KR20170089599A - Novel heterocyclic compounds and organic light-emitting diode including the same - Google Patents

Abstract

The present invention relates to a heterocyclic compound represented by chemical formula A, and an organic light-emitting device including the same. In the chemical formula A, Ar1 to Ar3 are the same as defined in the present specification. According to the present invention, the heterocyclic compound can be used in the production of excellent organic light-emitting devices.

Description

TECHNICAL FIELD The present invention relates to a novel heterocyclic compound and an organic light emitting device including the heterocyclic compound and an organic light emitting diode including the same.

The present invention relates to a novel heterocyclic compound that can be used in a light emitting layer in an organic light emitting device, and an organic light emitting device including the same.

BACKGROUND ART An organic light emitting device using an organic light emitting phenomenon that converts electric energy into light energy using an organic material usually has a structure including an anode, an anode, and an organic material layer therebetween.

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.

In an organic light emitting device, a light emitting material 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 a light emitting 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.

In order for the organic light emitting device to sufficiently exhibit the above-described excellent characteristics, materials constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material are supported by a stable and efficient material Should be preceded.

When current is applied to the organic light emitting device, holes and electrons are injected from the anode and the cathode, respectively, and the injected holes and electrons recombine in the light emitting layer through the respective hole transporting layers and electron transporting layers to form luminescent excitons. The luminescent excitons thus formed emit light while transitioning to the ground state. The light may be divided into fluorescence using a singlet exciton and phosphorescent triplet exciton according to a light emitting mechanism, and the fluorescence and phosphorescence may be used as a light source of an organic light emitting device.

On the other hand, fluorescence using only singlet excitons has a limit of luminous efficiency because the probability of occurrence of singlet excitons is 25%, while phosphorescence using triplet excitons is superior to fluorescence in many cases Is continuing.

However, in the case of a conventional material such as BAlq or CBP used as a host of a phosphorescent material, a device using a conventional phosphorescent material has a higher driving voltage than a device using a fluorescent material, There is no significant advantage in terms of power efficiency (lm / w), and it is disadvantageous in terms of life span. In addition, in order to use such a phosphorescent material as a light emitting device, the aromatic heterocycle is bonded to the skeleton of a 6-membered aromatic ring or a 6-membered heteroaromatic ring in Published Patent Application No. 10-2011-0013220 (2011.02.09) Japanese Patent Laid-Open Publication No. 2010-166070 (2010.7.29) discloses an organic compound in which an aryl or heteroaryl ring is bonded to a substituted or unsubstituted pyrimidine or quinazoline skeleton .

However, in spite of efforts to manufacture the light emitting material for an organic light emitting device, development of a material for low driving voltage or high light emitting efficiency is not sufficient, There is a continuing need to develop such an excellent luminescent material or a material for an electron transporting layer.

Japanese Patent Application Laid-Open No. 10-2011-0013220 (Feb., 2011)

Japanese Unexamined Patent Publication No. 2002-166070 (2010.7.29)

Accordingly, a first technical object of the present invention is to provide a novel heterocyclic compound which can be used in a light emitting layer of an organic light emitting device, has a long lifetime and low voltage driving characteristics and is excellent in light emitting efficiency.

A second object of the present invention is to provide an organic light emitting device including the organic compound.

In order to achieve the first technical object, the present invention provides a heterocyclic compound represented by the following formula (A).

(A)

In the above formula (A)

Ar 1 to Ar 3 are the same or different and are each 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 alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted C1-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C5- A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group , A substituted or unsubstituted alkylamine 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 C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 silyl group, a substituted or unsubstituted C1 to C30 carboxyl group, a thiol group, a cyano group, a hydroxy group, a nitro group, A halogen group, a selenium group, a tellurium group, an amino group, a substituted or unsubstituted ester group having 1 to 30 carbon atoms, or a substituent group represented by the following structural formula A,

At least one of Ar1 to Ar3 is a substituent represented by the following structural formula A,

When two or more of Ar 1 to Ar 3 are substituents represented by the following structural formula A, the substituents represented by the structural formula A are the same as or different from each other.

[Structural Formula A]

In the above formula A,

W is any one selected from O, S, or CR1R2;

The substituents R1, R2, R11 and R12 are the same or different and independently of each other

A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 alkyl group, A substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1- A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylamine 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 heteroaryl group having 2 to 50 carbon atoms, Or a substituted or unsubstituted C 1 -C 30 carboxyl group, a thiol group, a cyano group, a hydroxy group, a nitro group, a halogen group, a selenium group, a tellurium group, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms And an ester group having 1 to 30 carbon atoms, and may form a single ring or polycyclic ring of an alicyclic or aromatic group linked to the adjacent functional group;

The linking group L is a single bond, 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 alkynylene group having 2 to 60 carbon atoms, A substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C2-C60 hetero An arylene group;

m is 1 or 2,

p is an integer of 1 to 4, and when p is 2 or more, each R 11 is the same or different,

q is an integer of 1 to 3, and when q is 2 or more, each R 12 is the same as or different from each other,

n is an integer of 1 to 3, and when n is 2 or more, each L is the same or different from each other;

'- **' is bonded to the carbon atom of the triazine ring in the above formula (A)

Hydrogen or deuterium is bonded when the substituent of R < 11 > or R < 12 > is not bonded to the carbon atoms in both aromatic rings of the structural formula A.

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, An organic light emitting device comprising at least one heterocyclic compound of the present invention is provided.

The heterocyclic compound according to the present invention has long lifetime and low voltage driving characteristics when used as a phosphorescent host material, and has excellent luminescence efficiency, and thus can be used in the production of an excellent 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 present invention provides a heterocyclic compound which can be used in the light emitting layer of an organic light emitting device, which comprises a compound represented by the following formula (A).

(A)

In the above formula (A)

Ar 1 to Ar 3 are the same or different and are each 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 alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted C1-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C5- A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group , A substituted or unsubstituted alkylamine 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 C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 silyl group, a substituted or unsubstituted C1 to C30 carboxyl group, a thiol group, a cyano group, a hydroxy group, a nitro group, A halogen group, a selenium group, a tellurium group, an amino group, a substituted or unsubstituted ester group having 1 to 30 carbon atoms, or a substituent group represented by the following structural formula A,

At least one of Ar1 to Ar3 is a substituent represented by the following structural formula A,

When two or more of Ar 1 to Ar 3 are substituents represented by the following structural formula A, the substituents represented by the structural formula A are the same as or different from each other.

[Structural Formula A]

In the above formula A,

W is any one selected from O, S, or CR1R2;

The substituents R1, R2, R11 and R12 are the same or different and independently of each other

A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 alkyl group, A substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1- A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylamine 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 heteroaryl group having 2 to 50 carbon atoms, Or a substituted or unsubstituted C 1 -C 30 carboxyl group, a thiol group, a cyano group, a hydroxy group, a nitro group, a halogen group, a selenium group, a tellurium group, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms And an ester group having 1 to 30 carbon atoms, and may form a single ring or polycyclic ring of an alicyclic or aromatic group linked to the adjacent functional group;

The linking group L is a single bond, 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 alkynylene group having 2 to 60 carbon atoms, A substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C2-C60 hetero An arylene group;

m is 1 or 2,

p is an integer of 1 to 4, and when p is 2 or more, each R 11 is the same or different,

q is an integer of 1 to 3, and when q is 2 or more, each R 12 is the same as or different from each other,

n is an integer of 1 to 3, and when n is 2 or more, each L is the same or different from each other;

'- **' is bonded to the carbon atom of the triazine ring in the above formula (A)

Hydrogen or deuterium is bonded when a substituent of R < 11 > or R < 12 > is not bonded to carbon atoms in both aromatic rings of the structural formula A;

The "substituted" in the above "substituted or unsubstituted" means a group selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, , An alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 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 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 2 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, 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 5 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 5 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.

In addition, the aryl group used in the compound of the present invention includes 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 include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, crycenyl, naphthacenyl, fluororan And the like, but are not limited thereto.

At least one of the hydrogen atoms of the aryl group may be substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH2, -NH (R) 'And R' 'each independently represent an alkyl group having 1 to 10 carbon atoms, in this case, referred to as an "alkylamino group"), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, A halogenated 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, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, A heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms.

The heteroaryl group which is a substituent used in the compound of the present invention is a heteroaryl group having 2 to 6 carbon atoms which may contain 1 to 4 hetero atoms selected from N, O, P, Se, Te, Si, Ge or S in each ring in the aryl group. Quot; means a heteroaromatic radical of from 2 to 24 carbon atoms, 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.

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, 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.

The present invention relates to a heterocyclic compound represented by the above formula (A), wherein at least one of the substituents Ar1 to Ar3 in the heterocyclic compound is a substituent represented by a structural formula A, And the linking group L is bonded to any one of the six rings of the ring.

In the case of the heterocyclic compound having such a structure in the present invention, it can be used as a phosphorescent host for the light emitting layer.

In one embodiment, the linking groups L in the formula (A) of the present invention are the same or different and independently of each other, or may be 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]

Here, the carbon of the aromatic ring in Structural Formulas 1 to 9 may be bonded to hydrogen or deuterium.

In one embodiment, the substituents R 1, R 2, R 11, and R 12 in the formula (A) are the same or different and are independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C6 to C20 aryl; And a substituted or unsubstituted C2-C20 heteroaryl group.

In the present invention, all of B1 to B4 in the above formula (A) may not be a nitrogen source. That is, the aromatic ring forming the hexagonal ring in the structural formula Q may be composed of only hydrocarbon.

In one embodiment, m in the above formula (A) may be 1 or 2, preferably 1.

In one embodiment, only one of the substituents Ar1 to Ar3 in the triazine ring in the formula [A] is a substituent represented by the structure A or two of them may be a substituent represented by the formula A, May be a substituent represented by Structural Formula A. In this case, the substituent other than the substituent represented by the structural formula A among Ar1 to Ar3 may be the same or different and each is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In the present invention, a more specific example of the heterocyclic compound represented by the formula (A) may be any one selected from the following [compound 1] to [compound 120].

<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 &

<Compound 113> <Compound 114> <Compound 115> <Compound 116>

&Lt; Compound 117 > < Compound 118 > < Compound 119 &

In addition, the present invention can provide a composition for a light emitting layer of an organic light emitting device comprising the heterocyclic compound. Wherein the composition comprises a first host material and a second host material, wherein the first host material uses the heterocyclic compound of the present invention. In this case, the weight ratio of the first host material to the second host material may be in the range of 1:99 to 99: 1, and the second host material may be any known phosphorescent host, Or a combination thereof.

(3)

&Lt; Formula 4 >

&Lt; Formula 5 >

  (6)

In the above Chemical Formulas 3 to 6,

A represents a hydrogen 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 alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C1- 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 aryloxy group having 1 to 30 carbon atoms An alkylamine group, 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 heteroaryl group having 2 to 50 carbon atoms, A substituted or unsubstituted C1 to C30 silyl group, a substituted or unsubstituted C1 to C30 carboxyl group, a thiol group, a cyano group, a hydroxy group, a nitro group, a halogen group, a selenium group, a tellurium group, A substituted or unsubstituted ester group having 1 to 30 carbon atoms;

The linking group L is the same as L described above,

n1 is an integer of 1 to 3, and when n1 is 2 or more, each L is the same or different from each other;

Substituent R31 is the same as R1 and R2 described above,

n2 is an integer of 1 to 5, and when n2 is 2 or more, each R31 is the same or different from each other;

In formula (3), n3 is an integer of 1 to 6, and when n3 is 2 or more, each of [(L) n1- (R31) n2]

In formula (4), n3 is an integer of 1 to 8, and when [n3] is 2 or more, each [(L) n1- (R31) n2]

In formula 5, n3 is an integer from 1 to 14, n3 is 2 or more and if each of the [(L) n1- (R31) n2] are the same or different from each other, the ring including a nitrogen atom forms a five-membered ring ,

Y is any one selected from the group consisting of NR ₃ , CR ₄ R ₅ , SiR ₆ R ₇ , GeR ₈ R ₉ , O, S and Se, the ring containing Y is a 5-membered ring,

 n3 is an integer of 1 to 10, and each [(L) n1- (R31) n2] is the same or different from each other when n3 is 2 or more,

In this case, R3 to R9 may be defined in the same manner as R1 and R2 described above.

Specifically, preferred examples of the second host material are as follows.

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 comprises at least one of the heterocyclic compounds in the present invention; Or a composition for a light emitting layer of an organic light emitting device including the above heterocyclic compound can provide an organic light emitting device.

In the present invention, the phrase "(organic layer) contains at least one organic compound" means that one organic compound belonging to the category of the present invention (organic layer) or two or more different compounds belonging to the category of organic compound May be included.

The organic layer may include 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. At this time, the organic layer interposed between the first electrode and the second electrode includes a light emitting layer, and the light emitting layer comprises a host and a dopant, and the heterocyclic compound in the present invention can be used as a host.

In the present invention, a dopant material may be used for the light emitting layer in addition to the host. When the light emitting layer 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.

Meanwhile, when the heterocyclic compound of the present invention is used as a host, the organic layer may further include a hole blocking layer or an electron blocking layer.

In the present invention, as the electron transport layer material of the organic light emitting device, a well-known electron transport material can be used, which functions to stably transport electrons injected from an electron injection electrode. Examples of known electron transporting materials include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, Balq, beryllium bis (benzoquinolin-10- olate: Bebq2), ADN, compound 201, compound 202, oxadiazole derivative PBD, BMD, BND and the like may be used, but the present invention is not limited thereto.

TAZ BAlq

&Lt; Compound 201 > < Compound 202 > BCP

In addition, the electron transporting layer used in the present invention can be used alone or in combination with the electron transporting layer material as the organometallic compound represented by the formula (C).

&Lt; RTI ID = 0.0 &

In the above formula (C)

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 A ligand chelated by coordination bond with the single bond, and

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

The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, An aryl group, an aryl group, a heteroaryl group, germanium, phosphorus, and boron.

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 alkylamino group having 1 to 30 carbon atoms, an unsubstituted alkylamino group having 1 to 30 carbon atoms, 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 And may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

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.

Subsequently, an organic light emitting layer 50 is laminated on the hole transport layer 40, and a hole blocking layer (not shown) is selectively deposited on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method .

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.

As a material used for the hole blocking layer, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq _2, OXD-7, Liq, and although any one can be selected from any of formulas 1001) to (1007, but is not limited to such .

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

(1001)

 (1004)

1007

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.

The light emitting layer may be made of a host and a dopant.

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

The phosphorescent dopant used in the case where the light emitting layer utilizes phosphorescence may be one or more compounds selected from the compounds represented by the following formulas (A-1) to (J-1).

[General Formula A-1]

Wherein M is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, preferably Ir, Pt, Pd, Rh, Re , Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag. The ligands L ₁ , L ₂ and L ₃ are the same or different from each other and independently selected from the following structural formulas D, but are not limited thereto.

In the following structural formula D, &quot; * &quot; represents a site coordinated to the metal ion M. [

[Structural formula D]

Wherein R is different from or the same as each other and is independently selected from the group consisting of hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, Or a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2- A substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C30 arylamino group, and a substituted or unsubstituted C6- An arylsilyl group having 1 to 30 carbon atoms;

Each R is independently selected from an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen Which may be further substituted with one or more substituents;

And R may be connected to each adjacent substituent by alkylene or alkenylene to form a monocyclic ring and a monocyclic or polycyclic aromatic ring;

The L may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

As one example, the dopant represented by the above-mentioned [formula A-1] may be any one selected from the following compounds.

[Formula B-1]

In the general formula B-1,

M ^A1 represents the same metal ion as defined in the general formula (A1), also, Y ^{A11, A14} Y, Y and Y ^{A15 A18} each independently represent a carbon atom or a nitrogen atom, Y ^{A12, A13} Y, Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom, and L ^A11 , L ^A12 , L ^A13 and L ^A14 each represent a linking group And Q ^A11 and Q ^A12 represent a partial structure containing an atom bonding to M ^A1 .

Exemplary structures of the compound represented by the general formula B-1 include, but are not limited to, the following.

[Formula C-1]

In the general formula C-1,

M ^B1 eunil represents the same metal ion as defined in bansik ^{A-1, Y B11, Y} B14, Y B15 and Y ^B18 represents a carbon atom or a nitrogen atom, each ^{independently, Y B12, Y B13, Y} B16 and Y ^B17 each independently represent a substituted or unsubstituted carbon atoms, a substituted or unsubstituted nitrogen atom, an oxygen atom, a sulfur atom, a, L ^B11, L ^B12, L ^B13, L ^B14 represents a linking group, Q ^B11, Q ^B12 is M ^Lt ; RTI ID = 0.0 &gt; ^B1 . &^Lt; / RTI &gt;

Exemplary structures of the compound represented by the general formula C-1 include, but are not limited to, the following.

[Formula D-1]

In the general formula D-1,

M ^C1 represents a metal ion the same as defined in formula A-1, R ^C11 and R ^C12 each independently represent a hydrogen atom, a substituent which is connected to each other to form a 5-membered ring, R ^C13 and R ^C14 are each independently a hydrogen atom, a substituent which is mutually connected to form a 5-membered ring or a substituent which is not connected to each other, G ^C11 and G ^C12 each independently represent a nitrogen atom, a substituted or unsubstituted L ^C11 and L ^C12 represent a linking group, and Q ^C11 and Q ^C12 represent a partial structure containing an atom bonded to M ^C1 .

Exemplary structures of the compound represented by the general formula D-1 include, but are not limited to, the following.

      [Formula E-1]

In the general formula E-1,

M ^D1 represents the same metal ion as defined in formula (A-1), G ^D11 and G ^D12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and J ^D11 , J ^D12 , J ^D13 and J ^D14 each independently represents an atomic group necessary for forming a five-membered ring, and L ^D11 and L ^D12 represent a linking group.

Exemplary structures of the compound represented by the general formula E-1 include, but are not limited to, the following.

   [Formula F-1]

In the general formula F-1,

M ^E1 eunil represents the same metal ion as defined in bansik ^{A-1, J E11, J} E12 represents a group of atoms necessary haneundedo form a 5-membered ring, each ^{independently, G E11, G E12, G} E13 and G ^E14 are each Y ^E11 , Y ^E12 , Y ^E13, and Y ^E14 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and the like.

Exemplary structures of the compound represented by the general formula F-1 include, but are not limited to, the following.

       [Formula G-1]

In the general formula G-1,

M ^F1 represents the same metal ion as defined in formula A-1,

L ^F11, L ^F12 and L ^F13 represents a linking ^{group, R F11, R F12, R} F13 and R ^F14 represents a substituent, R ^F11 and R ^F12, R ^F12 and R ^F13, R ^F13 and R ^F14 are connected to each other And the ring formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 is a 5-membered ring. And Q ^F11 and Q ^F12 represent a partial structure containing an atom bonding to M ^F1 .

Exemplary structures of the compound represented by the general formula G-1 include, but are not limited to, the following.

[Formula H-1] [Formula H-2] [Formula H-3]

In the general formula H-1,

R ¹¹ and R ¹² are substituents of alkyl, aryl or heteroaryl; And q11 and q12 may be 0 to 4, preferably 0 to 2, and they may form a fused ring with substituents adjacent to each other.

When q11 and q12 are 2 to 4, plural R11 and R12 are the same or different,

L ¹ is a ligand which binds to platinum and is preferably a ligand capable of forming an ortho metal platinum complex, a nitrogen-containing heterocyclic ligand, a diketone ligand or a halogen ligand, more preferably an ortho metal metal) platinum complex, a bipyridyl ligand, or a phenanthroline ligand.

n ¹ is an integer of 0 to 3, preferably 0, m ¹ is 1 or 2, and preferably 2.

It is preferable that n ¹ and m ¹ denote the metal complex represented by the general formula H-1 as a neutral complex.

R ²¹ , R ²² , n ² , m ² , q ²² and L ² are the same as R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² and L ¹ in the general formula H-2, q ²¹ is an integer of 0 to 2, preferably 0.

Wherein R ³¹ , n ³ , m ³ and L ³ are the same as R ¹¹ , n ¹ , m ¹ and L ¹ , q ³¹ is an integer of 0 to 8, 2 is preferable, and 0 is more preferable.

Examples of the specific compounds of the above-mentioned general formulas H-1 to H-3 are as follows, but are not limited thereto.

[Formula I-1]

In the general formula I-1,

Ring A, ring B, ring C, and ring D represent a nitrogen-containing heterocyclic ring which may have a substituent, and the remaining two rings are an aryl ring or heteroaryl which may have a substituent And a condensed ring can be formed by ring A and ring B, ring A and ring C, and / or ring B and ring D, respectively. X ¹ , X ² , X ³ and X ^{4 each} represent a nitrogen atom in which two of the double bonds coordinate to a platinum atom, and the remaining two represent a carbon atom or a nitrogen atom. Q ¹ , Q ² and Q ³ each independently represent a divalent atom (or a bond), but Q ¹ , Q ² and Q ³ do not simultaneously represent a bond. ^{Two of} Z ¹ , Z ² , Z ³ and Z ⁴ represent coordinate bond, and the remaining two represent a covalent bond, an oxygen atom or a sulfur atom.

Examples of the specific compounds of the general formula I-1 include, but are not limited to, the following.

[Formula J-1]

In the general formula J-1,

M represents the same metal ion as defined in the general formula A-1, Ar1 represents a substituted or unsubstituted cyclic structure, and in the two azomethine bonds (-C = N-) bonded to the M, , And nitrogen atoms (N) are respectively bonded to the M and form a three-terminal ligand which is bonded at the 3-position to the M as a whole.

Further, in Ar 1, C represents a carbon atom constituting a ring structure represented by Ar 1. R 1 and R 2 may be the same or different and each represents a substituted or unsubstituted alkyl or aryl group, and L represents a one-dimensional ligand.

In the general formula J-1, M is preferably Pt. The above-mentioned Ar1 is preferably selected from a 5-membered ring, a 6-membered ring and condensed ring group thereof.

Examples of the specific compounds of the general formula J-1 include, but are not limited to, the following.

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

In the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer may be formed by a single molecular 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.

(Example)

Synthesis Example 1: Synthesis of Compound 1

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

Intermediate 1-a was synthesized according to Reaction Scheme 1 below.

<Reaction Scheme 1>

                                                    [Intermediate 1-a]

To a 2 L reactor was added the above 1,3,5-tribromobenzene (50 g, 159 mmol), 4-dibenzofuranboronic acid (67 g, 318 mmol), tetrakis (triphenylphosphine) palladium 3.17 mmol), potassium carbonate (65.7 g, 476 mmol), toluene (700 mL) and distilled water (200 mL) were added, and the mixture was stirred at 100 ° C for 12 hours. After cooling to room temperature, the organic layer was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain [intermediate 1-a]. (33 g, 43%).

Synthesis Example 1- (2): Synthesis of Intermediate 1-b

Intermediate 1-b was synthesized according to Reaction Scheme 2 below.

<Reaction Scheme 2>

         [Intermediate 1-a] [Intermediate 1-b]

500 mL of tetrahydrofuran and [Intermediate 1-a] (33 g, 72.6 mmol) obtained in Synthesis Example 1- (1) were added to a 1 L reaction vessel and the temperature was cooled to -78 ° C under a nitrogen atmosphere. After 30 minutes, 1.6M n-butyl lithium (50 mL, 80 mmol) was slowly added dropwise and stirred at -78 ° C for 1 hour. Trimethylborate (9.05 g, 87.1 mmol) was slowly added dropwise at -78 [deg.] C and the temperature was raised to room temperature. After stirring for 2 hours, an aqueous hydrochloric acid solution was added to terminate the reaction, and the organic layer was extracted and vacuum distilled. The solid was recrystallized from hexane, and the resulting solid was filtered and dried to obtain Intermediate 1-b. (27 g, 88%).

Synthesis Example 1- (3): Synthesis of Compound 1

Compound 1 was synthesized according to Reaction Scheme 3 below.

<Reaction Scheme 3>

  [Intermediate 1-b] [Compound 1]

 Instead of the 1,3,5-tribromobenzene used in Synthesis Example 1- (1), 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 4-dibenzofuranboronic acid [Compound 1] was synthesized in the same manner as in [Intermediate 1-b] except for using [Intermediate 1-b]. (8.3 g, 54%).

MS (MALDI-TOF): m / z 641.21 [M ^&lt; ⁺ &^gt;].

Synthesis Example 2: Synthesis of Compound 11

Synthesis Example 2- (1): Synthesis of Intermediate 2-a

Intermediate 2-a was synthesized according to Reaction Scheme 4 below.

<Reaction Scheme 4>

                                                   [Intermediate 2-a]

Except that 3-bromoiodobenzene was used instead of 1,3,5-tribromobenzene used in Synthesis Example 1- (1) and 4-dibenzothiophene boronic acid was used instead of 4-dibenzofuranboronic acid Were synthesized in the same manner as [Intermediate 2-a]. (29 g, 59%).

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

Intermediate 2-b was synthesized according to Reaction Scheme 5 below.

<Reaction Scheme 5>

        [Intermediate 2-a] [Intermediate 2-b]

Was synthesized in the same manner as Intermediate 2-b except for using [Intermediate 2-a] instead of [Intermediate 1-a] used in Synthesis Example 1- (2). (22 g, 79%).

Synthesis Example 2- (3): Synthesis of Compound 11

Compound 11 was synthesized according to Reaction Scheme 6 below.

<Reaction Scheme 6>

                         [Intermediate 2-b] [Compound 11]

(4-bromophenyl) -4,6-diphenyl-1,3,5-triazine instead of 1,3,5-tribromobenzene used in Synthesis Example 1- (1) [Compound 11] was obtained by the same method except for using [intermediate 2-b] instead of dibenzofuranboronic acid. (17 g, 61%).

MS (MALDI-TOF): m / z 567.18 [M ^&lt; ⁺ &^gt;].

Synthesis Example 3: Synthesis of Compound 23

Synthesis Example 3- (1): Synthesis of Intermediate 3-a

Intermediate 3-a was synthesized according to Scheme 7 below.

<Reaction Scheme 7>

                                                [Intermediate 3-a]

[Intermediate 3-a] was obtained by the same method except for using 2-bromo-9-9-dimethylfluorene instead of [Intermediate 1-a] used in Synthesis Example 1- (2) g, 82%)

Synthesis Example 3- (2): Synthesis of Intermediate 3-b

Intermediate 3-b was synthesized according to Scheme 8 below.

<Reaction Scheme 8>

      [Intermediate 3-a] [Intermediate 3-b]

(21 g, 74%) was obtained in the same manner as Intermediate 3-b except for using [Intermediate 3-a] instead of 4-dibenzothiophene boronic acid used in Synthesis Example 2- (1) )

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

Intermediate 3-c was synthesized according to Scheme 9 below.

<Reaction Scheme 9>

           [Intermediate 3-b] [Intermediate 3-c]

Intermediate 3-c] was obtained (17 g, 81%) except that [Intermediate 3-b] was used instead of [Intermediate 1-a] used in Synthesis Example 1- (2)

Synthesis Example 3- (4): Synthesis of Compound 23

Compound 23 was synthesized according to Reaction Scheme 10 below.

<Reaction formula 10>

[중간체3-c] [화합물 23]

[Intermediate 3-c] [Compound 23]

(14 g, 64%) was obtained by synthesizing [Compound 23], except that [Intermediate 3-c] was used instead of [Intermediate 3-c] used in Synthesis Example 2- (3)

MS (MALDI-TOF): m / z 577.25 [M ^&lt; ⁺ &^gt;

Synthesis Example 4: Synthesis of Compound 42

Synthesis Example 4- (1): Synthesis of Intermediate 4-a

Intermediate 4-a was synthesized according to Scheme 11 below.

<Reaction Scheme 11>

                                           [Intermediate 4-a]

(26 g, 79%) was obtained by synthesizing the intermediate 4-a, except that 2-bromodibenzofuran was used in place of [Intermediate 1-a] used in Synthesis Example 1- (2)

Synthesis Example 4- (2): Synthesis of Intermediate 4-b

Intermediate 4-b was synthesized according to Scheme 12 below.

<Reaction Scheme 12>

   [Intermediate 4-a] [Intermediate 4-b]

Intermediate 4-b] was obtained in the same manner as Intermediate 4-b except that 4-dibenzothiopheneboronic acid used in Synthesis Example 2- (1) was replaced by [Intermediate 4-a]. (21 g, 71% )

Synthesis Example 4- (3): Synthesis of Intermediate 4-c

Intermediate 4-c was synthesized according to Scheme 13 below.

<Reaction Scheme 13>

       [Intermediate 4-b] [Intermediate 4-c]

Intermediate 4-c] was obtained (16 g, 83%) except that [Intermediate 4-b] was used instead of [Intermediate 1-a] used in Synthesis Example 1- (2)

Synthesis Example 4- (4): Synthesis of Compound 42

Compound 42 was synthesized according to Reaction Scheme 14 below.

<Reaction Scheme 14>

[중간체4-c] [화합물 42]

[Intermediate 4-c] [Compound 42]

(11 g, 58%) was obtained by synthesizing [Compound 42], except that [Intermediate 4-c] was used in place of [Intermediate 4-c] used in Synthesis Example 2- (3)

MS (MALDI-TOF): m / z 551.20 [M ^&lt; ⁺ &^gt;

Synthesis Example 5: Synthesis of Compound 68

Synthesis Example 5- (1): Synthesis of Intermediate 5-a

Intermediate 5-a was synthesized according to Reaction Scheme 15 below.

<Reaction Scheme 15>

                                                 [Intermediate 5-a]

(26 g, 79%) was synthesized in the same manner as Intermediate 5-a except that 2-bromodibenzothiophene was used in place of [Intermediate 1-a] used in Synthesis Example 1- (2) )

Synthesis Example 5- (2): Synthesis of Intermediate 5-b

Intermediate 5-b was synthesized according to Scheme 16 below.

<Reaction Scheme 16>

      [Intermediate 5-a] [Intermediate 5-b]

Intermediate 5-b] was obtained by the same procedure as Intermediate 5-a instead of 4-dibenzothiophene boronic acid used in Synthesis Example 2- (1) (22 g, 74% )

Synthesis Example 5- (3): Synthesis of Intermediate 5-c

Intermediate 5-c was synthesized according to Scheme 17 below.

<Reaction Scheme 17>

[Intermediate 5-b] [Intermediate 5-c]

Intermediate 5-c] was obtained (16 g, 77%) except that [Intermediate 5-b] was used instead of [Intermediate 1-a] used in Synthesis Example 1- (2)

Synthesis Example 5- (4): Synthesis of Compound 68

Compound 68 was synthesized according to Scheme 18 below.

<Reaction Scheme 18>

                  [Intermediate 5-c] [Compound 68]

2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used instead of 1,3,5-tribromobenzene used in Synthesis Example 1- (1) (13 g, 52%) was obtained by synthesizing [Compound 68] except for using [Intermediate 5-c] instead of dibenzofuranboronic acid.

MS (MALDI-TOF): m / z 567.18 [M ^&lt; ⁺ &^gt;].

Synthesis Example 6: Synthesis of Compound 75

Synthesis Example 6- (1): Synthesis of Intermediate 6-a

Intermediate 6-a was synthesized according to Scheme 19 below.

<Reaction Scheme 19>

                                                         [Intermediate 6-a]

Dibenzofuranboronic acid was used instead of 4-dibenzothiophene boronic acid used in Synthesis Example 2- (1) to obtain [Intermediate 6-a] (31 g, 76%). %)

Synthesis Example 6- (2): Synthesis of Intermediate 6-b

Intermediate 6-b was synthesized according to Scheme 20 below.

<Reaction Scheme 20>

          [Intermediate 6-a] [Intermediate 6-b]

Intermediate 6-c] was obtained (26 g, 72%) except that [Intermediate 6-a] was used in place of [Intermediate 1-a] used in Synthesis Example 1- (2)

Synthesis Example 6- (3): Synthesis of Compound 75

Compound 75 was synthesized according to Reaction Scheme 21 below.

<Reaction Scheme 21>

                     [Intermediate 6-b] [Compound 75]

(18 g, 58%) was synthesized in the same manner as in [Synthesis Example 2- (3)], except that [Intermediate 6-b] was used instead of [Intermediate 2-b]

MS (MALDI-TOF): m / z 551.20 [M ^&lt; ⁺ &^gt;

Synthesis Example 7: Synthesis of Compound 89

Synthesis Example 7- (1): Synthesis of Compound 89

Compound 89 was synthesized according to Reaction Scheme 22 below.

<Reaction Formula 22>

                  [Intermediate 3-c] [Compound 89]

(12 g, 49%) was obtained by synthesizing [Compound 89] except for using [Intermediate 3-c] instead of [Intermediate 5-c] used in Synthesis Example 5- (4)

MS (MALDI-TOF): m / z 577.25 [M ^&lt; ⁺ &^gt;

Synthesis Example 8: Synthesis of Compound 108

Synthesis Example 8- (1): Synthesis of Intermediate 8-a

Intermediate 8-a was synthesized according to Reaction Scheme 23 below.

<Reaction Scheme 23>

                                                            [Intermediate 8-a]

Synthesis Example 1 (1) using 4-boronic acid instead of 9,9-dimethyl-furan benjyo -9 H in-fluorene by -2-yl-, except that the acid was synthesized in the same manner [Intermediate 8 a] was obtained (19 g, 41%).

Synthesis Example 8- (2): Synthesis of Intermediate 8-b

Intermediate 8-b was synthesized according to Scheme 24 below.

<Reaction Scheme 24>

         [Intermediate 8-a] [Intermediate 8-b]

[Intermediate 8-b] was obtained in the same manner except that [Intermediate 8-a] was used instead of [Intermediate 1-a] used in Synthesis Example 1- (2). (15 g, 84%).

Synthesis Example 8- (3): Synthesis of Compound 108

Compound 108 was synthesized according to Reaction Scheme 25 below.

<Reaction Scheme 25>

[중간체8-b] [화합물 108]

[Intermediate 8-b] [Compound 108]

[Compound 108] was obtained by the same method except for using [Intermediate 8-b] instead of [Intermediate 1-b] used in Synthesis Example 1- (3). (9.1 g, 62%).

MS (MALDI-TOF): m / z 693.31 [M ^&lt; ⁺ &^gt;].

Synthesis Example 9: Synthesis of Compound 115

Synthesis Example 9- (1): Synthesis of Compound 115

Compound 115 was synthesized according to Scheme 26 below.

<Reaction Scheme 26>

                  [Intermediate 3-c] [Compound 115]

Dichloro-6-phenyl-1,3,5-triazine was used instead of the 1,3,5-tribromobenzene used in Synthesis Example 1- (1), and [Intermediate 1-b 3-c] was used in place of the compound [115]. (6.7 g, 43%).

MS (MALDI-TOF): m / z 551.20 [M &lt; + &gt;

Examples 1 to 15 (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 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 coated on the ITO using HATCN (50 Å), NPD (900 Å), the compound prepared by the present invention And the green phosphorescent dopant (GD) was doped with 7% to form a 300 Å thick luminescent layer. The films were deposited in the order of ET: Liq = 1: 1 (300 Å), Liq (10 Å), and Al (1,000 Å).

[HATCN] [NPD]

[ET] [Liq] [GD]

Comparative Example

The organic light emitting device for the comparative example was fabricated in the same manner except that CBP, which is generally used as a phosphorescent host material, was used instead of the compound prepared by the invention in the device structures of Examples 1 to 15, It is as follows.

             <CBP>

The voltage, luminance, color coordinates, and lifetime of the organic light emitting device manufactured according to Examples 1 to 15 and Comparative Examples were measured, and the results are shown in Table 1 below. T ₉₅ means the time required for the luminance to decrease from the initial luminance (6000 cd / m ² ) to 95%.

Host Driving voltage
(V) The luminous efficiency (cd / A) CIEx CIEy T95
6000nit (h) Example 1 Compound 1 3.4 55 0.335 0.627 60 Example 2 Compound 11 3.4 48 0.339 0.631 50 Example 3 Compound 24 3.6 53 0.331 0.627 55 Example 4 Compound 34 3.7 52 0.324 0.636 70 Example 5 Compound 37 3.5 56 0.333 0.628 50 Example 6 Compound 42 3.4 48 0.334 0.629 60 Example 7 Compound 50 3.6 58 0.336 0.627 65 Example 8 Compound 61 3.5 52 0.328 0.632 65 Example 9 Compound 68 3.5 54 0.327 0.632 50 Example 10 Compound 70 3.8 55 0.328 0.633 70 Example 11 Compound 75 3.7 60 0.330 0.632 75 Example 12 Compound 89 3.6 58 0.338 0.626 50 Example 13 Compound 101 3.4 51 0.330 0.632 50 Example 14 Compound 108 3.7 49 0.326 0.634 65 Example 15 Compound 115 3.5 55 0.330 0.631 55 Comparative Example CBP 6.9 36 0.335 0.628 8

As shown in Table 1, the organic light emitting device using the organic compound according to the present invention has higher efficiency, lower driving voltage and longer life than the organic light emitting device according to the comparative example.

Claims (14)

A heterocyclic compound represented by the following formula (A).
(A)

In the above formula (A)
Ar 1 to Ar 3 are the same or different and are each 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 alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted C1-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C5- A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group , A substituted or unsubstituted alkylamine 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 C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 silyl group, a substituted or unsubstituted C1 to C30 carboxyl group, a thiol group, a cyano group, a hydroxy group, a nitro group, A halogen group, a selenium group, a tellurium group, an amino group, a substituted or unsubstituted ester group having 1 to 30 carbon atoms, or a substituent group represented by the following structural formula A,
At least one of Ar1 to Ar3 is a substituent represented by the following structural formula A,
When two or more of Ar 1 to Ar 3 are substituents represented by the following structural formula A, the substituents represented by the structural formula A are the same as or different from each other.
[Structural Formula A]

In the above formula A,
W is any one selected from O, S, or CR1R2;
The substituents R1, R2, R11 and R12 are the same or different and independently of each other
A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 alkyl group, A substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1- A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylamine 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 heteroaryl group having 2 to 50 carbon atoms, a substituted Or a substituted or unsubstituted C 1 -C 30 carboxyl group, a thiol group, a cyano group, a hydroxy group, a nitro group, a halogen group, a selenium group, a tellurium group, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms And an ester group having 1 to 30 carbon atoms, and may form a single ring or polycyclic ring of an alicyclic or aromatic group linked to the adjacent functional group;
The linking group L is a single bond, 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 alkynylene group having 2 to 60 carbon atoms, A substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C2-C60 hetero An arylene group;
m is 1 or 2,
p is an integer of 1 to 4, and when p is 2 or more, each R 11 is the same or different,
q is an integer of 1 to 3, and when q is 2 or more, each R 12 is the same as or different from each other,
n is an integer of 1 to 3, and when n is 2 or more, each L is the same or different from each other;
'- **' is bonded to the carbon atom of the triazine ring in the above formula (A)
Hydrogen or deuterium is bonded when a substituent of R &lt; 11 &gt; or R &lt; 12 &gt; is not bonded to carbon atoms in both aromatic rings of the structural formula A;
The "substituted" in the above "substituted or unsubstituted" means a group selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, , An alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 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 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 2 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, Group, and an aryloxy group having 6 to 24 carbon atoms. The method according to claim 1,
Wherein each of the linking groups L is the same or different and 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,
Substituents R 1, R 2, R 11 and R 12 in the formula [A] are the same or different and each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C6 to C20 aryl; A substituted or unsubstituted C2-C20 heteroaryl group, or a substituted or unsubstituted C2-C20 heteroaryl group. The method according to claim 1,
The heterocyclic compound according to claim 1, wherein m in formula (A) is 1. The method according to claim 1,
Wherein only one of Ar1 to Ar3 in the above-mentioned formula (A) is a substituent group represented by the formula (A). 6. The method of claim 5,
Wherein the substituents not represented by the structural formula A among Ar 1 to Ar 3 are the same or different and each is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. The method according to claim 1,
A heterocyclic compound represented by any one of the following [compound 1] to [compound 120].
<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 &

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

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

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

<Compound 113><Compound114><Compound115><Compound116>

&Lt; Compound 117 >< Compound 118 >< Compound 119 &

A composition for an organic light emitting device comprising a first host material and a second host material,
Wherein the first host material is a heterocyclic compound selected from the group consisting of the compounds represented by any one of claims 1 to 7 and the second host material is any one or more selected from compounds represented by the following formulas (3) to (6) Composition.
(3)

&Lt; Formula 4 >

&Lt; Formula 5 >

(6)

In the above Chemical Formulas 3 to 6,
A represents a hydrogen 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 alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C1- 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 aryloxy group having 1 to 30 carbon atoms An alkylamine group, 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 heteroaryl group having 2 to 50 carbon atoms, A substituted or unsubstituted C1 to C30 carboxyl group, a thiol group, a cyano group, a hydroxy group, a nitro group, a halogen group, a selenium group, a tellurium group, an amino group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms A substituted or unsubstituted ester group having 1 to 30 carbon atoms;
The linking group L is the same as L in claim 1,
n1 is an integer of 1 to 3, and when n1 is 2 or more, each L is the same or different from each other;
Substituent R31 is the same as R1 and R2 in claim 1,
n2 is an integer of 1 to 5, and when n2 is 2 or more, each R31 is the same or different from each other;
In formula (3), n3 is an integer of 1 to 6, and when n3 is 2 or more, each of [(L) n1- (R31) n2]
In formula (4), n3 is an integer of 1 to 8, and when [n3] is 2 or more, each [(L) n1- (R31) n2]
In formula (5), n3 is an integer of 1 to 14, and when n3 is 2 or more, each [(L) n1- (R31) n2] is the same or different from each other and the ring containing nitrogen atom forms a 5-membered ring ,
Y is any one selected from the group consisting of NR ₃ , CR ₄ R ₅ , SiR ₆ R ₇ , GeR ₈ R ₉ , O, S and Se, the ring containing Y is a 5-membered ring,
n3 is an integer of 1 to 10, and each [(L) n1- (R31) n2] is the same or different from each other when n3 is 2 or more,
In this case, R3 to R9 may be defined in the same manner as R1 and R2 described above. 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 at least one heterocyclic compound selected from the group consisting of the following 1 to 7; Or the composition of claim 8. 10. The method of claim 9,
Wherein the organic layer 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. 11. The method of claim 10,
An organic layer interposed between the first electrode and the second electrode includes a light emitting layer,
Wherein the light emitting layer comprises a host and a dopant, and the heterocyclic compound is used as a host. 12. The method of claim 11,
Wherein the organic layer further comprises a hole blocking layer or an electron blocking layer. 11. The method of claim 10,
Wherein at least one layer selected from the respective layers is formed by a deposition process or a solution process. 10. The method of claim 9,
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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