KR102088506B1 - Organic light emitting device - Google Patents

Abstract

The present invention provides an organic light emitting device.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

The present invention relates to an organic light emitting device.

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies have been conducted.

The organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layer structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, or an electron injection layer. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode and electrons are injected at the cathode, and excitons are formed when the injected holes meet the electrons. When it falls to the ground again, it glows.

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

Korean Patent Publication No. 10-2000-0051826

The present invention provides an organic light emitting device.

The present invention is an anode; A cathode provided opposite the anode; And one or more organic material layers provided between the anode and the cathode, wherein the organic material layer includes a hole injection layer adjacent to the anode, a hole transport layer provided on the hole injection layer, and a hole transport layer provided on the hole transport layer. An organic light-emitting device comprising a light emitting layer, the hole injection layer includes a compound selected from the group consisting of compounds represented by the following Chemical Formulas 1-1 to 1-2, and the hole transport layer includes a compound represented by the following Chemical Formula 2 Provides

[Formula 1-1] [Formula 1-2]

In Chemical Formula 1-1,

R ¹ to R ⁵ are each independently a cyano group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted O, N, Si and S containing at least one of 2 to 60 carbon atoms. Heteroaryl group,

In Chemical Formula 1-2,

R ¹⁵ to R ¹⁸ are each independently hydrogen, halogen, cyano group, alkyl group having 1 to 40 carbon atoms, haloalkyl group having 1 to 40 carbon atoms, haloalkoxy group having 1 to 40 carbon atoms, substituted or unsubstituted 6 to 60 carbon atoms. An aryl group, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms containing at least one of O, N, Si and S,

Y ³ and Y ⁴ are each independently CR ¹⁹ or N,

* R ¹⁹ each independently represents a cyano group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one of O, N, Si and S Ki,

[Formula 2]

In Chemical Formula 2,

Ar ¹ is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms including one or more of O, N, Si and S,

X ¹ is a non-bonding, single-bonding, alkylene group having 1 to 3 carbon atoms, O or S,

L ¹ and L ² are each independently a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms including one or more of O, N, Si and S. ego,

Ar ² and Ar ³ are each independently a substituent selected from the group consisting of the following substituents,

Ar ⁴ to Ar ⁶ are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms containing at least one of O, N, Si and S ego,

X ² and X ³ are each independently a single bond, O or S.

Compounds selected from the group consisting of the compounds represented by Formulas 1-1 to 1-2 described above are used as a material for the hole injection layer, and the compounds represented by Formula 2 described above are used as a material for the hole transport layer, so that the organic light emitting device is low Driving voltage and / or life characteristics can be improved.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is done.

Hereinafter, the present invention will be described in more detail to help understanding.

The present invention provides an organic light emitting device in which the hole injection layer includes a compound selected from the group consisting of compounds represented by Formulas 1-1 to 1-2, and the hole transport layer includes a compound represented by Formula 2 above.

In the present specification, non-bonding means a case in which there is no chemical bond in a portion represented by X ¹ . For example, if X ¹ in Formula 2 is unbound, it is represented as follows.

In addition, a single bond means a case where a separate atom does not exist in a portion represented by X ¹ to X ³ . For example, if X ^{1 in} Formula 2 is a single bond, it is represented as follows.

In this specification the term "substituted or unsubstituted" may be substituted or means a unsubstituted by R ^a, R ^a is heavy hydrogen, a halogen, a cyano group, a nitro group, an amino group, an alkyl group having 1 to 40 carbon atoms, 1 to 40 haloalkyl groups, substituted or unsubstituted O, N, Si and one or more of C 1 to 40 carbon atoms including one or more of substituted, unsubstituted O, N, Si and S It may be a hetero haloalkyl group having 1 to 40 carbon atoms, or an alkenyl group having 2 to 40 carbon atoms.

Halogen herein may be fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group having 1 to 40 carbon atoms may be a straight chain, branched chain, or cyclic alkyl group. Specifically, the alkyl group having 1 to 40 carbon atoms is a straight chain alkyl group having 1 to 40 carbon atoms; A straight-chain alkyl group having 1 to 20 carbon atoms; A straight-chain alkyl group having 1 to 10 carbon atoms; A branched or cyclic alkyl group having 3 to 40 carbon atoms; A branched or cyclic alkyl group having 3 to 20 carbon atoms; Or it may be a branched or cyclic alkyl group having 3 to 10 carbon atoms. More specifically, the alkyl group having 1 to 40 carbon atoms is a methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, t-butyl group, n-pentyl group, iso-pentyl group, neo-pentyl group or cyclohexyl group. However, it is not limited thereto.

In the present specification, a heteroalkyl group having 1 to 40 carbon atoms may be one or more carbons of the alkyl group, each independently substituted with O, N, Si or S. For example, as an example of a straight chain alkyl group, a heteroalkyl group in which 1 carbon of n-butyl group is substituted with O is an n-propoxy group, a heteroalkyl group substituted with N is an n-propylamino group, and a heteroalkyl group substituted with Si is n -It is a propyl silyl group, and the heteroalkyl group substituted by S is an n-propylthio group. And, as an example of a branched chain alkyl group, the heteroalkyl group in which the first carbon of the neo-pentyl group is substituted with O is a t-butoxy group, the heteroalkyl group substituted with N is a t-butylamino group, and the heteroalkyl group substituted with Si is t -Butylsilyl group, and the heteroalkyl group substituted with S is a t-butylthio group. In addition, as an example of the cyclic alkyl group, the heteroalkyl group in which the second carbon of the cyclohexyl group is substituted with O is a 2-tetrahydropyranyl group, and the heteroalkyl group substituted with N is a 2-piperidinyl group, The heteroalkyl group substituted with Si is a 1-sila-cyclohexyl group, and the heteroalkyl group substituted with S is a 2-tetrahydrothiopyranyl group. Specifically, a heteroalkyl group having 1 to 40 carbon atoms is a straight chain, branched chain or cyclic hydroxyalkyl group having 1 to 40 carbon atoms; A straight chain, branched chain or cyclic alkoxy group having 1 to 40 carbon atoms; A straight chain, branched chain or cyclic alkoxyalkyl group having 2 to 40 carbon atoms; A straight chain, branched chain or cyclic aminoalkyl group having 1 to 40 carbon atoms; A straight chain, branched chain or cyclic alkylamino group having 1 to 40 carbon atoms; A straight chain, branched chain or cyclic alkylaminoalkyl group having 1 to 40 carbon atoms; A straight chain, branched chain or cyclic silylalkyl (oxy) group having 1 to 40 carbon atoms; A straight chain, branched chain or cyclic alkyl (oxy) silyl group having 1 to 40 carbon atoms; A straight chain, branched chain or cyclic alkyl (oxy) silylalkyl (oxy) group having 1 to 40 carbon atoms; A straight chain, branched chain or cyclic mercaptoalkyl group having 1 to 40 carbon atoms; A straight chain, branched chain or cyclic alkylthio group having 1 to 40 carbon atoms; Or it may be a straight chain, branched chain, or cyclic alkylthioalkyl group having 2 to 40 carbon atoms. More specifically, the heteroalkyl group having 1 to 40 carbon atoms is hydroxymethyl group, methoxy group, ethoxy group, n-propoxy group, iso-propoxy group, t-butoxy group, cyclohexoxy group, methoxymethyl group, iso-pro Foxymethyl group, cyclohexoxymethyl group, 2-tetrahydropyranyl group, aminomethyl group, methylamino group, n-propylamino group, t-butylamino group, methylaminopropyl group, 2-piperidinyl group, n- Propylsilyl group, trimethylsilyl group, dimethylmethoxysilyl group, t-butylsilyl group, 1-sila-cyclohexyl group, n-propylthio group, t-butylthio group or 2-tetra And hydrothiopyranyl (2-tetrahydrothiopyranyl) groups. However, it is not limited thereto.

In the present specification, an alkenyl group having 2 to 40 carbon atoms may be a straight chain, branched chain, or cyclic alkenyl group. Specifically, an alkenyl group having 2 to 40 carbon atoms is a straight chain alkenyl group having 2 to 40 carbon atoms; A straight-chain alkenyl group having 2 to 20 carbon atoms; A straight-chain alkenyl group having 2 to 10 carbon atoms; A branched alkenyl group having 3 to 40 carbon atoms; A branched alkenyl group having 3 to 20 carbon atoms; A branched alkenyl group having 3 to 10 carbon atoms; A cyclic alkenyl group having 5 to 40 carbon atoms; A cyclic alkenyl group having 5 to 20 carbon atoms; Or it may be a cyclic alkenyl group having 5 to 10 carbon atoms. More specifically, the alkenyl group having 2 to 40 carbon atoms may be an ethenyl group, a propenyl group, a butenyl group, a pentenyl group, or a cyclohexenyl group. However, it is not limited thereto.

In this specification, the aryl group having 6 to 60 carbon atoms may be a monocyclic aryl group or a polycyclic aryl group. Specifically, an aryl group having 6 to 60 carbon atoms is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it may be a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms. More specifically, the aryl group having 6 to 60 carbon atoms may be a phenyl group, a biphenyl group or a terphenyl group as a monocyclic aryl group, and a naphthyl group, anthracenyl group, phenanthryl group, triphenylenyl group, pyre as a polycyclic aryl group. It may be a nil group, perylenyl group, chrysenyl group or fluorenyl group. However, it is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure. When the fluorenyl group is substituted,

It can be back. However, it is not limited thereto.

In the present specification, the heteroaryl group having 2 to 60 carbon atoms may be one or more carbons of the aryl group, each independently substituted with O, N, Si or S. For example, the heteroaryl group in which the 9th carbon of the fluorenyl group is substituted with O is a dibenzofuranyl group, the heteroaryl group substituted with N is a carbazoli group, and the heteroaryl group substituted with Si is a 9-sila-floorenyl group , S-substituted heteroaryl group is a dibenzothiophenyl group. Specifically, a heteroaryl group having 2 to 60 carbon atoms is a heteroaryl group having 2 to 30 carbon atoms; Or it may be a heteroaryl group having 2 to 20 carbon atoms. More specifically, a heteroaryl group having 2 to 60 carbon atoms is a thiophene group, a furan group, a pyrrol group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, Triazine group, triazole group, acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyra Genyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group (phenanthroline ), A thiazolyl group, an isooxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

In the present specification, the arylene group means a divalent organic group from which any one hydrogen radical of the above-described aryl group is removed, and the heteroarylene group means a divalent organic group from which any hydrogen radical of the above-described heteroaryl group is removed. .

In Formula 1-1, one of R ² and R ³ and one of R ⁴ and R ⁵ are cyano groups, and R ¹ ; The other of R ² and R ³ ; And the other of R ⁴ and R ⁵ are each independently a cyano group; An aryl group having 6 to 20 carbon atoms substituted with one or more selected from the group consisting of halogen and cyano groups; Or it may be a heteroaryl group having 2 to 20 carbon atoms including one or more of O, N, Si and S substituted with one or more substituents selected from the group consisting of halogen and cyano groups.

Specifically, in Formula 1-1, R ² and R ⁴ are cyano groups, and R ¹ , R ³ and R ⁵ may each independently be a phenyl group substituted with one or more selected from the group consisting of halogen and cyano groups. .

More specifically, the compound represented by Formula 1-1 may be the following compound.

In Formula 1-2, one of R ¹⁵ and R ¹⁶ and one of R ¹⁷ and R ¹⁸ are each independently a halogen, a cyano group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 1 to 5 carbon atoms. An aryl group having 6 to 20 carbon atoms substituted with at least one member selected from the group consisting of haloalkoxy groups; Or one or more of O, N, Si and S substituted with one or more selected from the group consisting of halogen, cyano group, alkyl group having 1 to 5 carbon atoms, haloalkyl group having 1 to 5 carbon atoms and haloalkoxy group having 1 to 5 carbon atoms. It is a heteroaryl group having 2 to 20 carbon atoms, and the other of R ¹⁵ and R ¹⁶ and the other of R ¹⁷ and R ¹⁸ may each independently be hydrogen, halogen, or a haloalkyl group having 1 to 5 carbon atoms.

In Formula 1-2, Y ³ and Y ⁴ are CR ¹⁹ , and R ¹⁹ are each independently a cyano group; An aryl group having 6 to 20 carbon atoms substituted with one or more selected from the group consisting of halogen and cyano groups; Or it may be a heteroaryl group having 2 to 20 carbon atoms including one or more of O, N, Si and S substituted with one or more substituents selected from the group consisting of halogen and cyano groups.

The compound represented by Chemical Formula 1-2 may be selected from the group consisting of the following compounds.

The compound represented by Chemical Formula 1-2 may be prepared by the same method as in Scheme A below. The manufacturing method may be more specific in the manufacturing examples to be described later.

[Scheme A]

In Reaction Scheme A, R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ are as described above, and additional substituents may be further included.

The reaction is a reaction for introducing malononitrile, and is preferably performed in the presence of a palladium catalyst and a base. In addition, the type of reactor and catalyst used in the above reaction formula can be appropriately changed. The manufacturing method may be more specific in the manufacturing examples to be described later.

In Formula 2, Ar ¹ is benzene, naphthalene, biphenyl, terphenyl, triphenylene, phenylnaphthalene, 9,9-dimethylfluorene, 9,9-diphenylfluorene and spiro [fluorene-9,9 ' -Fluorene] may be a monovalent residue derived from arenes selected from the group consisting of.

In Formula 2, L ¹ and L ² may each independently be a divalent residue derived from arenes selected from the group consisting of benzene, naphthalene, biphenyl, and terphenyl.

일 때, Ar⁴ 및 Ar⁵는 각각 독립적으로 벤젠, 나프탈렌, 바이페닐 및 터페닐로 구성된 군에서 선택된 아렌 유래의 1가 잔기일 수 있다. In Formula 2, Ar ² and / or Ar ³ is

In this case, Ar ⁴ and Ar ⁵ may each independently be a monovalent residue derived from arenes selected from the group consisting of benzene, naphthalene, biphenyl and terphenyl.

일 때, Ar⁶는 페닐일 수 있다. In Formula 2, Ar ² and / or Ar ³ is

, Ar ⁶ may be phenyl.

The compound represented by Chemical Formula 2 may be a compound represented by Chemical Formula 2-1.

[Formula 2-1]

In Chemical Formula 2-1,

Ar ¹ to Ar ³ and X ¹ are the same as in Chemical Formula 2,

L ³ to L ⁶ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted O, N, Si and S containing at least one of 2 to 50 carbon atoms. It is a heteroarylene group.

The compound represented by Chemical Formula 2 may be selected from the group consisting of the following compounds.

The compound represented by Chemical Formula 2 may be prepared by the same method as in Scheme B below. The manufacturing method may be more specific in the manufacturing examples to be described later.

[Scheme B]

In Scheme B, X ¹ , L ¹ , L ² , Ar ¹ and Ar ² are as described above, and additional substituents may be further included.

The reaction is a Suzuki coupling reaction, and is preferably performed in the presence of a palladium catalyst and a base. In addition, the type of reactor and catalyst used in the above reaction formula can be appropriately changed. The manufacturing method may be more specific in the manufacturing examples to be described later.

The organic light emitting device of the present invention includes an anode; A cathode provided opposite the anode; And one or more organic material layers provided between the anode and the cathode. The organic material layer has a multilayer structure in which three or more organic material layers are stacked. Specifically, the organic material layer includes a hole injection layer adjacent to the anode, a hole transport layer provided on the hole injection layer, and a light emitting layer provided on the hole transport layer.

In the present specification, the hole injection layer refers to a layer that receives holes from the anode and transfers them to other organic material layers as an organic material layer contacting the anode of the organic light emitting device. Accordingly, the hole injection layer may also be referred to as a charge generating layer. The hole transport layer is an organic material layer provided on the hole injection layer of the organic light emitting device, and refers to a layer that transmits holes transferred from the hole injection layer to the light emitting layer and prevents electrons transmitted from the light emitting layer from being transmitted to the hole injection layer. Accordingly, the hole transport layer may also be referred to as an electron suppressing layer.

In addition, the organic light emitting device may include an electron transport layer and an electron injection layer between the light emitting layer and the cathode. However, the structure of the organic light emitting device is not limited to this, and may include fewer organic material layers.

The organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate (normal type). Further, the organic light emitting device according to the present invention 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 the organic light emitting device according to an embodiment of the present invention is illustrated in FIG. 1.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 It is done. In this structure, the compound selected from the group consisting of compounds represented by Formulas 1-1 to 1-2 is included in the hole injection layer 5, and the compound represented by Formula 2 is a hole transport layer 6 It can be included to improve the low driving voltage and / or life characteristics.

The organic light emitting device according to the present invention includes a compound selected from the group consisting of compounds represented by Formulas 1-1 to 1-2 in the hole injection layer, and a compound represented by Formula 2 in the hole transport layer. It can be made of materials and methods known in the art, except as noted. Further, the plurality of organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking one electrode of an anode and a cathode, an organic material layer, and another electrode of the anode and a cathode on a substrate. At this time, a positive electrode is formed by depositing a metal or conductive metal oxide or an alloy of these on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. Then, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and a material that can be used as a cathode is deposited 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 a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

In addition, the compounds represented by Chemical Formulas 1-1 to 1-2 and the compounds represented by Chemical Formula 2 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 application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

The positive electrode material is preferably a material having a large work function so that hole injection into the organic material layer is smooth. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO: Al or SNO ₂ : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into an 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; There is a multilayer structure material such as LiF / Al or LiO ₂ / Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode, and a compound selected from the group consisting of compounds represented by Chemical Formulas 1-1 to 1-2 is used as a material for forming the hole injection layer. Since the compounds represented by Chemical Formulas 1-1 to 1-2 have been described above in detail, detailed descriptions thereof will be omitted.

The compounds represented by Chemical Formulas 1-1 to 1-2 have the ability to transport holes and thus have a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and an electron injection layer of exciton generated in the light emitting layer Alternatively, the movement of the electron injection material can be prevented. In addition, the compounds of Formulas 1-1 to 1-2 are excellent in thin film forming ability.

Meanwhile, the hole injection layer may further include a hole injection material known in the art to which the present invention pertains, in addition to the compounds of Formulas 1-1 to 1-2. As such a hole injection material, it is preferable that the highest occupied molecular orbital (HOMO) is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene. There are organic-based organic materials, anthraquinones, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As a material for forming the hole transport layer, a compound represented by Chemical Formula 2 is used. Since the compound represented by Chemical Formula 2 has been described in detail above, a detailed description is omitted here.

The compound represented by Chemical Formula 2 is suitable for transporting holes from the anode or the hole injection layer and transferring them to the light emitting layer because the mobility of the holes is large.

Meanwhile, the hole transport layer may further include a hole transport material known in the art to which the present invention pertains, in addition to the compound represented by Chemical Formula 2. Specific examples of the hole transport material include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in the visible region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

The light emitting layer may include a host material and a dopant material. The host material may be 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, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes arylamino groups such as pyrene, anthracene, chrysene, periplanten, and the substituted or unsubstituted styrylamine compound. A compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons Suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited to these. 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 those that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, an excellent electron injection effect on a light emitting layer or a light emitting material, and injects holes of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

The organic light emitting device according to the present invention may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.

Preparation of the compounds represented by Formulas 1-1 to 1-2, the compounds represented by Formula 2, and the organic light emitting device including the same will be described in detail in the Examples below. However, the following examples are intended to illustrate the invention, and the scope of the invention is not limited by them.

Manufacturing example

Manufacturing example  1: Synthesis of Compound 1-2-1

(1) Synthesis of Intermediate A

[Scheme 1-1]

Compound a Intermediate A

18.5 g (0.038 mol) of 1,4-dibromo-2,5-diiodobenzene (4-trifluoromethoxy) phenylboronic acid 16.0 g (0.078 mol), tetrakis (triphenylphosphine) palladium (0 ) 2.2 g, 2M potassium carbonate 114 ml, tetrahydrofuran 360 ml, and reflux stirring for 8 hours under nitrogen. After cooling, it was extracted with water and dichloromethane, and further separated by a silica gel column (developing solvent: ethyl acetate / hexane = 10/1) to obtain 8.0 g (38.0%) of a white solid (Compound a). Next, 8.5 g (15.3 mmol) of this white solid (compound a), 9.0 g (76.6 mmol) of nickel powder, 5.0 g (30.4 mmol) of potassium iodide, and 0.19 g (0.77 mmol) of iodine 20 ml of dimethylformaldehyde The mixture was mixed with and refluxed and stirred under argon conditions for 24 hours. After completion of the reaction, 100 ml of 3% dilute hydrochloric acid and 40 ml of diethyl ether were added. The nickel solid was removed, extracted with water and diethyl ether, and separated by a silica gel column (developing solvent: ethyl acetate / hexane = 10/1) to obtain 5.4 g (54.0%) of a white solid (Intermediate A).

(2) Synthesis of Compound 1-2-1

[Scheme 1-2]

Intermediate A Compound 1-2-1

After dissolving 1.7 g of malononitrile in 60 ml of 1,2-dimethoxyethane, it was cooled to -10 ° C under nitrogen conditions. Sodium hydride (1.3 g) was added dropwise in 4 portions, stirred at room temperature for 20 minutes, and then cooled to 0 ° C. 2 ', 5'-diiodo-4,4' '-bis (trifluoromethoxy) -1,1': 4 ', 1' '-terphenyl (Intermediate A) 3.60g (5.54mmol) and tetrakis (Triphenylphosphine) Palladium 0.64g (0.55mmol) was added and stirred for 8 hours under reflux conditions. Then, it was separated with dilute hydrochloric acid and ethyl acetate, dried over anhydrous sodium sulfate, and filtered. After distilling ethyl acetate under reduced pressure, it was separated by a silica gel column (developing solvent: ethyl acetate) to obtain 1.8 g (62.0%) of a solid.

Next, 1.8 g of the solid was dissolved in 30 ml of acetonitrile, and then 20 ml of diluted bromine water was added. After stirring for 20 minutes, excess distilled water was added to filter the precipitated solid and washed with distilled water. Then, it was recrystallized with acetonitrile to obtain 1.20 g of solid (Compound 1-2-1).

Manufacturing example  2: Synthesis of Compound 1-2-2

(1) Synthesis of Intermediate B

[Scheme 1-3]

Compound b-1 Compound b-2 Compound b-3 Intermediate B

Lithium 2,2,6,6-tetramethylpiperidide (100mmol) was dissolved in 120ml of tetrahydrofuran, and then cooled to -78 ° C under nitrogen. 27.2 g (100 mmol) of 1,4-dibromo-2,5-difluorobenzene was dissolved in 60 ml of tetrahydrofuran, and intubated under nitrogen conditions at -78 ° C, and the temperature was raised to room temperature. Then, the reaction was terminated with an aqueous sodium thiosulfate solution, separated with ethyl acetate, dried over anhydrous sodium sulfate, and filtered. Separated by silica gel column (developing solvent: ethyl acetate / hexane = 10/1) to obtain 26.3 g (66.0%) of a solid (Compound b-1).

Next, 2,2,6,6-tetramethylpiperidide lithium (100mmol) was dissolved in 120ml of tetrahydrofuran, and then cooled to -78 ° C under nitrogen conditions. Dissolve 39.8 g (100 mmol) of 1,4-dibromo-2,5-difluoro-3-iodobenzene (Compound b-1) in 60 ml of tetrahydrofuran, intubate at -78 ° C under nitrogen conditions. , The temperature was raised to room temperature. Then, the reaction was terminated with an aqueous sodium thiosulfate solution, separated with ethyl acetate, dried over anhydrous sodium sulfate, and filtered. Separated by silica gel column (developing solvent: ethyl acetate / hexane = 10/1) to obtain 30.3 g (58.0%) of a solid (Compound b-2).

Next, 19.9 g (0.038 mol) of 1,4-dibromo-2,5-difluoro-3,6-diiodobenzene (compound b-2) (2-fluoro-4-trifluoromethoxy) The mixture was mixed with 17.5 g of phenylboronic acid (0.078 mol), 2.2 g of tetrakis (triphenylphosphine) palladium (0), 114 ml of 2M potassium carbonate, and 360 ml of tetrahydrofuran, and refluxed and stirred under nitrogen conditions for 12 hours. After cooling, it was extracted with water and dichloromethane, and further separated by a silica gel column (developing solvent: ethyl acetate / hexane = 10/1) to obtain 7.8 g (34.7%) of a white solid (Compound b-3).

Next, 9.06 g (15.3 mmol) of this white solid (compound b-3), 9.0 g (76.6 mmol) of nickel powder, 5.0 g (30.4 mmol) of potassium iodide, and 0.19 g (0.77 mmol) of iodine in dimethylform The mixture was mixed with 20 ml of aldehyde and refluxed and stirred under argon conditions for 24 hours. After completion of the reaction, 100 ml of 3% dilute hydrochloric acid and 40 ml of diethyl ether were added. The nickel solid was removed, extracted with water and diethyl ether, and separated by a silica gel column (developing solvent: ethyl acetate / hexane = 10/1) to obtain 3.2 g (30.4%) of a white solid (Intermediate B).

(2) Synthesis of Compound 1-2-2

[Scheme 1-4]

Intermediate B compound 1-2-2

2 ', 5'-diiodo-4,4' '-bis (trifluoromethoxy) -1,1': 4 ', 1' '-terphenyl in the synthesis of compound 1-2-1 (Intermediate A) 3.60 g of 2 ', 5'-difluoro-3', 6'-diiodo-4,4 ''-bis (trifluoromethoxy) -1,1 ': 4', 1 ''-terphenyl ( Intermediate B) 0.84 g of solid (Compound 1-2-2) was obtained by reacting and purifying in the same manner except that 3.8 g was changed. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at M / Z = 560.

Manufacturing example  3: Synthesis of Compound 1-2-3

[Scheme 1-5]

Intermediate C compound 1-2-3

2 ', 5'-diiodo-4,4' '-bis (trifluoromethoxy) -1,1': 4 ', 1' '-terphenyl in the synthesis of compound 1-2-1 (Intermediate A) 3.60 g of 2,2 '-(4,4' '-bis (trifluoromethoxy)-[1,1': 4 ', 1' '-terphenyl] -2', 5'-diyl) bis ( 2- (pentafluorophenyl) acetonitrile) (Intermediate C) 0.8 g of solid (Compound 1-2-3) was obtained by reaction and purification in the same manner, except that it was changed to 2.2 g. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at M / Z = 806.

Manufacturing example  4: Synthesis of Compound 2-1

[Scheme 2-1]

Compound 3,6-dibromo-9-phenyl-9H-carbazole (5.67 g, 14.21 mmol), and compound a1 (8.94 g, 31.26 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere. Then, 2M potassium carbonate aqueous solution (120 mL) was added, tetrakis- (triphenylphosphine) palladium (0.49 g, 0.43 mmol) was added, followed by heating and stirring for 3 hours. The temperature was reduced to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 mL of ethyl acetate to prepare compound 2-1 (6.69 g, 64%).

MS [M + H] ⁺ = 730

Manufacturing example  5: Synthesis of Compound 2-2

[Scheme 2-2]

Compound 3,6-dibromo-9- (naphthalen-2-yl) -9H-carbazole (5.32 g, 11.85 mmol), and compound a1 (7.46 g, 26.07 mmol) are tetrahydro in a 500 mL round-bottom flask in a nitrogen atmosphere. After completely dissolving in 240 mL of furan, 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis- (triphenylphosphine) palladium (0.41 g, 0.36 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was reduced to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate 230 mL to prepare compound 2-2 (5.57 g, 60%).

MS [M + H] ⁺ = 780

Examples and comparative examples

(1) Preparation of Comparative Example 1-1

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as a detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice for 10 minutes with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner. In addition, after the substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum evaporator.

A hole injection layer was formed by thermally vacuum-depositing a compound of the following compound [HI1] and the following compound 1-1-1 to a ratio of 98: 2 (molar ratio) to a thickness of 100 MPa on the prepared ITO transparent electrode, which was prepared in this way (p- doping matrix).

A hole transport layer was formed by vacuum-depositing the following compound [HT1] (1150Å), which is a material for transporting holes on the hole injection layer. Subsequently, an electron blocking layer was formed by vacuum-depositing the following compound [EB1] with a thickness of 50 mm 2 on the hole transport layer.

Subsequently, a light emitting layer was formed by vacuum-depositing the following compound [BH] and compound [BD] at a weight ratio of 50: 1 with a thickness of 200 mm 2 on the electron blocking layer. On the light emitting layer, the compound [HB 1] was vacuum-deposited with a thickness of 50 mm 2 on the hole transport layer to form a hole blocking layer. Subsequently, on the hole blocking layer, the compound [ET1] and the compound [LiQ] (Lithium Quinolate) were vacuum-deposited at a weight ratio of 1: 1 to form a layer that simultaneously injected and transported electrons to a thickness of 310 MPa.

On the electron injection and transport layer, lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 2,000 순차적 were sequentially deposited to form a negative electrode. In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride of the negative electrode was maintained at a deposition rate of 0.3 Å / sec and aluminum at 2 Å / sec, and the vacuum degree during deposition was 2 진공 10-7. An organic light emitting device was manufactured by maintaining ~ 5 ⅹ10-6 torr.

(2) Preparation of Comparative Examples 1-2 to 1-16 and Examples 1-1 to 1-8

In Comparative Example 1-1, an organic light emitting device was manufactured in the same manner as in Comparative Example 1-1, except that the components shown in Table 1 were used as components of the hole injection layer and the hole transport layer.

division Hole injection layer Hole transport layer Voltage
(V) efficiency
(cd / A) T95
(hr) Comparative Example 1-1 [HI1]: 1-1-1: = 98: 2 HT1 4.26 5.85 115 Comparative Example 1-2 [HI1]: 1-1-1: = 98: 2 HT2 4.38 5.71 100 Comparative Example 1-3 [HI1]: 1-1-1: = 98: 2 HT3 4.25 5.82 115 Comparative Example 1-4 [HI1]: 1-1-1: = 98: 2 HT4 4.24 5.81 125 Comparative Example 1-5 1-2-1 HT1 4.40 5.63 130 Comparative Example 1-6 1-2-2 HT1 4.45 5.64 135 Comparative Example 1-7 1-2-3 HT1 4.48 5.59 140 Comparative Example 1-8 1-2-1 HT2 4.56 5.42 130 Comparative Example 1-9 1-2-1 HT3 4.42 5.65 140 Comparative Example 1-10 1-2-1 HT4 4.39 5.68 140 Comparative Example 1-11 1-2-2 HT2 4.58 5.45 135 Comparative Example 1-12 1-2-2 HT3 4.44 5.65 130 Comparative Example 1-13 1-2-2 HT4 4.38 5.63 145 Comparative Example 1-14 1-2-3 HT2 4.52 5.47 135 Comparative Example 1-15 1-2-3 HT3 4.48 5.57 145 Comparative Example 1-16 1-2-3 HT4 4.39 5.56 145 Example 1-1 [HI1]: 1-1-1: = 98: 2 Compound 2-1 3.82 6.25 155 Example 1-2 [HI1]: 1-1-1: = 98: 2 Compound 2-2 3.82 6.27 150 Example 1-3 1-2-1 Compound 2-1 4.08 6.06 160 Example 1-4 1-2-2 Compound 2-1 4.02 6.04 170 Example 1-5 1-2-3 Compound 2-1 4.05 6.03 165 Example 1-6 1-2-1 Compound 2-2 4.01 6.09 165 Example 1-7 1-2-2 Compound 2-2 4.06 6.07 175 Example 1-8 1-2-3 Compound 2-2 4.003 6.36 165

The blue organic light emitting devices of Comparative Examples 1-1 to 1-4 use a hole injection layer with [HI1]: 1-1-1: = 98: 2 (molar ratio), and the compounds of compounds HT1 to HT4 are used as the hole transport layer. It shows the characteristics of the basic p-doping device with the device structure used.

In the blue organic light emitting diodes of Comparative Examples 1-5 to 1-16, a compound of 1-2-1 to 1-2-3 was used as a hole injection layer, and a compound of compounds HT1 to HT4 was used as a hole transport layer to form a basic layer. It shows the characteristics of the type device.

In Examples 1-1 and 1-2, when the compounds of 2-1 and 2-2 were used as the hole transport layer instead of the compounds of HT-1 to HT-4 in the basic p-doping device, the luminous efficiency and driving of the organic light emitting device were driven. It can be seen that the voltage and life can be improved.

Examples 1-3 to 1-8 are 2-1 and 2- instead of the compounds of HT-1 to HT-4 in the layer type device using the compound of 1-2-1 to 1-2-3 as the hole injection layer. It can be seen that when the compound of 2 is used as the hole transport layer, it is possible to improve the luminous efficiency, driving voltage, and lifetime of the organic light emitting device.

HT1 having a Homo value of about 5.2eV and HT-3 having a degree of 5.8eV have a large barrier to adjacent layers, resulting in a large voltage increase. In the comparative example using a material of HT2 in which an amine group is directly connected to positions 3 and 6 of carbazole, the characteristics of the device were most poorly measured. Unlike Formula 2 of claim 1, HT4 is a meta-linked structure, and its efficiency is relatively low.

Through this, a compound of Formula 1-2 (including Tetracyanoquinodimethane: TCNQ core and derivatives thereof as a core) according to one embodiment of the present specification is used as a layer type hole injection layer material, or the compound of Formula 1-1 is p- It can be seen that in the device structure used as the doping hole injection layer material, the driving voltage, luminous efficiency, and lifetime characteristics of the blue organic light emitting device formed by combining the compound of Formula 2 as the hole transport layer can be improved.

1: Substrate
2: anode
4: Cathode
5: hole injection layer
6: hole transport layer
7: emitting layer
8: electron transport layer

Claims (13)

anode; A cathode provided opposite the anode; And one or more organic material layers provided between the anode and the cathode,
The organic material layer includes a hole injection layer adjacent to the anode, a hole transport layer provided on the hole injection layer, and a light emitting layer provided on the hole transport layer,
The hole injection layer includes a compound selected from the group consisting of compounds represented by the following Chemical Formulas 1-1 to 1-2,
The hole transport layer comprises a compound represented by the following formula 2-1, an organic light emitting device:
[Formula 1-1] [Formula 1-2]

In Chemical Formula 1-1,
R ¹ to R ⁵ are each independently a cyano group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted O, N, Si and S containing at least one of 2 to 60 carbon atoms. Heteroaryl group,
In Chemical Formula 1-2,
R ¹⁵ to R ¹⁸ are each independently hydrogen, halogen, cyano group, alkyl group having 1 to 40 carbon atoms, haloalkyl group having 1 to 40 carbon atoms, haloalkoxy group having 1 to 40 carbon atoms, substituted or unsubstituted 6 to 60 carbon atoms. An aryl group, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms containing at least one of O, N, Si and S,
Y ³ and Y ⁴ are each independently CR ¹⁹ or N,
R ¹⁹ are each independently a cyano group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms including one or more of O, N, Si and S. ego,
[Formula 2-1]

In Chemical Formula 2-1,
Ar ¹ is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms including one or more of O, N, Si and S,
X ¹ is a non-bonding, single-bonding, alkylene group having 1 to 3 carbon atoms, O or S,
L ³ to L ⁶ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted O, N, Si and S containing at least one of 2 to 50 carbon atoms. A heteroarylene group,
Ar ² and Ar ³ are each independently a substituent selected from the group consisting of the following substituents,

Ar ⁴ to Ar ⁶ are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms containing at least one of O, N, Si and S ego,
X ² and X ³ are each independently a single bond, O or S.
The method of claim 1, wherein one of R ² and R ³ and one of R ⁴ and R ⁵ is a cyano group,
R ¹ ; The other of R ² and R ³ ; And the other of R ⁴ and R ⁵ are each independently a cyano group; An aryl group having 6 to 20 carbon atoms substituted with one or more selected from the group consisting of halogen and cyano groups; Or a heteroaryl group having 2 to 20 carbon atoms containing at least one of O, N, Si and S substituted with one or more substituents selected from the group consisting of halogen and cyano groups, an organic light emitting device.
The method according to claim 1, wherein R ² and R ⁴ are cyano groups,
R ¹ , R ³ and R ⁵ are each independently an phenyl group substituted with one or more selected from the group consisting of halogen and cyano groups, an organic light-emitting device.
The organic light emitting device of claim 1, wherein the compound represented by Chemical Formula 1-1 is the following compound:

.
The method of claim 1, wherein one of R ¹⁵ and R ¹⁶ and one of R ¹⁷ and R ¹⁸ are each independently a halogen, cyano group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 1 to 5 carbon atoms. An aryl group having 6 to 20 carbon atoms substituted with at least one member selected from the group consisting of haloalkoxy groups; Or one or more of O, N, Si and S substituted with one or more selected from the group consisting of halogen, cyano group, alkyl group having 1 to 5 carbon atoms, haloalkyl group having 1 to 5 carbon atoms and haloalkoxy group having 1 to 5 carbon atoms. Heteroaryl group having 2 to 20 carbon atoms containing,
The other of R ¹⁵ and R ¹⁶ and the other of R ¹⁷ and R ¹⁸ are each independently hydrogen, halogen or a haloalkyl group having 1 to 5 carbon atoms, an organic light-emitting device.
The method according to claim 1, Y ³ and Y ⁴ is CR ¹⁹ ,
R ¹⁹ are each independently a cyano group; An aryl group having 6 to 20 carbon atoms substituted with one or more selected from the group consisting of halogen and cyano groups; Or a heteroaryl group having 2 to 20 carbon atoms containing at least one of O, N, Si and S substituted with one or more substituents selected from the group consisting of halogen and cyano groups, an organic light emitting device.
The organic light emitting device of claim 1, wherein the compound represented by Chemical Formula 1-2 is selected from the group consisting of the following compounds:

.
The method of claim 1, wherein Ar ¹ is benzene, naphthalene, biphenyl, terphenyl, triphenylene, phenylnaphthalene, 9,9-dimethylfluorene, 9,9-diphenylfluorene and spiro [fluorene-9, 9'-fluorene] is an organic light-emitting device, which is a monovalent residue derived from arenes selected from the group consisting of.
◈ Claim 9 was abandoned when payment of the set registration fee was made.◈ The organic light emitting device according to claim 1, wherein L ¹ and L ² are each independently a divalent residue derived from arenes selected from the group consisting of benzene, naphthalene, biphenyl and terphenyl.
The organic light emitting device according to claim 1, wherein Ar ⁴ and Ar ⁵ are each independently a monovalent residue derived from arenes selected from the group consisting of benzene, naphthalene, biphenyl and terphenyl.
The organic light emitting device according to claim 1, wherein Ar ⁶ is phenyl.
delete The organic light emitting device of claim 1, wherein the compound represented by Chemical Formula 2-1 is selected from the group consisting of the following compounds:

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