KR20160102881A - organic light-emitting diode with low operating voltage and High efficiency - Google Patents

Abstract

The present invention relates to an organic light emitting element which can be operated at a low voltage, and has high efficiency. More particularly, the organic light emitting element comprises: a first electrode; a second electrode facing the first electrode; and a luminous layer interposed between the first electrode and the second electrode. The luminous layer comprises compounds represented by chemical formula A and chemical formula D. The structures of the chemical formula A and chemical formula D are the same as described in the specification.

Description

(Organic light-emitting diode with low operating voltage and high efficiency)

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic light emitting device capable of being driven at a low voltage and having high efficiency, and more particularly, to an organic light emitting device including a host material and a dopant material having a specific structure used as a light emitting layer in an organic light emitting device.

The organic light emitting diode (OLED) is a display using a self-luminous phenomenon. The organic light emitting diode (OLED) has a wide viewing angle and is thinner and lighter than a liquid crystal display and has a fast response speed. ) Applications for display or illumination are expected.

A material used as an organic material layer in the organic light emitting device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism .

On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuating effect. A host-dopant system can be used as a light emitting material to increase the efficiency of light emission through the transition.

When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant used.

As a conventional art relating to a dopant compound in such a light emitting layer, Japanese Patent Application Laid-Open No. 10-1132635 (Apr. 04, 2012) discloses an organic light emitting device comprising an arylamine-bonded pyrene derivative. Japanese Patent Application Laid- (December, 2011) discloses an organic light emitting device having excellent brightness and long lifetime using an anthracene derivative as a host compound.

Korean Patent Application No. 10-2013-012194 discloses an organic luminescent device including an anthracene derivative usable as a fluorescence host as a prior art related to a host compound in a luminescent layer.

However, despite the prior art including the above-mentioned prior arts, there is a continuing demand for development of an organic light emitting device capable of driving at a low voltage and exhibiting high efficiency.

Korean Registered Patent No. 10-1132635 (Apr. 03, 2012)

Korean Patent Registration No. 10- 1092006 (December, 2011)

Korean Patent Application No. 10-2013-0121947

Accordingly, it is an object of the present invention to provide a novel organic light emitting diode (OLED) capable of being driven at a low voltage through a dopant and a host having a specific structure and exhibiting high efficiency.

According to an aspect of the present invention, there is provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And an emission layer interposed between the first electrode and the second electrode,

A pyrene derivative wherein the light emitting layer is represented by the following formula (A); And an anthracene derivative represented by the following formula (D).

(A)

In the above formula (A)

R 1 to R 6 are the same or different from each other and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, A substituted or unsubstituted C1 to C30 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, A substituted or unsubstituted C2-C30 hetero cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group , A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted C1 to C30 alkyl A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C6-C30 aryl group,

Hydrogen or deuterium is bonded to the carbon of the aromatic ring to which the substituent of R ₁ to R ₆ is not bonded,

P, q, r, and s are integers of 0 to 3, and when they are each 2 or more, each of R1 to R4 is the same or different,

R ₁ to R ₄ are connected to adjacent X ₁ to X _{8 ,} or when R ₁ to R ₄ are each 2 or more, R ₁ to R ₄ are connected to each other to form an alicyclic or aromatic group And the carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from N, O, P, Si, S, Ge, Se and Te ;

X ₁ to X ₈ are the same or different from each other and are each independently a substituent selected from hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

At least X _{1 ,} X _2, X ₅ and X ₆ of X ₁ to X ₈ are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms.

 [Chemical Formula D]

In the above formula (D)

Substituents R < ₁₁ > to R < ₁₅ &

A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, , A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number of 6 to 30 A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylamine group, A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S A substituted or unsubstituted C 1 -C 30 silyl group, a substituted or unsubstituted C 1 -C 30 germanium group, a substituted or unsubstituted C 1 -C 30 boron atom, a substituted or unsubstituted C 1 -C 30 aryl group, a cyano group, a nitro group, a halogen group, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aliphatic group having 1 to 30 carbon atoms, a substituted or unsubstituted aliphatic group having 1 to 30 carbon atoms, a carbonyl group, a phosphoryl group, an amino group, a thiol group, a hydroxy group, a selenium group, a tellurium group,

Hydrogen is bonded to the carbon of the aromatic ring to which the substituent of R ₁₁ to R ₁₅ is not bonded,

The linking group L is a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms;

j is an integer of 0 to 2, and when j is 2, each L is the same or different from each other,

k is an integer of 1 to 5,

1 to n are the same or different from each other and independently of one another are an integer of from 1 to 4,

o is an integer of 1 to 3,

When each of k to o is 2 or more, each of R ₁₁ to R ₁₅ is the same as or different from each other,

&Quot; *** " of X is a bonding site to be bonded to the linking group L,

The "substituted" in the "substituted or unsubstituted" in the above [Formula A] and [Formula D] is a substituent selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, A halogenated alkyl group, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, An aryl group or a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, An alkylsilyl group, an arylsilyl group having 6 to 24 carbon atoms, and an aryloxy group having 6 to 24 carbon atoms.

The organic light emitting device according to the present invention can drive the organic light emitting device at a low voltage as compared with the organic light emitting device according to the related art and can exhibit high efficiency.

1 is a schematic view of an organic light emitting device according to an embodiment of the present invention.

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

The present invention relates to a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And an emission layer interposed between the first electrode and the second electrode,

Wherein the light emitting layer comprises a pyrene derivative represented by the formula (A) and a compound represented by the formula (D).

Meanwhile, in the substituent in the compound of the present invention, the range of the alkyl or aryl group in the "substituted or unsubstituted C1-C30 alkyl group" or "substituted or unsubstituted C5-C50 aryl group" , The range of the carbon number of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms is not limited to the total of all the alkyl moieties constituting the alkyl moiety or the aryl moiety Means the number of carbon atoms. For example, a phenyl group substituted with a butyl group at the para position should be considered to correspond to an aryl group having 6 carbon atoms substituted with a butyl group having a carbon number of 4.

An aryl group, which is a substituent used in the compound of the present invention, refers to an aromatic system composed of a hydrocarbon containing at least one ring, and when the aryl group has a substituent, it is fused with neighboring substituents to further form a ring .

Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m- terphenyl group, p- terphenyl group, naphthyl group, anthryl group, An aromatic group such as a pyridyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylenyle, a crycenyl, a naphthacenyl, a fluoranthene and the like, and at least one hydrogen atom of the aryl group may be substituted with a deuterium atom, (-NH ₂ , -NH (R), -N (R ') (R "), R' and R" each independently represent an alkyl group having 1 to 10 carbon atoms A hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkyl group having 1 to 24 carbon atoms, An alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, It may be substituted with a heteroaryl group of a small number of 6 to 24 aryl group, C 6 -C 24 arylalkyl group, having 2 to 24 carbon atoms or heteroaryl group having 2 to 24.

The heteroaryl group which is a substituent used in the compound of the present invention is a heteroaryl group having 2 to 24 carbon atoms in which the heteroaryl group includes 1,2 or 3 hetero atoms selected from N, O, P, Si, S, Ge, Refers to a ring aromatic system, which rings may be fused to form a ring. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the aryl group.

In the present invention, the aromatic heterocyclic ring means that at least one of aromatic carbons in the aromatic hydrocarbon ring is substituted with at least one hetero atom selected from N, O, P, Si, S, Ge, Se and Te.

Specific examples of the alkyl group as the substituent used in the present invention include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl and hexyl. The hydrogen atom may be substituted with a substituent similar to that of the aryl group.

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group used as the substituent in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, Butylsilyl, dimethylpurylsilyl and the like, and at least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

In the organic light emitting device according to the present invention, the pyrene derivative represented by the above formula (A) may be combined with arylamine at positions 3 and 8 in the pyrene structure shown in the following FIG.

[그림 1]

[Figure 1]

Here, at least one aryl group of each of the aryl groups bonded to the nitrogen atom of the two arylamines to be bonded to the pyrene is a substituted or unsubstituted aryl group having 1 to 20 carbon atoms in the ortho- Lt; / RTI > to 20 carbon atoms.

That is, in the pyrene derivative represented by the above formula (A), at least X _{1 ,} X _2, X ₅ and X ₆ of X ₁ to X ₈ are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms.

In this case, substituents adjacent to each other among the substituents included in the aryl group may be connected to each other to form a monocyclic or polycyclic ring of alicyclic or aromatic, and the carbon ring of the formed alicyclic or aromatic monocyclic or polycyclic ring May be substituted with any one or more heteroatoms selected from N, O, P, Si, S, Ge, Se and Te.

As shown in FIG. 2, the compound represented by the formula (D) in the present invention has a linking group L to be bonded to the 9-position of the anthracene ring, or an anthracene group in the absence of the linking group, Is bonded to the carbon atom at position 1 or 2 of either phenyl ring of the dibenzofuran.

[그림 2]

[Figure 2]

The light emitting layer of the organic light emitting device according to the present invention comprises a host and a dopant,

The pyrene derivative represented by the above-mentioned formula (A) is used as a dopant in the light emitting layer, and the compound represented by the above formula (D), which is another component of the light emitting layer in the present invention, It can be driven at a low voltage as compared with the light emitting element, and can also have an effect of high efficiency.

In the present invention, when the alkyl group is substituted at the ortho-position in the phenyl group in the arylamine used as a dopant, the efficiency can be increased compared with a compound in which the alkyl group is not substituted (for example, a compound substituted with hydrogen) When the linking group L or the anthracene group is bonded to the 1- or 2-position of one of the phenyl groups of benzofuran, the organic luminescent device can be driven at a low voltage, and the pyrene derivative represented by the formula (A) By using the anthracene derivatives to be displayed together, it is possible to have an effect of increasing the efficiency as the driving voltage is lowered.

In one embodiment, R 1 to R 6 in the formula (A) of the present invention are the same or different from each other and independently represent hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, And an arylsilyl group having 5 to 30 carbon atoms.

In one embodiment, the substituents R5 and R6 in the pyrene derivative represented by the above formula (A) may each be hydrogen.

In the present invention, the pyrene derivative may have the same or different two amine groups, and when the two amine groups are the same, they may be obtained by reacting the same kind of amine with a halogenated pyrene such as dibromopyrene And when two amine groups are different, they can be obtained by sequentially reacting each different kind of amine.

When a different amine is sequentially reacted as described above, the pyrene derivative having an amine group bonded thereto as an intermediate may be purified and then reacted with a new amine in the next step. When the two amines are different as described above, the resulting pyrene derivative is obtained as an asymmetric compound.

In the present invention, the linking group L of the anthracene derivative of the above formula (D) may be a single bond or any one selected from the following formulas (22) and (30).

[Structural Formula 22] [Structural Formula 23] [Structural Formula 24] [Structural Formula 25]

[Structural Formula 26] [Structural Formula 27] [Structural Formula 28] [Structural Formula 29]

[Structural Formula 30]

The carbon residue of the aromatic ring in the linking group L may be bonded to hydrogen or deuterium.

In addition, at least one of the substituents R ₁₁ to R ₁₅ in the formula (D) of the present invention may be deuterium.

In one embodiment, the substituent R < ₁₁ > is deuterium and k may be 5.

In one embodiment, R ₁₂ and / or R ₁₃ is deuterium, and l may be two or more, or m may be two or more.

In one embodiment, R ₁₂ and R ₁₃ are deuterium at the same time, and 1 and m each may be 2 or more.

In one embodiment, R ₁₄ and / or R ₁₅ is deuterium, n is 2 or more, or o is 2 or more.

In one embodiment, R ₁₄ and R ₁₅ are simultaneously deuterium, and n and o may be two or more.

In the present invention, the compound represented by the formula (A) may be any one selected from the following formulas (1) to (45).

≪ Formula 1 > (2) (3)

≪ Formula 4 > ≪ Formula 5 > (6)

≪ Formula 7 > (8) ≪ Formula 9 >

≪ Formula 10 > ≪ Formula 11 > ≪ Formula 12 >

≪ Formula 13 > ≪ Formula 14 > ≪ Formula 15 >

≪ Formula 16 > ≪ Formula 17 > ≪ Formula 18 >

(19) (20) ≪ Formula 21 >

(22) ≪ Formula 23 > ≪ EMI ID =

≪ Formula 25 > (26) ≪ Formula 27 >

(28) (29) (30)

(31) (32) ≪ Formula 33 >

(34) ≪ Formula 35 > ≪ EMI ID =

(37) ≪ Formula 38 > ≪ EMI ID =

≪ EMI ID = ≪ EMI ID = (42)

&Lt; Formula 43 > &Lt; Formula 44 > <Formula 45>

In the present invention, the anthracene derivative represented by the above formula (D) may be any one of organic compounds selected from the following [compounds 1] to [138].

Compounds represented by the following [compounds 1] to [138], which are the compounds used as a host, include a linking group L which binds to the 9-position of the anthracene ring, or a substituted or unsubstituted anthracene group Is bonded to the carbon atom at the 1st or 2nd position of either phenyl ring of benzofuran.

&Lt; Compound 1 >    <Compound 2> <Compound 3>

<Compound 4>    <Compound 5> <Compound 6>

<Compound 7>    <Compound 8> <Compound 9>

<Compound 10>    <Compound 11> <Compound 12>

<Compound 13>    <Compound 14> <Compound 15>

<Compound 16>    <Compound 17> <Compound 18>

&Lt; Compound 19 > < Compound 20 > <Compound 21>

<Compound 22>    <Compound 23> <Compound 24>

<Compound 25>    <Compound 26> <Compound 27>

<Compound 28>    <Compound 29> <Compound 30>

<Compound 31>    <Compound 32> <Compound 33>

<Compound 34>    <Compound 35> <Compound 36>

<Compound 37>    <Compound 38> <Compound 39>

&Lt; Compound 40 > < Compound 41 > <Compound 42>

<Compound 43>    <Compound 44> <Compound 45>

<Compound 46>    <Compound 47> <Compound 48>

<Compound 49>    <Compound 50> <Compound 51>

<Compound 52>    <Compound 53> <Compound 54>

<Compound 55>    <Compound 56> <Compound 57>

<Compound 58>    <Compound 59> <Compound 60>

<Compound 61>    <Compound 62>  <Compound 63>

<Compound 64>    <Compound 65> <Compound 66>

<Compound 67>    <Compound 68> <Compound 69>

&Lt; Compound 70 > < Compound 71 > <Compound 72>

&Lt; Compound 73 > < Compound 74 > <Compound 75>

<Compound 76>       <Compound 77> <Compound 78>

<Compound 79>       <Compound 80> <Compound 81>

<Compound 82>       <Compound 83> <Compound 84>

<Compound 85> <Compound 86> <Compound 87>

<Compound 88>       <Compound 89> <Compound 90>

<Compound 91>       <Compound 92> <Compound 93>

<Compound 94>       &Lt; Compound 95 > <Compound 96>

&Lt; Compound 97 >       &Lt; Compound 98 > &Lt; Compound 99 >

<Compound 100> &Lt; Compound 101 > &Lt; Compound 102 >

&Lt; Compound 103 > < Compound 104 > < Compound 105 >

&Lt; Compound 106 > < Compound 107 >   <Compound 108>

&Lt; Compound 109 > < Compound 110 >   <Compound 111>

<Compound 112> <Compound 113>   <Compound 114>

<Compound 115> <Compound 116>   <Compound 117>

<Compound 118> <Compound 119>   <Compound 120>

<Compound 121> <Compound 122>   <Compound 123>

<Compound 124> <Compound 125>   <Compound 126>

<Compound 127> <Compound 128>   <Compound 129>

<Compound 130> <Compound 131>   <Compound 132>

<Compound 133> <Compound 134>   <Compound 135>

<Compound 136> <Compound 137>   <Compound 138>

As one embodiment of the present invention, the present invention provides a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And a light emitting layer interposed between the first electrode and the second electrode, wherein at least one of the pyrene derivatives represented by the formula (A) in the present invention is contained as a dopant in the light emitting layer, ] As the host in the light emitting layer.

Herein, "(organic layer) contains at least one organic compound" in the present invention means that one or more organic compounds belonging to the category of the present invention (organic layer) Compound "as used herein.

In this case, the content of the dopant in the light emitting layer may be selected from the range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

The light emitting layer may further include various dopants and various hosts as well as the dopant and the host.

By appropriately selecting the substituent of the pyrene derivative represented by the above-mentioned formula (A) in the present invention and by appropriately selecting an anthracene derivative represented by the formula (D) as a host compound to be used in the light emitting layer comprising the host and the dopant, Driving and high-efficiency devices can be realized.

In addition, the organic light emitting device of the present invention may further include at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer in addition to the light emitting layer can do.

In the present invention, as the electron transporting layer material, a known electron transporting material can be used as a material that stably transports electrons injected from an electron injection electrode (cathode). Examples of known electron transporting materials include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, Balq, beryllium bis (benzoquinolin-10- but are not limited to, materials such as olate: Bebq2), ADN, compound 201, compound 202, BCP, oxadiazole derivative PBD, BMD, BND and the like.

TAZ BAlq

&Lt; Compound 201 > < Compound 202 > < BCP &

Hereinafter, the organic light emitting device of the present invention will be described with reference to FIG.

1 is a cross-sectional view showing a structure of an organic light emitting device of the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60, and a cathode 80, An injection layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, the organic light emitting device of the present invention and a method of manufacturing the same will be described below. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

The hole injection layer material is not particularly limited as long as it is conventionally used in the art. For example, 2-TNATA [4,4 ', 4 "-tris (2-naphthylphenyl-phenylamino) -triphenylamine] , NPD [N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'- biphenyl-4,4'-diamine], DNTPD [N, N'-diphenyl-N, N'-bis- [4- ], Etc. However, the present invention is not limited thereto.

The material for the hole transport layer is not particularly limited as long as it is commonly used in the art and includes, for example, N, N'-bis (3-methylphenyl) -N, N'- Biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (a-NPD). However, the present invention is not necessarily limited thereto.

A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

Further, according to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 ANGSTROM.

In the present invention, at least one layer selected from the functional layer having the hole injecting layer, the hole transporting layer, the hole injecting function and the hole transporting function, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer, A deposition method or a solution process. Here, the deposition method refers to a method of forming a thin film by evaporating a material used as a material for forming each of the layers through heating or the like under vacuum or low pressure, Refers to a method of mixing a material used as a material with a solvent and forming the thin film by a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating or the like.

Further, the organic light emitting device of the present invention may be a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a single-color or white-colored flexible lighting device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

(Examples) I. Preparation Example of Dopant Compound

Synthesis Example 1: Synthesis of [Formula 1]

Synthesis of [Reaction Scheme 1-1] [Intermediate 1-a]

                                              [Intermediate 1-a]

(6.2 g, 0.050 mol), palladium acetate (0.22 g, 1 mmol) and 2,2'-bis (diphenylphosphino) -1- 1'-binaphthyl (1.3 g, 2 mmol) and sodium tertiarybutoxide (12.2 g, 0.120 mol) were added to 100 mL of toluene and refluxed for 12 hours. The reaction mixture was cooled to room temperature, extracted with ethyl acetate, and then subjected to column chromatography to obtain 7.3 g (yield: 73%) of Intermediate 1-a.

[Reaction 1-2] Synthesis of [Formula 1]

                                                  [Chemical Formula 1]

(5.0 g, 0.025 mol) synthesized in the above Reaction Scheme 1-1, sodium terephthalate (5.3 g, 0.011 mol) synthesized in the above Reaction Scheme 1-1, 1,6-dibromopyrene (4 g, 0.055 mol), palladium acetate (0.1 g, 0.44 mmol), and tri-tertiary butylphosphine (0.36 g, 1.7 mmol) were added to 50 mL of toluene and refluxed for 24 hours. The mixture was cooled to room temperature, extracted with ethyl acetate, and then separated by column chromatography to obtain 3.1 g (yield: 48%) of [Formula 1].

Synthesis Example 2: Synthesis of [Formula 2]

Synthesis of [Reaction Scheme 2-1] [Intermediate 2-a]

                                         [Intermediate 2-a]

[Intermediate 2-a] (yield 75%) was obtained in the same manner as in [Reaction Scheme 1-1] above using 2,6-diethylaniline instead of 2,6-dimethylaniline.

[Reaction Scheme 2-2] Synthesis of [Formula 2]

                                                    (2)

(Yield: 63%) was obtained in the same manner as in [Reaction formula 1-2] using [Intermediate 2-a] synthesized in the above Reaction Scheme 2-1 instead of Intermediate 1-a.

Synthesis Example 3: Synthesis of [Formula 3]

Synthesis of [Reaction Scheme 3-1] [Intermediate 3-a]

                                             [Intermediate 3-a]

[Intermediate 3-a] (yield 75%) was obtained in the same manner as in [Reaction Scheme 1-1] above using 2,6-diisopropylaniline instead of 2,6-dimethylaniline.

[Reaction formula 3-2] Synthesis of [formula 3]

                                                     (3)

(Yield: 56%) was obtained in the same manner as in [Intermediate 3-a] synthesized in the above Reaction Scheme 3-1 instead of Intermediate 1-a in Reaction Scheme 1-2 above.

Synthesis Example 4: Synthesis of [Formula 6]

Synthesis of [Reaction Scheme 4-1] [Intermediate 4-a]

                                                   [Intermediate 4-a]

[Intermediate 4-a] (yield 78%) was obtained in the same manner as in [Reaction Scheme 1-1] except that 1-bromo-4-trimethylsilylbenzene was used instead of bromobenzene.

[Reaction Scheme 4-2] Synthesis of [Formula 6]

                                                    [Chemical Formula 6]

(Yield: 70%) was obtained in the same manner as in [Intermediate 4-a] synthesized in the above Reaction Scheme 4-1 instead of [Intermediate 1-a] in the above Reaction Scheme 1-2.

Synthesis Example 5: Synthesis of [Formula 7]

Synthesis of [Reaction Scheme 5-1] [Intermediate 5-a]

                                                  [Intermediate 5-a]

[Intermediate 5-a] (yield: 77%) was obtained in the same manner as in [Reaction Scheme 1-1] except that 1-bromo-4-tert-butylbenzene was used instead of bromobenzene.

[Reaction Scheme 5-2] Synthesis of [Formula 7]

                                             (7)

(Yield 75%) was obtained in the same manner as in [Intermediate 5-a] synthesized in the above Reaction Scheme 5-1 instead of [Intermediate 1-a] in the above Reaction Scheme 1-2.

II. Production Example of Host Compound

Synthetic example  11: Synthesis of compound 1

Synthesis Example 11- (1): Synthesis of Intermediate 11-a

Intermediate 11-a was synthesized according to Scheme 11 below:

<Reaction Scheme 11>

                             <Intermediate 11-a>

To a 500 mL round-bottom flask reactor was added a solution of (10-phenyl (d5) -anthracene-9-boronic acid (38.6 g, 127 mmol), 1-bromo-4-iodobenzene (30.0 g, 150 mL of toluene, 150 mL of tetrahydrofuran, and 60 mL of water were charged, and the temperature of the reactor was raised to 90 degrees and the mixture was stirred overnight. After the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate and the organic layer was separated. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain <Intermediate 11-a> (35.0 g, 79.7%

Synthesis Example 11- (2): Synthesis of Intermediate 11-b

Intermediate 11-b was synthesized according to Scheme 12 below:

<Reaction Scheme 12>

                                    <Intermediate 11-b>

1,3-dimethoxybenzene (100.0 g, 0.724 mol) and 800 ml of tetrahydrofuran were placed in a well-dried 2 L round bottom flask reactor. The reaction solution was cooled to -10 degrees in a nitrogen atmosphere, and then n-butyl lithium (543 ml, 0.868 mol) was slowly added dropwise. The mixture was stirred at the same temperature for 4 hours and then cooled to -78 ° C. Trimethylboride (112.8 g, 1.086 mol) was slowly added dropwise over 30 minutes while maintaining the same temperature, followed by stirring at room temperature overnight. After completion of the reaction, 2N HCl was slowly added dropwise to acidify it. The organic layer was extracted with water and ethyl acetate, and water was removed with magnesium sulfate. The material was concentrated under reduced pressure and then crystallized with heptane. The resulting solid was filtered and washed with heptane to obtain <Intermediate 11-b> (92.0 g, 69%).

Synthesis Example 11- (3): Synthesis of Intermediate 11-c

Intermediate 11-c was synthesized according to Scheme 13 below:

<Reaction Scheme 13>

                    <Intermediate 11-b> <Intermediate 11-c>

(80.0 g, 0.457 mol), <intermediate 11-b> (91.5 g, 0.503 mol), tetrakis (triphenylphosphine) palladium (11.6 g , 0.01 mol) and potassium carbonate (126.4 g, 0.914 mol) were placed, 400 mL of toluene, 400 mL of tetrahydrofuran and 160 mL of water were added. The temperature of the reactor was raised to 80 ° C and stirred overnight. When the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain <Intermediate 11-c> (85.0 g, 80%).

Synthesis Example 11- (4): Synthesis of intermediate 11-d

Intermediate 11-d was synthesized according to Scheme 14 below:

<Reaction Scheme 14>

<Intermediate 11-c> <Intermediate 11-d>

<Intermediate 11-c> (85.0 g, 0.366 mol) was added to a 2 L round-bottom flask reactor, and 510 ml of acetic acid and 340 ml of hydrobromic acid were added thereto. When the reaction was completed, the reaction mixture was cooled to room temperature and then added dropwise to 1000 ml of cold water. The solution was extracted with water and ethyl acetate to separate the organic layer. The organic layer was washed with 400 ml of an aqueous solution of sodium hydrogencarbonate and concentrated under reduced pressure. The material was separated and purified by column chromatography to obtain < intermediate 11-d >. (71 g, 95%).

Synthesis Example 11- (5): Synthesis of Intermediate 11-e

Intermediate 11-e was synthesized according to Scheme 15 below:

<Reaction Scheme 15>

<Intermediate 11-d> <Intermediate 11-e>

<Intermediate 11-d> (71.0, 39 mmol), potassium carbonate (96.1 g, 0.695 mol) and 1-methyl-2-pyrrolidinone (1060 ml) were placed in a 2 L round bottom flask reactor and stirred overnight at 120 ° C. After completion of the reaction, the mixture was cooled to room temperature and added dropwise to 1000 ml of cold water. After extraction with water and ethyl acetate, the organic layer was separated and concentrated under reduced pressure. The material was separated and purified by column chromatography to obtain <Intermediate 11-e>. (60.0 g, 93.7%).

Synthesis Example 11- (6): Synthesis of Intermediate 11-f

Intermediate 11-f was synthesized according to Scheme 16 below:

<Reaction Scheme 16>

<Intermediate 11-e> <Intermediate 11-f>

<Intermediate 11-e> (60.0 g, 0.326 mol) and 600 ml of methylene chloride were placed in a 2 L round bottom flask reactor, and pyridine (38.7 g, 0.489 mol) was slowly added thereto and stirred at room temperature for 30 minutes. The reaction solution was cooled to 0 ° C., and then trifluoromethanesulfonyl anhydride (137.8 g, 0.489 mol) was added dropwise at the same temperature. After stirring at room temperature for 5 hours, 100 ml of water was slowly added to the reaction solution and stirred for 10 minutes. The mixture was extracted with water and ethyl acetate, and the organic layer was separated and concentrated under reduced pressure. The material was separated and purified by column chromatography to obtain <Intermediate 11-f>. (87 g, 84.5%).

Synthesis Example 11- (7): Synthesis of intermediate 11-g

Intermediate 11-g was synthesized according to Scheme 17 below:

<Reaction Scheme 17>

<Intermediate 11-f> <Intermediate 11-g>

(87.0 g, 0.275 mol), bis (pinacolato) diboron (83.8 g, 0.330 mol) and 1,1'-bis (diphenylphosphino) ferrocene- Palladium (II) dichloride (4.5 g, 0.006 mol), potassium acetate (54.0 g, 0.550 mol) and 870 ml of 1,4-dioxane were added and the mixture was refluxed overnight. After completion of the reaction, the solution was passed through a celite pad, and the filtrate was concentrated under reduced pressure. The material was separated and purified by column chromatography to obtain <Intermediate 11-g>. (65.3 g, 80.7%)

Synthesis Example 11- (8): Synthesis of Compound 1

Compound 1 was synthesized according to Scheme 18 below:

<Reaction Scheme 18>

<Intermediate 11-a> <Intermediate 11-g> <Compound 1>

<Intermediate 11-a> (5.5 g, 13 mmol), Intermediate 11-g (4.7 g, 16 mmol), tetrakis (triphenylphosphine) palladium (0.46 g, 3 mmol), potassium Carbonate (3.67 g, 26.5 mmol), 30 mL of toluene, 30 mL of 1,4-dioxane and 11 mL of water were added. The temperature of the reactor was raised to 90 ° C and stirred overnight. When the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and then separated by column chromatography. Recrystallization from toluene and acetone gave <compound 1> (3.2 g, 48%).

MS: m / z 502.2 [M ^&lt; ⁺ &^gt;] [

Synthesis Example 12: Synthesis of Compound 13

Synthesis Example 12- (1): Synthesis of <Intermediate 12-a>

Intermediate 12-a was synthesized according to Scheme 19 below:

<Reaction Scheme 19>

                            <Intermediate 12-a>

To a 2 L round bottom flask reactor was added 2-bromodibenzofuran (70.0 g, 0.283 mol), bis (pinacolato) diboron (86.3 g, 0.340 mol), 1,1'-bis (diphenylphosphino) Palladium (II) dichloride (4.6 g, 0.006 mol), potassium acetate (56.6 g, 0.567 mol) and 1,4-dioxane (700 ml) were added and the mixture was refluxed overnight. After completion of the reaction, the solution was passed through a celite pad, and the filtrate was concentrated under reduced pressure. The material was separated and purified by column chromatography to obtain < intermediate 12-a >. (66.4 g, 79%)

Synthesis Example 12- (2): Synthesis of Compound 13

Compound 13 was synthesized according to Scheme 20 below:

<Reaction Scheme 20>

<Intermediate 11-a> <Intermediate 12-a> <Compound 13>

<Compound 13> (3.0 g, 66.1%) was obtained using the same method as in Synthesis Example 11- (8), except that <Intermediate 12-a> was used instead of <Intermediate 11-g>.

MS: m / z 502.2 [M ^&lt; ⁺ &^gt;] [

Synthesis Example 13: Synthesis of Compound 22

Synthesis Example 13- (1): Synthesis of Intermediate 13-a

Intermediate 13-a was synthesized according to Scheme 21 below:

<Reaction Scheme 21>

                                  <Intermediate 13-a>

<Intermediate 13-a> (32 g, 10 mmol) was obtained using the same method except that 1-bromo-3-iodobenzene was used in place of 1-bromo- 72.8%).

Synthesis Example 13- (2): Synthesis of Compound 22

Compound 22 was synthesized according to the following scheme 22:

<Reaction Formula 22>

<Intermediate 13-a> <Intermediate 11-g> <Compound 22>

<Compound 22> (3.5 g, 57.8%) was obtained using the same method except that <Intermediate 13-a> was used in place of <Intermediate 11-a> in Synthesis Example 11- (8).

MS: m / z 502.2 [M ^&lt; ⁺ &^gt;] [

Synthesis Example 14: Synthesis of Compound 31

Synthesis Example 14- (1): Synthesis of Compound 31

Compound 31 was synthesized according to Scheme 23 below:

<Reaction Scheme 23>

<Intermediate 13-a> <Intermediate 12-a> <Compound 31>

<Compound 31> (2.7 g, 44.6%) was obtained using the same method as in Synthesis Example 12- (2), except that <Intermediate 13-a> was used in place of Intermediate 11-a.

MS: m / z 502.2 [M ^&lt; ⁺ &^gt;] [

Synthesis Example 15: Synthesis of Compound 43

Synthesis Example 15- (1): Synthesis of Intermediate 15-a

Intermediate 15-a was synthesized according to Scheme 24 below:

<Reaction Scheme 24>

                                <Intermediate 15-a>

<Intermediate 15-a> (29 g, 59.5%) was obtained by using the same method except that 1,4-dibromonaphthalene was used in place of 1-bromo-4-iodobenzene in Synthesis Example 11- (1) ).

Synthesis Example 15- (2): Synthesis of Compound 43

Compound 43 was synthesized according to Scheme 25 below:

<Reaction Scheme 25>

<Intermediate 15-a> <Intermediate 11-g> <Compound 43>

<Compound 43> (4.2 g, 69.4%) was obtained using the same method except that <Intermediate 15-a> was used in place of <Intermediate 11-a> in Synthesis Example 11- (8).

MS: m / z 552.2 [M ^&lt; ⁺ &^gt;] [

Synthesis Example 16: Synthesis of Compound 52

Synthesis Example 16- (1): Synthesis of Compound 52

Compound 52 was synthesized according to Scheme 26 below:

<Reaction Scheme 26>

<Intermediate 15-a> <Intermediate 12-a> <Compound 52>

<Compound 52> (4.0 g, 67.4%) was obtained using the same method as in Synthesis Example 12- (2), except that <Intermediate 15-a> was used in place of Intermediate 11-a.

MS: m / z 552.2 [M ^&lt; ⁺ &^gt;] [

Synthesis Example 17: Synthesis of Compound 61

Synthesis Example 17- (1): Synthesis of Intermediate 17-a

Intermediate 17-a was synthesized according to Scheme 27 below:

<Reaction Scheme 27>

                 <Intermediate 17-a>

<Intermediate 17-a> (244 g, 95%) was obtained using the same method except that 1,4-dihydroxynaphthalene was used in place of <Intermediate 11-e> in Synthesis Example 11- (6) .

Synthesis Example 17- (2): Synthesis of Intermediate 17-b

Intermediate 17-b was synthesized according to Scheme 28 below:

<Reaction Scheme 28>

&Lt; Intermediate 17-a > < Intermediate 17-b &

(110.0 g, 0.259 mol), 10-phenyl (d5) -anthracene-9-boronic acid (78.6 g, 0.259 mol)), tetrakis (triphenylphosphine ) Palladium (6.0 g, 5 mmol) and potassium carbonate (71.7 g, 0.519 mol) were placed, and 770 mL of toluene, 330 mL of ethanol and 220 mL of water were added. The temperature of the reactor was raised to 60 ° C and stirred for 1 hour. When the reaction was completed, the temperature of the reactor was lowered to room temperature and the resulting solid was filtered. The filtrate was extracted with water and ethyl acetate, and the organic layer was separated and concentrated under reduced pressure. The material was dissolved in toluene and recrystallized from methanol to give <Intermediate 17-b>. (100.0 g, 72.3%).

Synthesis Example 17- (3): Synthesis of Compound 61

Compound 61 was synthesized according to Scheme 29 below:

<Reaction Scheme 29>

<Intermediate 17-b> <Intermediate 11-g> <Compound 61>

<Compound 61> (2.8 g, 54%) was obtained in the same manner as in Synthesis Example 11- (8) except that <Intermediate 17-b> was used instead of <Intermediate 11-a>.

MS: m / z 552.2 [M ^&lt; ⁺ &^gt;] [

Synthesis Example 18: Synthesis of Compound 70

Synthesis Example 18- (1): Synthesis of Compound 70

Compound 70 was synthesized according to Reaction Scheme 30 below.

<Reaction Scheme 30>

<Intermediate 17-b> <Intermediate 12-a> <Compound 70>

<Compound 70> (2.4 g, 46%) was obtained using the same method as in Synthesis Example 12- (2), except that <Intermediate 17-b> was used instead of <Intermediate 11-a>.

MS: m / z 552.2 [M ^&lt; ⁺ &^gt;] [

Synthesis Example 19: Synthesis of Compound 118

Synthesis Example 19- (1): Synthesis of Compound 118

Compound 118 was synthesized according to the following Reaction Scheme 31

<Reaction Scheme 31>

                <Intermediate 19-a> <Compound 118>

(D5) -anthracene-9-boronic acid and 10-phenyl (H5) -anthracene-9-boronic acid instead of <Intermediate 17-b> in Synthesis Examples 17- (2) and 17- <Compound 118> (3.5 g, 58%) was obtained using the same method except that <Intermediate 19-a> was used.

MS: m / z 547.2 [M ^&lt; ⁺ &^gt;] [

Synthesis Example 20: Synthesis of Compound 84

Synthesis Example 20- (1): Synthesis of Compound 84

Intermediate 20-a was synthesized according to the following reaction scheme 32

<Reaction equation 32>

                                <Intermediate 20-a>

1,2-Dihydroxynaphthalene (50.0 g, 0.312 mol), hydrochloric acid (17 ml) and methanol (500 ml) were placed in a 1 L round bottom flask reactor and stirred at room temperature for 3 days. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the resultant product was separated and purified by column chromatography to obtain <Intermediate 20-a> (40.0 g, 73%).

Synthesis Example 20- (2): Synthesis of Intermediate 20-b

Intermediate 20-b was synthesized according to Scheme 33 below

<Reaction Scheme 33>

&Lt; Intermediate 20-a > < Intermediate 20-b &

<Intermediate 20-b> (65.2 g, 92%) was obtained in the same manner as in Synthesis Example 11- (6) except that <Intermediate 20-a> was used in place of Intermediate 11-e.

Synthesis Example 20- (3): Synthesis of Intermediate 20-c

Intermediate 20-c was synthesized according to the following reaction scheme 34

<Reaction formula 34>

<Intermediate 20-b> <Intermediate 20-c>

<Intermediate 20-c> (12.0 g, 59%) was obtained using the same method except that <Intermediate 20-b> was used in place of <Intermediate 17-a> in Synthesis Example 17- (2).

Synthesis Example 20- (4): Synthesis of Intermediate 20-d

Intermediate 20-d was synthesized according to the following reaction scheme 35

<Reaction Scheme 35>

<Intermediate 20-b> <Intermediate 20-d>

<Intermediate 20-b> (12.0 g, 0.028 mol) and 180 ml of dichloromethane were placed in a 500 ml round bottom flask reactor and cooled to 0 ° C. Boron tromide (43.3 g, 0.043 mol) was slowly added dropwise to the cooled reaction solution and stirred at room temperature. After completion of the reaction, the reaction solution was cooled to 0 degree. 20 ml of water was slowly added dropwise to the reaction solution, which was then extracted with water and ethyl acetate. The organic layer was separated, concentrated under reduced pressure, and recrystallized from acetonitrile and acetone to obtain Intermediate 20-d (10.0 g, 86.2%).

Synthesis Example 20- (5): Synthesis of Intermediate 20-e

Intermediate 20-e was synthesized according to the following reaction scheme 36

<Reaction Formula 36>

<Intermediate 20-d> <Intermediate 20-e>

<Intermediate 20-e> (11.2 g, 84%) was obtained using the same method except that <Intermediate 20-d> was used in place of <Intermediate 11-e> in Synthesis Example 11- (6).

Synthesis Example 20- (6): Synthesis of Compound (84)

84 was synthesized according to the following Reaction Scheme 37

(Reaction Scheme 37)

<Intermediate 20-e> <Intermediate 11-g> <Compound 84>

<Compound 84> (3.8 g, 54%) was obtained in the same manner as in Synthesis Example 11- (8) except that <Intermediate 20-e> was used instead of <Intermediate 11-a>.

MS: m / z 552.2 [M ^&lt; ⁺ &^gt;] [

Example 1: Preparation of organic light emitting device

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the ITO glass was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 ^-7 torr, and HAT-CN (50 Å) and α-NPD (600 Å) were sequentially formed on the ITO. (E-1) and (E-2) were mixed in a ratio of 1: 1 as an electron transporting layer after forming a film (200 Å) by mixing the host shown in the following Table 1 and a dopant (E-1) as an electron injecting layer in the order of 10 Å and Al (1000 Å), respectively, to prepare an organic light emitting device. The luminescent characteristics of the organic light emitting device were measured at 0.4 mA.

     [HAT-CN] [[alpha] -NPD]

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

Comparative Example 1

An organic light emitting device was fabricated in the same manner as in Example 1 except that [BD1] was used as a dopant instead of the dopant compound. The structure of [BD1] was as follows.

[BD1]

Comparative Examples 2 to 5

An organic light emitting device was prepared in the same manner as in Example 1 except that the host compound represented by the following [BH1] to [BH4] was used instead of the host compound used in Example 1. The structures of [BH1] to [BH4] .

[BH1]   [BH2] [BH3]    [BH4]

Comparative Examples 6 to 7

An organic light emitting device was prepared using the dopant used in Comparative Example 1 and using [BH1] and [BH3] as a host.

The results of measuring the driving voltage and efficiency of the organic light-emitting device manufactured according to Example 1 and Comparative Examples 1 to 7 are shown in Table 1 below.

Host Dopant The driving voltage (V) Efficiency (cd / A) Example 1 Compound 70 Formula 1 3.5 6.5 Example 2 Compound 13 Formula 1 3.3 6.5 Example 3 Compound 22 (2) 3.4 6.8 Example 4 Compound 31 (2) 3.2 6.7 Example 5 Compound 31 (3) 3.5 6.6 Example 6 Compound 43 6 3.4 6.7 Example 7 Compound 61 Formula 7 3.4 6.8 Example 8 Compound 118 Formula 7 3.3 6.6 Comparative Example 1 Compound 70 BD 1 3.5 6.1 Comparative Example 2 BH 1 Formula 1 3.9 6.2 Comparative Example 3 BH 2 Formula 1 3.8 6.5 Comparative Example 4 BH 3 Formula 1 3.9 6.1 Comparative Example 5 BH 4 Formula 1 3.9 6.3 Comparative Example 6 BH 1 BD 1 3.9 5.8 Comparative Example 7 BH 3 BD 1 3.9 5.5

As shown in Table 1, the organic light emitting device according to the present invention can drive an organic light emitting device at a low voltage as compared with an organic light emitting device using a compound according to a comparative example as a host or a dopant, It can be seen that the device is highly applicable as a device.

Claims (16)

A first electrode;
A second electrode facing the first electrode; And
And an emission layer interposed between the first electrode and the second electrode,
A pyrene derivative wherein the light emitting layer is represented by the following formula (A); And an anthracene derivative represented by the following formula (D).
(A)

In the above formula (A)
R 1 to R 6 are the same or different from each other and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, A substituted or unsubstituted C1 to C30 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, A substituted or unsubstituted C2-C30 hetero cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group , A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, a cyano group,
Hydrogen or deuterium is bonded to the carbon of the aromatic ring to which the substituent of R ₁ to R ₆ is not bonded,
P, q, r, and s are integers of 0 to 3, and when they are each 2 or more, each of R1 to R4 is the same or different,
R ₁ to R ₄ are connected to adjacent X ₁ to X _{8 ,} or when R ₁ to R ₄ are each 2 or more, R ₁ to R ₄ are connected to each other to form an alicyclic or aromatic group And the carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from N, O, P, Si, S, Ge, Se and Te ;
X ₁ to X ₈ are the same or different from each other and are each independently a substituent selected from hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
At least X _{1 ,} X _2, X ₅ and X ₆ of X ₁ to X ₈ are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms.
[Chemical Formula D]

In the above formula (D)
Substituents R &lt; ₁₁ &gt; to R &lt; ₁₅ &
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, , A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number of 6 to 30 A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylamine group, A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S A substituted or unsubstituted C 1 -C 30 silyl group, a substituted or unsubstituted C 1 -C 30 germanium group, a substituted or unsubstituted C 1 -C 30 boron group, a substituted or unsubstituted C 1 -C 30 aryl group, a cyano group, a nitro group, a halogen group, , A substituted or unsubstituted aliphatic group having 1 to 30 carbon atoms, a carbonyl group, a phosphoryl group, an amino group, a thiol group, a hydroxyl group, a selenium group, a tellurium group, an amide group,
Hydrogen is bonded to the carbon of the aromatic ring to which the substituent of R ₁₁ to R ₁₅ is not bonded,
The linking group L is a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms;
j is an integer of 0 to 2, and when j is 2, each L is the same or different from each other,
k is an integer of 1 to 5,
1 to n are the same or different from each other and independently of one another are an integer of from 1 to 4,
o is an integer of 1 to 3,
When each of k to o is 2 or more, each of R11 to R15 is the same as or different from each other,
&Quot; *** &quot; of X is a bonding site to be bonded to the linking group L,
The "substituted" in the "substituted or unsubstituted" in the above [Formula A] and [Formula D] is a substituent selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, A halogenated alkyl group, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, An aryl group or a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, An alkylsilyl group, an arylsilyl group having 6 to 24 carbon atoms, and an aryloxy group having 6 to 24 carbon atoms. The method according to claim 1,
Wherein the light emitting layer of the organic light emitting device comprises a host and a dopant,
The pyrene derivative represented by the above formula [A] is used as a dopant, and the compound represented by the above formula [D] is used as a host. The method according to claim 1,
R 1 to R 6 in the above formula (A) are the same or different and are independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, &Lt; / RTI &gt; The method according to claim 1,
And R5 and R6 are each hydrogen. The method according to claim 1,
Wherein the pyrene derivative has the same two amine groups. The method according to claim 1,
Wherein the pyrene derivative is asymmetric with the two amine groups being different from each other. The method according to claim 1,
Wherein the linking group L of the anthracene derivative of the formula (D) is a single bond or any one selected from the following formulas (22) and (30).
[Structural Formula 22] [Structural Formula 23] [Structural Formula 24] [Structural Formula 25]

[Structural Formula 26] [Structural Formula 27] [Structural Formula 28] [Structural Formula 29]

[Structural Formula 30]

The carbon residue of the aromatic ring in the linking group L may be bonded to hydrogen or deuterium. The method according to claim 1,
Wherein at least one of the substituents R &lt; ₁₁ &gt; to R &lt; ₁₅ &gt; in the formula (D) comprises deuterium. The method according to claim 1,
Wherein R &lt; ₁₁ &gt; is deuterium and k is 5. The method according to claim 1,
Wherein R ₁₂ and / or R ₁₃ is deuterium, l is 2 or more, or m is 2 or more. The method according to claim 1,
Wherein R ₁₄ and / or R ₁₅ is deuterium, n is 2 or more, or o is 2 or more. The method according to claim 1,
Wherein the pyrene derivative represented by the above formula (A) is any one selected from the following formulas (1) to (45).
&Lt; Formula 1 >< EMI ID =

&Lt; Formula 4 &gt;&lt; EMI ID =

&Lt; Formula 7 >< EMI ID =

&Lt; Formula 10 &gt;&lt; EMI ID =

&Lt; Formula 13 >< EMI ID =

&Lt; Formula 16 &gt;&lt; EMI ID =

&Lt; Formula 19 >< EMI ID =

&Lt; Formula 22 &gt;&lt; EMI ID =

&Lt; Formula 25 >< EMI ID = 26.0 >

&Lt; Formula 28 >< EMI ID = 29.0 >

&Lt; Formula 31 >< EMI ID =

&Lt; Formula 34 &gt;&lt; EMI ID =

&Lt; Formula 37 >< EMI ID = 38.0 >

&Lt; Formula 40 >< EMI ID =

&Lt; General Formula 43 &gt;

The method according to claim 1,
Wherein the anthracene derivative represented by the formula [D] is any one selected from the group consisting of the following [compounds 1] to [138].
&Lt; Compound 1 >< Compound 2 >< Compound 3 &

&Lt; Compound 4 >< Compound 5 >< Compound 6 &

&Lt; Compound 7 >< Compound 8 >< Compound 9 &

&Lt; Compound 10 >< Compound 11 >< Compound 12 &

&Lt; Compound 13 >< Compound 14 >< Compound 15 &

&Lt; Compound 16 >< Compound 17 >< Compound 18 &

&Lt; Compound 19 >< Compound 20 >< Compound 21 &

&Lt; Compound 22 >< Compound 23 >< Compound 24 &

&Lt; Compound 25 >< Compound 26 >< Compound 27 &

&Lt; Compound 28 >< Compound 29 >< Compound 30 &

&Lt; Compound 31 >< Compound 32 >< Compound 33 &

&Lt; Compound 34 >< Compound 35 >< Compound 36 &

&Lt; Compound 37 >< Compound 38 >< Compound 39 &

&Lt; Compound 40 >< Compound 41 >< Compound 42 &

&Lt; Compound 43 >< Compound 44 >< Compound 45 >

&Lt; Compound 46 >< Compound 47 >< Compound 48 &

&Lt; Compound 49 >< Compound 50 >< Compound 51 &

&Lt; Compound 52 >< Compound 53 >< Compound 54 &

&Lt; Compound 55 >< Compound 56 >< Compound 57 >

&Lt; Compound 58 >< Compound 59 >< Compound 60 &

&Lt; Compound 61 >< Compound 62 >< Compound 63 >

&Lt; Compound 64 >< Compound 65 >< Compound 66 >

&Lt; Compound 67 >< Compound 68 >< Compound 69 >

&Lt; Compound 70 >< Compound 71 >< Compound 72 >

&Lt; Compound 73 >< Compound 74 >< Compound 75 >

&Lt; Compound 76 >< Compound 77 >< Compound 78 >

&Lt; Compound 79 >< Compound 80 >< Compound 81 >

&Lt; Compound 82 >< Compound 83 >< Compound 84 >

&Lt; Compound 85 >< Compound 86 >< Compound 87 >

&Lt; Compound 88 >< Compound 89 >< Compound 90 >

&Lt; Compound 91 >< Compound 92 >< Compound 93 >

&Lt; Compound 94 >< Compound 95 >< Compound 96 >

&Lt; Compound 97 >< Compound 98 >< Compound 99 >

&Lt; Compound 100 >< Compound 101 >< Compound 102 &

&Lt; Compound 103 >< Compound 104 >< Compound 105 >

&Lt; Compound 106 >< Compound 107 >< Compound 108 &

&Lt; Compound 109 >< Compound 110 >< Compound 111 >

&Lt; Compound 112 >< Compound 113 >< Compound 114 >

&Lt; Compound 115 >< Compound 116 >< Compound 117 >

&Lt; Compound 118 >< Compound 119 >< Compound 120 &

&Lt; Compound 121 >< Compound 122 >< Compound 123 &

&Lt; Compound 124 >< Compound 125 >< Compound 126 &

&Lt; Compound 127 >< Compound 128 >< Compound 129 &

&Lt; Compound 130 >< Compound 131 >< Compound 132 >

&Lt; Compound 133 >< Compound 134 >< Compound 135 >

<Compound 136><Compound137><Compound138>

The method according to claim 1,
Wherein the organic light emitting device further comprises at least one layer selected from a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, an electron transporting layer, and an electron injecting layer in addition to the light emitting layer. Light emitting element. 15. The method of claim 14,
Wherein at least one layer selected from the respective layers is formed by a deposition process or a solution process. The method according to claim 1,
The organic light emitting device includes a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a device for flexible illumination of a single color or a white color.

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