KR20180027195A - Novel organic compounds and organic light-emitting diode therewith - Google Patents

Abstract

The present invention relates to an organic compound represented by chemical formula A or chemical formula B and an organic light emitting diode comprising the same, wherein R1 to R14, L1, L2, Ar1 to Ar3, n and m in chemical formulas A and B are described in specifications of the invention.

Description

TECHNICAL FIELD [0001] The present invention relates to novel organic compounds and organic light-

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel organic compound and an organic light emitting device including the organic compound. More particularly, the present invention relates to a novel organic compound capable of realizing device characteristics such as high efficiency, long life and low- To 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.

Generally, an organic light emitting phenomenon refers to a phenomenon in which an organic material is used to convert electrical energy into light energy. The organic light emitting device using the organic light emitting phenomenon typically has a structure including an anode, an anode, and an organic layer between the anode and the cathode.

Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

The material used as the 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, an electron injecting material, Or a hole blocking layer may be added.

Of these, in order to produce an organic compound having excellent electron transporting ability and hole blocking ability, excellent luminous efficiency and high stability in a thin film state, as a prior art related to an electron transporting layer material, it is disclosed in Korean Patent Publication No. 10-2012-0104204 (2012.09.20) describes an organic compound in which a pyridoindole derivative is bonded to a substituted anthracene ring structure, and in JP-A-2010-168363 (2010.08.05), an external quantum efficiency and a driving voltage Discloses an anthracene derivative having a pyridine naphthyl group, which has excellent characteristics.

On the other hand, as a conventional technique related to the hole transporting layer, in JP-A 10-1074193 (Oct. 2011, Oct. 14, 2011), organic compounds using a compound having a core structure in which at least one benzene ring is condensed in a carbazole structure as a hole transporting layer compound Emitting device is disclosed in Japanese Patent Application Laid-Open No. 10-1455156 (Publication Date: Oct. 24, 2014, Oct. 27, 2014), an emission assistant having a HOMO energy level between a hole transport layer HOMO energy level and a light emission layer HOMO energy level is provided between a hole transport layer and a light emission layer Emitting layer having a layer formed thereon is disclosed.

However, although various methods for manufacturing an organic light emitting device having more efficient light emitting characteristics have been attempted in the prior art including the above-mentioned prior arts, it is still possible to operate at a low voltage, and the organic light emitting device having improved luminous efficiency and long life There is a continuing need to develop a material that can be used as an electron transport layer and a hole transport layer for a light emitting device.

Japanese Patent Application Laid-Open No. 10-2012-0104204 (2012.09.20)

Japanese Unexamined Patent Application Publication No. 2010-168363 (Aug. 05, 2010)

Patent Registration No. 10-1074193 (Published on October 14, 2011)

Patent Registration No. 10-1455156 (Publication date: Oct. 27, 2014)

Accordingly, the first technical object of the present invention is to provide an organic compound having a specific structure capable of having high efficiency, low voltage, and long life characteristics by using it in an electron transporting layer or a hole transporting layer in an organic light emitting device.

A second object of the present invention is to provide a novel organic light emitting device including the organic compound in an electron transport layer or a hole transport layer.

In order to achieve the above technical problems, the present invention provides an organic compound represented by the following formula (A) or (B).

(A)

[Chemical Formula B]

In the above formulas (A) and (B)

Each of the substituents R 1 to R 4 is the same or different and is 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,

The substituents R5 to R12 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, , A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, a cyano group, a nitro group, a halogen group, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms , A substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a carbonyl group, a phosphoryl group, an amino group, a thiol group, a hydroxyl group, a selenium group, a tellurium group, An ester group,

R13 and R14 are the same or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3- To 50 heteroaryl groups, and R13 and R14 may be connected to each other to form a condensed ring,

In the above formula (A), one or two substituents of the substituents R5 to R12 are a single bond which binds to the A1,

In the above formula (B), one or two substituents of the substituents R5 to R12 are a single bond bonding to the A2, Ar2 and L2 in A2 may be connected to each other to form a condensed ring, and Ar3 and L2 may be They may be connected to each other to form a condensed ring,

The linking groups L 1 and L 2 are the same or different and independently represent a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted C2- A substituted or unsubstituted C2-C60 alkynylene group, a substituted or unsubstituted C3-C60 cycloalkylene group, a substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, And an unsubstituted heteroarylene group having 2 to 60 carbon atoms,

n and m are the same or different and independently of each other an integer of 0 to 3, and when each of these is 2 or more, each of the linking groups L1 and L2 is the same or different from each other,

The substituents Ar 1 to Ar 3 are the same or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to another 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 organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises at least one organic compound of the present invention.

The organic light emitting device comprising the compound represented by the formula (A) or (B) according to the present invention in the electron transporting layer or the hole transporting layer can have high efficiency, low voltage and long life characteristics as compared with the conventional organic light emitting device.

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 organic compound according to the present invention has a structure represented by the following formula (A) or (B).

(A)

[Chemical Formula B]

In the above formulas (A) and (B)

Each of the substituents R 1 to R 4 is the same or different and is 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,

The substituents R5 to R12 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, , A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, a cyano group, a nitro group, a halogen group, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms , A substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a carbonyl group, a phosphoryl group, an amino group, a thiol group, a hydroxyl group, a selenium group, a tellurium group, An ester group,

R13 and R14 are the same or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3- To 50 heteroaryl groups, and R13 and R14 may be connected to each other to form a condensed ring,

In the above formula (A), one or two substituents of the substituents R5 to R12 are a single bond which binds to the A1,

In the above formula (B), one or two substituents of the substituents R5 to R12 are a single bond bonding to the A2, Ar2 and L2 in A2 may be connected to each other to form a condensed ring, and Ar3 and L2 may be They may be connected to each other to form a condensed ring,

The linking groups L 1 and L 2 are the same or different and independently represent a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted C2- A substituted or unsubstituted C2-C60 alkynylene group, a substituted or unsubstituted C3-C60 cycloalkylene group, a substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, And an unsubstituted heteroarylene group having 2 to 60 carbon atoms,

n and m are the same or different and independently of each other an integer of 0 to 3, and when each of these is 2 or more, each of the linking groups L1 and L2 is the same or different from each other,

The substituents Ar 1 to Ar 3 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,

The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group, 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, a heteroaryl group having 2 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An aryloxy group, an aryloxy group, an arylsilyl group, and an aryloxy group having 6 to 24 carbon atoms.

In consideration of the range of the alkyl or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms" and "substituted or unsubstituted aryl group having 6 to 50 carbon atoms" in the present invention, The carbon number of the alkyl group having 1 to 30 carbon atoms and the aryl group having 6 to 50 carbon atoms means the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when it is considered that the substituent is not substituted without considering the substituted moiety will be. 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.

The aryl group which is a substituent used in the compound of the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen elimination and includes a single or fused ring system containing 5 to 7 atoms, preferably 5 or 6 atoms, When a substituent is present in the aryl group, the adjacent substituent may be fused with each other to 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 2 to 20 carbon atoms, An alkenyl group having 2 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, having 7 to 24 of the 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, isoamyloxy, 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, diphenylvinylsilyl, methylcyclobutylsilyl , And dimethylpurylsilyl. At least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

In detail, the compound represented by the above formula (A) or (B) according to the present invention will be described in more detail. A 5-membered ring containing a carbon atom connected to a 6-membered aromatic carbon ring- - an aromatic carbon ring having 14 carbon atoms (phenanthrene skeleton) containing R5 to R12 'are condensed with each other, and one or two substituents of the substituents R5 to R12 in these condensed rings are bonded to the above-mentioned A1 or A2 Is a single bond.

In one embodiment, the substituents Ar1 to Ar3 are the same or different and each independently selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, .

In the above formulas (A) and (B), the substituents R13 and R14 are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted C6- Lt; / RTI >

In this case, the substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms represented by the following structural formulas A to S And can be any one selected.

[Structural Formula A] [Structural formula B] [Structural formula C]

[Structural formula D] [Structural formula E] [Structural formula F]

[Structural formula G] [Structural formula H] [Structural formula I]

[Structural formula J] [Structural formula K] [Structural formula L]

[Structural formula M] [Structural formula N] [Structural formula O]

[Structural formula P] [Structural formula Q]

[Structural formula R] [Structural formula S]

The substituents R in the structural formulas A to S are the same as R 5 to R 12 defined above,

K is an integer of 1 to 7, and when k is 2 or more, each substituent R is the same or different,

When k is 2 or more, each substituent R may be bonded to adjacent substituent R to form a saturated or unsaturated ring.

On the other hand, the organic compound according to the present invention may be an organic compound in which one of the substituents R5 to R12 in the formulas (A) and (B) is a single bond bonding with Al or A2.

In the compound according to the present invention represented by the above formula (B), Ar2 and Ar3 may be the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment according to the present invention, among the substituents R5 to R12 in the above formulas (A) and (B), the substituent which is not connected to A1 or A2 may be hydrogen or deuterium.

In one embodiment of the present invention, the linking groups L 1 and L 2 in the above formulas (A) and (B) are the same or different and each independently a single bond or a group selected from the following Structural Formulas It can be one.

[Structural Formula 1] [Structural Formula 2] [Structural Formula 3] [Structural Formula 4]

[Structural formula 5] [Structural formula 6] [Structural formula 7]

[Structural formula 8] [Structural formula 9]

In the structural formulas 1 to 9, the carbon of the aromatic ring is bonded to hydrogen or deuterium.

Specific examples of the organic compound represented by the above formula (A) or (B) according to the present invention may be a compound represented by any one selected from the group consisting of the following [compounds 1] to [111] Do not.

<Compound 1> <Compound 2> <Compound 3> <Compound 4>

&Lt; Compound 5 > < Compound 6 > < Compound 7 > < Compound 8 &

&Lt; Compound 9 > < Compound 10 > < Compound 11 &

&Lt; Compound 13 > < Compound 14 > < Compound 15 > < Compound 16 &

&Lt; Compound 17 > < Compound 18 > < Compound 19 &

&Lt; Compound 21 > < Compound 22 > < Compound 23 &

<Compound 25> <Compound 26> <Compound 27> <Compound 28>

&Lt; Compound 29 > < Compound 30 > < Compound 31 &

<Compound 33> <Compound 34> <Compound 35> <Compound 36>

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

&Lt; Compound 41 > < Compound 42 > < Compound 43 &

<Compound 45> <Compound 46> <Compound 47> <Compound 48>

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

<Compound 53> <Compound 54> <Compound 55> <Compound 56>

&Lt; Compound 57 > < Compound 58 > < Compound 59 > < Compound 60 &

&Lt; Compound 61 > < Compound 62 > < Compound 63 > < Compound 64 &

<Compound 65> <Compound 66> <Compound 67> <Compound 68>

&Lt; Compound 69 > < Compound 70 > < Compound 71 > < Compound 72 &

<Compound 73> <Compound 74> <Compound 75> <Compound 76>

&Lt; Compound 77 > < Compound 78 > < Compound 79 > < Compound 80 &

<Compound 81> <Compound 82> <Compound 83> <Compound 84>

&Lt; Compound 85 > < Compound 86 > < Compound 87 > < Compound 88 &

<Compound 89> <Compound 90> <Compound 91> <Compound 92>

<Compound 93> <Compound 94> <Compound 95> <Compound 96>

&Lt; Compound 97 > < Compound 98 > < Compound 99 > < Compound 100 &

&Lt; Compound 101 > < Compound 102 > < Compound 103 > < Compound 104 &

<Compound 105> <Compound 106> <Compound 107> <Compound 108>

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

The present invention also provides a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes the organic compound according to the present invention described above.

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.

At this time, the organic layer containing the organic compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer .

Further, the organic compound of the present invention can be used for a hole transporting layer or for an electron transporting layer.

As the material of the hole transporting layer used in the organic light emitting device according to the present invention, the organic compound represented by the above formula (A) or (B) of the present invention may be used.

 In the case where the organic compound represented by the above formula (A) or (B) is not used, a material for a hole transport layer commonly used in the art can be used.

As the material for the hole transport layer, the organic compound represented by the formula (A) or the formula (B) of the present invention may be used, and in addition to the organic compound represented by the formula (A) or (B) In the case where the organic compound represented by the above formula (A) or (B) is not used, a hole transport layer commonly used in the art can be used.

As such a hole transporting layer material, electron donating molecules having a small ionization potential can be used, and diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is widely used, and for example, N, N'- Bis (3-methylphenyl) -N, N'-diphenyl- [1,1-biphenyl] -4,4'- diamine (TPD) or N, N'- N'-diphenylbenzidine (a-NPD), and the like.

A HIL (Hole Injection Layer) may be additionally deposited on the lower portion of the hole transport layer. The hole injection layer material may also be formed using an organic compound represented by the formula (A) or (B) And when the organic compound represented by the above formula (A) or (B) of the present invention is not used, a hole injecting layer commonly used in the art can be used.

Such conventionally used hole injection layers include, for example, copper phthalocyanine (CuPc) or starburst type amine TCTA (4,4 ', 4 "-tri (N-carbazolyl) triphenylamine), m- 4 ', 4 "-tris- (3-methylphenylphenylamino) triphenylamine) and the like can be used.

In addition, the light emitting layer in the organic light emitting device of the present invention may be composed of a host and a dopant. In this case, the host used in the light emitting layer may include at least one compound represented by the following formula (H) .

[Formula H] &lt;

In the above formula (H)

X ₁ to X ₁₀ are the same or different from each other and each independently represent a hydrogen atom, a deuterium atom, 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 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 aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted 5 A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S, a substituted or unsubstituted hetero atom, a substituted Is a group selected from the group consisting of an unsubstituted silicon group, a substituted or unsubstituted boron group, a substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a hydroxyl group, a nitro group, a halogen group, an amide group and an ester group And the groups adjacent to each other may form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero.

More specifically, the host may be represented by any one selected from the group consisting of [compounds 201] to [396], but is not limited thereto.

[Compound 201] [Compound 202] [Compound 203] [Compound 204]

[Compound 205] [Compound 206] [Compound 207] [Compound 208]

[Compound 209] [Compound 210] [Compound 211] [Compound 212]

[Compound 213] [Compound 214] [Compound 215] [Compound 216]

[Compound 217] [Compound 218] [Compound 219] [Compound 220]

[Compound 221] [Compound 222] [Compound 223] [Compound 224]

[Compound 225] [Compound 226] [Compound 227] [Compound 228]

[Compound 229] [Compound 230] [Compound 231] [Compound 232]

[Compound 233] [Compound 234] [Compound 235] [Compound 236]

[Compound 237] [Compound 238] [Compound 239] [Compound 240]

[Compound 241] [Compound 242] [Compound 243] [Compound 244]

[Compound 245] [Compound 246] [Compound 247] [Compound 248]

[Compound 249] [Compound 250] [Compound 251] [Compound 252]

[Compound 253] [Compound 254] [Compound 255] [Compound 256]

[Compound 257] [Compound 258] [Compound 259] [Compound 260]

[Compound 261] [Compound 262] [Compound 263] [Compound 264]

[Compound 265] [Compound 266] [Compound 267] [Compound 268]

[Compound 269] [Compound 270] [Compound 271] [Compound 272]

[Compound 273] [Compound 274] [Compound 275] [Compound 276]

[Compound 277] [Compound 278] [Compound 279] [Compound 280]

[Compound 281] [Compound 282] [Compound 283] [Compound 284]

[Compound 285] [Compound 286] [Compound 287] [Compound 288]

[Compound 289] [Compound 290] [Compound 291] [Compound 292]

[Compound 293] [Compound 294] [Compound 295] [Compound 296]

[Compound 297] [Compound 298] [Compound 299] [Compound 300]

[Compound 301] [Compound 302] [Compound 303] [Compound 304]

[Compound 305] [Compound 306] [Compound 307] [Compound 308]

[Compound 309] [Compound 310] [Compound 311] [Compound 312]

[Compound 313] [Compound 314] [Compound 315] [Compound 316]

[Compound 317] [Compound 318] [Compound 319] [Compound 320]

[Compound 321] [Compound 322] [Compound 323] [Compound 324]

[Compound 325] [Compound 326] [Compound 327] [Compound 328]

[Compound 329] [Compound 330] [Compound 331] [Compound 332]

[Compound 333] [Compound 334] [Compound 335] [Compound 336]

[Compound 337] [Compound 338] [Compound 339] [Compound 340]

[Compound 341] [Compound 342] [Compound 343] [Compound 344]

[Compound 345] [Compound 346] [Compound 347] [Compound 348]

[Compound 349] [Compound 350] [Compound 351] [Compound 352]

[Compound 353] [Compound 354] [Compound 355] [Compound 356]

[Compound 357] [Compound 358] [Compound 359] [Compound 360]

[Compound 361] [Compound 362] [Compound 363] [Compound 364]

[Compound 365] [Compound 366] [Compound 367] [Compound 368]

[Compound 369] [Compound 370] [Compound 371] [Compound 372]

[Compound 373] [Compound 374] [Compound 375] [Compound 376]

[Compound 377] [Compound 378] [Compound 379] [Compound 380]

[Compound 381] [Compound 382] [Compound 383] [Compound 384]

[Compound 385] [Compound 386] [Compound 387] [Compound 388]

[Compound 389] [Compound 390] [Compound 391] [Compound 392]

[Compound 393] [Compound 394] [Compound 395] [Compound 396]

Meanwhile, the dopant used in the light emitting layer in the organic light emitting device of the present invention may be a compound represented by the following formula (1) or (2), and various known dopant materials may be used.

            [Chemical Formula 1] &lt; EMI ID =

Among the above-mentioned formulas (1) and (2)

A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, an optionally substituted arylene group having 6 to 60 carbon atoms , A substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms having a hetero atom O, N or S, and the like.

More specifically, A is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a single bond, preferably an anthracene, pyrene, phenanthrene, indenophenanthrene, klysene, naphthacene, Perylene, pentacene, and more particularly, the A may be a substituent represented by any one of the following formulas (A1) to (A10).

[Formula A1] [Formula A2] [Formula A3]

[Chemical Formula A4] [Chemical Formula A5] [Chemical Formula A6]

[Chemical formula A7] [Chemical formula A8] [Chemical formula A9]

(A10)

Wherein Z ₁ to Z ₂ in the formula [A3] are each independently selected from the group consisting of hydrogen, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted Or an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 2 to 60 carbon atoms (Substituted or unsubstituted C1-C60 alkyl) amino group, or a substituted or unsubstituted C6-C60 aryl) amino group, a substituted or unsubstituted C1-C60 alkylamino group, , (Substituted or unsubstituted aryl group having 6 to 60 carbon atoms) amino group, and Z ₁ to Z ₂ are the same or different from each other and can form a condensed ring with adjacent groups.

In the above formula (1)

X ₁ and X ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, X ₁ and X ₂ may be bonded to each other,

Y ₁ and Y ₂ are each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted Or a substituted or unsubstituted C1 to C24 heteroalkyl group, a substituted or unsubstituted C3 to C24 cycloalkyl group, a substituted or unsubstituted C1 to C24 alkoxy group, a cyano group, a halogen group, a substituted or unsubstituted carbon number A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium, and hydrogen. more selected species and, Y ₁ to Y ₂ each are the same or different each other, may form a fused ring group of the aliphatic, aromatic, aliphatic hetero, or aromatic heterocyclic group which are adjacent to each other It was,

Each of l and m is an integer of 1 to 20, and n is an integer of 1 to 4.

In the above formula (2)

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each cycloalkane may be in a fused form, Each of which may be substituted with deuterium or alkyl, and may be the same as or different from each other.

In addition, Is a single bond or - [C (R ₅ ) (R ₆ )] _p -, and p is an integer of 1 to 3; when p is 2 or more, R ₅ and R ₆ are the same or different from each other;

Wherein _{R 1, R 2, R 3} , R 5 and R ₆ are, each independently, hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms , A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, Or beach (Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms), a di (substituted or unsubstituted alkyl group having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, An aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron,

a is an integer of 1 to 4, and when a is 2 or more, R ₃ of 2 or more are the same or different, and when R ₃ is plural, each R ₃ may be in fused form, and n is 1 to 4 It is an integer.

The amine group bonded to A in the formulas (1) and (2) may be represented by any one selected from the group consisting of the following [substituents 1] to [52], but is not limited thereto.

[Substituent 1]  [Substituent 2]    [Substituent 3]   

  [Substituent group 4] [Substituent group 5] [Substituent group 6]

[Substituent group 7]     [Substituent group 8] [Substituent group 9]

 [Substituent 10] [Substituent group 11]       [Substituent group 12]

 [Substituent group 13] [Substituent group 14] [Substituent 15]

 [Substituent group 16] [Substituent group 17] [Substituent 18]

 [Substituent group 19] [Substituent group 20] [Substituent group 21]

 [Substituent 22]     [Substituent group 23] [Substituent group 24]

[Substituent 25] [Substituent 26] [Substituent 27]

[Substituent 28]     [Substituent group 29] [Substituent group 30]

[Substituent 31]  [Substituent group 32]     [Substituent group 33]

[Substituent 34] [Substituent 35] [Substituent 36]

[Substituent group 37]    [Substituent group 38] [Substituent group 39]

[Substituent 40]  [Substituent 41]  [Substituent 42]

[Substituent 43] [Substituent 44]       [Substituent 45]

[Substituent group 46] [Substituent group 47]     [Substituent group 48]

[Substituent group 49] [Substituent group 50] [Substituent group 51]

[Substituent 52]

In the above substituents, R may be the same or different from each other and is selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted C1 to C60 alkoxy group, A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, (Substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a substituted or unsubstituted aryl (having 6 to 60 carbon atoms) amino group, di (substituted or unsubstituted A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, and each has 1 To 12 carbon atoms, and each of the substituents may form a condensed ring with adjacent groups.

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

When the light emitting layer according to the present invention includes a host and a dopant, the dopant 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.

On the other hand, the electron transporting layer used in the present invention may be formed by using the organic compound represented by the above-mentioned [Formula A] or [Formula B] of the present invention, or a commonly used electron transporting layer material, Or when the organic compound represented by the above formula (A) or (B) is not used in the present invention, a commonly used compound may be used.

Examples of commonly used electron transporting layer compounds include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, BAlq, beryllium bis (benzoquinolyl- (benzoquinolin-10-olate: Bebq2), BCP, compound 201, compound 202, oxadiazole derivative PBD, BMD, BND and the like may be used.

TAZ BAlq

&Lt; Compound 201 > < Compound 202 > BCP

As the electron transporting layer compound in the invention, the organometallic compounds represented by the above formula (F) may be used singly or in combination.

 [Chemical Formula F]

In the above formula (F)

Y is a moiety selected from C, N, O and S, which is directly bonded to M to form a single bond, and any moiety selected from C, N, O and S is a moiety coordinating to M And is a ligand chelated by coordination bond with the single bond; Wherein M is an alkali metal, an alkaline earth metal, an aluminum (Al), or a boron (B) atom, and OA is a monovalent ligand capable of single bond or coordination bond with M,

O is oxygen,

A represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C2 to C20 Substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, and substituted or unsubstituted hetero atoms having 2 to 50 carbon atoms having O, N or S, An aryl group,

M is 1 and n is 0 when M is a metal selected from an alkali metal,

M = 1, n = 1, or m = 2 and n = 0 when M is a metal selected from alkaline earth metals,

M is 1 to 3 when M is boron or aluminum, and n is any of 0 to 2 and satisfies m + n = 3.

In the present invention, Y may be the same or different and independently of each other may be any one selected from the following formulas [C1] to [C39], but is not limited thereto.

[Structural formula C1] [Structural formula C2] [Structural formula C3]

[Structural formula C4] [Structural formula C5] [Structural formula C6]

[Structural formula C7] [Structural formula C8] [Structural formula C9] [Structural formula C10]

[Structural formula C11] [Structural formula C12] [Structural formula C13]

[Structural formula C14] [Structural formula C15] [Structural formula C16]

[Structural formula C17] [Structural formula C18] [Structural formula C19] [Structural formula C20]

[Structural formula C21] [Structural formula C22] [Structural formula C23]

[Structural formula C24] [Structural formula C25] [Structural formula C26]

[Structural formula C27] [Structural formula C28] [Structural formula C29] [Structural formula C30]

[Structural formula C31] [Structural formula C32] [Structural formula C33]

[Structural formula C34] [Structural formula C35] [Structural formula C36]

[Structural formula C37] [Structural formula C38] [Structural formula C39]

In the above Structural Formula C1 to Structural Formula C39,

R is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring. Herein, the 'substitution' in the 'substituted or unsubstituted' refers to a substituent selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, heteroarylamino group, An aryl group, a heteroaryl group, germanium, phosphorus, and boron. The term &quot; substituted aryl group &quot;

Meanwhile, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. The electron injection layer material As long as it is commonly used in the related art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO can be used.

The deposition conditions of the electron injection layer may vary depending on the compound used, but may generally be selected from the same range of conditions as the formation of the hole injection layer.

The thickness of the electron injecting layer may be from about 1 A to about 100 A, and from about 3 A to about 90 A. When the thickness of the electron injection layer satisfies the above-described range, satisfactory electron injection characteristics can be obtained without substantially increasing the driving voltage.

In the present invention, the negative electrode may be formed of a material selected from the group consisting of Li, Mg, Al, Al-Li, Ca, Mg- Mg-Ag), or a transmissive negative electrode using ITO or IZO can be used to obtain a top-emitting device.

In the present invention, at least one layer selected from the functional layer having the hole injection layer, the hole transport layer, the hole injection function and the hole transport function, the light emitting layer, the electron transport layer, and the electron injection layer may be formed by a deposition process 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 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.

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.

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.

Synthesis Example 1. Synthesis of [Compound 1]

Synthetic example  1-1. Synthesis of [intermediate 1-a]

                                                 [Intermediate 1-a]

44.7 g (187 mmol) of dimethylfluorene-3-boronic acid, 50 g (187 mmol) of 2-iodo-3-chlorobenzaldehyde, 4.3 g (3.7 mmol) of tetrakistriphenylphosphine palladium, 52 g (375 mmol) of potassium, 600 ml of toluene and 150 ml of water were put under a nitrogen atmosphere and refluxed for 12 hours. After completion of the reaction, the reaction mixture was subjected to layer separation, and the organic layer was concentrated under reduced pressure, followed by separation by column chromatography to obtain 43 g of Intermediate 1-a. (Yield: 75%)

Synthesis Example 1-2. Synthesis of [intermediate 1-b]

                                            [Intermediate 1-b]

To a round-bottomed flask containing 200 ml of tetrahydrofuran was added 65 ml (97.8 mmol) of 1 M potassium tetrasulfate tetoxide, the temperature was lowered to 0 ° C under a nitrogen atmosphere, and then (methoxymethyl) triphenylphosphonium chloride 33.5 g (97.8 mmol) is dissolved in 200 ml of tetrahydrofuran and then slowly added dropwise. After 30 minutes, 20 g (65.2 mmol) of Intermediate 1-a was dissolved in 200 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was washed with water, and the organic layer was concentrated under reduced pressure, followed by separation by column chromatography to obtain 20.7 g of [intermediate 1-b]. (Yield: 95%)

Synthesis Example 1-3. [Synthesis of intermediate 1-c]

                                           [Intermediate 1-c]

20 g (59.7 mmol) of Intermediate 1-b, 1.9 g (2.9 mmol) of bismuth (III) trifluoromethanesulfonate and 300 ml of 1,2-dichloroethane were placed in a round bottom flask under a nitrogen atmosphere at room temperature And the mixture was stirred for 3 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 10.2 g of [intermediate 1-c]. (Yield: 52%)

Synthesis Example 1-4. Synthesis of [intermediate 1-d]

                                          [Intermediate 1-d]

10 g (30.4 mmol) of Intermediate 1-c, 10 g (39.5 mmol) of bispinacolato diboron, 1.1 g (1.5 mmol) of diphenylphosphinoferrocene palladium dichloride, 8.8 g g (91.2 mmol) of triethylamine and 100 ml of toluene. After completion of the reaction, the reaction mixture was concentrated and then separated by column chromatography to obtain 8.9 g of [intermediate 1-d]. (70% yield)

Synthesis Example 1-5. Synthesis of [Compound 1]

                                                 [Compound 1]

To a round bottom flask was added 8 g (19 mmol) of Intermediate 1-d, 5.6 g (20 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, tetrakistriphenylphosphine palladium 0.4 g (0.3 mmol) of potassium carbonate, 5.2 g (38 mmol) of toluene, 40 ml of toluene, 40 ml of 1,4-dioxane and 20 ml of water were added under nitrogen and refluxed for 12 hours. After completion of the reaction, the reaction mixture was subjected to layer separation, and the organic layer was concentrated under reduced pressure, followed by separation by column chromatography to obtain 7 g of [Compound 1]. (70% yield)

MS (MALDI-TOF): m / z 525.22 [M] ^&lt; ^{+ &}

Synthesis Example 2. Synthesis of [Compound 3]

Synthesis Example 2-1. Synthesis of [intermediate 2-a]

                                         [Intermediate 2-a]

Dichloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5, [Intermediate 2-a] was obtained by the same method except for using 1-naphthalene boronic acid instead of Intermediate 1-d. (Yield: 42%)

Synthesis Example 2-2. Synthesis of [Compound 3]

                                              [Compound 3]

Was synthesized in the same manner as in Synthesis Example 1-5 except that [Intermediate 2-a] was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5 to give [Compound 3] . (Yield: 71%)

MS (MALDI-TOF): m / z 575.24 [M] ^&lt; ^{+ &}

Synthesis Example 3. Synthesis of [Compound 4]

Synthesis Example 3-1. Synthesis of [intermediate 3-a]

                                         [Intermediate 3-a]

Dichloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5, Except that benzofuran-1-boronic acid was used in place of Intermediate 1-d]. [Intermediate 3-a] was obtained. (Yield: 42%)

Synthesis Example 3-2. Synthesis of [Compound 4]

                                              [Compound 4]

Was synthesized in the same manner as in Synthesis Example 1-5 except that [Intermediate 3-a] was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5 to give [Compound 4] . (Yield 67%)

MS (MALDI-TOF): m / z 615.23 [M] ^&lt; ^{+ &}

Synthesis Example 4. Synthesis of [Compound 41]

Synthesis Example 4-1. Synthesis of [intermediate 4-a]

[Intermediate 4-a]

Was synthesized in the same manner as in Synthesis Examples 1-1 to 1-4 using diethylfluorene-3-boronic acid instead of dimethylfluorene-3-boronic acid used in Synthesis Example 1-1 to obtain [Intermediate 4-a] . (Yield: 53%)

Synthesis Example 4-2. [Synthesis of intermediate 4-b]

                           [Intermediate 4-b]

37 g (156 mmol) of (3-amino-benzofuran-2-yl) -phenyl-methanone, 16.9 g (281 mmol) of urea and 185 mL of acetic acid are placed in a 500 mL reactor and stirred under reflux for 12 hours. After completion of the reaction, excess water is added to the reaction product, which is then filtered out. The mixture was hot-slurried with methanol, filtered, hot-slurried with toluene, and then filtered to obtain 24 g of [intermediate 4-b]. (Yield: 59%)

Synthesis Example 4-3. [Synthesis of intermediate 4-c]

                         [Intermediate 4-c]

Add 15 g (44 mmol) of [intermediate 4-b] and 150 mL of phosphorus oxychloride to a 500 mL reactor and stir at reflux for 3 hours. After completion of the reaction, slowly add the reactant to an excess of water at 0 ° C, precipitate it, and filter it. The resultant product was separated by column chromatography to obtain 21 g of [intermediate 4-c]. (Yield: 81%)

Synthesis Example 4-4. Synthesis of [Compound 41]

                                                 [Compound 41]

[Intermediate 4-a] was used in the place of [2-chloro-4,6-diphenyl-1,3,5-triazine used in Preparation Example 1-5 and [Intermediate 4-a] Was used to synthesize [Compound 41]. (Yield 66%)

MS (MALDI-TOF): m / z 566.24 [M] ^&lt; ^{+ &}

Synthesis Example 5. Synthesis of [Compound 56]

Synthesis Example 5-1. Synthesis of [Compound 56]

                                               [Compound 56]

5 g (15.5 mmol) of Intermediate 1-c, 5.1 g (15.5 mmol) of bis-biphenyl-4-yl-amine, 0.2 g (0.3 mmol) of trisdibenzylideneacetone dipalladium, g (1.5 mmol), sodium tertiarybutoxide (3 g, 31.1 mmol) and toluene (50 ml) were added under nitrogen and refluxed for 12 hours. After completion of the reaction, the reaction mixture was subjected to layer separation, and the organic layer was concentrated under reduced pressure, followed by separation by column chromatography to obtain 6.7 g of [Compound 56]. (Yield: 71%)

MS (MALDI-TOF): m / z 613.28 [M] ^&lt; ^{+ &}

Synthesis Example 6. Synthesis of [Compound 61]

Synthesis Example 6-1. Synthesis of [intermediate 6-a]

[Intermediate 6-a]

Was synthesized in the same manner as in Synthesis Examples 1-1 to 1-3 using 2-iodo-5-bromobenzaldehyde instead of 2-iodo-3-chlorobenzaldehyde used in Synthesis Example 1-1 to obtain Intermediate 6-a ]. (Yield 50%)

Synthesis Example 6-2. Synthesis of [Compound 61]

                                                 [Compound 61]

(9,9-dimethoxyphenyl) -amine was used in place of [Intermediate 6-a] instead of [Intermediate 1-c] used in Synthesis Example 5-1 and bis-biphenyl- Dimethylfluoren-2-yl) amine was used in place of the compound [61]. (Yield: 76%)

MS (MALDI-TOF): m / z 653.31 [M] ^&lt; ^{+ &}

Synthesis Example 7. Synthesis of [Compound 74]

Synthesis Example 7-1. [Synthesis of intermediate 7-a]

                           [Intermediate 7-a]

2.3 g (24.7 mmol) of aniline, 7.4 g (30 mmol) of 1-bromodibenzofuran, 0.4 g (0.3 mmol) of palladium acetate, 4.2 g (43 mmol) of sodium tertiarybutoxide, 0.1 g (0.3 mmol) of phosphine and 100 ml of toluene were placed, and the mixture was refluxed with stirring for 13 hours. After completion of the reaction, the reaction mixture was filtered, and the filtrate was concentrated and separated by column chromatography to obtain 4.0 g of Intermediate 7-a. (Yield: 63%)

Synthesis Example 7-2. [Synthesis of intermediate 7-b]

[Intermediate 7-b]

Dibromobenzaldehyde was used instead of 2-iodo-3-chlorobenzaldehyde used in Synthesis Example 1-1 to obtain [Intermediate 7-b] . (Yield: 54%)

Synthesis Example 7-3. Synthesis of [Compound 74]

                                             [Compound 74]

Except that [Intermediate 7-a] was used instead of [Intermediate 7-b] instead of [Intermediate 1-c] used in Synthesis Example 5-1 and [Bis-biphenyl-4-yl- To thereby give [Compound 74]. (Yield: 73%)

MS (MALDI-TOF): m / z 551.22 [M] ^&lt; ^{+ &}

Synthesis Example 8. Synthesis of [Compound 85]

Synthesis Example 8-1. [Synthesis of intermediate 8-a]

                           [Intermediate 8-a]

(0.1 mol) of 4-chlorotoluene, 18.2 g (0.1 mol) of 9-aminocarbazole, 0.08 g (0.32 mmol) of palladium acetate and 2,2'-bis (diphenylphosphino) 0.26 g (0.42 mmol) of binaphthyl and 15.2 g (0.16 mol) of sodium tertiary butoxide were placed in 150 mL of toluene and refluxed for 12 hours. The mixture was cooled to room temperature, washed with methanol, and recrystallized from dichloromethane and methanol to obtain 15.3 g of [intermediate 8-a]. (Yield: 73%)

Synthesis Example 8-2. Synthesis of [Compound 85]

                                           [Compound 85]

Except that [Intermediate 8-a] was used instead of [Intermediate 6-a] instead of [Intermediate 1-c] used in Synthesis Example 5-1 and bis-biphenyl-4-yl- To obtain [Compound 85]. (Yield: 75%)

MS (MALDI-TOF): m / z 564.26 [M] ^&lt; ^{+ &}

Examples 1 to 4: Preparation of organic light emitting diode - electron transport layer

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was adjusted to have a pressure of 1 × 10 ^-6 torr. Then, an organic material was deposited on the ITO using HATCN (50 Å), NPD (650 Å), [BH] + Blue dopant (300 Å), Liq (10 Å), and Al (1,000 Å) were deposited in this order and measured at 0.4 mA. The structures of [HATCN], [NPD], [BD], [BH], and [Liq] are as follows.

[HATCN] [NPD] [BD]

[BH] [Liq]

Comparative Example 1

The organic light emitting diode device for Comparative Example 1 was fabricated in the same manner as in Example 1 except that ET, which is generally used as an electron transport layer material, was used instead of the compound manufactured by the invention. Are as follows.

  [ET]

Comparative Example 2

The organic light emitting diode device for Comparative Example 2 was fabricated in the same manner except that [Formula A-1] was used in place of the compound prepared by the invention in the device structure of the above example, and the structure of the [Formula A-1] It is as follows.

[A-1]

The voltage, luminance, color coordinates, and lifetime of the organic EL device manufactured according to Examples 1 to 4, Comparative Example 1 and Comparative Example 2 were measured, and the results are shown in Table 1 below. T95 means the time required for the luminance to be reduced to 95% compared with the initial luminance (2000 cd / m ² )

division ETL V Cd / A CIEx CIEy T ₉₅ (Hrs) Comparative Example 1 ET 4.3 6.5 0.133 0.129 13 Comparative Example 2 A-1 4.0 6.8 0.133 0.129 20 Example 1 Formula 1 3.7 8.0 0.132 0.130 34 Example 2 (3) 3.6 7.9 0.133 0.128 28 Example 3 Formula 4 3.5 7.9 0.132 0.126 32 Example 4 Formula 41 3.9 7.6 0.133 0.125 35

As shown in Table 1, the organic compound obtained according to the present invention has higher efficiency, lower driving voltage and longer life than ET, which is widely used as an electron transport layer material in the prior art.

Examples 5 to 8: Preparation of organic light emitting diode - Hole transport layer

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber and the base pressure was adjusted to ¹ × 10 ^-6 torr, an organic material was coated on the ITO using HATCN (50 Å) as the hole transport layer, the compound (650 Å) Doped with a host (BH) + blue dopant (BD) of 5% to form a 200 Å thick light emitting layer. Thereafter, the compound ET: Liq = 1: 1 (300 ANGSTROM), the electron injecting layer Liq (10 ANGSTROM) and Al (1,000 ANGSTROM) were sequentially deposited as the electron transporting layer.

Comparative Example 3

The organic light emitting diode device for Comparative Example 3 was fabricated in the same manner as in Example 5 except that NPD, which is widely used as a hole transport layer material in the prior art, was used instead of the compound prepared by the present invention .

Comparative Example 4

The organic light emitting diode device for Comparative Example 4 was fabricated in the same manner except that the compound of Formula B-1 was used instead of the compound of the present invention in the device structure of the above Example, and the structure of Formula B-1 is It is as follows.

[Formula B-1]

The voltage, current, luminance, color coordinates and lifetime of the organic EL device manufactured according to Examples 5 to 8 and Comparative Examples 3 and 4 were measured, and the results are shown in Table 2 below.

division HTL V Cd / A CIEx CIEy T ₉₅ (Hrs) Comparative Example 3 NPD 4.3 6.5 0.133 0.129 13 Comparative Example 4 Formula B 4.1 6.7 0.133 0.129 18 Example 5 Formula 56 3.4 8.3 0.132 0.130 32 Example 6 61 3.3 8.3 0.133 0.128 29 Example 7 74 3.4 8.5 0.132 0.126 33 Example 8 Formula 85 3.5 8.4 0.132 0.126 30

As shown in Table 2, the organic compound obtained by the present invention has higher efficiency, lower driving voltage and longer life than NPD, which is widely used as a hole transport layer material in the prior art.

Claims (16)

An organic compound represented by the following formula (A) or (B).
(A)

[Chemical Formula B]

In the above formulas (A) and (B)
Each of the substituents R 1 to R 4 is the same or different and is 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,
The substituents R5 to R12 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, , A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, a cyano group, a nitro group, a halogen group, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms , A substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a carbonyl group, a phosphoryl group, an amino group, a thiol group, a hydroxyl group, a selenium group, a tellurium group, An ester group,
R13 and R14 are the same or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3- To 50 heteroaryl groups, and R13 and R14 may be connected to each other to form a condensed ring,
In the above formula (A), one or two substituents of the substituents R5 to R12 are a single bond which binds to the A1,
In the above formula (B), one or two substituents of the substituents R5 to R12 are a single bond bonding to the A2, Ar2 and L2 in A2 may be connected to each other to form a condensed ring, and Ar3 and L2 may be They may be connected to each other to form a condensed ring,
The linking groups L 1 and L 2 are the same or different and independently represent a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted C2- A substituted or unsubstituted C2-C60 alkynylene group, a substituted or unsubstituted C3-C60 cycloalkylene group, a substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, And an unsubstituted heteroarylene group having 2 to 60 carbon atoms,
n and m are the same or different and independently of each other an integer of 0 to 3, and when each of these is 2 or more, each of the linking groups L1 and L2 is the same or different from each other,
The substituents Ar 1 to Ar 3 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,
The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group, 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, a heteroaryl group having 2 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An aryloxy group, an aryloxy group, an arylsilyl group, and an aryloxy group having 6 to 24 carbon atoms. The method according to claim 1,
Wherein the substituents Ar 1 to Ar 3 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 30 carbon atoms A heteroaryl group, and a heteroaryl group. The method according to claim 1,
The substituents R13 and R14 in the above formulas (A) and (B) are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted group having 6 to 20 carbon atoms Gt; is an aryl group. The method according to claim 1,
Wherein Ar 1 in the above [Formula A] is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. 5. The method of claim 4,
Wherein the substituent Ar1 in the above formula (A) is any one selected from the following structural formulas A to S.
[Structural formula A] [Structural formula B] [Structural formula C]

[Structural formula D] [Structural formula E] [Structural formula F]

[Structural formula G] [Structural formula H] [Structural formula I]

[Structural formula J] [Structural formula K] [Structural formula L]

[Structural formula M] [Structural formula N] [Structural formula O]

[Structural formula P] [Structural formula Q]

[Structural formula R] [Structural formula S]

The substituents R in the structural formulas A to S are the same as those of R 5 to R 12 defined in claim 1,
K is an integer of 1 to 7, and when k is 2 or more, each R is the same or different,
When k is 2 or more, each substituent R may be bonded to adjacent substituent R to form a saturated or unsaturated ring. The method according to claim 1,
Wherein one of the substituents R5 to R12 is a single bond bonded to Al or A2, in the above formulas (A) and (B). The method according to claim 1,
Wherein Ar 2 and Ar 3 are the same or different and independently of each other, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. The method according to claim 1,
Wherein the substituent R &lt; 5 &gt; to R &lt; 12 &gt; in the above formulas (A) and (B) is hydrogen or deuterium. The method according to claim 1,
Wherein the linking groups L 1 and L 2 in the above formulas (A) and (B) are the same or different from each other and each independently a single bond or any one selected from the following structural formulas (1) to (9).
[Structural Formula 1] [Structural Formula 2] [Structural Formula 3] [Structural Formula 4]

[Structural formula 5] [Structural formula 6] [Structural formula 7]

[Structural formula 8] [Structural formula 9]

In the structural formulas 1 to 9, the carbon of the aromatic ring is bonded to hydrogen or deuterium. The method according to claim 1,
Wherein the compound represented by the above formula (A) or (B) is any one selected from the group consisting of the following compounds [1] to [111].

<Compound 1><Compound2><Compound3><Compound4>

&Lt; Compound 5 >< Compound 6 >< Compound 7 >< Compound 8 &

&Lt; Compound 9 >< Compound 10 >< Compound 11 &

&Lt; Compound 13 >< Compound 14 >< Compound 15 >< Compound 16 &

&Lt; Compound 17 >< Compound 18 >< Compound 19 &

&Lt; Compound 21 >< Compound 22 >< Compound 23 &

<Compound 25><Compound26><Compound27><Compound28>

&Lt; Compound 29 >< Compound 30 >< Compound 31 &

<Compound 33><Compound34><Compound35><Compound36>

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

&Lt; Compound 41 >< Compound 42 >< Compound 43 &

<Compound 45><Compound46><Compound47><Compound48>

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

<Compound 53><Compound54><Compound55><Compound56>

&Lt; Compound 57 >< Compound 58 >< Compound 59 >< Compound 60 &

&Lt; Compound 61 >< Compound 62 >< Compound 63 >< Compound 64 &

<Compound 65><Compound66><Compound67><Compound68>

&Lt; Compound 69 >< Compound 70 >< Compound 71 >< Compound 72 &

<Compound 73><Compound74><Compound75><Compound76>

&Lt; Compound 77 >< Compound 78 >< Compound 79 >< Compound 80 &

<Compound 81><Compound82><Compound83><Compound84>

&Lt; Compound 85 >< Compound 86 >< Compound 87 >< Compound 88 &

<Compound 89><Compound90><Compound91><Compound92>

<Compound 93><Compound94><Compound95><Compound96>

&Lt; Compound 97 >< Compound 98 >< Compound 99 >< Compound 100 &

Compound 101 &gt;&lt; Compound 102 &gt;&lt; Compound 103 &gt;&lt; Compound 104 &

<Compound 105><Compound106><Compound107><Compound108>

&Lt; Compound 109 >< Compound 110 >< Compound 111 > A first electrode;
A second electrode facing the first electrode; And
And an organic layer interposed between the first electrode and the second electrode,
Wherein the organic layer comprises the organic compound according to any one of claims 1 to 10. 12. The method of claim 11,
Wherein the organic light emitting device comprises at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting layer, an electron transporting layer, and an electron injecting layer. 12. The method of claim 11,
Wherein the organic compound is used for a hole transport layer. 12. The method of claim 11,
Wherein the organic compound is used for an electron transport layer. 13. The method of claim 12,
Wherein at least one layer selected from the respective layers is formed by a deposition process or a solution process. 12. The method of claim 11,
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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