KR101953818B1

KR101953818B1 - Hetero-cyclic compound and organic light emitting device comprising the same

Info

Publication number: KR101953818B1
Application number: KR1020150057428A
Authority: KR
Inventors: 차용범; 김진주; 홍성길
Original assignee: 주식회사 엘지화학
Priority date: 2015-04-23
Filing date: 2015-04-23
Publication date: 2019-03-04
Also published as: KR20160126420A

Abstract

The present invention provides a heterocyclic compound and an organic light emitting device including the heterocyclic compound.

Description

[0001] HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME [0002]

TECHNICAL FIELD The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same.

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 Publication No. 2000-0051826

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,

A is substituted or unsubstituted fluoranthene,

L is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

B 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 cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio 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 arylheteroarylamine 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 or may be bonded to adjacent groups to form a substituted or unsubstituted ring,

R1 to R4 are the same or different from each other and each independently 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 cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio 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 arylheteroarylamine 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, or may be bonded to adjacent groups to form a substituted or unsubstituted ring,

a is an integer of 0 to 2,

b is an integer of 0 to 4,

m is an integer of 0 to 10,

When a, b, and m are each 2 or more, the structures in parentheses are the same or different.

In addition, one embodiment of the present disclosure includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of 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, light emitting, electron transporting, or electron injecting materials. In addition, the compounds described in the present specification can be preferably used as a light emitting layer, an electron transporting or electron injecting material.

According to one embodiment of the present disclosure, the compounds described herein can be used as red or blue hosts, or n-type Green host materials, which in this case can improve efficiency, lower drive voltage and / .

Further, according to one embodiment of the present disclosure, the compounds described herein can be used as blue dopants by linking appropriate substituents.

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.
Figure 3 illustrates one embodiment of the compounds of the present invention.

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; A silyl group substituted or unsubstituted with an alkyl 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; Phosphine oxide 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 one embodiment of the present disclosure, the term "substituted or unsubstituted" preferably includes deuterium; A halogen group; A nitrile group; An alkyl group; A silyl group substituted with an alkyl group; Arylphosphine groups; Phosphine oxide groups; An arylamine group; A heteroarylamine group; An arylheteroarylamine group; An aryl group; And a heterocyclic group, which may be substituted or unsubstituted.

As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

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 a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. 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 -SiRR'R ", wherein R, R 'and R "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 -BRR'R ", wherein R, R 'and R "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, examples of the halogen group include fluorine, chlorine, bromine or iodine.

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 20 carbon atoms. According to another 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 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 this 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 30 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, 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 the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, no.

When the fluorenyl group is substituted,

,

,

, And

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. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, Benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazyl group And dibenzofuranyl groups, but are not limited thereto.

In the present specification, the description of the aforementioned heterocyclic group can be applied, except that the heteroaryl group is aromatic.

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 in the heteroaryl group, the heteroarylamine group and the arylheteroarylamine group can be applied to the description of the above-mentioned heterocyclic group.

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

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

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

In the present specification, the term " forming a ring by bonding to adjacent groups " means forming a ring by bonding to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; A substituted or unsubstituted aromatic heterocycle; Or a condensed ring thereof.

In the present specification, an aliphatic hydrocarbon ring means a ring which is a non-aromatic ring and consists only of carbon and hydrogen atoms.

In the present specification, examples of the aromatic hydrocarbon ring include a phenyl group, a naphthyl group, and an anthracenyl group, but are not limited thereto.

In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing at least one hetero atom.

As used herein, an aromatic heterocyclic ring means an aromatic ring containing at least one heteroatom.

In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.

According to one embodiment of the present disclosure, A may be represented by the following structure.

In the above structure,

Represents a site to which A is connected,

The structure may 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 fluoranthene which is substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, halogen, alkyl group, aryl group and heterocyclic group.

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (2) or (3).

(2)

(3)

In the general formulas (2) and (3)

R 1 to R 4, B, L, m, a and b are as defined in the formula (1).

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

According to one embodiment of the present disclosure, L is a direct bond; Or arylene.

According to one embodiment of the present disclosure, L is a direct bond; Or a substituted or unsubstituted monocyclic to tricyclic arylene.

According to one embodiment of the present disclosure, L is a direct bond; Or arylene of 1 to 4 rings.

According to one embodiment of the present disclosure, L may be a direct bond or any one selected from the following structures.

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 disclosure, B is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, S, O and P.

According to one embodiment of the present disclosure, B is a substituted or unsubstituted aryl group of 1 to 3 rings; Or a substituted or unsubstituted 1 to 6-membered heterocyclic group containing at least one of N, S, O and P. [

According to one embodiment of the present invention, B is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted pyrimidyl; A substituted or unsubstituted triazine group; A substituted or unsubstituted quinolinyl group; A substituted or unsubstituted quinoxaline group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzocarbazole group; A substituted or unsubstituted 3-membered heterocyclic group containing 2 N; A substituted or unsubstituted 5-or 6-membered heterocyclic group containing 2 N; Or a substituted or unsubstituted 4-membered heterocyclic group containing 3 N atoms.

According to one embodiment of the present invention, B is a group selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, a silyl group substituted with an alkyl group, an arylphosphine group, a phosphine oxide group, an arylamine group, a heteroarylamine group, A phenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group, an aryl group, and a heterocyclic group; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A biphenyl group substituted or unsubstituted with at least one substituent selected from R < 1 > An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A substituted or unsubstituted naphthyl group; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A substituted or unsubstituted terphenyl group; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A phenanthryl group substituted or unsubstituted with at least one substituent selected from -O-; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A fluorenyl group which is substituted or unsubstituted with at least one substituent selected from R < 1 > An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A substituted or unsubstituted triphenylene group; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A dibenzofuranyl group substituted or unsubstituted with at least one substituent selected from -S-; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A dibenzothiophene group substituted or unsubstituted with at least one substituent selected from R < 1 > An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A dibenzocarbazolyl group substituted or unsubstituted with at least one substituent selected from R < 1 > An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A carbazolyl group substituted or unsubstituted with at least one substituent selected from R < 1 > An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, An amine group substituted or unsubstituted with at least one substituent selected from -O-; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A benzoxazole group substituted or unsubstituted with at least one substituent selected from -O-; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A benzimidazole group substituted or unsubstituted with at least one substituent selected from -O-; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A benzothiazole group substituted or unsubstituted with at least one substituent selected from -O-; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A substituted or unsubstituted pyridyl group; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A substituted or unsubstituted pyrimidyl group; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A substituted or unsubstituted triazine group; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A substituted or unsubstituted quinoline group; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, An isoquinoline group substituted or unsubstituted with at least one substituent selected from R < 1 > An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A quinazoline group substituted or unsubstituted with at least one substituent selected from R < 1 > An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A pyridopyrimidyl group substituted or unsubstituted with at least one substituent selected from -O-; An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A triple ring heterocyclic group containing two N substituted or unsubstituted with at least one substituent selected from R < 3 > An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, A 5- or 6-membered heterocyclic group containing two N substituted or unsubstituted with at least one substituent selected from R < 2 > An aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, a heterocyclic group, Lt; 3 > is a substituted or unsubstituted 4-membered heterocyclic group containing 3 N's.

According to one embodiment of the present invention, B is a group selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, an alkyl group, a trimethylsilyl group, an arylamine group, a phosphine oxide group substituted with an aryl group, an aryl group and a heterocyclic group A phenyl group substituted or unsubstituted with at least one selected substituent; A biphenyl group; Naphthyl group; A terphenyl group; A phenanthryl group; A fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group; Triphenylene group; A dibenzofuranyl group; A dibenzothiophene group; A dibenzocarbazole group substituted or unsubstituted with phenyl; A carbazolyl group substituted or unsubstituted with an aryl group; An amine group substituted or unsubstituted with an alkyl group or an unsubstituted aryl group; benzoxazole group; A benzimidazole group substituted or unsubstituted with an aryl group; Benzothiazole group; A pyridyl group substituted or unsubstituted with an aryl group; A pyrimidyl group substituted or unsubstituted with an aryl group; A triazine group substituted or unsubstituted with an aryl group; A quinolyl group substituted or unsubstituted with an aryl group; An isoquinoline group substituted or unsubstituted with an aryl group; A quinazoline group substituted or unsubstituted with an aryl group substituted or unsubstituted with an alkyl group; A quinazoline group substituted with a heterocyclic group; A pyridopyrimidyl group; A three-membered heterocyclic group containing two N; A 5-or 6-membered heterocyclic group containing 2 N; Or a four-membered heterocyclic group containing three N's.

According to an embodiment of the present invention, B may be any one selected from the following structures.

According to one embodiment of the present invention, the compound of Formula 1 may be any one selected from the following compounds.

The compound represented by the above formula (1) can be produced based on the following production example. According to one embodiment, it can be prepared in the same manner as in the following Reaction Scheme 1.

[Reaction Scheme 1]

- Core Synthesis of A

The compound 3-bromofluoranthene (30 g, 98 mmol) and 2-amino-9,9-dimethylfluorene (20.5 g, 98 mmol) were completely dissolved in 200 ml of toluene in a nitrogen atmosphere and then NaOt-Bu (11.3 g, 117.6 mmol) The mixture was stirred while increasing the temperature. When refluxing began, Bis (tri-tert-butylphosphine) palladium (0) (0.5 g, 0.98 mmol) was slowly added dropwise. After 3 hours, the reaction was terminated, the temperature was lowered to room temperature, the reaction mixture was concentrated under reduced pressure, and then subjected to column purification to obtain 31.9 g of intermediate A.

MS [M + H] < + > = 410

Intermediate A (31.9 g, 73.3 mmol) and potassium carbonate (10.1 g, 73.3 mmol) were added to 146 ml of pivalic acid. The temperature was heated to 120 ° C and palladium acetate (0.99 g, 4.4 mmol) was added and stirred in an oxygen atmosphere. After 48 hours, the reaction was terminated, the temperature was lowered to room temperature, the reaction mixture was concentrated under reduced pressure, and then purified to obtain 9.5 g of Core B.

MS [M + H] < + > = 408

- Core Synthesis of B

The compound 2-bromofluoranthene (30 g, 98 mmol) and 2-amino-9,9-dimethylfluorene (20.5 g, 98 mmol) were completely dissolved in 200 ml of toluene under a nitrogen atmosphere and then NaOt-Bu (11.3 g, 117.6 mmol) The mixture was stirred while increasing the temperature. When refluxing began, Bis (tri-tert-butylphosphine) palladium (0) (0.5 g, 0.98 mmol) was slowly added dropwise. After 3 hours, the reaction was terminated, the temperature was lowered to room temperature, the reaction mixture was concentrated under reduced pressure, and then subjected to column purification to obtain 28.4 g of intermediate B.

MS [M + H] < + > = 410

Intermediate A (28.4 g, 70.1 mmol) and potassium carbonate (9.12 g, 70.1 mmol) were added to 146 ml of pivalic acid. The temperature was raised to 120 ° C and palladium acetate (0.91 g, 4.0 mmol) was added and stirred in an oxygen atmosphere. The reaction was terminated after 36 hours, the temperature was lowered to room temperature, the reaction mixture was concentrated under reduced pressure, and then purified by column purification to prepare Core B (11.2 g).

MS [M + H] < + > = 408

Also, the present invention provides an organic light emitting device comprising the compound represented by Formula 1.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1.

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.

In one embodiment of the present invention, the organic material layer includes a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, (1).

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound of the general formula (1).

In one embodiment of the present invention, the organic layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound of the above formula (1).

In one embodiment of the present invention, the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and injects electrons includes the compound of the above formula (1).

In another embodiment, the organic material layer includes a light emitting layer and an electron transporting layer, and the electron transporting layer includes the compound of the above formula (1).

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.

In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.

For example, the structure of the organic light emitting device according to one embodiment of the present disclosure is illustrated in FIGS.

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. In such a structure, the compound may be included in the light emitting layer.

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. In such a structure, the compound may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound of the present invention, i.e., the compound of the above formula (1).

When the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode; Wherein at least one of the two or more organic compound layers includes the heterocyclic compound. 2. The organic light emitting device according to claim 1, wherein the organic compound layer comprises at least one organic compound. In one embodiment, the two or more organic layers may be selected from the group consisting of an electron transporting layer, an electron injecting layer, a layer that simultaneously transports electrons and an electron injecting layer, and a hole blocking layer.

In one embodiment of the present invention, the organic material layer includes two or more electron transporting layers, and at least one of the two or more electron transporting layers includes the heterocyclic compound. Specifically, in one embodiment of the present specification, the heterocyclic compound may be contained in one of the two or more electron transporting layers, and may be included in each of two or more electron transporting layers.

In one embodiment of the present invention, when the heterocyclic compound is contained in each of the two or more electron transporting layers, the materials other than the heterocyclic compound may be the same or different from each other.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of Formula 1, that is, the compound represented by Formula 1.

For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

In addition to such a method, an organic light emitting device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

In another embodiment, the first electrode is a cathode and the second electrode is a cathode.

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-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), 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.

The hole injecting material is a layer for injecting holes from the electrode. The hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material. A compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be 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 porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material 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 light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting material is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. 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 electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material with a low work function followed by an aluminum layer or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

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

In one embodiment of the present invention, the compound of Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

The preparation of the compound represented by Formula 1 and the organic light emitting device comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

< Manufacturing example >

< Manufacturing example 1>

- Synthesis of Compound 1

Add Core A (5g, 12.3mmol), bromobenzene (1.8g, 11.5mmol) and NaOt-Bu (1.3g, 13.8mmol) into 30ml of toluene, and raise the temperature with stirring. After warming up, begin to reflux and slowly drop the bis (tri-tertbutylphosphine) palladium (0.11 g, 0.23 mmol). After 5 hours, the reaction was terminated, the temperature was lowered to room temperature, the reaction mixture was concentrated under reduced pressure, and then the column was purified to obtain 5.27 g of Compound 1.

MS [M + H] < + > = 484

< Manufacturing example 2>

- Synthesis of Compound 2

4.9 g of Compound 2 was prepared in the same manner as in the synthesis of Compound 1 except that Core A (5 g, 12.3 mmol) and para-bromobenzonitrile (2.09 g, 11.5 mmol) were used.

MS [M + H] < + > = 509

< Manufacturing example 3>

- Synthesis of Compound 3

5.0 g of Compound 3 was prepared in the same manner as in the synthesis of Compound 1 except that Core A (5 g, 12.3 mmol) and bromobenzene-d5 (1.86 g, 11.5 mmol) were used.

MS [M + H] < + > = 489

< Manufacturing example 4>

- Synthesis of Compound 4

6.1 g of Compound 4 was prepared in the same manner as in the synthesis of Compound 1 except that Core A (5 g, 12.3 mmol) and 4-bromo-1,1'-biphenyl (2.68 g, 11.5 mmol)

MS [M + H] < + > = 560

< Manufacturing example 5>

- Synthesis of Compound 5

6.0 g of Compound 5 was prepared in the same manner as in the synthesis of Compound 1 except that Core A (5 g, 12.3 mmol) and 9-bromophenanthrene (2.94 g, 11.5 mmol) were used.

MS [M + H] < + > = 584

< Manufacturing example 6>

- Synthesis of Compound 6

6.5 g of Compound 6 was prepared in the same manner as in the synthesis of Compound 1 except that Core A (5 g, 12.3 mmol) and 2-bromo-9,9-dimethyl-9H-fluorene (3.13 g, 11.5 mmol) .

MS [M + H] < + > = 600

< Manufacturing example 7>

- Synthesis of Compound 7

5.8 g of Compound 7 was prepared in the same manner as in the synthesis of Compound 1 except that Core A (5 g, 12.3 mmol) and 2-bromonaphthalene (2.37 g, 11.5 mmol) were used.

MS [M + H] < + > = 534

< Manufacturing example 8>

- Synthesis of Compound 8

Add Core A (5 g, 12.3 mmol), 4-bromo-N, N-diphenylaniline (4.11 g, 12.8 mmol) and NaOt-Bu (1.3 g, 13.8 mmol) in 40 ml of toluene and raise the temperature with stirring. After refluxing, tri-tert-butylphosphine palladium (0.13 g, 0.23 mmol) is slowly added dropwise.

After 7 hours, the reaction was terminated, the temperature was lowered to room temperature, the reaction mixture was concentrated under reduced pressure, and then purified by column chromatography to obtain 6.7 g of Compound 8.

MS [M + H] < + > = 651

< Manufacturing example 9>

- Synthesis of Compound 9

Synthesis and purification of Compound 8 were performed except that Core A (5 g, 12.3 mmol) and N- (4-bromophenyl) -N-phenyl- [1,1'- biphenyl] -4 -amine (4.32 g, 12.8 mmol) 7.4 g of Compound 9 was prepared in the same manner.

MS [M + H] < + > = 727

< Manufacturing example 10>

- Synthesis of Compound 10

4-yl) -N- (4-bromophenyl) - [1,1'-biphenyl] -4-amine (5.86 g, 12.3 mmol) 7.6 g of Compound 10 was prepared in the same manner as in the synthesis of Compound 8 except that the compound 10 was used.

MS [M + H] < + > = 803

< Manufacturing example 11>

- Synthesis of Compound 11

Synthesis of Compound 8 above except that Core A (5 g, 12.3 mmol) and N- (4-bromophenyl) -9,9-dimethyl-N-phenyl-9H- fluoren- 7.8 g of the compound 11 was prepared.

MS [M + H] < + > = 767

< Manufacturing example 12>

- Synthesis of Compound 12

4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren-2-amine (7.12 g, 12.3 mmol) , 12.8 mmol), 8.9 g of Compound 12 was prepared.

MS [M + H] < + > = 843

< Manufacturing example 13>

- Synthesis of Compound 13

Add CoreA (5g, 12.3mmol), 9- (4-bromophenyl) -9H-carbazole (3.98g, 12.8mmol) and NaOt-Bu (1.3g, 13.8mmol) into 40ml of toluene and increase the temperature with stirring. After refluxing, tri (tert-butylphosphine) palladium (0.11 g, 0.23 mmol) is slowly added dropwise. The reaction was terminated after 5 hours, the temperature was lowered to room temperature, the reaction mixture was concentrated under reduced pressure, and then purified by column chromatography to obtain 6.9 g of Compound 13.

MS [M + H] < + > = 649

< Manufacturing example 14>

- Synthesis of compound 14

6.7 g of Compound 14 was prepared in the same manner as in the synthesis of Compound 13 except that Core A (5 g, 12.3 mmol) and 9- (3-bromophenyl) -9H-carbazole (3.98 g, 12.9 mmol)

MS [M + H] < + > = 649

< Manufacturing example 15>

- Synthesis of compound 15

6.8 g of Compound 15 was prepared in the same manner as in the synthesis of Compound 13 except that Core A (5 g, 12.3 mmol) and 3-bromo-9-phenyl-9H-carbazole (3.98 g, 12.8 mmol)

MS [M + H] < + > = 649

< Manufacturing example 16>

- Synthesis of Compound 16

6.7 g of Compound 16 was prepared in the same manner as in the synthesis of Compound 13 except that Core A (5 g, 12.3 mmol) and 2-bromo-9-phenyl-9H-carbazole (3.98 g, 12.8 mmol)

MS [M + H] < + > = 649

< Manufacturing example 17>

- Synthesis of Compound 17

7.2 g of Compound 17 was obtained in the same manner as in the synthesis of Compound 13 except that Core A (5 g, 12.3 mmol) and 3- (4-bromophenyl) -9-phenyl-9H- .

MS [M + H] < + > = 725

< Manufacturing example 18>

- Synthesis of compound 18

7.0 g of Compound 18 was synthesized in the same manner as in the synthesis of Compound 1 except that Core A (5 g, 12.3 mmol) and 2- (4-bromophenyl) -9-phenyl-9H- .

MS [M + H] < + > = 725

< Manufacturing example 19>

- Synthesis of Compound 19

7.4 g of Compound 19 was synthesized in the same manner as in the synthesis of Compound 13 except that Core A (5 g, 12.3 mmol) and 3- (3-bromophenyl) -9-phenyl-9H- .

MS [M + H] < + > = 725

< Manufacturing example 20>

- Synthesis of compound 20

6.9 g of Compound 20 was synthesized in the same manner as in the synthesis of Compound 13 except that Core A (5 g, 12.3 mmol) and 2- (3-bromophenyl) -9-phenyl-9H- .

MS [M + H] < + > = 725

< Manufacturing example 21>

- Synthesis of Compound 21

6.3 g of Compound 21 was synthesized in the same manner as in the synthesis of Compound 13 except that Core A (5 g, 12.3 mmol) and 3-bromo-9- (naphthalen2-yl) -9H- .

MS [M + H] < + > = 699

< Manufacturing example 22>

- Synthesis of Compound 22

(4.1 g, 12.8 mmol) and 2- (4-bromophenyl) dibenzo [b, d] thiophene and NaOt-Bu (1.3 g, 13.8 mmol) were added to 40 ml of toluene, . After refluxing, tri (tert-butylphosphine) palladium (0.11 g, 0.23 mmol) is slowly added dropwise. After 9 hours, the reaction was terminated, the temperature was lowered to room temperature, the reaction mixture was concentrated under reduced pressure, and then purified by column chromatography to obtain 6.5 g of Compound 22.

MS [M + H] < + > = 666

< Manufacturing example 23>

- Synthesis of Compound 23

(3.98g, 12.8mmol) and NaOt-Bu (1.3g, 13.8mmol) were added to 40ml of toluene, followed by stirring at room temperature . After refluxing, tri (tert-butylphosphine) palladium (0.11 g, 0.23 mmol) is slowly added dropwise. After 6 hours, the reaction was terminated, the temperature was lowered to room temperature, the reaction mixture was concentrated under reduced pressure, and then subjected to column purification to obtain 6.1 g of Compound 23.

MS [M + H] < + > = 650

< Manufacturing example 24>

- Synthesis of Compound 24

6.3 g of Compound 24 was prepared in the same manner as in the synthesis of Compound 22 except that Core A (5 g, 12.3 mmol) and 4- (4-bromophenyl) dibenzo [b, d] thiophene (4.11 g, 12.8 mmol) Respectively.

MS [M + H] < + > = 666

< Manufacturing example 25>

- Synthesis of compound 25

6.2 g of Compound 25 was prepared in the same manner as in the synthesis of Compound 23 except that Core A (5 g, 12.3 mmol) and 4- (4-bromophenyl) dibenzo [b, d] furan Respectively.

MS [M + H] < + > = 650

< Manufacturing example 26>

- Synthesis of compound 26

Core A (5g, 12.3mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.53g, 12.8mmol) and K3PO4 (4.88g, 23mmol) were placed in 21ml of xylene and 7ml of DMAC The temperature is raised while stirring. After the temperature was elevated, reflux was started. After 7 hours, the reaction was terminated. The temperature was lowered to room temperature, and the reaction mixture was concentrated under reduced pressure, followed by column purification to obtain 6.7 g of Compound 26.

MS [M + H] < + > = 639

< Manufacturing example 27>

- Synthesis of Compound 27

Add Core A (5 g, 12.3 mmol), 2-chloro-4,6-diphenylpyrimidine (3.38 g, 12.7 mmol) and K3PO4 (4.88 g, 23 mmol) into 21 ml of xylene and 7 ml of DMAC. After the temperature was elevated, reflux was started. After 5 hours, the reaction was terminated. The temperature was lowered to room temperature, and the reaction mixture was concentrated under reduced pressure and then purified by column chromatography to obtain 6.9 g of Compound 27.

MS [M + H] < + > = 638

< Manufacturing example 28>

- Synthesis of compound 28

Add Core A (5 g, 12.3 mmol), 2-chloro-4,6-diphenylpyridine (3.37 g, 12.7 mmol) and K3PO4 (4.88 g, 23 mmol) into 21 ml of xylene and 7 ml of DMAC. After the temperature was elevated, reflux was started. After 9 hours, the reaction was completed. The temperature was lowered to room temperature, and the mixture was concentrated under reduced pressure and then purified by filtration to obtain 6.4 g of Compound 28.

MS [M + H] < + > = 637

< Manufacturing example 29>

- Synthesis of Compound 29

(6.1 g, 12.7 mmol) and NaOt-Bu (1.3 g, 13.8 mmol) were dissolved in 40 ml of toluene And the temperature is raised while stirring. After refluxing, tri (tert-butylphosphine) palladium (0.11 g, 0.23 mmol) is slowly added dropwise. After 6 hours, the reaction was terminated, the temperature was lowered to room temperature, the reaction mixture was concentrated under reduced pressure and then subjected to column purification to obtain 7.3 g of Compound 29.

MS [M + H] < + > = 715

< Manufacturing example 30>

- Synthesis of compound 30

Add Core A (5g, 12.3mmol), 2- (4-bromophenyl) 4,6-diphenylpyrimidine (6.15g, 12.7mmol) and NaOt-Bu (1.3g, 13.8mmol) into 40ml of toluene and raise the temperature with stirring . After refluxing, tri (tert-butylphosphine) palladium (0.11 g, 0.23 mmol) is slowly added dropwise. After 8 hours, the reaction was terminated, the temperature was lowered to room temperature, the reaction mixture was concentrated under reduced pressure and then subjected to column purification to obtain 7.0 g of Compound 30.

MS [M + H] < + > = 714

< Manufacturing example 31>

- Synthesis of Compound 31

6.8 g of Compound 31 was prepared in the same manner as in the synthesis of Compound 30 except that Core A (5 g, 12.3 mmol) and 2- (4-bromophenyl) 4,6-diphenylpyridine (6.15 g, 12.8 mmol)

MS [M + H] < + > = 713

< Manufacturing example 32>

- Synthesis of Compound 32

The same procedure as in the synthesis of Compound 31 was conducted except that Core A (5 g, 12.3 mmol) and 2- (3-bromophenyl) 4,6-diphenyl-1,3,5-triazine (6.14 g, 12.8 mmol) g of Compound 32 was prepared.

MS [M + H] < + > = 715

< Manufacturing example 33>

- Synthesis of Compound 33

7.0 g of Compound 33 was prepared in the same manner as in the synthesis of Compound 32 except that Core A (5 g, 12.3 mmol) and 2- (3-bromophenyl) 4,6-diphenylpyrimidine (5.64 g, 12.8 mmol) were used.

MS [M + H] < + > = 714

< Manufacturing example 34>

- Synthesis of Compound 34

6.8 g of Compound 34 was prepared in the same manner as in the synthesis of Compound 33 except that Core A (5 g, 12.3 mmol) and 2- (3-bromophenyl) 4,6-diphenylpyridine (5.63 g, 12.8 mmol)

MS [M + H] < + > = 713

< Manufacturing example 35>

- Synthesis of compound 35

Add Core A (5 g, 12.3 mmol), 2-chloro-4-phenylquinazoline (3.05 g, 12.7 mmol) and K3PO4 (4.88 g, 23 mmol) into 21 ml of xylene and 7 ml of DMAC. After the temperature was elevated, reflux was started. After 5 hours, the reaction was terminated. The temperature was lowered to room temperature, and the reaction mixture was concentrated under reduced pressure and then subjected to column purification to obtain 6.0 g of Compound 35.

MS [M + H] < + > = 612

< Manufacturing example 36>

- Synthesis of Compound 36

6.7 g of Compound 36 was prepared in the same manner as in the synthesis of Compound 35 except that Core A (5 g, 12.3 mmol) and 2-chloro-4- (naphthalene-2-yl) quinazoline (3.68 g, 12.7 mmol) Respectively.

MS [M + H] < + > = 662

< Manufacturing example 37>

- Synthesis of Compound 37

The same procedure as in the synthesis of the compound 35 was conducted except that Core A (5 g, 12.3 mmol) and 4 - ([1,1'-biphenyl] -4-yl) 2-chloroquinazoline (4.01 g, 12.7 mmol) Of Compound 37 was prepared.

MS [M + H] < + > = 688

< Manufacturing example 38>

- Synthesis of compound 38

Except that Core A (5 g, 12.3 mmol) and 2-chloro-4- (9,9-dimethyl-9H-fluoren-2-yl) quinazoline (4.52 g, 12.7 mmol) 7.6 g of Compound 38 was prepared.

MS [M + H] < + > = 728

< Manufacturing example 39>

- Synthesis of Compound 39

7.2 g of Compound 39 was prepared in the same manner as in the synthesis of Compound 35 except that Core A (5 g, 12.3 mmol) and 2-chloro-4- (phenanthren-2-yl) quinazoline (4.32 g, 12.7 mmol) Respectively.

MS [M + H] < + > = 712

< Manufacturing example 40>

- Synthesis of compound 40

7.0 g of Compound 40 was prepared in the same manner as in the synthesis of Compound 35 except that Core A (5 g, 12.3 mmol) and 2-chloro-4- (phenanthren-3-yl) quinazoline (4.32 g, 12.7 mmol) Respectively.

MS [M + H] < + > = 712

< Manufacturing example 41>

The following compounds 41 to 80 were prepared in the same manner as in the preparation of compounds 1 to 40 except that Core B was used instead of Core A in Production Examples 1 to 40.

< Example >

< Experimental Example 1-1>

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as 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 washed with a solvent of isopropyl alcohol, acetone, and methanol, 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.

N-phenylamino] biphenyl (NPB) (300 Å) was vacuum-deposited on the hole injection layer to form a hole transport layer, which is a material for transporting holes, and the following compound 4-4'-bis [N- (1-naphthyl) Respectively.

Subsequently, the following compound 1 was vacuum deposited on the hole transport layer to a thickness of 100 ANGSTROM to form an electron blocking layer.

Subsequently, BH and BD were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 25: 1 to form a light emitting layer.

The compound ET1 and the compound LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 Å. 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.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of the lithium fluoride of the cathode was 0.3 Å / sec and the deposition rate of the aluminum was 2 Å / sec. To 5 x 10 < -6 > torr. Thus, an organic light emitting device was fabricated.

< Experimental Example 1-2>

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

< Experimental Example 1-3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 3 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 4 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-5>

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

< Experimental Example 1-6>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 6 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-7>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 7 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-8>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 8 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-9>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 9 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-10>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 10 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-11>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 11 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-12>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 12 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-13>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 13 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-14>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 14 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-15>

Except that Compound 15 was used instead of Compound 1 in Experimental Example 1-1

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1.

< Experimental Example 1-16>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 16 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-17>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 17 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-18>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 18 was used in place of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-19>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 19 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-20>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 20 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-21>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 21 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-22>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 22 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-23>

An organic light emitting device was prepared in the same manner as in Experimental Example 1-1, except that Compound 23 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-24>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 24 was used in place of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-25>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 25 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-26>

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

< Experimental Example 1-27>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that Compound 42 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-28>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 43 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-29>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 44 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-30>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 45 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-31>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 46 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-32>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 47 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-33>

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

< Experimental Example 1-34>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 49 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-35>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 50 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-36>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 51 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-37>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 52 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-38>

An organic light emitting device was prepared in the same manner as in Experimental Example 1-1, except that Compound 53 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-39>

An organic light emitting device was prepared in the same manner as in Experimental Example 1-1, except that Compound 54 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-40>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 55 was used in place of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-41>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 56 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-42>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 57 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-43>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 58 was used in place of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-44>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 59 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-45>

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

< Experimental Example 1-46>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 61 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-47>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 62 was used instead of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-48>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 63 was used in place of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-49>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 64 was used in place of Compound 1 in Experimental Example 1-1.

< Experimental Example 1-50>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 65 was used instead of Compound 1 in Experimental Example 1-1.

< Comparative Example 1-1>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that EB 1 (TCTA) was used instead of Compound 1 in Experimental Example 1-1.

< Comparative Example 1-2>

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

< Comparative Example 1-3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that EB 3 was used instead of Compound 1 in Experimental Example 1-1.

[EB 3]

The results shown in Table 1 were obtained when current was applied to the organic light emitting devices fabricated in Experimental Examples 1-1 to 1-50 and Comparative Examples 1-1 to 1-3.

[Table 1]

As shown in Table 1, the compounds 51 to 75 having the core A as the center and the core B as the center are not only TCTA (Comparative Example 1) frequently used as the electron suppressing layer in the organic light emitting device but also the core is the naphthalene Which is lower than that of Comparative Examples 2 and 3, and exhibits high efficiency. In particular, it can be seen that the compounds 51 to 75 having a core B as a center have excellent properties.

The compound represented by the formula according to the present invention has excellent electron suppression ability and exhibits characteristics of low voltage and high efficiency and can be applied to organic light emitting devices.

< Experimental Example 2>

< Experimental Example 2-1 ~ Experimental Example 2-25>

The same experiment was conducted except that EB 1 was used as the electron blocking layer in Experimental Example 1 and the compounds of Experimental Examples 1-1 to 50 were used instead of NPB as the hole transport layer.

< Comparative Example 2-1>

The same experiment was performed except that EB 1 was used as the electron blocking layer and HT 1 (NPB) was used as the hole transporting layer in Experimental Example 1.

< Comparative Example 2-2>

The same experiment was performed except that EB 1 was used as the electron blocking layer and HT 2 was used as the hole transporting layer in Experimental Example 1.

The results shown in Table 2 were obtained when current was applied to the organic light-emitting devices manufactured in Experimental Examples 2-1 to 2-25 and Comparative Examples 2-1 to 2-2.

[Table 2]

As shown in Table 1, the compounds 51 to 75, in which the core A is the center and the core B are the center, are compared with the compounds of Comparative Examples 2 and 3 in which HT1 (NPB) and HT2 frequently used as the major transport layer in the organic light emitting device Low voltage, and high efficiency. In particular, it can be seen that the compounds 51 to 75 having a core B as a center have excellent properties. The compound represented by the chemical formula according to the present invention exhibits low voltage and high efficiency due to its excellent hole transporting ability and can be applied to organic light emitting devices.

< Experimental Example 3-1>

The compounds synthesized in Synthesis Examples were subjected to high purity sublimation purification by a conventionally known method, and then a green organic light emitting device was prepared in the following manner.

The glass substrate coated with ITO (ndium tin oxide) with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as 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 washed with a solvent of isopropyl alcohol, acetone, and methanol, 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.

(60 nm) / TCTA (80 nm) / Compound 26 + 10% Ir (ppy) 3 (300 nm) / BCP (10 nm) / Alq 3 (30 nm) using the compound 26 as a host on the ITO transparent electrode prepared as described above. nm) / LiF (1 nm) / Al (200 nm) were fabricated in this order to produce an organic EL device. The structures of m-MTDATA, TCTA, Ir (ppy) ₃ and BCP are as follows.

< Experimental Example 3-2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1 except that Compound 27 was used instead of Compound 26 in Experimental Example 3-1.

< Experimental Example 3-3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1, except that Compound 28 was used instead of Compound 26 in Experimental Example 3-1.

< Experimental Example 3-4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1, except that Compound 29 was used instead of Compound 26 in Experimental Example 3-1.

< Experimental Example 3-5>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1 except that Compound 30 was used instead of Compound 26 in Experimental Example 3-1.

< Experimental Example 3-6>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1, except that Compound 31 was used instead of Compound 26 in Experimental Example 3-1. .

< Experimental Example 3-7>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1, except that Compound 32 was used instead of Compound 26 in Experimental Example 3-1.

< Experimental Example 3-8>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1 except that Compound 33 was used instead of Compound 26 in Experimental Example 3-1.

< Experimental Example 3-9>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1 except that Compound 34 was used instead of Compound 26 in Experimental Example 3-1.

< Experimental Example 3-10>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1, except that Compound 66 was used instead of Compound 26 in Experimental Example 3-1.

< Experimental Example 3-11>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1, except that Compound 67 was used instead of Compound 26 in Experimental Example 3-1.

< Experimental Example 3-12>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1 except that Compound 68 was used instead of Compound 26 in Experimental Example 3-1.

< Experimental Example 3-13>

An organic light emitting device was prepared in the same manner as in Experimental Example 3-1, except that Compound 69 was used instead of Compound 26 in Experimental Example 3-1.

< Experimental Example 3-14>

An organic light emitting device was prepared in the same manner as in Experimental Example 3-1, except that Compound 70 was used instead of Compound 26 in Experimental Example 3-1. .

< Experimental Example 3-15>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1 except that Compound 71 was used instead of Compound 26 in Experimental Example 3-1.

< Experimental Example 3-16>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1 except that Compound 72 was used instead of Compound 26 in Experimental Example 3-1.

< Experimental Example 3-17>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1, except that Compound 73 was used instead of Compound 26 in Experimental Example 3-1.

< Experimental Example 3-18>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1, except that Compound 74 was used instead of Compound 26 in Experimental Example 3-1.

< Comparative Example 1>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1 except that GH 1 (CBP) was used instead of Compound 26 in Experimental Example 3-1.

The results shown in Table 3 were obtained when current was applied to the organic light-emitting devices manufactured in Experimental Examples 3-1 to 3-18 and Comparative Example 1.

[Table 3]

As a result of the experiment, the green organic EL devices of Experimental Examples 3 to 1 to 18 using the compound represented by the present invention as the host material of the light emitting layer showed higher current efficiency and driving performance than the green organic EL device of Comparative Example 1 using CBP And it was confirmed that it exhibits excellent performance in terms of voltage.

< Experimental Example 4-1>

The compounds synthesized in Synthesis Examples were subjected to high purity sublimation purification by a conventionally known method, and red organic light emitting devices were prepared as follows. 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 doped with DNTPD (700 Å), α-NPB (300 Å) (100 Å) of Alq3 (350 Å), LiF (5 Å) and Al (1,000 Å) were deposited in the same manner as in Example 1, and the following (piq) 2Ir (acac) , And 0.4 mA.

The structures of DNTPD, alpha -NPB, (piq) 2Ir (acac) and Alq3 are as follows.

< Experimental Example 4-2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that Compound 27 was used instead of Compound 26 in Experimental Example 4-1.

< Experimental Example 4-3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that Compound 28 was used instead of Compound 26 in Experimental Example 4-1.

< Experimental Example 4-4>

An organic light emitting device was prepared in the same manner as in Experimental Example 4-1, except that Compound 35 was used instead of Compound 26 in Experimental Example 4-1.

< Experimental Example 4-5>

Except that Compound 36 was used instead of Compound 26 in Experimental Example 4-1

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1.

< Experimental Example 4-6>

Except that Compound 37 was used instead of Compound 26 in Experimental Example 4-1

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1. .

< Experimental Example 4-7>

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that Compound 38 was used instead of Compound 26 in Experimental Example 4-1.

< Experimental Example 4-8>

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that Compound 39 was used instead of Compound 26 in Experimental Example 4-1.

< Experimental Example 4-9>

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that Compound 40 was used instead of Compound 26 in Experimental Example 4-1.

< Experimental Example 4-10>

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that Compound 66 was used instead of Compound 26 in Experimental Example 4-1.

< Experimental Example 4-11>

An organic light emitting device was prepared in the same manner as in Experimental Example 4-1, except that Compound 67 was used instead of Compound 26 in Experimental Example 4-1.

< Experimental Example 4-12>

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1 except that Compound 68 was used instead of Compound 26 in Experimental Example 4-1.

< Experimental Example 4-13>

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that Compound 75 was used instead of Compound 26 in Experimental Example 4-1.

< Experimental Example 4-14>

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that Compound 76 was used instead of Compound 26 in Experimental Example 4-1. .

< Experimental Example 4-15>

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that Compound 77 was used instead of Compound 26 in Experimental Example 4-1.

< Experimental Example 4-16>

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that Compound 78 was used instead of Compound 26 in Experimental Example 4-1.

< Experimental Example 4-17>

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that Compound 79 was used instead of Compound 26 in Experimental Example 4-1.

< Experimental Example 4-18>

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that Compound 80 was used in place of Compound 26 in Experimental Example 4-1.

< Comparative Example 1>

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that RH 1 (CBP) was used instead of Compound 26 in Experimental Example 4-1.

The voltage, the current density, the luminance, the color coordinate, and the lifetime were measured for the organic electroluminescent device manufactured according to the following Experimental Examples 4-1 to 4-9 and Comparative Example 4-1, and the results are shown in Table 4 below . T95 means the time required for the luminance to decrease from the initial luminance (5000 nits) to 95%.

[Table 4]

As a result, it was found that the red organic EL devices of Experimental Examples 4-1 to 4-18 using the compound according to the present invention as a host material of the light emitting layer had higher current efficiency and driving voltage than the red organic EL device of Comparative Example 1 using CBP And excellent performance in terms of life span.

While the present invention has been described with reference to the preferred embodiments (the electron suppression layer, the hole transport layer, the green emission layer, and the red emission layer), the present invention is not limited thereto. And it is also within the scope of the invention.

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

Claims

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

In Formula 1,
A is fluoranthene,
L is a direct bond; A divalent phenyl group; A divalent biphenyl group; A divalent carbazole group; Or a divalent quinazoline group,
B is an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a nitrile group, a deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heterocyclic group having 3 to 30 carbon atoms; An amine group substituted with an aryl group having 6 to 30 carbon atoms or an alkylaryl group having 6 to 30 carbon atoms; Or an aryl group having 6 to 30 carbon atoms or a heterocyclic group having 3 to 30 carbon atoms including N, O, or S, which is unsubstituted or substituted with an alkylaryl group having 6 to 30 carbon atoms,
R1 and R2 are methyl,
R3 and R4 are hydrogen,
a is 2,
b is 4,
m is an integer of 0 to 10,
When m is 2 or more, the structures in parentheses are the same or different from each other.

delete

The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 2 or 3:
(2)

(3)

In the general formulas (2) and (3)
R 1 to R 4, B, L, m, a and b are as defined in the formula (1).

delete

[3] The compound according to claim 1, wherein B is a phenyl group substituted or unsubstituted with a nitrile group, a deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Naphthyl; Biphenyl; Terphenyl; A fluorene substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 30 carbon atoms or an alkylaryl group having 6 to 30 carbon atoms; A carbazole substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms; Dibenzofuran; Dibenzothiophene; A triazine group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms or an alkylaryl group having 6 to 30 carbon atoms; An aryl group having 6 to 30 carbon atoms, or a pyrimidine group substituted or unsubstituted with an alkylaryl group having 6 to 30 carbon atoms; An aryl group having 6 to 30 carbon atoms, or a pyridine group substituted or unsubstituted with an alkylaryl group having 6 to 30 carbon atoms; Quinoline substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms; An aryl group having 6 to 30 carbon atoms, or an alkylaryl group having 6 to 30 carbon atoms; Benzoimidazole substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms; Benzothiazole group; Benzoxazole group; Or a pyridopyrimidine group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.

2. The compound according to claim 1, wherein B is any one selected from the following structures:

The compound according to claim 1, wherein the compound of formula (1) is any one selected from the following compounds:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers is formed by a method according to any one of claims 1, 3, 6, 7 and 8 Wherein the compound is a compound represented by the following formula.

[Claim 12] The organic electroluminescent device according to claim 9, wherein the organic compound layer comprising the compound comprises a hole injection layer; A hole transport layer; Or a layer which simultaneously injects holes and transports holes.

[Claim 11] The organic electroluminescent device according to claim 9, wherein the organic compound layer containing the compound comprises an electron injection layer; An electron transport layer; Or an electron injection and electron transporting layer simultaneously.

The organic light emitting device according to claim 9, wherein the organic compound layer containing the compound is a light emitting layer.