KR20160111780A - Organic light emitting device - Google Patents

Abstract

The present invention provides an organic light emitting device.

Description

ORGANIC LIGHT EMITTING DEVICE

The present disclosure relates to an organic light emitting device.

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

The present invention provides an organic light emitting device.

One embodiment of the present disclosure

anode;

A negative electrode opposed to the positive electrode;

A light emitting layer provided between the anode and the cathode;

A first organic layer provided between the anode and the light emitting layer; And

And a second organic layer disposed between the cathode and the light emitting layer,

Wherein the first organic layer comprises a compound represented by the following formula (1)

And the second organic compound layer comprises a compound represented by the following general formula (2).

[Chemical Formula 1]

(2)

In the above formulas (1) and (2)

L1 is a direct bond; Substituted or unsubstituted arylene,

Ar 1 to Ar 5 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

X1 and X2 are the same or different and are each independently CR or N,

R and R1 to R3 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,

p is an integer of 0 to 10,

a and b are the same or different and each independently represents an integer of 0 to 4,

c is an integer of 0 to 3,

When a, b, c and p are each 2 or more, the structures in parentheses are equal to or different from each other.

The organic light emitting device according to one embodiment of the present invention can improve lifetime characteristics and / or efficiency characteristics of the device.

According to one embodiment of the present invention, a compound of Formula 2 including triazine, pyrimidine, and pyridine forms having excellent ability to inject electrons into the compound of Chemical Formula 1 is injected into an electron injection Layer, or an electron transport layer (A) Excellent hole injection property; (B) high hole mobility; (C) Good electronic blocking power; (D) a stable thin film state; And / or (E) has excellent heat resistance and exhibits characteristics of low voltage, high efficiency and long life.

1 shows an example of an organic light-emitting device 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 this specification, when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where there is another member between the two members.

In this specification, when a section is referred to as "including " an element, it is to be understood that this section may include other elements as well, without departing from the other elements unless specifically stated otherwise.

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

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or 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.

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, examples of the arylamine group include a substituted or unsubstituted monocyclic diarylamine group, a substituted or unsubstituted polycyclic diarylamine group, or a substituted or unsubstituted monocyclic and polycyclic diaryl Amine group.

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, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group, a fluorenyl group and a triphenylene group.

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

,

,

, 및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.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, S, P, Si and Se, and 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 this specification, the meaning of forming a substituted or unsubstituted ring by bonding to adjacent groups means that a substituted or unsubstituted aliphatic hydrocarbon ring is bonded to adjacent groups to form a substituted or unsubstituted ring; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; A substituted or unsubstituted aromatic heterocycle; Or a substituted or unsubstituted aliphatic or fused 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 invention, Ar 3 to Ar 5 are the same or different and each independently represents a substituted or unsubstituted aryl group having 1 to 3 rings; Or a substituted or unsubstituted heterocyclic group of 1 to 3 rings.

According to one embodiment of the present invention, Ar 3 to Ar 5 are the same or different and each independently represents a substituted or unsubstituted aryl group having 1 to 3 rings; Or a substituted or unsubstituted heterocyclic group of 1 or 2 rings.

According to one embodiment of the present invention, Ar 3 to Ar 5 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted pyrimidyl; A substituted or unsubstituted triazine group; A substituted or unsubstituted pyrazinyl group; A substituted or unsubstituted quinolinyl group; Or a substituted or unsubstituted isoquinolinyl group.

According to one embodiment of the present invention, Ar3 to Ar5 are the same or different and are each independently a phenyl group substituted or unsubstituted with an aryl group or a heterocyclic group; A naphthyl group substituted or unsubstituted with an aryl group or a heterocyclic group; A biphenyl group substituted or unsubstituted with an aryl group or a heterocyclic group; A terphenyl group substituted or unsubstituted with an aryl group or a heterocyclic group; A fluorenyl group substituted or unsubstituted with an alkyl group, an aryl group or a heterocyclic group; A phenanthryl group substituted or unsubstituted with an aryl group or a heterocyclic group; A pyridyl group substituted or unsubstituted with an aryl group or a heterocyclic group; A pyrimidyl group substituted or unsubstituted with an aryl group or a heterocyclic group; A triazine group substituted or unsubstituted with an aryl group or a heterocyclic group; A pyrazinyl group substituted or unsubstituted with an aryl group or a heterocyclic group; A quinolinyl group substituted or unsubstituted with an aryl group or a heterocyclic group; Or an isoquinolinyl group substituted or unsubstituted with an aryl group or a heterocyclic group.

According to one embodiment of the present disclosure, X1 is N.

According to one embodiment of the present disclosure, X1 and X2 are N.

According to one embodiment of the present disclosure, p is 0 or 1.

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

(3)

In Formula 3,

L2 is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

X3 to X6 are the same or different and are each independently CR or N,

Ar6 and Ar7 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R, Ar8 and Ar9 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,

q is an integer of 0 to 10,

When q is 2 or more, the structures in parentheses are the same or different from each other.

According to one embodiment of the present disclosure, L2 is a direct bond; A substituted or unsubstituted monocyclic to tricyclic arylene; Or a substituted or unsubstituted monocyclic or bicyclic heteroarylene.

According to one embodiment of the present disclosure, L2 is a direct bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted biphenylene; Substituted or unsubstituted terphenylene; Substituted or unsubstituted quaterphenylene; Substituted or unsubstituted naphthylene; Substituted or unsubstituted phenanthrylene; Substituted or unsubstituted fluorenylenes; A substituted or unsubstituted divalent pyridyl group; A substituted or unsubstituted divalent pyrimidyl; A substituted or unsubstituted divalent pyranyl group; A substituted or unsubstituted divalent triazine group; A substituted or unsubstituted divalent quinoline group; Or a substituted or unsubstituted divalent isoquinolinyl group.

According to one embodiment of the present disclosure, L2 is a direct bond; Phenylene; Biphenyllylene; Terphenylene; Quaterphenylene; Naphthylene; Phenanthrylene; Substituted or unsubstituted fluorenylenes; A divalent pyridyl group; A divalent pyrimidyl group; A divalent pyrazinyl group; A bivalent triazine group; A divalent quinoline group; Or a divalent isoquinolinyl group.

According to one embodiment of the present disclosure, L2 is a direct bond; Or substituted or unsubstituted arylene.

According to one embodiment of the present disclosure, L2 is a direct bond; Or a substituted or unsubstituted monocyclic to tricyclic arylene.

According to one embodiment of the present disclosure, L2 is a direct bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted biphenylene; Substituted or unsubstituted terphenylene; Substituted or unsubstituted quaterphenylene; Substituted or unsubstituted naphthylene; Substituted or unsubstituted phenanthrylene; Or substituted or unsubstituted fluorenylenes.

According to one embodiment of the present disclosure, L2 is a direct bond; Phenylene; Biphenyllylene; Terphenylene; Quaterphenylene; Naphthylene; Phenanthrylene; Or fluorenylene.

According to one embodiment of the present invention, Ar6 to Ar9 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, when Ar6 to Ar9 are aryl groups, the aryl group may be substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted phenanthryl group.

According to one embodiment of the present invention, when Ar6 to Ar9 are a heterocyclic group, the heterocyclic group may be substituted or unsubstituted pyridyl group; A substituted or unsubstituted pyrimidyl; A substituted or unsubstituted triazine group; A substituted or unsubstituted pyrazinyl group; A substituted or unsubstituted quinolinyl group; Or a substituted or unsubstituted isoquinolinyl group.

According to one embodiment of the present invention, Ar6 to Ar9 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted pyrimidyl; A substituted or unsubstituted triazine group; A substituted or unsubstituted pyrazinyl group; A substituted or unsubstituted quinolinyl group; Or a substituted or unsubstituted isoquinolinyl group.

According to one embodiment of the present disclosure, q is 0 or 1.

According to one embodiment of the present disclosure, L1 is a direct bond; Or a substituted or unsubstituted monocyclic to tricyclic arylene.

According to one embodiment of the present disclosure, L1 is a direct bond; Or a substituted or unsubstituted monocyclic or bicyclic arylene.

According to one embodiment of the present disclosure, L1 is a direct bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted naphthylene; Substituted or unsubstituted biphenylene; Or substituted or unsubstituted fluorenylenes.

According to one embodiment of the present disclosure, L1 is a direct bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted naphthylene; Or substituted or unsubstituted biphenyl rylene.

According to one embodiment of the present disclosure, L1 is a direct bond; Substituted or unsubstituted phenylene; Or substituted or unsubstituted biphenyl rylene.

According to one embodiment of the present disclosure, L1 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; Or a heterocyclic group, which may be substituted or unsubstituted.

According to one embodiment of the present disclosure, L1 is a direct bond; Phenylene; Naphthylene; Or biphenyl rylene.

According to one embodiment of the present disclosure, L1 is phenylene; Naphthylene; Or biphenyl rylene.

According to one embodiment of the present disclosure, L1 is a direct bond; Phenylene; Or biphenyl rylene.

According to one embodiment of the present disclosure, L1 is a direct bond; Or substituted or unsubstituted phenylene.

According to one embodiment of the present disclosure, L1 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; Or a heterocyclic group, which may be substituted or unsubstituted.

According to one embodiment of the present disclosure, L1 is a direct bond; Or phenylene.

According to one embodiment of the present disclosure, L1 is a direct bond.

According to one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group containing at least one of N, O and S.

According to one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted monocyclic to tricyclic aryl group; Or a substituted or unsubstituted 1 to 4 heteroaryl group.

According to one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted monocyclic to tricyclic aryl group; Or a substituted or unsubstituted tricyclic heteroaryl group.

According to one embodiment of the present invention, Ar 1 and Ar 2 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted quaterphenyl 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; Or a substituted or unsubstituted dibenzothiophene group.

According to one embodiment of the present invention, Ar 1 and Ar 2 are the same or different and are each independently a phenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group and a heterocyclic group; A biphenyl group; A terphenyl group; A quaterphenyl group; Naphthyl group; A phenanthryl group; A fluorenyl group substituted with an alkyl group; Triphenylene group; A dibenzofuranyl group; Or a dibenzothiophene group.

According to one embodiment of the present invention, at least one of Ar1 and Ar2 is a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, at least one of Ar1 and Ar2 is a fluorenyl group which is substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group, an aryl group and a heterocyclic group.

According to one embodiment of the present disclosure, R1 to R3 are hydrogen.

According to one embodiment of the present disclosure, X1 and X2 are N.

According to one embodiment of the present invention, L1 is substituted or unsubstituted phenylene, Ar1 is a substituted or unsubstituted fluorenyl group, Ar2 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted o-biphenyl group; Or a substituted or unsubstituted p-biphenyl group.

According to one embodiment of the present disclosure, L 1 is phenylene, Ar 1 is a fluorenyl group, Ar 2 is a phenyl group; o-biphenyl; Or a p-biphenyl group.

According to one embodiment of the present invention, L1 is substituted or unsubstituted phenylene, Ar1 is a substituted or unsubstituted fluorenyl group, Ar2 is a substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophene group.

According to one embodiment of the present invention, L 1 is phenylene, Ar 1 is a fluorenyl group, and Ar 2 is a dibenzofuranyl group or a dibenzothiophene group.

According to one embodiment of the present invention, the formula (1) may be any one selected from the following structures.

According to one embodiment of the present invention, the formula (2) may be any one selected from the following structures.

The compound of Formula 1 has a structure in which an arylamine group is substituted with a core structure represented by Formula 1, that is, triphenylene and a linking group.

Triphenylene has a very high triplet energy of about 2.6 to 2.7. In addition, it has excellent hole transporting ability and broad band gap as compared with conventional materials, and is widely used as a host material of a light emitting layer.

In the present invention, compounds having various energy bandgaps can be synthesized by introducing various substituents at the 2-position of the core structure having a large energy band gap as described above. Usually, it is easy to control the energy band gap by introducing a substituent to a core structure having a large energy band gap. However, when the core structure has a small energy band gap, it is difficult to control the energy band gap by introducing a substituent. In the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing various arylamine groups into the core structure having the above structure.

According to one embodiment of the present invention, the compound of Formula 1 has an arylamine structure in its core structure, and thus may have an appropriate energy level as a hole injecting and / or hole transporting material in an organic light emitting device. In the present invention, a compound having an appropriate energy level according to the substituent among the compounds of the formula (1) is selected and used in an organic light emitting device, thereby realizing a device having a low driving voltage and a high light efficiency.

For example, the compound of the formula (1-1) of Example 1 of the present invention described below is a compound having an energy band gap and an energy level, As the amine-introduced compound, the HOMO is 5.35 eV and thus has an energy level suitable for use as a hole transport layer. On the other hand, the band gap of the compound of the formula (1-1) of Example 1 is still 3.14 eV, which is much larger than that of the NPB used as the hole transport layer material, and thus the LUMO value of this compound is also very high, about 2.21 eV .

According to one embodiment of the present invention, when a compound having such a high LUMO value is used as the hole transport layer, it is possible to increase the energy wall of the material used as the light emitting layer with the LUMO so that electrons flow from the light emitting layer to the hole transport layer Can be prevented. That is, it functions as an exciton blocking layer so that excitons are confined within the light emitting layer, thereby preventing light leakage. Accordingly, such a compound can improve the luminous efficiency of the organic light emitting device compared to the conventional NPB (HOMO 5.4 eV, LUMO 2.3 eV, energy gap 3.1 eV).

In the present invention, the energy band gap was calculated using a general method calculated by the UV-VIS spectrum.

Further, according to one embodiment of the present invention, the compound of the formula (1-1) in the following Example 1 exhibits a stable redox property. The stability against oxidation and reduction can be confirmed by CV (cyclovoltammetry) method. As a specific example, when the compound of formula (1-1) of Example 1 was oxidized at the same voltage and applied with the same voltage repeatedly, the same amount of current was exhibited. This indicates that the compound has excellent stability against oxidation .

Meanwhile, according to another embodiment of the present invention, the compound of Chemical Formula 1 has a high glass transition temperature (Tg) and thus is excellent in thermal stability. For example, the compound of Formula 1-1 of Example 1 of the present invention has a glass transition temperature of 133C, which is significantly higher than that of NPB (Tg: 96 ° C), which has been generally used. This increase in thermal stability is an important factor in providing drive stability to the device.

Finally, when the arylamine containing a fluorene group is connected to a compound of the formula (1) according to an embodiment of the present invention by a substituent, the hole mobility is remarkably increased and the effect of lowering the driving voltage is remarkably reduced.

That is, according to one embodiment of the present invention, the compound of Formula 2 including the triazine, pyrimidine, and pyridine forms having a very high ability to inject electrons into the compound of Formula 1 having such characteristics, (A) excellent hole injection characteristics when used as an electron injection layer or an electron transport layer provided between the anode and the cathode; (B) high hole mobility; (C) Good electronic blocking power; (D) a stable thin film state; And / or (E) has excellent heat resistance and exhibits characteristics of low voltage, high efficiency and long life.

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.

In one embodiment of the present invention, the organic material layer includes an electron injection layer, an electron transporting layer, or a layer simultaneously injecting and transporting electrons.

In one embodiment of the present invention, the organic layer includes an electron blocking layer.

In one embodiment of the present invention, the first organic layer includes an electron blocking layer, and the electron blocking layer includes a compound represented by the general formula (1).

In one embodiment of the present invention, the first organic layer includes a hole transporting layer and an electron blocking layer, and the electron blocking layer includes a compound represented by the above formula (1).

In one embodiment of the present invention, the electron blocking layer is provided in contact with the light emitting layer.

In one embodiment of the present invention, the second organic layer includes an electron transporting layer, and the electron transporting layer includes a compound represented by the general formula (2).

In one embodiment of the present invention, the second organic layer includes an electron transporting layer, and the electron transporting layer includes a compound represented by the above-mentioned general formula (3).

In one embodiment of the present invention, the second organic layer includes an electron transporting layer and an electron injecting layer, and the electron transporting layer includes a compound represented by the above formula (2).

In one embodiment of the present invention, the second organic layer includes an electron transporting layer and an electron injecting layer, and the electron transporting layer includes a compound represented by the above formula (3).

In one embodiment of the present invention, the first organic material layer or the second organic material layer includes a hole transporting layer and a hole injecting layer, and the hole transporting layer or the hole injecting layer includes the compound of the above formula (1) or (2).

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; A light emitting layer provided between the first electrode and the second electrode; And two or more organic layers provided between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, wherein at least one of the two or more organic layers is a compound represented by the formula 1 or 2 . 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 compound of the above formula (1). Specifically, in one embodiment of the present specification, the 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 addition, in one embodiment of the present specification, when the compound is contained in each of the two or more electron transporting layers, the materials other than the above compounds may be the same or different from each other.

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 compound layer, and an anode are sequentially stacked on a substrate.

For example, the structure of an organic light emitting device according to one embodiment of the present specification is illustrated in FIG.

1 shows an example of an organic light-emitting device 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.

The organic luminescent device of the present invention is not particularly limited as long as the first organic material layer includes the compound represented by Formula 1 and the second organic material layer includes the compound represented by Formula 2 or 3 Materials and methods.

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.

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 compounds of Chemical Formulas 1 to 3 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, 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.

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 layer is a layer that receives electrons from the electron injection 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. .

Specific examples of the electron transporting material used for the electron transport layer 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 having a low work function followed by an aluminum layer or a 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, perylene tetracarboxylic 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.

One embodiment of the present invention provides a display device including the organic light emitting device. In the display device, the organic light emitting diode may serve as a pixel or a backlight. In addition, the configuration of the display device can be applied to those known in the art.

One embodiment of the present invention provides a lighting apparatus including the organic light emitting element. In the illumination device, the organic light emitting element plays a role of a light emitting portion. In addition, the configuration required for the lighting apparatus can be applied to those known in the art.

The structure according to one embodiment of the present disclosure can act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organophotoreceptors, organic transistors and the like.

The organic luminescent device of the present invention is not particularly limited as long as the first organic material layer includes the compound represented by Formula 1 and the second organic material layer includes the compound represented by Formula 2 or 3 Materials and methods.

The production of the organic light emitting device 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.

< Example >

< Experimental Example  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 N - ([1,1'-bisphenyl] -4-yl) -N- (4- (11 - ([1,1'-biphenyl] -4 -yl) -11H-benzo [a] carbazole-5-yl) phenyl) - [1,1'-biphenyl] -4-amine (100A) was vacuum deposited thereon 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.

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

< Experimental Example  1-1>

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

< Experimental Example  1-2>

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

< Experimental Example  1-3>

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

< Experimental Example  1-4>

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

< Experimental Example  1-5>

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

< Experimental Example  1-6>

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

< Experimental Example  1-7>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-15 was used instead of Compound EB-1 in Experimental Example 1.

< Experimental Example  1-8>

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

< Experimental Example  1-9>

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

< Experimental Example  1-10>

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

< Experimental Example  1-11>

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

< Experimental Example  1-12>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-37 was used in place of Compound EB-1 in Experimental Example 1.

< Experimental Example  1-13>

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

< Experimental Example  1-14>

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

< Experimental Example  1-15>

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

< Experimental Example  1-16>

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

< Experimental Example  1-17>

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

< Experimental Example  1-18>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-68 was used in place of Compound EB-1 in Experimental Example 1.

< Experimental Example  1-19>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-70 was used in place of Compound EB-1 in Experimental Example 1.

< Experimental Example  1-20>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-87 was used in place of Compound EB-1 in Experimental Example 1.

< Experimental Example  1-21>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-90 was used in place of Compound EB-1 in Experimental Example 1.

< Experimental Example  1-22>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-97 was used in place of Compound EB-1 in Experimental Example 1.

< Experimental Example  1-23>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-98 was used in place of Compound EB-1 in Experimental Example 1.

< Experimental Example  1-24>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-100 was used in place of Compound EB-1 in Experimental Example 1.

< Experimental Example  1-25>

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

< Experimental Example  1-26>

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

< Experimental Example  1-27>

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

< Experimental Example  1-28>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-6 was used in place of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-29>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-9 was used in place of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-30>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the compound 2-19 was used instead of the compound ET-1 in Experimental Example 1.

< Experimental Example  1-31>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-21 was used in place of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-32>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-33 was used instead of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-33>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 2-38 was used in place of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-34>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-45 was used in place of Compound ET-1 in Experimental Example 1 above.

< Experimental Example  1-35>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-46 was used in place of Compound ET-1 in Experimental Example 1 above.

< Experimental Example  1-36>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-47 was used in place of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-37>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-49 was used in place of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-38>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-50 was used in place of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-39>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-56 was used instead of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-40>

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

< Experimental Example  1-41>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-68 was used in place of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-42>

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

< Experimental Example  1-43>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3-8 was used in place of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-44>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3-12 was used in place of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-45>

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

< Experimental Example  1-46>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3-38 was used in place of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-47>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3-40 was used in place of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-48>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3-44 was used in place of Compound ET-1 in Experimental Example 1.

< Experimental Example  1-49>

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

< Experimental Example  1-50>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-2 was used instead of Compound EB-1 in Experimental Example 1, and Compound 2-50 was used in place of Compound ET-1 .

< Experimental Example  1-51>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-2 was used instead of Compound EB-1 in Experimental Example 1, and Compound 3-8 was used in place of Compound ET-1 .

< Experimental Example  1-52>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-2 was used instead of Compound EB-1 in Experimental Example 1, and Compound 3-40 was used in place of Compound ET-1 .

< Experimental Example  1-53>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-2 was used instead of Compound EB-1 in Experimental Example 1, and Compound 3-44 was used in place of Compound ET-1 .

< Experimental Example  1-54>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-7 was used instead of Compound EB-1 in Experimental Example 1 and Compound 2-1 was used in place of Compound ET-1 .

< Experimental Example  1-55>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-7 was used instead of Compound EB-1 in Experimental Example 1, and Compound 2-50 was used in place of Compound ET-1 .

< Experimental Example  1-56>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-7 was used instead of Compound EB-1 in Experimental Example 1, and Compound 3-8 was used in place of Compound ET-1 .

< Experimental Example  1-57>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-7 was used instead of Compound EB-1 in Experimental Example 1, and Compound 3-40 was used in place of Compound ET-1 .

< Experimental Example  1-58>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-7 was used instead of Compound EB-1 in Experimental Example 1, and Compound 3-44 was used in place of Compound ET-1 .

< Experimental Example  1-59>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that Compound 1-25 was used instead of Compound EB-1 in Experimental Example 1 and Compound 2-1 was used in place of Compound ET-1 .

< Experimental Example  1-60>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-25 was used instead of Compound EB-1 in Experimental Example 1 and Compound 2-50 was used in place of Compound ET-1 .

< Experimental Example  1-61>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-25 was used instead of Compound EB-1 in Experimental Example 1, and Compound 3-8 was used in place of Compound ET-1 .

< Experimental Example  1-62>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-25 was used instead of Compound EB-1 in Experimental Example 1, and Compound 3-40 was used in place of Compound ET-1 .

< Experimental Example  1-63>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-25 was used instead of Compound EB-1 in Experimental Example 1, and Compound 3-44 was used in place of Compound ET-1 .

< Experimental Example  1-64>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-37 was used in place of Compound EB-1 in Experimental Example 1 and Compound 2-1 was used instead of Compound ET-1 .

< Experimental Example  1-65>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-37 was used in place of Compound EB-1 in Experimental Example 1, and Compound 2-50 was used in place of Compound ET-1 .

< Experimental Example  1-66>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-37 was used in place of Compound EB-1 in Experimental Example 1, and Compound 3-8 was used in place of Compound ET-1 .

< Experimental Example  1-67>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-37 was used in place of Compound EB-1 in Experimental Example 1, and Compound 3-40 was used in place of Compound ET-1 .

< Experimental Example  1-68>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-37 was used in place of Compound EB-1 in Experimental Example 1, and Compound 3-44 was used in place of Compound ET-1 .

< Experimental Example  1-69>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-62 was used in place of Compound EB-1 in Experimental Example 1, and Compound 2-1 was used in place of Compound ET-1 .

< Experimental Example  1-70>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-62 was used in place of Compound EB-1 in Experimental Example 1, and Compound 2-50 was used in place of Compound ET-1 .

< Experimental Example  1-71>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-62 was used in place of Compound EB-1 in Experimental Example 1 and Compound 3-8 was used instead of Compound ET-1 .

< Experimental Example  1-72>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-62 was used in place of Compound EB-1 in Experimental Example 1, and Compound 3-40 was used in place of Compound ET-1 .

< Experimental Example  1-73>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-62 was used instead of Compound EB-1 in Experimental Example 1, and Compound 3-44 was used in place of Compound ET-1 .

< Experimental Example  1-74>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-100 was used instead of Compound EB-1 in Experimental Example 1, and Compound 2-1 was used instead of Compound ET-1 .

< Experimental Example  1-75>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-100 was used instead of Compound EB-1 in Experimental Example 1, and Compound 2-50 was used in place of Compound ET-1 .

< Experimental Example  1-76>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-100 was used instead of Compound EB-1 in Experimental Example 1, and Compound 3-8 was used instead of Compound ET-1 .

< Experimental Example  1-77>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that Compound 1-100 was used instead of Compound EB-1 in Experimental Example 1, and Compound 3-40 was used in place of Compound ET-1 .

< Experimental Example  1-78>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-100 was used instead of Compound EB-1 in Experimental Example 1, and Compound 3-44 was used in place of Compound ET-1 .

[Table 1]

When an electric current was applied to the organic light-emitting device manufactured by Experimental Examples 1-1 to 1-78, the results shown in Table 1 were obtained. In the experimental example of the present invention, the blue organic light emitting device is a structure in which EB-1 is used as an electron blocking layer and ET-1 is used as an electron transporting layer.

According to the above Table 1, the compounds of the formula (1) were used instead of the compounds of the formula (1), and the compounds of the formula (1-25) 1 and Formula 2 are separately used, the basic characteristics of the device are shown.

Experimental Examples 1-49 to 1-78 show the characteristics of the device when the compounds of Formula 1 were used instead of EB-1 and the compounds of Formula 2 were used in place of ET-1 in one device.

In Experimental Examples 1-54 to 1-58, when the derivatives of Formulas 2 and 3 were used as ET-1 with the formula 1-7 as EB-1, the voltage was lowest. In Experimental Examples 1-69 to 1-73, when the derivatives 1-32 were used as EB-1 and the derivatives 2-3 were used as ET-1, the longest life was measured. In terms of the luminous efficiency, it was measured higher than in Experimental Examples 1-1 to 1-48.

(1), which is an electron blocking layer material (EB-1) having the structure of the present invention (the structure in which amine is directly or linker-connected to triphenylene core) of the present invention, Emitting efficiency and lifetime characteristics of a blue organic light-emitting device formed by combining the compound of Formula 2 including a pyridine form with an electron transport layer material (ET-1) provided between the anode and the light-emitting layer .

< Experimental Example  2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that HT-1 was used instead of EB-1 in Experimental Example 1. Except that 1-7, 1-32, 1-37, 1-65, and 1-70 were used in place of HT-1 in Experimental Examples 1-49 to 1-78 in combination of Formula 1 and Formula 2, -1, 2-50, 3-14, 3-44, 3-46 were used.

[Table 2]

When an electric current was applied to the organic light-emitting device manufactured by Experimental Examples 1-1 to 1-78, the results shown in Table 1 were obtained. In the experimental example of the present invention, the blue organic light emitting device is a structure in which HT-1 is used as a hole transport layer and ET-1 is used as an electron transport layer.

According to Table 1, in Experimental Examples 1-1 to 1-24, the compound of Chemical Formula 1 was used instead of HT-1, and in Experimental Examples 1-25 to 1-48, the compound of Chemical Formula 2 was used instead of ET- 1 and Formula 2 are separately used, the basic characteristics of the device are shown.

Experimental Examples 1-49 to 1-78 show the characteristics of the device when the compounds of Formula 1 were used instead of HT-1 and the compounds of Formula 2 were used in place of ET-1 in one device.

In Experimental Examples 1-49 to 1-53, when the derivatives 1-7 were used as HT-1 and the derivatives 2 and 3 were used as ET-1, the voltage dropped by 10% or more. It can be seen from the results in Experimental Example 1 that the compound of the formula 1-7 is excellent in not only the function of electron suppression but also the function of hole transport when the compounds of the formulas 2 and 3 are combined with ET-1. In Experimental Examples 1-69 to 1-73, when the derivatives 1-32 and 1-37 were used as HT-1 and the derivatives 2 and 3 were used as ET-1, the lifetime was increased by about 25% to 30%. In terms of luminous efficacy, it was measured to be about 10% higher than in Experimental Examples 1-1 to 1-48.

As a result, the hole transport layer material (HT-1) of the present invention represented by Formula 1 (structure in which amine is directly or linker-linked to triphenylene core) is used as a hole transport layer material (HT-1) and triazine, pyrimidine, Emitting efficiency and lifetime characteristics of a blue organic light-emitting device formed by combining the compound of Formula 2 including the electron-transporting material (ET-1) with the electron-transporting layer material (ET-1) provided between the anode and the light- .

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

Claims (15)

anode;
A negative electrode opposed to the positive electrode;
A light emitting layer provided between the anode and the cathode;
A first organic layer provided between the anode and the light emitting layer; And
And a second organic layer disposed between the cathode and the light emitting layer,
Wherein the first organic layer comprises a compound represented by the following formula (1)
Wherein the second organic compound layer comprises a compound represented by Formula 2: &lt; EMI ID =
[Chemical Formula 1]

(2)

In the above formulas (1) and (2)
L1 is a direct bond; Substituted or unsubstituted arylene,
Ar 1 to Ar 5 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
X1 and X2 are the same or different and are each independently CR or N,
R and R1 to R3 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,
p is an integer of 0 to 10,
a and b are the same or different and each independently represents an integer of 0 to 4,
c is an integer of 0 to 3,
When a, b, c, and p are each 2 or more, the structures in parentheses are the same or different. The compound according to claim 1, wherein Ar3 to Ar5 are the same or different and each independently represents a substituted or unsubstituted monocyclic to tricyclic aryl group; Or a substituted or unsubstituted monocyclic or bicyclic heterocyclic group. The organic electroluminescent device according to claim 1, wherein the compound represented by Formula 2 is represented by Formula 3:
(3)

In Formula 3,
L2 is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,
X3 to X6 are the same or different and are each independently CR or N,
Ar6 and Ar7 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R, Ar8 and Ar9 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,
q is an integer of 0 to 10,
When q is 2 or more, the structures in parentheses are the same or different from each other. 4. The compound according to claim 3, wherein L2 is a direct bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted biphenylene; Substituted or unsubstituted terphenylene; Substituted or unsubstituted quaterphenylene; Substituted or unsubstituted naphthylene; Substituted or unsubstituted phenanthrylene; Or substituted or unsubstituted fluorenylene. [2] The compound according to claim 1, wherein L1 is a direct bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted naphthylene; Substituted or unsubstituted biphenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted fluorenylene. [2] The compound according to claim 1, wherein Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted quaterphenyl 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; Or a substituted or unsubstituted dibenzothiophene group. The organic electroluminescent device according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following structural formulas:

The organic electroluminescent device according to claim 1, wherein the compound of formula (2) is any one selected from the following formulas:

[2] The organic light emitting device of claim 1, wherein the first organic layer comprises an electron blocking layer, and the electron blocking layer comprises a compound represented by the general formula (1). The organic light emitting device according to claim 1, wherein the first organic layer comprises a hole transporting layer and an electron blocking layer, and the electron blocking layer comprises a compound represented by the general formula (1). The organic light emitting device according to claim 9 or 10, wherein the electron blocking layer is provided in contact with the light emitting layer. The organic light emitting diode according to claim 1, wherein the second organic layer includes an electron transporting layer, and the electron transporting layer comprises a compound represented by the general formula (2). [4] The organic light emitting device according to claim 3, wherein the second organic material layer comprises an electron transporting layer, and the electron transporting layer comprises a compound represented by the general formula (3). The organic light emitting device according to claim 1, wherein the second organic material layer comprises an electron transporting layer and an electron injecting layer, and the electron transporting layer comprises a compound represented by the general formula (2). [4] The organic light emitting diode according to claim 3, wherein the second organic material layer comprises an electron transporting layer and an electron injecting layer, and the electron transporting layer comprises a compound represented by the general formula (3).

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