embodiment of the present specification, L is a divalent biphenyl group.

According to yet an embodiment of the present disclosure, the spiro compound of Formula 1 may be represented by the following structural formula.

According to an exemplary embodiment of the present specification, the spiro compound of Formula 1 may be prepared according to the following scheme, but is not limited thereto. In the following schemes, the type and number of substituents can synthesize various kinds of intermediates as those skilled in the art appropriately select known starting materials. Reaction type and reaction conditions may be used those known in the art.

By properly combining the formulas described in the examples herein and the intermediates based on common technical knowledge, all of the spiro compounds of Formula 1 described herein can be prepared.

The organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described compound.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention includes a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers may include the aforementioned spiro compound.

However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.

For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic material layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.

1 illustrates an organic light emitting diode and is not limited thereto.

2 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic material layer 3, a light emitting layer 4, and a second electrode 5 are sequentially stacked on a substrate 1.

2 illustrates an organic light emitting device, and is not limited thereto, and may further include an additional organic material layer between the light emitting layer 4 and the second electrode 5.

The organic light emitting device of the present invention may include a structure in which a first electrode, an organic material layer, and a second electrode are sequentially stacked on a substrate, and the organic material layer may include the compound of Formula 1.

The organic light emitting device of the present invention may include a structure in which a first electrode, a light emitting layer, a hole suppression layer, and a second electrode are sequentially stacked on a substrate, and the hole suppression layer may include the compound of Formula 1.

The organic light emitting device of the present invention includes a structure in which a first electrode, a hole transport layer, a light emitting layer, a hole suppression layer, an electron transport layer, and a second electrode are sequentially stacked on a substrate, and the hole suppression layer or the electron transport layer is represented by Chemical Formula 1 It may include a compound of.

The organic light emitting device of the present invention includes a structure in which a first electrode, a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole suppression layer, an electron injection and transport layer, and a second electrode are sequentially stacked on the substrate. The hole suppression layer or the electron transport layer may include the compound of Formula 1.

In one embodiment of the present invention, the organic material layer includes a hole injection layer, a hole transport layer, a hole injection and transport layer, or an electron suppression layer, the hole injection layer, a hole transport layer, a hole injection and transport layer, or an electron suppression layer It may include a spiro compound of Formula 1.

In an exemplary embodiment of the present invention, the organic material layer includes an electron injection layer, an electron transport layer, an electron injection and transport layer, or a hole suppression layer, and includes an electron injection layer, an electron transport layer, an electron injection and transport layer, or a hole suppression layer. It may include a spiro compound of Formula 1.

In an exemplary embodiment of the present invention, the organic material layer may include a hole suppression layer, and the hole suppression layer may include a spiro compound of Chemical Formula 1.

In an exemplary embodiment of the present invention, the organic material layer may include an electron transport layer, and the electron transport layer may include a spiro compound of Chemical Formula 1.

For example, the organic light emitting device according to the present invention uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate. To form an anode, an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an organic material layer including the spiro compound of Formula 1 thereon, and then a material that can be used as a cathode thereon. It can be prepared by vapor deposition. In addition to the above 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.

As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methyl compound), poly [3,4- (ethylene-1,2-dioxy) compound] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic compounds, anthraquinones and polyaniline and poly-compounds of conductive polymers, and the like, but are not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion, but are not limited thereto.

The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

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

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.

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

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

Dopant materials include aromatic spiro compounds, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic spiro compound is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene and periplanthene having an arylamino group, and a styrylamine compound is substituted or unsubstituted. At least one arylvinyl group is substituted with the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As an electron transporting material, a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Do. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or silver layer in each case.

The electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, 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, It is not limited to this.

The hole suppression layer is a layer for suppressing the reaching of the cathode of the hole, generally can be formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

The 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 according to a material used.

The manufacturing method of the spiro compound of Formula 1 and the manufacture of an organic light emitting device using the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

< Production Example  1>

One) Preparation of Compound 1

                                  [Compound 1]

In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound A (5.12 g, 10.71 mmol) and a-1 (4.35 g, 12.32 mmol) were completely dissolved in 280 ml of tetrahydrofuran, followed by adding 2M potassium carbonate solution (140 ml). -(Triphenylphosphine) palladium (0.37g, 0.32mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 160 ml of tetrahydrofuran to prepare compound 1 (5.23 g, 69%).

MS [M + H] ⁺ = 708

< Production Example  2>

One) Preparation of Compound 2

                              [Compound 2]

In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound A (4.67 g, 9.77 mmol) and a-2 (3.97 g, 11.24 mmol) were completely dissolved in 200 ml of tetrahydrofuran, followed by adding 2 M aqueous potassium carbonate solution (100 ml). -(Triphenylphosphine) palladium (0.34g, 0.29mmol) was added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 220 ml of ethyl acetate to obtain Compound 2 (4.19 g, 61%).

MS [M + H] ⁺ = 708

< Production Example  3>

One) Preparation of Compound 3

                               [Compound 3]

In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound A (5.36 g, 13.14 mmol) and a-3 (4.55 g, 12.90 mmol) were completely dissolved in 220 ml of tetrahydrofuran, and then 2M aqueous potassium carbonate solution (110 ml) was added thereto. -(Triphenylphosphine) palladium (0.39 g, 0.34 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 ml of acetone to prepare compound 3 (4.64 g, 58%).

MS [M + H] ⁺ = 707

< Production Example  4>

One) Preparation of Compound 4

                          [Compound 4]

In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound A (5.29 g, 11.07 mmol) and a-4 (4.49 g, 12.73 mmol) were completely dissolved in 240 ml of tetrahydrofuran, followed by adding 2M potassium carbonate solution (120 ml). -(Triphenylphosphine) palladium (0.38g, 0.33mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and recrystallized with acetone 220ml to prepare compound 4 (3.97g, 51%).

MS [M + H] ⁺ = 706

< Production Example  5>

One) Preparation of Compound 5

                            [Compound 5]

In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound B (6.13 g, 12.82 mmol) and a-1 (5.21 g, 14.75 mmol) were completely dissolved in 260 ml of tetrahydrofuran, followed by adding 2M potassium carbonate solution (130 ml). -(Triphenylphosphine) palladium (0.44g, 0.38mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of ethyl acetate to obtain compound 5 (6.85 g, 75%).

MS [M + H] ⁺ = 708

< Production Example  6>

One) Preparation of Compound 6

                                  [Compound 6]

In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound C (5.36 g, 11.21 mmol) and a-2 (4.55 g, 12.90 mmol) were completely dissolved in 240 ml of tetrahydrofuran, followed by adding 2M potassium carbonate solution (120 ml). -(Triphenylphosphine) palladium (0.39 g, 0.34 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 220 ml of ethyl acetate to obtain compound 6 (4.56 g, 57%).

MS [M + H] ⁺ = 708

< Production Example  7>

One) Preparation of Compound 7

                                 [Compound 7]

In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound A-1 (7.19 g, 13.66 mmol) and a-5 (4.26 g, 12.42 mmol) were completely dissolved in 200 ml of tetrahydrofuran, followed by adding 2M aqueous potassium carbonate solution (100 ml). Tetrakis- (triphenylphosphine) palladium (0.43g, 3755mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with acetonitrile 220ml to obtain compound 7 (6.37g, 72%).

MS [M + H] ⁺ = 708

< Production Example  8>

One) Preparation of Compound 8

                                  [Compound 8]

In a 500 ml round bottom flask in nitrogen atmosphere, completely dissolve Compound B-1 (7.88 g, 14.98 mmol) and a-5 (4.67 g, 13.62 mmol) in 200 ml of tetrahydrofuran, and then add 2M aqueous potassium carbonate solution (100 ml). Tetrakis- (triphenylphosphine) palladium (0.47g, 0.41mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of acetonitrile to prepare compound 8 (5.89 g, 61%).

MS [M + H] ⁺ = 708

< Production Example  9>

One) Preparation of Compound 9

                                  [Compound 9]

In a 500 ml round bottom flask in a nitrogen atmosphere, Compound C-1 (8.30 g, 15.78 mmol) and a-6 (4.92 g, 14.34 mmol) were completely dissolved in 260 ml of tetrahydrofuran and 2M aqueous potassium carbonate solution (130 ml) was added thereto. Tetrakis- (triphenylphosphine) palladium (0.50g, 0.43mmol) was added thereto, followed by heating and stirring for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with acetonitrile 230ml to prepare compound 9 (6.23 g, 61%).

MS [M + H] ⁺ = 708

< Production Example  10>

One) Preparation of Compound 10

                                  [Compound 10]

In a 500 ml round bottom flask in a nitrogen atmosphere, Compound A-1 (7.73 g, 14.70 mmol) and a-6 (4.77 g, 13.36 mmol) were completely dissolved in 280 ml of tetrahydrofuran, followed by adding 2M aqueous potassium carbonate solution (140 ml). Tetrakis- (triphenylphosphine) palladium (0.64 g, 0.55 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of acetonitrile to prepare compound 10 (5.14 g, 54%).

MS [M + H] ⁺ = 722

< Production Example  11>

One) Preparation of Compound 11

                                  [Compound 11]

In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound B-1 (9.70 g, 18.44 mmol) and a-7 (4.51 g, 16.77 mmol) were completely dissolved in 200 ml of tetrahydrofuran, followed by adding 2M aqueous potassium carbonate solution (100 ml). Tetrakis- (triphenylphosphine) palladium (0.58g, 0.50mmol) was added thereto, followed by stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 ml of acetonitrile to prepare compound 11 (7.03 g, 66%).

MS [M + H] ⁺ = 634

< Production Example  12>

One) Preparation of Compound 12

                                  [Compound 12]

In a 500 ml round bottom flask in a nitrogen atmosphere, Compound C-1 (6.47 g, 12.30 mmol) and a-8 (4.17 g, 11.18 mmol) were completely dissolved in 200 ml of tetrahydrofuran, followed by adding 2M aqueous potassium carbonate solution (100 ml). Tetrakis- (triphenylphosphine) palladium (0.39 g, 0.30 mmol) was added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of acetonitrile to prepare Compound 12 (5.19 g, 63%).

MS [M + H] ⁺ = 738

< Production Example  13>

One) Preparation of Compound 13

                                  [Compound 13]

In a 500 ml round bottom flask in a nitrogen atmosphere, Compound A-1 (7.29 g, 13.85 mmol) and a-9 (5.44 g, 12.59 mmol) were completely dissolved in 200 ml of tetrahydrofuran, followed by adding 2M aqueous potassium carbonate solution (100 ml). Tetrakis- (triphenylphosphine) palladium (0.44 g, 0.38 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and recrystallized with acetonitrile 230ml to prepare compound 13 (7.16g, 71%).

MS [M + H] ⁺ = 797

< Production Example  14>

One) Preparation of Compound 14

                                [Compound 14]

In a 500 ml round bottom flask in a nitrogen atmosphere, Compound B (4.96 g, 10.38 mmol) and a-10 (5.12 g, 11.93 mmol) were completely dissolved in 240 ml of tetrahydrofuran, followed by adding 2M aqueous potassium carbonate solution (120 ml). -(Triphenylphosphine) palladium (0.36g, 0.31mmol) was added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of tetrahydrofuran to prepare compound 14 (6.34 g, 78%).

MS [M + H] ⁺ = 784

< Production Example  15>

One) Preparation of Compound 15

                                  [Compound 15]

In a 500 ml round bottom flask in a nitrogen atmosphere, Compound D-1 (9.53 g, 14.67 mmol) and a-11 (3.56 g, 13.33 mmol) were completely dissolved in 200 ml of tetrahydrofuran, followed by adding 2M aqueous potassium carbonate solution (100 ml). Tetrakis- (triphenylphosphine) palladium (0.46g, 0.40mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of acetonitrile to prepare Compound 15 (6.39 g, 63%).

MS [M + H] ⁺ = 756

< Production Example  16>

One) Preparation of Compound 16

                                  [Compound 16]

In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound E-1 (10.07 g, 15.49 mmol) and a-11 (3.76 g, 14.08 mmol) were completely dissolved in 200 ml of tetrahydrofuran, followed by adding 2M aqueous potassium carbonate solution (100 ml). Tetrakis- (triphenylphosphine) palladium (0.49 g, 0.42 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of acetonitrile to prepare compound 16 (5.67 g, 53%).

MS [M + H] ⁺ = 756

Example  1-1

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. In this case, Fischer Co. was used as a detergent, and distilled water was filtered secondly as a filter of Millipore Co. as a distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

The compound of the following compound HI1 and the following compound HI2 was thermally vacuum deposited to a thickness of 100 kPa so that the ratio of 98: 2 (molar ratio) was formed on the ITO transparent electrode as the anode thus prepared, thereby forming a hole injection layer. Compound (1150.) Represented by the following formula HT1 was vacuum deposited on the hole injection layer to form a hole transport layer. Subsequently, the electron suppression layer was formed by vacuum depositing a compound of EB1 on the hole transport layer with a film thickness of 50 GPa. Subsequently, the light emitting layer was formed by vacuum depositing the compound represented by the following formula BH and the compound represented by the following formula BD at a weight ratio of 50: 1 on the electron suppressing layer with a film thickness of 200 kPa. A hole suppression layer was formed by vacuum depositing the compound of Preparation Example 1 on the light emitting layer with a film thickness of 50 GPa. Subsequently, the compound represented by the following formula ET1 and the compound represented by the following formula LiQ were vacuum-deposited at a weight ratio of 1: 1 on the hole suppression layer to form an electron injection and transport layer at a thickness of 30 kPa. Lithium fluoride (LiF) and aluminum were deposited on the electron injection and transport layer sequentially to a thickness of 12 Å to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å / sec, the lithium fluoride of the cathode was maintained at 0.3 Å / sec, the aluminum was maintained at the deposition rate of 2 Å / sec, the vacuum degree during deposition is 2 ⅹ 10 ^-7 ~ The organic light emitting device was manufactured by maintaining ⁵ × 10 ⁻⁶ torr.

Example  1-2 to Example  1-8

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using the compound shown in Table 1 below instead of the compound of Preparation Example 1.

Comparative example  1-1 and 1-2

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using the compound shown in Table 1 below instead of the compound of Preparation Example 1. The compounds of HB2 and HB3 used in Table 1 below are as follows.

When the current was applied to the organic light emitting devices manufactured by Examples 1-1 to 1-8, Comparative Examples 1-1, and Comparative Examples 1-2, voltage, efficiency, color coordinates, and lifetime were measured, and the results are described below. Table 1]. T95 means the time it takes for the luminance to decrease to 95% from the initial luminance of 1600 nits.

compound
(Hole suppression layer) Voltage
(V @ 20mA
/ cm ² ) efficiency
(cd / A @ 20mA
/ cm ² ) Color coordinates
(x, y)
T95
(hr) Experimental Example 1-1 Compound 1 4.21 6.34 (0.143, 0.047) 255 Experimental Example 1-2 Compound 2 4.32 6.52 (0.142, 0.045) 285 Experimental Example 1-3 Compound 5 4.23 6.88 (0.143, 0.047) 275 Experimental Example 1-4 Compound 6 4.36 6.87 (0.143, 0.046) 260 Experimental Example 1-5 Compound 7 4.17 6.79 (0.144, 0.044) 275 Experimental Example 1-6 Compound 8 4.28 6.44 (0.141, 0.047) 255 Experimental Example 1-7 Compound 9 4.39 6.60 (0.142, 0.047) 280 Experimental Example 1-8 Compound 14 4.21 6.43 (0.143, 0.046) 270 Comparative Example 1-1 HB 2 4.51 5.81 (0.145, 0.049) 185 Comparative Example 1-2 HB 3 5.80 5.02 (0.148, 0.051) 55

As shown in Table 1, the organic light emitting device manufactured by using the compound of the present invention as a hole suppression layer exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device. It showed lower voltage, higher efficiency and longer life than the organic light emitting device manufactured by using the compound of spirobifluorene which is the core of the present invention and the substituted compound whose carbonyl group is substituted in the core of the present invention as the hole suppression layer. .

Example  2-1 to Example  2-11

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound of HB1 was used instead of the compound of Preparation Example 1 in Example 1-1, and the compound of Table 2 was used instead of ET1. Prepared.

Comparative example  2-1 and 2-2

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound of HB1 was used instead of the compound of Preparation Example 1 in Example 1-1, and the compound of Table 2 was used instead of ET1. Prepared. The compounds of ET2 and ET3 used in Table 2 below are as follows.

When the current was applied to the organic light emitting diodes produced in Examples 2-1 to 2-11, Comparative Example 2-1 and Comparative Example 2-2, voltage, efficiency, color coordinates and lifetime were measured and the results are described below. Table 2]. T95 means the time it takes for the luminance to decrease to 95% from the initial luminance of 1600 nits.

compound
(Electronic transport layer) Voltage
(V @ 20mA
/ cm ² ) efficiency
(cd / A @ 20mA
/ cm ² ) Color coordinates
(x, y)
T95
(hr) Experimental Example 2-1 Compound 3 4.30 6.32 (0.144, 0.046) 285 Experimental Example 2-2 Compound 4 4.35 6.87 (0.144, 0.044) 325 Experimental Example 2-3 Compound 7 4.46 6.55 (0.142, 0.044) 335 Experimental Example 2-4 Compound 8 4.34 6.79 (0.144, 0.044) 300 Experimental Example 2-5 Compound 9 4.27 6.61 (0.143, 0.046) 280 Experimental Example 2-6 Compound 10 4.48 6.56 (0.145, 0.045) 350 Experimental Example 2-7 Compound 11 4.49 6.78 (0.145, 0.047) 280 Experimental Example 2-8 Compound 12 4.35 6.67 (0.145, 0.046) 275 Experimental Example 2-9 Compound 13 4.32 6.54 (0.146, 0.045) 320 Experimental Example 2-10 Compound 15 4.24 6.43 (0.146, 0.046) 290 Experimental Example 2-11 Compound 16 4.15 6.62 (0.144, 0.045) 295 Comparative Example 2-1 ET 2 4.91 5.80 (0.142, 0.048) 230 Comparative Example 2-2 ET 3 5.92 4.25 (0.143, 0.052) 40

As shown in Table 1, the organic light emitting device manufactured by using the compound of the present invention as an electron transport layer exhibits excellent characteristics in terms of efficiency, driving voltage, and / or stability of the organic light emitting device. The low-voltage, high-efficiency, and long-life characteristics of the organic light-emitting device manufactured by using a compound of spirobifluorene, a core of the present invention, and a substituted compound in which a carbonyl group is substituted in the core of the present invention as an electron transporting layer.

Although preferred embodiments of the present invention (hole suppression layer, electron transport layer) have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention. This also belongs to the scope of the invention.

1: substrate
2: first electrode
3: organic material layer
4: light emitting layer
5: second electrode

Claims (8)

Spiro compounds represented by the following formula (1):
[Formula 1]

In Chemical Formula 1
X1 to X3 are the same as or different from each other, and each independently N or CR,
At least one of X1 to X3 is N,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents are bonded to each other to be substituted or unsubstituted An aliphatic ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted hetero ring,
L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
R and R1 to R6 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group, or substituted Or an unsubstituted heteroaryl group,
a is an integer of 0 to 8,
b is an integer of 0 to 7,
When a is a plurality, R5 is the same as or different from each other,
When b is a plurality, R6 is the same as or different from each other. The spiro compound of claim 1, wherein Formula 1 is represented by any one of Formulas 2 to 4.
[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4, the definitions of X1 to X3, R1 to R6, Ar1, Ar2, L, a, and b are as defined in Chemical Formula 1. The method according to claim 1, Ar1 and Ar2 are the same as or different from each other, each independently containing a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted N, O, or S 3 to 3 carbon atoms Spiro compound which is a heteroaryl group of 30. The spiro compound of claim 1, wherein L is a direct bond or a polycyclic substituted or unsubstituted arylene group having 10 to 30 carbon atoms. The spiro compound of claim 1, wherein Formula 1 is any one selected from the following compounds:

A first electrode; A second electrode provided to face the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the spiro compound of any one of claims 1 to 5. Organic light emitting device. The organic light emitting device of claim 6, wherein the organic material layer comprises a hole suppression layer, and the hole suppression layer comprises the spiro compound. The organic light emitting device of claim 6, wherein the organic material layer includes an electron transport layer, and the electron transport layer includes the spiro compound.

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