KR20170116974A - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a heterocyclic compound represented by Chemical Formula 1 and an organic light emitting device comprising the same.

Description

HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME [0002]

The present application claims the benefit of Korean Patent Application No. 10-2016-0044992 filed on April 12, 2016, the entire contents of which are incorporated herein by reference.

The present invention relates to heterocyclic compounds and organic light emitting devices containing them.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer 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.

Development of new materials for such organic light emitting devices has been continuously required.

Korean Patent Laid-Open Publication No. 2013-0108635

Heterocyclic compounds and organic light emitting devices containing them are described in this specification.

One embodiment of the present disclosure provides compounds represented by Formula 1:

[Chemical Formula 1]

In Formula 1,

L is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

L is a linking group connected to any one of R ₁ to R ₁₁ and any one of R ₁₂ to R ₁₉ ,

n is an integer from 0 to 4,

When n is 2 or more, L is the same or different from each other,

A is a substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heteroaryl group,

Any one of R ₁ to R ₁₁ and any one of R ₁₂ to R ₁₉ is connected to L,

A group not connected to L of R ₁ to R ₁₉ is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

One embodiment of the present disclosure is an organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, And a compound represented by the general formula (1).

The compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can improve the efficiency, lower driving voltage and / or lifetime characteristics in the organic light emitting device. In particular, the compounds described herein can be used as hole injecting, hole transporting, hole injecting and hole transporting, electron suppressing, luminescence, hole blocking, electron transporting, or electron injecting materials.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.
2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.
FIG. 3 is a diagram showing a mass spectrum result of the intermediate A-1. FIG.
4 shows mass spectral results of the intermediate A-2.
5 shows mass spectral results of intermediate A-6.
FIG. 6 is a diagram showing mass spectral results of the compound 1-1-2A. FIG.
7 is a graph showing a mass spectrum result of the compound 5-2-2A.
8 is a diagram showing mass spectral results of Compound 1-1-41A.
9 is a graph showing the mass spectrum results of the compound 1-2-41A.

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

An embodiment of the present invention provides a compound represented by the above formula (1).

Illustrative examples of such substituents are set forth below, but are not limited thereto.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; And a heterocyclic group, or a substituted or unsubstituted one in which at least two of the above-exemplified substituents are connected to each other. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with an ester group oxygen by a straight-chain, branched or cyclic alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiR _a R _b R _c , wherein R _a , R _b and R _c are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and phenylsilyl groups. Do not.

In the present specification, the boron group may be represented by the formula of -BR _a R _b , wherein R _a and R _b are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to one embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

Substituents comprising the alkyl groups, alkoxy groups and other alkyl moieties described herein include both straight chain and branched forms.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the number of carbon atoms of the alkylamine group is not particularly limited, but is preferably 1 to 40. Specific examples of the alkylamine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, Group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, and the like, but are not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing two or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methylphenylamine, 4-methyl-naphthylamine, 2-methyl- But are not limited to, cenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine group containing at least two heterocyclic groups may contain a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group at the same time.

In the present specification, the arylheteroarylamine group means an aryl group and an amine group substituted with a heterocyclic group.

In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or a stilbene group as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

, A spirofluorenyl group

(9,9-dimethylfluorenyl group), and

(9,9-diphenylfluorenyl group), and the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, P, S, Si and Se, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is from 1 to 30. [

Examples of the heterocyclic group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, A thiadiazole group, a thiadiazole group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a pyrazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, A phenanthridinyl group, a diazanaphthalenyl group, a triazinylidene group, an indole group, an indolyl group, a thiomorpholinyl group, a thiomorpholinyl group, a thienylthio group, a thiomorpholinyl group, , Indolinyl group, indolizinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group , Benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl , A carbazole group, a benzocarbazole group, a dibenzocarbazole group, an indolocarbazole group, an indenocarbazole group, a phenazinyl group, an imidazopyridine group, a phenoxazinyl group, a phenanthroline group, a phenanthroline group, Phenothiazine group, imidazopyridine group, imidazophenanthridine group. A benzoimidazoquinazolinyl group, a benzoimidazophenanthridin group, and the like, but are not limited thereto.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the arylphosphine group, the aralkyl group, the aralkylamine group, the aralkenyl group, the alkylaryl group, the arylamine group and the arylheteroarylamine group, The description of one aryl group may be applied.

In the present specification, the alkyl group in the alkylthio group, the alkylsulfoxy group, the aralkyl group, the aralkylamine group, the alkylaryl group and the alkylamine group can be applied to the alkyl group described above.

In the present specification, the heteroaryl group, the heteroarylamine group, and the heteroaryl group in the arylheteroarylamine group may be aromatic, and the description of the above-mentioned heterocyclic group may be applied.

In the present specification, the alkenyl group in the aralkenyl group can be applied to the description of the alkenyl group described above.

In this specification, the description of the aryl group described above can be applied, except that the alkylene group is a divalent group. In one embodiment, the alkylene group is an alkylene group having 1 to 30 carbon atoms.

In the present specification, the description of the aryl group described above can be applied, except that the arylene group is a divalent group.

In the present specification, the description of the above-mentioned heterocyclic group can be applied, except that the heteroarylene group is aromatic and divalent.

According to one embodiment of the present invention, the compound represented by Formula 1 may be represented by any of Formula 2 to Formula 4 below.

(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 2 to 4,

L, n and A are the same as in the formula (1)

R ₁₀₁ to R ₁₀₄ are hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

p is an integer of 0 to 4,

q and r are the same or different and each independently represents an integer of 0 to 3,

s is an integer of 0 to 7,

When n, p, q, r and s are each 2 or more in the general formula (2), the structures in the parentheses are the same or different from each other,

When n, p, q-1, r + 1 and s are each 2 or more in the general formula (3), the structures in parentheses are the same or different from each other,

When n, p-1, q, r + 1 and s are each 2 or more in the general formula (4), the structures in parentheses are the same or different from each other.

According to one embodiment of the present invention, the compound represented by Formula 1 may be represented by any one of Chemical Formulas 5 to 26 below.

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

[Chemical Formula 21]

[Chemical Formula 22]

(23)

≪ EMI ID =

(25)

(26)

In the above Chemical Formulas 5 to 26,

L, n and A are the same as in the formula (1)

The definition of R ₁₀₁ to R ₁₀₄ , p, q, r and s is the same as in formula (2).

According to one embodiment of the present disclosure, L is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

According to another embodiment, L is a direct bond; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

According to another embodiment, L is a direct bond; An alkylene group having 1 to 30 carbon atoms; An arylene group having 6 to 60 carbon atoms; Or a heteroarylene group having 2 to 60 carbon atoms.

According to another embodiment, L is a direct bond; Or a phenylene group.

According to one embodiment of the present invention, the compound represented by the formula (1) may be represented by any one of the following formulas (27) to (92).

(27)

(28)

[Chemical Formula 29]

(30)

(31)

(32)

(33)

(34)

(35)

(36)

(37)

(38)

[Chemical Formula 39]

(40)

(41)

(42)

(43)

(44)

[Chemical Formula 45]

(46)

(47)

(48)

(49)

(50)

(51)

(52)

(53)

(54)

(55)

(56)

(57)

(58)

[Chemical Formula 59]

(60)

(61)

(62)

(63)

≪ EMI ID =

(65)

(66)

(67)

(68)

(69)

(70)

(71)

(72)

(73)

≪ EMI ID =

(75)

[Formula 76]

[Formula 77]

(78)

(79)

(80)

[Formula 81]

(82)

(83)

(84)

(85)

≪ EMI ID =

[Chemical Formula 87]

[Formula 88]

(89)

(90)

[Formula 91]

≪ EMI ID =

In the above Chemical Formulas 27 to 92,

The definition of A is the same as in formula (1)

The definition of R ₁₀₁ to R ₁₀₄ , p, q, r and s is the same as in formula (2).

According to one embodiment of the present invention, L is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

According to one embodiment of the present invention, L is a direct bond; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms.

According to one embodiment of the present invention, L is a direct bond; A substituted or unsubstituted methylene group; A substituted or unsubstituted ethylene group; A substituted or unsubstituted propylene group; A substituted or unsubstituted n-propylene group; A substituted or unsubstituted isopropylene group; A substituted or unsubstituted butylene group; A substituted or unsubstituted n-butylene group; A substituted or unsubstituted isobutylene group; A substituted or unsubstituted tert-butylene group; A substituted or unsubstituted sec-butylene group; A substituted or unsubstituted 1-methyl-butylene group; A substituted or unsubstituted 1-ethyl-butylene group; A substituted or unsubstituted pentylene group; A substituted or unsubstituted hexylene group; A substituted or unsubstituted heptyl group; A substituted or unsubstituted octylene group; A substituted or unsubstituted nonylene group; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted quaterphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted pyrenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted perylenylene group; A substituted or unsubstituted tetracenylene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluoranthenylene group; And a substituted or unsubstituted fluorenylene group.

According to one embodiment of the present invention, L is a direct bond or a substituted or unsubstituted arylene group.

According to one embodiment of the present invention, L is a direct bond or an arylene group.

According to one embodiment of the present invention, L is a direct bond or a substituted or unsubstituted phenylene group.

According to one embodiment of the present invention, L is a direct bond or a phenylene group.

According to one embodiment of the present invention, A is a substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted phosphine oxide.

According to one embodiment of the present invention, A is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted crecenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted tetracenyl group; A substituted or unsubstituted pentacenyl group; A substituted or unsubstituted phenylamine group; A substituted or unsubstituted biphenylamine group; A substituted or unsubstituted naphthylamine group; A substituted or unsubstituted anthracene amine group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenylbiphenylamine group; A substituted or unsubstituted diphenylterphenylamine group; A substituted or unsubstituted phenylphenanthrene amine group; A substituted or unsubstituted dinaphthylamine group; A substituted or unsubstituted phenylfluorenamine group; A substituted or unsubstituted biphenylfluorene amine group; A substituted or unsubstituted triphenylamine group; A substituted or unsubstituted diphenyl biphenyl amine group; A substituted or unsubstituted phenyldiphenylamine group; A substituted or unsubstituted naphthylphenylbiphenylamine group; A substituted or unsubstituted triphenylamine group; A substituted or unsubstituted diphenylnaphthylamine group; A substituted or unsubstituted diphenylfluorene amine group; A substituted or unsubstituted phenylbiphenylfluorene amine group; A substituted or unsubstituted pyridinyl group; A substituted or unsubstituted pyrimidinyl group; A substituted or unsubstituted thiazinyl group; A substituted or unsubstituted quinazolinyl group; A substituted or unsubstituted quinoxalinyl group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted benzcarbazolyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted spirofluorenyl group; A substituted or unsubstituted indolocarbazole group; Or a substituted or unsubstituted phosphine oxide group.

In one embodiment, A is a phenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a nitrile group, an aryl group and a heterocyclic group; A biphenyl group; Naphthyl group; A phenanthrenyl group; A fluorenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group, an aryl group, and a heterocyclic group; A triphenylrenyl group substituted or unsubstituted with an aryl group; An anthracenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group and an aryl group substituted with a nitrile group; A pentacenyl group substituted or unsubstituted with an aryl group; A phenylamine group substituted or unsubstituted with an aryl group; A biphenylamine group substituted or unsubstituted with an aryl group; A naphthylamine group substituted or unsubstituted with an aryl group; Anthracene amine group substituted or unsubstituted with an aryl group; A diphenylamine group substituted or unsubstituted with an aryl group; A phenylbiphenylamine group substituted or unsubstituted with an aryl group; A diphenylterphenylamine group substituted or unsubstituted with an aryl group; A phenylphenanthreneamine group substituted or unsubstituted with an aryl group; A dinaphthylamine group substituted or unsubstituted with an aryl group; A phenylfluorenamine group substituted or unsubstituted with an aryl group; A biphenylfluorenamine group substituted or unsubstituted with an aryl group; A triphenylamine group substituted or unsubstituted with an aryl group; A diphenyl biphenylamine group substituted or unsubstituted with an aryl group; A phenyldiphenylamine group substituted or unsubstituted with an aryl group; A naphthylphenylbiphenylamine group substituted or unsubstituted with an aryl group; A substituted or unsubstituted triphenylamine group; A diphenylnaphthylamine group substituted or unsubstituted with an aryl group; A diphenylfluoreneamine group substituted or unsubstituted with an aryl group; A phenylbiphenylfluorenamine group substituted or unsubstituted with an aryl group; A pyrimidinyl group substituted with at least one substituent selected from the group consisting of a silyl group substituted with an aryl group and an aryl group; A pyridazinyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a silyl group substituted with an aryl group and an aryl group; An aryl group which is substituted or unsubstituted with a nitrile group or a pyridine group, and a heterocyclic group which is substituted or unsubstituted with a nitrile group or a pyridyl group, or a substituted or unsubstituted thiazinyl group substituted with at least one substituent selected from the group consisting of: A phosphine oxide group substituted or unsubstituted with an aryl group; A carbazole group substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group and a hetero group; A phenanthridine group; Or a phenanthroline group.

In another embodiment, A is a phenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a nitrile group, a phenyl group, a triphenylenyl group and a thiophene group; A biphenyl group; Naphthyl group; A phenanthrenyl group; A fluorenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a methyl group and a phenyl group; A triphenylrenyl group substituted or unsubstituted with a phenyl group; Anthracenyl group substituted or unsubstituted with a fluorenyl group substituted with a nitrile group; A silyl group substituted with a phenyl group, a pyrimidinyl group substituted with at least one substituent selected from the group consisting of a phenyl group, a biphenyl group and a fluorenyl group; A phenyl group substituted or unsubstituted with a pyridyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group substituted with a methyl group, a pyridyl group, a dibenzofurane group and a di A thiazolyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a benzothiophene group; A phenyl group; A phosphine oxide group substituted or unsubstituted with at least one substituent selected from the group consisting of a naphthyl group and a biphenyl group; A carbazole group substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group and a hetero group; A phenanthridine group; Or a phenanthroline group.

According to one embodiment of the present invention, A may be any one selected from the following structures, and the following structures may be further substituted.

The structures include deuterium; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amine group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; An arylheteroarylamine group; Arylphosphine groups; And a heterocyclic group, which may be substituted or unsubstituted.

According to one embodiment of the present invention, A is a phenyl group; A triazinyl group substituted or unsubstituted with a phenyl group; Or a quinazolinyl group substituted or unsubstituted with a phenyl group.

A group not connected to L of R ₁ to R ₁₉ and R ₁₀₁ to R ₁₀₄ are hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

A group not connected to L of R ₁ to R ₁₉ and R ₁₀₁ to R ₁₀₄ are hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 1 to 30 carbon atoms.

A group not connected to L of R ₁ to R ₁₉ and R ₁₀₁ to R ₁₀₄ are hydrogen; heavy hydrogen; A methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert- N-pentyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentene group, naphthyl group, naphthyl group, isopentyl group, neopentyl group, An ethyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an isobutyl group, Ethylhexyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, An alkyl group such as an acyl group, a 4-methylhexyl group and a 5-methylhexyl group; An aryl group such as a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a klycenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group and a fluorenyl group; A pyridyl group, a pyridyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, A triazinylidene group, a triazinylidene group, a triazinylidene group, a triazinylidene group, a triazinylidene group, a triazinylidene group, a triazinylidene group, a thiazolidinyl group, a thiazolidinyl group, A carbazolyl group, a benzothiophenyl group, a benzofuranyl group, a benzimidazole group, a benzofuranyl group, a benzopyranyl group, a benzofuranyl group, a benzofuranyl group, , A benzothiazole group, a benzoxazole group, a benzocarbazole group, a dibenzothiophene group, a dibenzofuranyl group, a dibenzocarbazole group, an indolocarbazole group, an indenocarbazole group, a phenanthroline group, a phenazinyl group , A phenoxazinyl group, a phenothiazinyl group, an imidazopyridinyl group, a The jope I dingi tree. A benzoimidazoquinazolinyl group, a benzoimidazophenanthridinyl group, and these may be further substituted.

Specifically, among R ₁ to R ₁₉ , the group which is not connected to L and R ₁₀₁ to R ₁₀₄ are deuterium; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amine group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; An arylheteroarylamine group; Arylphosphine groups; And a heterocyclic group, which may be substituted or unsubstituted.

In one embodiment of the present invention, the compound of Chemical Formula 1 may be represented by any one of Chemical Formulas 1-1 to 1-4.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In one embodiment of the present invention, the compound of Formula 1 may be represented by any one of the following Formulas 2-1 to 2-4.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

In one embodiment of the present invention, the compound of Formula 1 may be represented by any one of the following Formulas 3-1 to 3-4.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Chemical Formula 3-4]

In one embodiment of the present invention, the compound of Formula 4 may be represented by any one of the following Formulas 4-1 to 4-4.

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

[Formula 4-4]

In one embodiment of the present invention, the compound of Formula 1 may be represented by any one of the following Formulas 5-1 to 5-4.

[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

[Formula 5-4]

In one embodiment of the present invention, the compound of Formula 1 may be represented by any one of the following Formulas 6-1 to 6-4.

[Formula 6-1]

[Formula 6-2]

[Formula 6-3]

[Formula 6-4]

In one embodiment of the present invention, the compound of Formula 1 may be represented by any one of the following Formulas (7-1) to (7-4).

[Formula 7-1]

[Formula 7-2]

[Formula 7-3]

[Chemical Formula 7-4]

In one embodiment of the present invention, the compound of Formula 1 may be represented by any one of the following Formulas 8-1 to 8-4.

[Formula 8-1]

[Formula 8-2]

[Formula 8-3]

[Formula 8-4]

In one embodiment of the present invention, the compound of Formula 1 may be represented by any one of the following Formulas 9-1 to 9-4.

[Formula 9-1]

[Formula 9-2]

[Formula 9-3]

[Formula 9-4]

In one embodiment of the present invention, the compound of Chemical Formula 1 may be represented by any of Chemical Formulas 10-1 to 10-4.

[Formula 10-1]

[Formula 10-2]

[Formula 10-3]

[Formula 10-4]

In one embodiment of the present invention, the compound of Formula 1 may be represented by any one of the following Formulas 11-1 to 11-4.

[Formula 11-1]

[Formula 11-2]

[Formula 11-3]

[Formula 11-4]

According to one embodiment of the present invention, in the above formula (1-1), the substituents L and A are selected from the following [Table 1] to [Table 3].

[Table 1]

[Table 2]

[Table 3]

According to another embodiment, the substituents L and A in the formula 1-2 are selected from the above-mentioned [Table 1] to [Table 3].

According to another embodiment, the substituents L and A in the above formulas 1-3 are selected from the above-mentioned [Table 1] to [Table 3].

According to another embodiment, the substituents L and A in the formula 1-4 are selected from the above-mentioned [Table 1] to [Table 3].

According to another embodiment, in the above formula (2-1), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (2-2), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, the substituents L and A in the above formula (2-3) are selected from the above [Table 1] to [Table 3].

According to another embodiment, the substituents L and A in the above formula (2-4) are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (3-1), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (3-2), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, the substituents L and A in the formula 3-3 are selected from the above-mentioned [Table 1] to [Table 3].

According to another embodiment, the substituents L and A in the formula 3-4 are selected from the above [Table 1] to [Table 3].

According to another embodiment, the substituents L and A in the above formula (4-1) are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (4-2), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (4-3), substituents L and A are selected from the above-mentioned [Table 1] to [Table 3].

According to another embodiment, the substituents L and A in the above formula (4-4) are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (5-1), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (5-2), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (5-3), substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (5-4), the substituents L and A are selected from the above-mentioned [Table 1] to [Table 3].

According to another embodiment, in the above formula (6-1), substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (6-2), substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (6-3), substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, the substituents L and A in the formula (6-4) are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (7-1), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (7-2), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (7-3), substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (7-4), substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (8-1), substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (8-2), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (8-3), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, the substituents L and A in the above formula (8-4) are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (9-1), substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (9-2), substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (9-3), substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (9-4), substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (10-1), substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (10-2), substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (10-3), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (10-4), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (11-1), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (11-2), substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (11-3), the substituents L and A are selected from the above [Table 1] to [Table 3].

According to another embodiment, in the above formula (11-4), the substituents L and A are selected from the above [Table 1] to [Table 3].

In the present specification, the numbers of the compounds having substituents shown in [Table 1] to [Table 3] are the same as in the above-mentioned formulas 1-1 to 1-4, 2-1 to 2-4, 3-1 to 3-4 , 4-1 to 4-4, 5-1 to 5-4, 6-1 to 6-4, 7-1 to 7-4, 8-1 to 8-4, 9-1 to 9-4, 10 -1 to 10-4 and 11-1 to 11-4 can be displayed after attaching the symbols denoted by # in [Table 1] to [Table 3] above. For example, 1-1-1A has a compound of the following structural formula.

[Compound 1-1-1A]

The conjugation length of the compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.

In the present invention, compounds having various energy bandgaps can be synthesized by introducing various substituents to the core structure. Usually, it is easy to control the energy band gap by introducing a substituent to a core structure having a large energy band gap. However, when the core structure has a small energy band gap, it is difficult to control the energy band gap by introducing a substituent. In the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents to the core structure.

Further, by introducing various substituents to the core structure, it is possible to synthesize a compound having the intrinsic characteristics of the introduced substituent. For example, by introducing a substituent mainly used in a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic light emitting device into the core structure, a material meeting the requirements of each organic layer is synthesized .

Also, the organic light emitting device according to the present invention is an organic light emitting device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers Which comprises the above compound.

The organic light emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic compound layers are formed using the above-described compounds.

The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.

Therefore, in the organic light emitting device of the present invention, the organic material layer may include at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, Lt; / RTI >

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the general formula (1). As one example, the compound represented by Formula 1 may be included as a host of the light emitting layer. As another example, the compound represented by Formula 1 may be included as a phosphorescent host in the light emitting layer.

As another example, the organic compound layer containing the compound represented by Formula 1 may include a compound represented by Formula 1 as a host, and may include another organic compound, metal, or metal compound as a dopant.

As another example, the organic material layer containing the compound represented by Formula 1 may include a compound represented by Formula 1 as a host, and may be used together with an iridium (Ir) dopant.

In addition, the organic material layer may include at least one of an electron transporting layer, an electron injecting layer, and a layer that simultaneously performs electron transport and electron injection, and at least one of the layers may include the compound.

In another embodiment, the organic material layer of the organic electronic device includes a hole transporting layer, and the hole transporting layer includes a compound represented by the above formula (1).

In such an organic layer having a multi-layer structure, the compound may be included in a light emitting layer, a layer that simultaneously transports holes and holes, a layer that simultaneously transports light and electrons, or a layer that simultaneously transports electrons and emits light.

For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.

1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated on a substrate 1. In FIG. In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic light emitting device in which an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 are sequentially laminated on a substrate 1 Structure is illustrated. In such a structure, the compound may be included in the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 7, or the electron transporting layer 8.

For example, the organic light emitting device according to the present invention may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate, To form an anode, an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and a material which can be used as a cathode is deposited thereon. In addition to such a method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. The organic material layer may be formed using a variety of polymeric materials by a method such as a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Layer.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methyl compounds), poly [3,4- (ethylene-1,2-dioxy) compounds] (PEDT), polypyrrole and polyaniline.

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

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , An anthraquinone, and a conductive polymer of polyaniline and a poly-compound, but the present invention is not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The organic material layer containing the compound represented by Formula 1 includes the compound represented by Formula 1 as a host, and may be used together with an iridium (Ir) dopant.

For example, an iridium complex used as a phosphorescent dopant is as follows. May include at least one of the following compounds Dp-1 to Dp-37, but is not limited to the structure described below.

The above-mentioned structure is not limited to a dopant compound.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

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

The compound according to the present invention may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors and the like.

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

<Production Example>

&Lt; Preparation Example 1 &

Synthesis of Intermediates A and A-1 to A-6

(1) Preparation of intermediate A-1

To a 2000 ml round bottom flask in a nitrogen atmosphere was added 100.0 g (54.58 mmol, 1 eq) of 10H-phenoxazine and 156.2 g (65.50 mmol, 1 eq) of 1-chloro-2-iodobenzene , 1.2 eq), bis (tri-tert-butylphosphine) palladium (0) (13.9 g, 2.7 mmol, 0.05 eq), sodium tert-butoxide sodium tert-butoxide (157 g, 163.7 mol, 3 eq) were added to 1000 ml of xylene and the mixture was heated with stirring for 5 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 25 to prepare Intermediate A-1 (117 g, yield: 73%).

FIG. 3 is a data showing the result of mass spectrometry to confirm that intermediate A-1 was generated by the progress of the reaction.

(2) Preparation of intermediate A-2

Intermediate A-1 117 g (39.83 mmol , 1.0 eq) in _{Pd (OAc) 2 4.47 g (} 19.92 mmol, 0.05 eq), PPh 3 10.45 g (3.98 mmol, 0.1 eq), K2CO3 110 g (79.66 mmol, 2.0 eq ) And 55.3 g (19.91 mmol, 0.5 eq) of tetra- n- butylammonium chloride were placed in 1000 mL of dimethylacetamide. The reaction solution was stirred at 150 ° C for 20 hours, and then the solvent was concentrated under reduced pressure. The concentrate was completely dissolved in CHCl ₃ and washed with water. The solution in which the product was dissolved was concentrated under reduced pressure and purified by column chromatography. 56.6 g (yield: 58%) of Intermediate A-2 was obtained.

FIG. 4 is a graph showing mass spectrum results showing that intermediate A-2 was generated by the progress of the reaction.

(3) Preparation of intermediate A

56.6 (22.00 mmol, 1 eq) of Intermediate A-2 was dissolved in 500 ml of DMF, and NBS (43.07 g, 24.20 mmol, 1.1 eq) was added in 5 portions at 0 ° C, followed by stirring at room temperature for 3 hours. Thereafter, the solution was reduced in pressure, dissolved in ethyl acetate, washed with water with water, the organic layer was separated, and the solvent was removed by decompression. This was subjected to column chromatography to obtain 112 g (yield: 83%) of intermediate A.

(4) Preparation of intermediates A-3 and A-4

Except that 4-bromo-2-chloro-1-iodobenzene was used instead of 1-chloro-2-iodobenzene , And Compound A-3 was prepared in the same manner as Compound A-1. Then, Compound A-4 was prepared in the same manner as Intermediate A-2 was prepared.

(5) Preparation of intermediates A-5 and A-6

Except that 4-bromo-1-chloro-2-iodobenzene was used instead of 1-chloro-2-iodobenzene And the compound A-5 was prepared in the same manner as the compound A-1. Then, Compound A-6 was prepared in the same manner as Intermediate A-2 was prepared.

FIG. 5 is a data showing the result of mass spectrometry to confirm that intermediate A-6 was generated by the progress of the reaction.

Synthesis of Intermediates B-1 to B-6

(1) Preparation of intermediate B-1

(9H-carbazol-2-yl) boronic acid (13.8 g, 6.54 mmol) was added to a 500 ml round-bottomed flask under nitrogen atmosphere. (triphenylphosphine) palladium (1.37 g, 0.12 mmol, 0.02 eq) was added to the solution, and the mixture was stirred for 6 hours Followed by heating and stirring. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The intermediate B-1 (20 g, yield: 80%) was prepared by a column with tetrahydrofuran: hexane = 1:16.

(2) Preparation of intermediate B-2

(9H-carbazol-3-yl) boronic acid instead of (9H-carbazol-2-yl) boronic acid ), The intermediate B-2 was prepared in the same manner as the intermediate B-1.

(3) Preparation of intermediate B-3

Intermediate B-3 was prepared in the same manner as Intermediate B-1 except for using Intermediate A-4 instead of Intermediate A.

(4) Preparation of intermediate B-4

Intermediate B-4 was prepared in the same manner as Intermediate B-1 except for using Intermediate A-6 instead of Intermediate A.

(5) Preparation of intermediate B-5

Intermediate B-5 was prepared in the same manner as Intermediate B-2 except for using Intermediate A-4 instead of Intermediate A.

(6) Preparation of intermediate B-6

Intermediate B-6 was prepared in the same manner as Intermediate B-2 except for using Intermediate A-6 instead of Intermediate A.

Synthesis of Intermediates C-1 to C-5

(1) Preparation of intermediate C-1

Intermediate A 50 g (14.87 mmol, 1.0 eq), 4,4,5,5-tetramethyl- [l, 3,2] -dioxabororane (4,4,5,5- 3,2] -dioxaborolane) 45.32 g (17.85 mmol, 1.2 eq), Pd (dba) 2 4.28 g (0.74 mmol, 0.05eq), PCy 3 4.17 g (1.48 mmol, 0.1 eq), KOAc 43.79 g (44.62 mmol , 3.0 eq) was placed in 500 mL of dioxane and stirred at reflux for 8 hours. The temperature was lowered to room temperature and the solvent was concentrated under reduced pressure. The concentrate was completely dissolved in CHCl ₃ and washed with water. The solution in which the product was dissolved was concentrated under reduced pressure and purified by column chromatography. 50 g (yield 88%) of Intermediate C-1 was obtained.

(2) Preparation of intermediate C-2

(9H-carbazol-2-yl) boronic acid (20.0 g, 9.47 mmol, 1 eq), 1-chloro-4-iodobenzene (2-chloro-4-iodobenzene) (24.86 g, 10.4 mmol, 1.1 eq) was dissolved in 150 ml of tetrahydrofuran, and 2M potassium carbonate aqueous solution (100 ml) was added. Tetrakis- (triphenylphosphine) palladium g, 0.19 mmol), and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the water layer was removed. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The intermediate C-2 (20 g, yield: 70%) was prepared by column chromatography with tetrahydrofuran: hexane = 1:15.

(3) Preparation of intermediate C-3

Intermediate C-1 (20 g, 5.06 mmol) and Intermediate C-2 (16.8 g, 5.57 mmol) were dissolved in 280 ml of tetrahydrofuran in a 500 ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (140 ml) Tetrakis- (triphenylphosphine) palladium (0.62 g, 0.54 mmol) was added thereto, followed by heating with stirring for 5 hours. The temperature was lowered to room temperature, and the aqueous layer was removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 200 ml of ethyl acetate to obtain 23.5 g (yield: 87%) of Intermediate C-3.

(4) Preparation of intermediate C-4

Method for producing intermediate C-2 except that 1-chloro-4-iodobenzene was used instead of 1-chloro-4-iodobenzene , The intermediate C-4 was prepared.

(5) Preparation of intermediate C-5

Intermediate C-5 was prepared in the same manner as Intermediate C-3 except for using Intermediate C-4 instead of Intermediate C-2.

&Lt; Preparation Example 2 &

1) Synthesis of the following compound 1-1-2A

                                    [Compound 1-1-2A]

To a 500 ml round bottom flask under nitrogen was added intermediate B-1 (10.0 g, 23.7 mmol), 4-bromo-1,1'-biphenyl (6.07 g, 26.0 mmol ) Was completely dissolved in 100 ml of xylene, sodium tert-butoxide (6.82 g, 23.29 mol) was added, bis (tri- tert-butylphosphine) palladium (0) tert-butylphosphine palladium (0)) (0.09 g, 71 mmol) were added thereto, followed by heating with stirring for 5 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 20 to prepare Compound 1-1-2A (9.92 g, yield: 73%).

FIG. 6 is a graph showing mass spectral results to confirm that Compound 1-1-2A was produced in the course of Production Example 2, and MS [M + H] ⁺ = 575.4.

MS [M + H] &lt; ⁺ &gt; = 575

&Lt; Preparation Example 3 &

1) Synthesis of the following compound 1-2-2A

                                     [Compound 1-2-2A]

By the same method as how to prepare a compound 1-1-2A except using Intermediate B-1 was used instead of Intermediate B-2 was produced the compound 1-2-2A.

MS [M + H] &lt; ⁺ &gt; = 575

&Lt; Preparation Example 4 &

1) Synthesis of the following compound 5-1-2A

                                                   [Compound 5-1-2A]

By the same method as how to prepare a compound 1-1-2A except that Intermediate B-1 was used instead of Intermediate B-3 was prepared in the compound compound 5-1-2A.

MS [M + H] &lt; ⁺ &gt; = 575

&Lt; Production Example 5 &

1) Synthesis of the following compound 6-1-2A

                                                 [Compound 6-1-2A]

By the same method as the method for preparing a compound 1-1-2A except using Intermediate B-1 was used instead of Intermediate B-4 was prepared in the compound 6-1-2A.

MS [M + H] &lt; ⁺ &gt; = 575

&Lt; Production Example 6 &

1) Synthesis of the following compound 5-2-2A

                                                [Compound 5-2-2A]

By the same method as how to prepare a compound 1-1-2A except using Intermediate B-1 was used instead of Intermediate B-5 to prepare the compound 5-2-2A.

FIG. 7 shows mass spectrometry results showing that Compound 5-2-2A was produced by the progress of Production Example 6, and MS [M + H] ⁺ = 575.4.

MS [M + H] &lt; ⁺ &gt; = 575

&Lt; Production Example 7 >

1) Synthesis of the following compound 6-2-2A

                                                  [Compound 6-2-2A]

By the same method as how to prepare a compound 1-1-2A except using Intermediate B-1 was used instead of Intermediate B-6 was prepared in the compound 6-2-2A.

MS [M + H] &lt; ⁺ &gt; = 575

&Lt; Production Example 8 &

1) Synthesis of the following compound 1-1-2B

                             [Compound 1-1-2B]

By the same method as how to prepare a compound 1-1-2A except that Intermediate B-1 was used instead of Intermediate C-3 was prepared in the compound 1-1-2B.

MS [M + H] &lt; ⁺ &gt; = 651

&Lt; Production Example 9 &

1) Synthesis of the following compound 1-1-2C

                                [Compound 1-1-2C]

By the same method as how to prepare a compound 1-1-2A except using Intermediate B-1 was used instead of Intermediate C-5 was prepared in the compound 1-1-2C.

MS [M + H] &lt; ⁺ &gt; = 651

&Lt; Production Example 10 &

1) Synthesis of the following compound 1-1-29A

                                [Compound 1-1-29A]

(7.0 g, 16.6 mmol), 5'-bromo-1,1 ': 3', 1 "-terphenyl (5'-bromo-1,1 ' : Sodium tert-butoxide (4.78 g, 49.7 mol) was added to the mixture, followed by the addition of bis (tri (tert-butylphosphine) palladium (0) (0.42 g, 0.8 mmol) was added and the mixture was heated with stirring for 2 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 18 to prepare the compound 1-1-29A (8.95 g, yield: 83%).

MS [M + H] &lt; ⁺ &gt; = 651

&Lt; Production Example 11 &

1) Synthesis of the following compound 1-1-17A

                               [Compound 1-1-17A]

(4-bromo-N, diphenylaniline) was used instead of 4-bromo-1,1'-biphenyl , The compound 1-1-17A was prepared in the same manner as the compound 1-1-2A .

MS [M + H] &lt; ⁺ &gt; = 666

&Lt; Production Example 12 &

1) Synthesis of the following compound 1-1-35A

                                     [Compound 1-1-35A]

Chloro-4,6-diphenyl-1,3,5-triazine instead of 4-bromo-1,1'-biphenyl , 6-diphenyl-1,3,5-triazine), the compound 1-1-35A was prepared in the same manner as the compound 1-1-2A .

MS [M + H] &lt; ⁺ &gt; = 654

&Lt; Production Example 13 >

1) Synthesis of the following compound 5-1-35B

By the same method as how to prepare a compound 1-1-35A except that Intermediate B-1 was used instead of Intermediate B-7 was prepared in the compound 5-1-35B.

MS [M + H] &lt; ⁺ &gt; = 730

&Lt; Production Example 14 >

1) Synthesis of the following compound 6-1-35B

By the same method as how to prepare a compound 1-1-35A except that Intermediate B-1 was used instead of Intermediate B-8 it was prepared in the compound 6-1-35B.

MS [M + H] &lt; ⁺ &gt; = 730

&Lt; Production Example 15 >

1) Synthesis of the following compound 1-1-41A

[Intermediate B-1]                                      [Compound 1-1-41A]

Instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (prepared as described in Example 1) instead of 4-bromo-1,1'- The compound 1-1-41A was prepared in the same manner as the compound 1-1-2A except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine was used. Respectively.

8 is a mass spectral data showing that Compound 1-1-41A was generated by the progress of Production Example 15 and MS [M + H] ⁺ = 730.5.

MS [M + H] &lt; ⁺ &gt; = 730

&Lt; Production Example 16 &

1) Synthesis of the following compound 1-2-41A

                                  [Compound 1-2-41A]

Intermediate B-2 was used in the place of Intermediate B-1, and 2- (3-chlorophenyl) -4,6-dibromobutane was used instead of 4-bromo-1,1'- - how to prepare a compound 1-1-2A except that diphenyl-1,3,5-triazine (2- (3-chlorophenyl) -4,6 -diphenyl-1,3,5-triazine) The compound 1-2-41A was prepared.

FIG. 9 shows Mass Spectrum results showing that Compound 1-2-41A was generated by the progress of Production Example 16, and MS [M + H] ⁺ = 730.4.

MS [M + H] &lt; ⁺ &gt; = 730

<Production Example 17>

1) Synthesis of the following compound 5-1-41A

                                            [Compound 5-1-41A]

Intermediate B-3 was used in the place of Intermediate B-1, and 2- (3-chlorophenyl) -4,6-dioxaborolane was used instead of 4-bromo-1,1'- - how to prepare a compound 1-1-2A except that diphenyl-1,3,5-triazine (2- (3-chlorophenyl) -4,6 -diphenyl-1,3,5-triazine) The compound 5-1-41A was prepared.

MS [M + H] &lt; ⁺ &gt; = 730

&Lt; Production Example 18 >

1) Synthesis of the following compound 1-1-48A

                                 [Compound 1-1-48A]

Using 2-chloro-4,6-diphenylpyrimidine instead of 4-bromo-1,1'-biphenyl, , Compound 1-1-48A was prepared in the same manner as Compound 1-1-2A .

MS [M + H] &lt; ⁺ &gt; = 653

&Lt; Production Example 19 &

1) Synthesis of the following compound 5-1-48A

                                                   [Compound 5-1-48A]

Intermediate B-3 was used in the place of Intermediate B-1, and 2-chloro-4,6-diphenylpyrimidine was used instead of 4-bromo-1,1'-biphenyl with (2-chloro-4,6-diphenylpyrimidine ) and method for producing a compound 1-1-2A, except for using the same method to prepare the compound 5-1-48A.

MS [M + H] &lt; ⁺ &gt; = 653

&Lt; Production Example 20 &

1) Synthesis of the following compound 1-1-56A

                                          [Compound 1-1-56A]

4-bromo-1,1'-biphenyl (4-bromo-1,1'-biphenyl ) instead of the compound except for using 2-chloro-4-phenyl-quinazoline (2-chloro-4-phenylquinazoline ) 1 -1-2A, the compound 1-1-56A was prepared.

MS [M + H] &lt; ⁺ &gt; = 627

&Lt; Preparation Example 21 &

1) Synthesis of the following compound 5-1-56A

                                                [Compound 5-1-56A]

Intermediate B-3 was used in the place of Intermediate B-1 and 2-chloro-4-phenylquinazoline (2- (4-bromo-1,1'-biphenyl) chloro-4-phenylquinazoline), the compound 5-1-56A was prepared in the same manner as the compound 1-1-2A .

MS [M + H] &lt; ⁺ &gt; = 627

&Lt; Production Example 22 >

1) Synthesis of the following compound 1-1-60A

                                         [Compound 1-1-60A]

4-chlorodibenzo [b, d] furan was used instead of 4-bromo-1,1'-biphenyl The compound 1-1-60A was prepared in the same manner as the compound 1-1-2A .

MS [M + H] &lt; ⁺ &gt; = 589

&Lt; Production Example 23 >

1) Synthesis of the following compound 1-1-60B

                                       [Compound 1-1-60B]

By the same method as how to prepare a compound 1-1-60A except that Intermediate B-1 was used instead of Intermediate C-3 was prepared in the compound 1-1-60B.

MS [M + H] &lt; ⁺ &gt; = 665

<Experimental Example 1>

The glass substrate coated with ITO (indium tin oxide) film with a thickness of 1,500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, the detergent was a product of Fischer Co., and distilled water, which was filtered with a filter of Millipore Co., was used as the distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol in order, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

[LINE]

N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (400 angstroms) as a material for transporting holes was thermally vacuum deposited thereon to form a hole transport layer.

[NPB]

Subsequently, Compound 1-1-2A synthesized in the above Production Example was vacuum deposited on the hole transport layer to a film thickness of 300 ANGSTROM at a concentration of 12% with Ir (ppy) 3 dopant to form a light emitting layer

[ET1]

The compound ET1 as an electron transporting material was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injecting and transporting layer. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, the degree of vacuum upon deposition ⅹ10 2 ^-7 To 5 x 10 &lt; ^-6 &gt; torr, thereby fabricating an organic light emitting device.

<Experimental Example 2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-1-2B was used instead of Compound 1-1-2A in Experimental Example 1.

<Experimental Example 3>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-1-2C was used instead of Compound 1-1-2A in Experimental Example 1.

<Experimental Example 4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 5-2-2A was used in place of Compound 1-1-2A in Experimental Example 1.

<Experimental Example 5>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-1-60B was used instead of Compound 1-1-2A in Experimental Example 1.

<Experimental Example 6>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-1-41A was used instead of Compound 1-1-2A in Experimental Example 1.

<Experimental Example 7>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound 1-2-41A was used instead of the compound 1-1-2A in Experimental Example 1.

 <Experimental Example 8>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 5-1-35B was used instead of Compound 1-1-2A in Experimental Example 1.

<Experimental Example 9>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-1-48A was used instead of Compound 1-1-2A in Experimental Example 1.

<Experimental Example 10>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 5-1-56A was used in place of Compound 1-1-2A in Experimental Example 1.

&Lt; Comparative Example 1 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the following H1 was used instead of the compound 1-1-2A in Experimental Example 1.

&Lt; Comparative Example 2 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the following H2 was used instead of the compound 1-1-2A in Experimental Example 1.

&Lt; Comparative Example 3 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the following H3 was used instead of the compound 1-1-2A in Experimental Example 1.

&Lt; Comparative Example 4 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the following H4 was used instead of the compound 1-1-2A in Experimental Example 1.

Table 4 shows the results of devices manufactured using the compounds of Examples 1 to 10 and Comparative Examples 1 to 4 as a light emitting layer.

No. HOST Dopant Doping concentration (%) The driving voltage (V) The luminous efficiency (cd / A) λ _max
(nm) Experimental Example 1 Formula 1-1-2A Ir (ppy) 3 12 4.5 44.5 430 Experimental Example 2 Formula 1-1-2B Ir (ppy) 3 12 4.7 44.0 439 Experimental Example 3 1-1-2C Ir (ppy) 3 12 4.6 44.9 435 Experimental Example 4 5-2-2A Ir (ppy) 3 12 4.4 44.2 431 Experimental Example 5 Formula 1-1-60B Ir (ppy) 3 12 4.6 46.1 431 Experimental Example 6 Formula 1-1-41A Ir (ppy) 3 12 4.9 50.1 514 Experimental Example 7 1-2-41A Ir (ppy) 3 12 4.8 51.8 526 Experimental Example 8 5-1-35B Ir (ppy) 3 12 5.0 50.4 517 Experimental Example 9 Formula 1-1-48A Ir (ppy) 3 12 4.7 53.2 516 Experimental Example 10 Formula 5-1-56A Ir (ppy) 3 12 5.0 49.9 532 Comparative Example 1 H1 Ir (ppy) 3 12 4.9 43.1 430 Comparative Example 2 H2 Ir (ppy) 3 12 5.0 42.1 433 Comparative Example 3 H3 Ir (ppy) 3 12 5.2 44.3 498 Comparative Example 4 H4 Ir (ppy) 3 12 5.1 44.1 448

When current was applied to the organic light-emitting device manufactured in Experimental Examples 1 to 10, the results shown in Table 1 were obtained. In the experimental examples of the present invention, green organic light emitting devices are referred to as materials that are widely used.

As can be seen from the above Table 1, it can be seen that the compounds of the present invention can be used as the host of the green light emitting layer. In particular, it was confirmed that the organic light emitting devices of Experimental Examples 1 to 5, which are the compounds of the present invention, had lower driving voltage characteristics than the organic light emitting devices of Comparative Examples 1 to 4. In Experimental Examples 6 to 10, the luminous efficiency was found to be higher than about 10% as a whole, and it was confirmed that the luminous efficiency was high. In addition, as compared with Comparative Examples 1 and 2, the PL peak is red shifted by about 80 to 100 nm to emerge from the long wavelength region, overlapping with the emission spectrum of the dopant, so that it can be deduced that it is advantageous for energy transfer.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: Hole injection layer
6: hole transport layer
7:
8: Electron transport layer

Claims (11)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
L is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
L is a linking group connected to any one of R ₁ to R ₁₁ and any one of R ₁₂ to R ₁₉ ,
n is an integer from 0 to 4,
When n is 2 or more, L is the same or different from each other,
A is a substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heteroaryl group,
Any one of R ₁ to R ₁₁ and any one of R ₁₂ to R ₁₉ is connected to L,
A group not connected to L of R ₁ to R ₁₉ is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (2) to (4)
(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 2 to 4,
L, n and A are the same as in the formula (1)
R ₁₀₁ to R ₁₀₄ are hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
p is an integer of 0 to 4,
q and r are the same or different and each independently represents an integer of 0 to 3,
s is an integer of 0 to 7,
When n, p, q, r and s are each 2 or more in the general formula (2), the structures in the parentheses are the same or different from each other,
When n, p, q-1, r + 1 and s are each 2 or more in the general formula (3), the structures in parentheses are the same or different from each other,
When n, p-1, q, r + 1 and s are each 2 or more in the general formula (4), the structures in parentheses are the same or different from each other. The compound according to claim 2, wherein the formula (1) is represented by any one of the following formulas (5) to (26)
[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

[Chemical Formula 21]

[Chemical Formula 22]

(23)

&Lt; EMI ID =

(25)

(26)

In the above Chemical Formulas 5 to 26,
L, n and A are the same as in the formula (1)
The definition of R ₁₀₁ to R ₁₀₄ , p, q, r and s is the same as in formula (2). The compound according to claim 1, wherein A is a phenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a nitrile group, an aryl group and a heterocyclic group; A biphenyl group; Naphthyl group; A phenanthrenyl group; A fluorenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group and an aryl group; A triphenylrenyl group substituted or unsubstituted with an aryl group; An anthracenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group substituted with a nitrile group; A pyrimidinyl group substituted with at least one substituent selected from the group consisting of a silyl group substituted with an aryl group and an aryl group; A triazinyl group substituted or unsubstituted with an aryl group; A phosphine oxide group substituted or unsubstituted with an aryl group; A carbazole group substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group and a hetero group; A phenanthridine group; Or a phenanthroline group. The compound according to claim 1, wherein A is any one selected from the following structures:

[2] The compound according to claim 1, wherein the compound represented by Formula 1 is represented by the following Formulas 1-1 to 1-4, Formula 2-1 to 2-4, Formula 3-1 to 3-4, Formula 4-1 to 4-4, (5-1 to 5-4, 6-1 to 6-4, 7-1 to 7-4, 8-1 to 8-4, 9-1 to 9-4, 10-1 to 10-4, 10-4, and 11-1 to 11-4,
The compounds of formulas 1-1 to 1-4, formulas 2-1 to 2-4, formulas 3-1 to 3-4, formulas 4-1 to 4-4, formulas 5-1 to 5-4, formulas 6-1 To 6-4, 7-1 to 7-4, 8-1 to 8-4, 9-1 to 9-4, 10-1 to 10-4 and 11-1 to 11-4 Wherein substituents L and A are selected from the following Tables 1 to 3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Chemical Formula 3-4]

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

[Formula 4-4]

[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

[Formula 5-4]

[Formula 6-1]

[Formula 6-2]

[Formula 6-3]

[Formula 6-4]

[Formula 7-1]

[Formula 7-2]

[Formula 7-3]

[Chemical Formula 7-4]

[Formula 8-1]

[Formula 8-2]

[Formula 8-3]

[Formula 8-4]

[Formula 9-1]

[Formula 9-2]

[Formula 9-3]

[Formula 9-4]

[Formula 10-1]

[Formula 10-2]

[Formula 10-3]

[Formula 10-4]

[Formula 11-1]

[Formula 11-2]

[Formula 11-3]

[Formula 11-4]

[Table 1]

[Table 2]

[Table 3]

An organic light emitting device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is formed by a method according to any one of claims 1 to 6 &Lt; RTI ID = 0.0 &gt; 1, &lt; / RTI &gt; The organic electroluminescent device according to claim 7, wherein the organic material layer includes at least one of an electron injection layer and an electron transport layer, and at least one of the electron injection layer and the electron transport layer contains the compound. The organic light emitting device according to claim 7, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a host of the light emitting layer. 8. The organic electroluminescent device according to claim 7, wherein the organic material layer comprises at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, wherein one of the layers includes the compound Organic light emitting device. 8. The organic light emitting device according to claim 7, wherein the organic compound layer contains the compound as a host and contains another organic compound, metal or metal compound as a dopant.

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