KR101968216B1 - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

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,

Ar1, Ar2, R3 and 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,

c and d are the same or different and independently of one another an integer of 0 to 4,

When c and d are each 2 or more, the structures in parentheses are the same or different from each other,

R1 and R2 are combined with a structure represented by the following formula (2) to form a ring,

(2)

In Formula 2,

X is O, S, SO, SO ₂ , C (R 6) (R 7) or Si (R 8)

Ar 3 and R 5 to R 9 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,

e is an integer of 0 to 4,

When e is 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. More preferably, according to one embodiment of the present invention, the compound can be used as a material for the hole injecting layer, the hole transporting layer, or the electron blocking layer.

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.

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.

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).

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, 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, 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 invention, the formula (1) may be represented by the following formula (3) or (4).

(3)

[Chemical Formula 4]

In the above formulas (3) and (4)

The definitions of Ar1 to Ar3, X, R3 to R5, c, d and e are as shown in formula (1).

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (5) to (15).

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

In the above Formulas 5 to 15,

The definitions of Ar1 to Ar3, R3 to R9, c, d and e are as shown in formula (1).

According to one embodiment of the present disclosure, X is O.

According to one embodiment of the present disclosure, X is S.

According to one embodiment of the present disclosure, X is SO ₂ .

According to one embodiment of the present disclosure, X is SO.

According to one embodiment of the present disclosure, X is C (R6) (R7).

According to one embodiment of the present disclosure, X is Si (R8) (R9).

According to one embodiment of the present invention, R6 to R9 are the same or different and each independently represents a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, R6 to R9 are the same or different from each other, and each independently an alkyl group; An aryl group; Or a heterocyclic group.

According to one embodiment of the present invention, R6 to R9 are the same or different and are each independently a substituted or unsubstituted alkyl group.

According to one embodiment of the present invention, R6 to R9 are the same or different from each other and each independently an alkyl group.

According to one embodiment of the present invention, R6 to R9 are the same or different and are each independently a methyl group.

According to one embodiment of the present invention, at least one of Ar1 to Ar3 is a substituted or unsubstituted aryl group.

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

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

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different from each other and each independently represents an aryl group substituted with at least one substituent selected from the group consisting of an alkyl group, an aryl group, an arylamine group and a heterocyclic group group; Or a heterocyclic group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different from each other and each independently represents an aryl group substituted with at least one substituent selected from the group consisting of an alkyl group, an aryl group, an arylamine group and a heterocyclic group group; A carbazolyl group substituted or unsubstituted with an aryl group; Parlyldyl 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; Or a quinazoline group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different from each other and each independently represents an aryl group substituted with at least one substituent selected from the group consisting of an alkyl group, an aryl group, an arylamine group and a heterocyclic group group; A carbazole group substituted with an aryl group; A pyridyl group substituted with an aryl group; A pyrimidyl group substituted with an aryl group; A triazine group substituted with an aryl group; Or a quinazoline group substituted with an aryl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and are each independently a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and each independently represents a substituted or unsubstituted 1 to 5-membered aryl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 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 naphthyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, Ar1 to Ar3 are the same or different and each independently represents one or more substituents selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, a trimethylsilyl group, an alkyl group and a heterocyclic group A substituted or unsubstituted phenyl group; A biphenyl group; A terphenyl group; Naphthyl group; A phenanthryl group; Triphenylene group; Or a fluorenyl group substituted with an alkyl group.

According to one embodiment of the present invention, at least one of Ar1 to Ar3 may be represented by the following general formula (1-1).

[Formula 1-1]

In Formula 1-1,

X 1 to X 3 are the same or different and each independently N or CR,

R, Ar4 and Ar5 are the same or different 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,

L3 is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

p is an integer of 0 to 5,

When p is 2 or more, the structures in parentheses are the same or different.

According to one embodiment of the present invention, Ar4 and Ar5 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, Ar4 and Ar5 are the same or different from each other and are each independently a phenyl group; A biphenyl group; Naphthyl group; A pyridyl group; Pyrimidyl; Triazine; Or a fluorenyl group substituted with an alkyl group.

According to one embodiment of the present invention, at least one of Ar1 to Ar3 may be represented by the following general formula (1-2).

[Formula 1-2]

In Formula 1-2,

Ar6 and Ar7 are the same or different 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.

According to one embodiment of the present invention, at least one of Ar1 to Ar3 may be represented by the following Formula 1-3.

[Formula 1-3]

In Formula 1-3,

Ar8 and Ar9 are the same or different 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.

According to one embodiment of the present invention, at least one of Ar1 to Ar3 may be represented by the following general formula (1-4).

[Formula 1-4]

In Formula 1-4,

Y1 and Y2 are the same or different and are each independently CR, N, S or O,

R, R 21 and R 22 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 is bonded to an adjacent group to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, at least one of Ar1 to Ar3 may be represented by the following general formula (1-5).

[Formula 1-5]

In Formula 1-5,

Ar10 to Ar12 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.

According to one embodiment of the present invention, at least one of Ar1 to Ar3 may be represented by the following general formulas 1-6 or 1-7.

[Chemical Formula 1-6]

[Chemical Formula 1-7]

In the above formulas 1-6 and 1-7,

X4 is CR, N, S or O,

R, A1 and A2 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,

a1 is an integer of 0 to 7,

a2 is an integer of 0 to 8,

When a1 and a2 are each 2 or more, the structures in parentheses are the same or different from each other.

According to one embodiment of the present invention, at least one of Ar1 to Ar3 is a substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphtho benzofuranyl group; Or a substituted or unsubstituted naphthobenzothiophene group.

According to one embodiment of the present disclosure, at least one of Ar1 to Ar3 is an unsubstituted carbazole group; A carbazole group substituted with an aryl group; An unsubstituted benzocarbazole group; A benzocarbazole group substituted with an aryl group; An unsubstituted dibenzofuranyl group; An unsubstituted dibenzothiophene group; A dibenzofuranyl group substituted with an aryl group; A dibenzothiophen group substituted with an aryl group; An unsubstituted naphtho benzofuranyl group; Or an unsubstituted naphthobenzothiophene group.

According to one embodiment of the present invention, at least one of Ar1 to Ar3 may be represented by the following Chemical Formulas 1-8.

[Chemical Formula 1-8]

In Formula 1-8,

Y3 and Y4 are the same or different and are each independently N, O or S,

A3 and A4 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,

a3 is an integer of 0 to 3,

a4 is an integer of 0 to 4,

When a3 and a4 are each 2 or more, the structures in parentheses are the same or different from each other.

According to an embodiment of the present invention, at least one of Ar1 to Ar3 may be 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 invention, the compound of Formula 1 may be any one selected from the following compounds.

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

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

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

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

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 following manner.

[Reaction Scheme 1]

[Reaction Scheme 2-1]

[Reaction Scheme 2-2]

[Reaction Scheme 2-3]

[Reaction Scheme 2-4]

In the above reaction formulas, the definitions of substituents are as shown in formula (1).

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 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 an 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.

< Synthetic example  1>

<Production Example 1> Synthesis of Compound 1-1

Dihydro-5H-diindolo [2,3-a: 2 ', 3'-c] phenothiazine (15.0 g, 0.28 mol), 3-bromo -9-phenyl-9H-carbazole ( 10.01g, 0.31mol) , and then completely dissolved in Xylene 240ml was added sodium tert-butoxide (3.27g, 0.34mol ) and, Bis (tri- tert -butylphosphine) palladium (0) ( 0.07 g, 0.0014 mol) was added thereto, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and removing the base by filtration, the xylene was concentrated under reduced pressure, and the resulting product was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to prepare the compound 1-1 (18.47 g, yield: 88%).

MS [M + H] &lt; ⁺ &gt; = 771

<Preparation Example 2> Synthesis of compound 1-2 to compound

6-dihydro-5H-diindolo [2,3-a: 2 ', 3'-c] phenothiazine (15.0 g, 0.28 mol) and 9- 4-bromophenyl) -9H-carbazole ( 11.01g, 0.34mol) , and then completely dissolved in Xylene 300ml was added sodium tert-butoxide (3.59g, 0.37mol ) and, Bis (tri- tert -butylphosphine) palladium (0) ( 0.11 g, 0.0021 mol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 3 to prepare the compound 1-2 (19.51 g, yield: 93%).

MS [M + H] &lt; ⁺ &gt; = 771

<Production Example 3> Synthesis of Compound 1-3

(15.0 g, 0.28 mol), bromobenzene (5.50 g, 0.28 mol), and the like were placed in a 500 ml round-bottomed flask under a nitrogen atmosphere. g, 0.34mol), and then was completely dissolved in Xylene 230ml was added sodium tert-butoxide (3.59g, 0.37mol ) , insert a Bis (tri- tert -butylphosphine) palladium ( 0) (0.11g, 0.0021mol) 5 Lt; / RTI &gt; After the temperature was lowered to room temperature and the base was removed by filtration, the xylene was concentrated under reduced pressure and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 10 to prepare the compound 1-3 (13.11 g, yield: 85%).

MS [M + H] &lt; ⁺ &gt; = 606

<Production Example 4> A compound of Compound 1-4 Synthesis

Dihydro-5H-diindolo [2,3-a: 2 ', 3'-c] phenothiazine (15.0 g, 0.28 mol) and 2-chloro 4,6-diphenyl-1,3,5-triazine (8.37g, 0.34mol) was completely dissolved in 300ml of xylene, sodium tert-butoxide (3.59g, 0.37mol) was added and bis (tri- tert -butylphosphine ) palladium (0) (0.11 g, 0.0021 mol) were added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to prepare the compound 1-4 (13.47 g, yield: 88%).

MS [M + H] &lt; ⁺ &gt; = 761

<Production Example 5> Synthesis of compound 1-5 to compound

Dihydro-5H-diindolo [2,3-a: 2 ', 3'-c] phenothiazine (15.0 g, 0.28 mol) and 2-chloro 4,6-diphenylpyrimidine (8.37g, 0.34mol) was completely dissolved in 300ml of xylene, sodium tert-butoxide (3.59g, 0.37mol) was added and bis (tri- tert -butylphosphine) palladium , 0.0021 mol), and the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and removing the base by filtration, the xylene was concentrated under reduced pressure, and the obtained product was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to prepare the above compound 1-5 (18.59 g, yield: 85%).

MS [M + H] &lt; ⁺ &gt; = 760

<Production Example 6> A compound of Compound 1-6 Synthesis

Dihydro-5H-diindolo [2,3-a: 2 ', 3'-c] phenothiazine (15.0 g, 0.28 mol) and 2-chloro 4,6-diphenylpyridine (8.37g, 0.34mol) was completely dissolved in 300ml of xylene, sodium tert-butoxide (3.59g, 0.37mol) was added and bis (tri- tert -butylphosphine) palladium , 0.0021 mol), and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to prepare the compound 1-6 (17.78 g, yield: 84%).

MS [M + H] &lt; ⁺ &gt; = 761

<Production Example 7> A compound of Compound 1-7 Synthesis

Dihydro-5H-diindolo [2,3-a: 2 ', 3'-c] phenothiazine (15.0 g, 0.28 mol) and 2-chloro 4-phenylquinazoline (8.42 g, 0.34 mol) was completely dissolved in 300 ml of xylene. To the mixture was added sodium tert-butoxide (3.59 g, 0.37 mol) and bis (tri- tert -butylphosphine) palladium mol), and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 3 to prepare the compound 1-7 (16.17 g, yield: 82%).

MS [M + H] &lt; ⁺ &gt; = 761

<Production Example 8> A compound of Compound 1-8 Synthesis

To a 500 ml round bottom flask in a nitrogen atmosphere was added 16-phenyl-5- (4-phenylquinazolin-2-yl) -6,16-dihydro-5H-diindolo [2,3-a: 2 ', 3'-c] phenothiazine (Tert-butoxide) (3.59g, 0.37mol) was added to the solution, and bis (tri-tert-butoxide) tert- butylphosphine palladium (0) (0.11 g, 0.0021 mol) was added thereto, followed by heating with stirring for 5 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 10 to prepare the compound 1-8 (15.11 g, yield: 95%).

MS [M + H] &lt; ⁺ &gt; = 810

<Production Example 9> A compound of Compound 1-9 Synthesis

Dihydro-5H-diindolo [2,3-a] pyridine was prepared in a 500 ml round-bottomed flask under a nitrogen atmosphere by placing 5- (4,6-diphenyl-1,3,5-triazin- (15.0 g, 0.23 mol) and 2-bromo-9,9-dimethyl-9H-fluorene (5.50 g, 0.34 mol) were dissolved in 250 ml of xylene and sodium tert-butoxide g, 0.37 mol) was added, and Bis (tri- tert- butylphosphine) palladium (0) (0.11 g, 0.0021 mol) was added and the mixture was heated with stirring for 5 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 15 to prepare the above compound 1-9 (11.11 g, yield: 74%).

MS [M + H] &lt; ⁺ &gt; = 877

<Production Example 10> A compound of the compound 1-10 Synthesis

N, diphenyl-4- (5-phenyl-5,6-dihydro-16H-diindolo [2,3-a: 2 ', 3'-c] phenothiazin-16-yl ) aniline (15.0g, 0.22mol), bromobenzene (5.5g 0.34mol) , and then completely dissolved in Xylene 180ml was added sodium tert-butoxide (3.59g, 0.37mol ), and Bis (tri- tert -butylphosphine) palladium ( 0 ) (0.11 g, 0.0021 mol) were added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 10 to prepare the compound 1-10 (13.11 g, yield: 85%).

MS [M + H] &lt; ⁺ &gt; = 773

<Production Example 11> A compound of the compound 1-11 Synthesis

N, diphenyl-4- (5-phenyl-5,6-dihydro-16H-diindolo [2,3-a: 2 ', 3'-c] phenothiazin-16-yl ) aniline (15.0g, 0.22mol), bromobenzene (5.5g 0.34mol) , and then completely dissolved in Xylene 200ml sodium tert-butoxide (3.59g , 0.37mol) was added and, Bis (tri- tert -butylphosphine) palladium (0 ) (0.11 g, 0.0021 mol) were added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure, and the residue was subjected to column chromatography using tetrahydrofuran: hexane = 1: 10 to prepare the compound 1-11 (13.11 g, yield: 85%).

MS [M + H] &lt; ⁺ &gt; = 712

<Production Example 12> A compound of the compound 1-12 Synthesis

(Dibenzo [b, d] furan-2-yl) -5-phenyl-6,16-dihydro-5H-diindolo [2,3-a: 2 ', 3'- c] phenothiazine (15.0g, 0.22mol) , bromobenzene (5.5g 0.34mol) , and then completely dissolved in Xylene 200ml was added sodium tert-butoxide (3.59g, 0.37mol ) and, Bis (tri- tert -butylphosphine) palladium ( 0) (0.11 g, 0.0021 mol) was added thereto, followed by heating and stirring for 5 hours. After the temperature was lowered to room temperature and the base was removed by filtration, the xylene was concentrated under reduced pressure and the residue was subjected to column chromatography using tetrahydrofuran: hexane = 1: 10 to prepare the compound 1-12 (13.11 g, yield: 85%).

MS [M + H] &lt; ⁺ &gt; = 696

<Production Example 13> A compound of the compounds 1-13 ~ 1-24 Synthesis

The compounds 1-13 to 1-24 were synthesized in the same manner as in the preparation of the compounds 1-1 to 1-12 except that the starting materials in Preparation Examples 1 to 12 were those in which X = O was used instead of X = S. .

<Production Example 14> A compound of the compounds 1-25 ~ 1-36 Synthesis

In the same manner as in the production of the compound 1-1 to 1-12 except that the starting material was the same as the compound X = C (CH ₃ ) ₂ instead of X═S, the compound 1-25 ~ 1-36.

<Production Example 15> A compound of the synthesized compounds 1-37 ~ 1-48

The compounds 1-37 to 1-48 were synthesized in the same manner as in the preparation of the compounds 1-1 to 1-12 except that the starting materials in Preparation Examples 1 to 12 were those in which X = Si instead of X = S was used. .

<Production Example 16> A compound of the synthesized compounds 1-49 ~ 1-60

The compounds 1-49 to 1-60 were synthesized in the same manner as in the preparation of the above compounds 1-1 to 1-12 except that the starting materials in Preparation Examples 1 to 12 were those in which X = SO 2 was used instead of X = S. .

<Production Example 17> A compound of the synthesized compounds 1-61 ~ 1-72

The compounds 1-61 to 1-72 were synthesized in the same manner as in the preparation of the above compounds 1-1 to 1-12 except that the starting materials in Preparation Examples 1 to 12 were those in which X = SO was used instead of X = S. .

< 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.

[LINE]

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.

[NPB]

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

[1-1]

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.

[BH]

[BD]

[ET1]

[LiQ]

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 1-2 was used instead of EB1 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 1-3 was used in place of EB1 in Experimental Example 1.

 <Experimental Example 1-3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-10 was used instead of Compound EB1 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 1-11 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-5>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-12 was used instead of Compound EB1 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 1-13 was used instead of Compound EB1 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 1-14 was used instead of Compound EB1 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 1-21 was used instead of EB1 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 1-22 was used instead of Compound EB1 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 1-23 was used instead of Compound EB1 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 1-24 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-12>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-25 was used in place of Compound EB1 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 1-26 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-14>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-27 was used instead of Compound EB1 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 1-34 was used in place of Compound EB1 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 1-35 was used in place of Compound EB1 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 1-36 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-18>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-37 was used instead of Compound EB1 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 1-38 was used in place of Compound EB1 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 1-39 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-21>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-46 was used in place of Compound EB1 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 1-47 was used in place of Compound EB1 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 1-48 was used in place of Compound EB1 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 1-49 was used in place of Compound EB1 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 1-50 was used in place of Compound EB1 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 1-51 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-27>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-58 was used in place of Compound EB1 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 1-59 was used in place of Compound EB1 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 1-60 was used in place of Compound EB1 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 Compound 1-61 was used instead of Compound EB1 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 1-62 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-32>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-63 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-33>

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 EB1 in Experimental Example 1.

<Experimental Example 1-34>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-71 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-35>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-72 was used instead of Compound EB1 in Experimental Example 1.

&Lt; Comparative Example 1 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound HT1 was used in place of Compound EB1 in Experimental Example 1.

[HT1]

&Lt; Comparative Example 2 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound HT2 was used in place of Compound EB1 in Experimental Example 1.

[HT2]

&Lt; Comparative Example 3 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound HT3 was used in place of Compound EB1 in Experimental Example 1.

[HT3]

&Lt; Comparative Example 4 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound HT4 was used in place of Compound EB1 in Experimental Example 1.

[HT4]

&Lt; Comparative Example 5 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound HT5 was used in place of Compound EB1 in Experimental Example 1.

[HT5]

The results shown in Table 1 were obtained when current was applied to the organic light-emitting device manufactured in Experimental Example 1, Experimental Examples 1-1 to 35 and Comparative Examples 1 to 5.

compound
(Electron inhibiting layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 1 Compound 1-1 3.89 6.45 (0.138, 0.127) Experimental Example 1-1 Compound 1-2 3.94 6.35 (0.139, 0.122) Experimental Example 1-2 Compound 1-3 3.85 6.36 (0.138, 0.126) Experimental Example 1-3 Compound 1-10 3.96 6.31 (0.138, 0.127) Experimental Examples 1-4 Compound 1-11 3.93 6.42 (0.137, 0.125) Experimental Examples 1-5 Compound 1-12 3.82 6.47 (0.136, 0.125) Experimental Example 1-6 Compound 1-13 3.80 6.51 (0.136, 0.127) Experimental Example 1-7 Compound 1-14 3.87 6.35 (0.136, 0.125) Experimental Examples 1-8 Compound 1-15 3.86 6.34 (0.137, 0.125) Experimental Examples 1-9 Compound 1-22 3.85 6.31 (0.138, 0.125) Experimental Example 1-10 Compound 1-23 3.85 6.33 (0.136, 0.125) Experimental Example 1-11 Compound 1-24 3.81 6.32 (0.137, 0.125) Experimental Example 1-12 Compound 1-25 3.89 6.30 (0.136, 0.125) Experimental Example 1-13 Compound 1-26 3.89 6.50 (0.138, 0.126) Experimental Example 1-14 Compound 1-27 3.84 6.52 (0.137, 0.125) Experimental Example 1-15 Compound 1-34 3.80 6.50 (0.136, 0.127) Experimental Example 1-16 Compound 1-35 3.81 6.55 (0.135, 0.127) Experimental Example 1-17 Compound 1-36 3.84 6.51 (0.138, 0.127) Experimental Example 1-18 Compound 1-37 3.78 6.59 (0.137, 0.125) Experimental Example 1-19 Compound 1-38 3.84 6.46 (0.137, 0.125) Experimental Example 1-20 Compound 1-39 3.88 6.42 (0.136, 0.125) Experimental Example 1-21 Compound 1-46 3.89 6.46 (0.138, 0.126) Experimental Example 1-22 Compound 1-47 3.81 6.44 (0.137, 0.125) Experimental Example 1-23 Compound 1-48 3.85 6.40 (0.136, 0.127) Experimental Example 1-24 Compound 1-49 3.84 6.46 (0.135, 0.127) Experimental Example 1-25 Compound 1-50 3.88 6.42 (0.137, 0.125) Experimental Example 1-26 Compound 1-51 3.89 6.46 (0.138, 0.125) Experimental Example 1-27 Compound 1-58 3.85 6.44 (0.136, 0.125) Experimental Example 1-28 Compound 1-59 3.85 6.50 (0.136, 0.127) Experimental Example 1-29 Compound 1-60 3.85 6.50 (0.136, 0.127) Experimental Example 1-30 Compound 1-61 3.88 6.42 (0.137, 0.125) Experimental Examples 1-31 Compound 1-62 3.89 6.40 (0.138, 0.125) Experimental Example 1-32 Compound 1-63 3.95 6.44 (0.136, 0.125) Experimental Example 1-33 Compound 1-70 3.75 6.43 (0.136, 0.127) Experimental Example 1-34 Compound 1-71 3.87 6.48 (0.136, 0.127) Experimental Example 1-35 Compound 1-72 3.85 6.47 (0.136, 0.127) Comparative Example 1 HT1 4.23 5.91 (0.136, 0.127) Comparative Example 2 HT2 4.27 5.95 (0.136, 0.127) Comparative Example 3 HT3 4.45 5.52 (0.135, 0.125) Comparative Example 4 HT4 4.44 5.73 (0.135, 0.130) Comparative Example 5 HT5 4.48 5.65 (0.135, 0.130)

As shown in Table 1, in the case of the organic light emitting device prepared by using the compound of the present invention as an electron blocking layer, the compound of the present invention has an electron blocking effect when compared with the case of using the materials of Comparative Examples 1 to 5 And thus exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device.

Specifically, the trifused carbazole type exhibited more voltage increase and efficiency reduction characteristics than the indolocarbazole type, and the experimental examples 1-1 to 1-35 showed a voltage reduction of 10 to 20% Also, it shows more than 20% higher characteristics.

As shown in Table 1, it was confirmed that the compounds of the present invention are excellent in electron blocking ability and applicable to organic light emitting devices.

< Experimental Example  2>

In Experimental Example 1, the same experiment was conducted except that the compounds of Experimental Examples 1-1 to 35 were used instead of NPB as the hole transport layer.

The results shown in Table 2 were obtained when current was applied to the organic light-emitting device manufactured in Experimental Example 2, Experimental Examples 2-1 to 35 and Comparative Examples 1 to 5.

compound
(Electron inhibiting layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 2 Compound 1-1 4.45 5.45 (0.138, 0.127) Experimental Example 2-1 Compound 1-2 4.52 5.35 (0.139, 0.122) EXPERIMENTAL EXAMPLE 2-2 Compound 1-3 4.48 5.36 (0.138, 0.126) Experimental Example 2-3 Compound 1-10 4.59 5.39 (0.138, 0.127) Experimental Example 2-4 Compound 1-11 4.55 5.42 (0.137, 0.125) Experimental Example 2-5 Compound 1-12 4.46 5.47 (0.136, 0.125) Experimental Examples 2-6 Compound 1-13 4.48 5.51 (0.136, 0.127) Experimental Example 2-7 Compound 1-14 4.53 5.35 (0.136, 0.125) Experimental Examples 2-8 Compound 1-15 4.49 5.34 (0.137, 0.125) Experimental Examples 2-9 Compound 1-22 4.52 5.38 (0.138, 0.125) Experimental Example 2-10 Compound 1-23 4.54 5.46 (0.136, 0.125) Experimental Example 2-11 Compound 1-24 4.46 5.36 (0.137, 0.125) Experimental Examples 2-12 Compound 1-25 4.41 5.31 (0.136, 0.125) Experimental Example 2-13 Compound 1-26 4.50 5.50 (0.138, 0.126) Experimental Example 2-14 Compound 1-27 4.43 5.52 (0.137, 0.125) Experimental Example 2-15 Compound 1-34 4.57 5.58 (0.136, 0.127) Experimental Example 2-16 Compound 1-35 4.56 5.55 (0.135, 0.127) Experimental Example 2-17 Compound 1-36 4.44 5.51 (0.138, 0.127) Experimental Example 2-18 Compound 1-37 4.41 5.59 (0.137, 0.125) Experimental Example 2-19 Compound 1-38 4.58 5.46 (0.137, 0.125) Experimental Example 2-20 Compound 1-39 4.49 5.45 (0.136, 0.125) Experimental Example 2-21 Compound 1-46 4.57 5.46 (0.138, 0.126) Experimental Example 2-22 Compound 1-47 4.52 5.44 (0.137, 0.125) Experimental Example 2-23 Compound 1-48 4.43 5.40 (0.136, 0.127) Experimental Example 2-24 Compound 1-49 4.45 5.36 (0.135, 0.127) Experimental Example 2-25 Compound 1-50 4.57 5.42 (0.137, 0.125) Experimental Example 2-26 Compound 1-51 4.46 5.46 (0.138, 0.125) Experimental Example 2-27 Compound 1-58 4.54 5.44 (0.136, 0.125) EXPERIMENTAL EXAMPLE 2-28 Compound 1-59 4.53 5.53 (0.136, 0.127) Experimental Example 2-29 Compound 1-60 4.41 5.51 (0.136, 0.127) Experimental Example 2-30 Compound 1-61 4.45 5.42 (0.137, 0.125) EXPERIMENTAL EXAMPLE 2-31 Compound 1-62 4.59 5.40 (0.138, 0.125) Experimental Example 2-32 Compound 1-63 4.41 5.44 (0.136, 0.125) Experimental Example 2-33 Compound 1-70 4.58 5.43 (0.136, 0.127) Experimental Example 2-34 Compound 1-71 4.50 5.48 (0.136, 0.127) Experimental Example 2-35 Compound 1-72 4.46 5.47 (0.136, 0.127) Comparative Example 1 HT1 5.06 4.91 (0.136, 0.127) Comparative Example 2 HT2 5.11 4.95 (0.136, 0.127) Comparative Example 3 HT3 5.18 4.52 (0.135, 0.125) Comparative Example 4 HT4 5.22 4.73 (0.135, 0.130) Comparative Example 5 HT5 5.39 4.65 (0.135, 0.130)

As shown in Table 2, in the case of the organic light emitting device manufactured by using the compound of the present invention as a hole transporting layer, the compound of the present invention has an electron blocking function as compared with the case of using the materials of Comparative Examples 1 to 5 Exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device.

Specifically, in Experimental Examples 2-1 to 2-35, the voltage is decreased by 10% or more and the efficiency is also 20% or more higher than the comparative example.

As shown in Table 1, it was confirmed that the compounds of the present invention are excellent in electron blocking ability and applicable to organic light emitting devices.

As shown in Tables 1 and 2, it was confirmed that the compounds according to the present invention are applicable not only to electron blocking ability but also to hole transporting ability and thus to organic light emitting devices.

< Experimental Example  3>

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) / CBP + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) using CBP as a host on the prepared ITO transparent electrode. ) / 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 , CBP and BCP are as follows.

<Experimental Example 3-1>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-4 was used instead of CBP in Experimental Example 3.

 <Experimental Example 3-2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-5 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-6 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-4>

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

<Experimental Example 3-5>

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

<Experimental Example 3-6>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-9 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-7>

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

 <Experimental Example 3-8>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-16 was used instead of Compound CBP in Experimental Example 3.

<Experimental Example 3-9>

An organic light emitting device was prepared in the same manner as in Experimental Example 3, except that Compound 1-17 was used instead of Compound CBP in Experimental Example 3.

<Experimental Example 3-10>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-18 was used instead of Compound CBP in Experimental Example 3.

<Experimental Example 3-11>

An organic light emitting device was prepared in the same manner as in Experimental Example 3, except that Compound 1-19 was used instead of Compound CBP in Experimental Example 3.

<Experimental Example 3-12>

An organic light emitting device was prepared in the same manner as in Experimental Example 3, except that Compound 1-20 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-13>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-21 was used instead of Compound CBP in Experimental Example 3.

<Experimental Example 3-14>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-24 was used instead of CBP in Experimental Example 3.

 <Experimental Example 3-15>

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

<Experimental Example 3-16>

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

<Experimental Example 3-17>

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

<Experimental Example 3-18>

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

<Experimental Example 3-19>

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

<Experimental Example 3-20>

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

 <Experimental Example 3-21>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-36 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-22>

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

<Experimental Example 3-23>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-41 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-24>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-42 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-25>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-43 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-26>

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

<Experimental Example 3-27>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-45 was used instead of CBP in Experimental Example 3.

 <Experimental Example 3-28>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-48 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-29>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-52 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-30>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-53 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-31>

An organic light emitting device was prepared in the same manner as in Experimental Example 3, except that Compound 1-54 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-32>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-55 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-33>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-56 was used in place of CBP in Experimental Example 3.

 <Experimental Example 3-34>

An organic light emitting device was prepared in the same manner as in Experimental Example 3, except that Compound 1-57 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-35>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-60 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-35>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-64 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-35>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 1-65 was used in place of Compound CBP in Experimental Example 3.

<Experimental Example 3-35>

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

<Experimental Example 3-35>

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

<Experimental Example 3-40>

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

<Experimental Example 3-41>

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

<Experimental Example 3-42>

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

&Lt; Comparative Example 1 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound GH1 was used in place of Compound CBP in Experimental Example 1.

[GH1]

&Lt; Comparative Example 2 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that the following compound GH2 was used instead of the compound CBP in Experimental Example 3.

[GH2]

&Lt; Comparative Example 3 &

An organic light emitting device was prepared in the same manner as in Experimental Example 3, except that the following compound GH3 was used in place of the compound CBP in Experimental Example 3.

[GH3]

&Lt; Comparative Example 4 &

An organic light emitting device was prepared in the same manner as in Experimental Example 3, except that the following compound GH4 was used in place of the compound CBP in Experimental Example 3.

[GH4]

&Lt; Comparative Example 5 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that the following compound GH5 was used in place of the compound CBP in Experimental Example 3.

[GH5]

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 42 and Comparative Examples 1 to 5.

compound
(Host) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) EL peak
(nm) Experimental Example 3 CBP 7.32 38.12 516 Experimental Example 3-1 Compound 1-4 6.70 42.93 517 Experimental Example 3-2 Compound 1-5 6.72 42.24 516 Experimental Example 3-3 Compound 1-6 6.71 42.72 517 Experimental Example 3-4 Compound 1-7 6.72 42.65 518 Experimental Example 3-5 Compound 1-8 6.70 42.31 517 Experimental Example 3-6 Compound 1-9 6.73 42.63 517 Experimental Example 3-7 Compound 1-12 6.71 42.62 516 Experimental Examples 3-8 Compound 1-16 6.72 42.64 517 Experimental Examples 3-9 Compound 1-17 6.72 42.08 516 Experimental Example 3-10 Compound 1-18 6.71 42.72 518 Experimental Example 3-11 Compound 1-19 6.72 42.70 517 Experimental Examples 3-12 Compound 1-20 6.73 42.76 516 Experimental Example 3-13 Compound 1-21 6.70 44.93 517 Experimental Examples 3-14 Compound 1-24 6.66 45.24 516 Experimental Example 3-15 Compound 1-28 6.5 44.72 518 Experimental Examples 3-16 Compound 1-29 6.59 44.65 517 Experimental Example 3-17 Compound 1-30 6.58 44.31 515 Experimental Example 3-18 Compound 1-31 6.63 44.63 516 Experimental Example 3-19 Compound 1-32 6.64 44.62 516 Experimental Example 3-20 Compound 1-33 6.57 44.64 517 Experimental Example 3-21 Compound 1-36 6.64 45.08 518 Experimental Example 3-22 Compound 1-40 6.66 44.72 517 Experimental Example 3-23 Compound 1-41 6.62 44.70 517 Experimental Example 3-24 Compound 1-42 6.73 44.76 517 Experimental Example 3-25 Compound 1-43 6.73 43.93 518 Experimental Example 3-26 Compound 1-44 6.76 43.24 517 Experimental Example 3-27 Compound 1-45 6.75 43.72 517 Experimental Example 3-28 Compound 1-48 6.72 43.65 516 Experimental Example 3-29 Compound 1-52 6.70 43.31 517 Experimental Example 3-30 Compound 1-53 6.73 43.63 518 Experimental Example 3-31 Compound 1-54 6.71 43.62 517 Experimental Example 3-32 Compound 1-55 6.77 43.64 517 Experimental Example 3-33 Compound 1-56 6.74 43.08 516 Experimental Example 3-34 Compound 1-57 6.71 43.72 517 Experimental Example 3-35 Compound 1-60 6.72 43.70 516 Experimental Example 3-36 Compound 1-64 6.73 43.76 518 Experimental Example 3-37 Compound 1-65 6.72 43.62 517 EXPERIMENTAL EXAMPLE 3-38 Compound 1-66 6.70 43.64 518 Experimental Example 3-39 Compound 1-67 6.74 43.08 518 Experimental Example 3-40 Compound 1-68 6.76 43.72 517 Experimental Example 3-41 Compound 1-69 6.72 43.70 517 Experimental Example 3-42 Compound 1-72 6.73 43.76 516 Comparative Example 1 GH1 7.28 38.15 515 Comparative Example 2 GH2 7.15 39.70 515 Comparative Example 3 GH3 7.22 38.39 516 Comparative Example 4 GH4 7.35 37.51 517 Comparative Example 5 GH5 7.30 37.64 517

As a result of the experiment, the green organic EL devices of Experimental Examples 3 to 1 to 42 using the compound represented by the present invention as a host material of the light emitting layer were compared with the green organic EL of Experimental Example 3 using Conventional CBP and Comparative Examples 1 to 5 It was confirmed that the device exhibited better current efficiency and better driving voltage than the device. It can be seen that the above compounds having substituents of triazines, pyrimidines, pyridines, quinazolines, and dibenzofurans as substituents are suitable as green light emitting organic devices.

< Experimental Example  4>

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, and then an organic material was deposited on the ITO using DNTPD (700 Å), α-NPB (300 Å) 1-7, 1-8, 1-9, 1-16, 1-19, 1-20, 1-21, 1-28, 1-31, 1-32, 1-33, 43, 1-44, 1-45, 1-52, 1-55, 1-56, 1-57, 1-64, 1-67, 1-68, 1-72 as hosts (90 wt%) and, to as a dopant (piq) ₂ Ir (acac), and co-deposited (300 Å) to (10 wt%), was deposited to the order of Alq3 (350 Å), LiF ( 5 Å), Al (1,000 Å) , And 0.4 mA.

The structures of DNTPD, alpha-NPB, (piq) 2Ir (acac), Alq3 and [compound 1] to [compound 8] are as follows.

&Lt; Comparative Example 1 &

The organic light emitting device for Comparative Example 1 was fabricated in the same manner except that CBP which is widely used as a general phosphorescent host material instead of the organic light emitting compound prepared by the present invention as a host of a light emitting layer in the device structure of the above embodiment was used.

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 Examples 1 to 24 and Comparative Example 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%.

division Host
Dopant Voltage Luminance
(V) CIEx
(cd / m &lt; 2 & CIEy T95 (hr) Example 1 1-4 [(piq) 2Ir (acac)] 4.3 1860 0.670 0.329 465 Example 2 1-7 [(piq) 2Ir (acac)] 4.2 1850 0.674 0.325 415 Example 3 1-8 [(piq) 2Ir (acac)] 4.1 1900 0.672 0.327 440 Example 4 1-9 [(piq) 2Ir (acac)] 4.3 1840 0.673 0.335 435 Example 5 1-16 [(piq) 2Ir (acac)] 4.0 1790 0.675 0.333 405 Example 6 1-19 [(piq) 2Ir (acac)] 4.2 1810 0.670 0.339 420 Example 7 1-20 [(piq) 2Ir (acac)] 4.3 1970 0.671 0.338 445 Example 8 1-21 [(piq) 2Ir (acac)] 4.3 1860 0.668 0.329 465 Example 9 1-28 [(piq) 2Ir (acac)] 4.2 1950 0.673 0.325 415 Example 10 1-31 [(piq) 2Ir (acac)] 4.1 1900 0.670 0.327 440 Example 11 1-32 [(piq) 2Ir (acac)] 4.3 1940 0.671 0.335 435 Example 12 1-33 [(piq) 2Ir (acac)] 4.0 1990 0.674 0.333 405 Example 13 1-40 [(piq) 2Ir (acac)] 4.2 1910 0.675 0.339 420 Example 14 1-43 [(piq) 2Ir (acac)] 4.3 1970 0.671 0.338 445 Example 15 1-44 [(piq) 2Ir (acac)] 4.3 1960 0.668 0.329 465 Example 16 1-45 [(piq) 2Ir (acac)] 4.2 1950 0.674 0.325 415 Example 17 1-52 [(piq) 2Ir (acac)] 4.1 1800 0.672 0.327 440 Example 18 1-55 [(piq) 2Ir (acac)] 4.3 1840 0.669 0.335 435 Example 19 1-56 [(piq) 2Ir (acac)] 4.0 1890 0.668 0.333 405 Example 20 1-57 [(piq) 2Ir (acac)] 4.2 1810 0.669 0.339 420 Example 21 1-64 [(piq) 2Ir (acac)] 4.3 1870 0.668 0.338 445 Example 22 1-67 [(piq) 2Ir (acac)] 4.0 1890 0.668 0.333 405 Example 23 1-68 [(piq) 2Ir (acac)] 4.2 1810 0.669 0.339 420 Example 24 1-69 [(piq) 2Ir (acac)] 4.3 1870 0.668 0.338 445 Comparative Example 1 CBP [(piq) 2Ir (acac)] 5.5 920 0.679 0.339 120

As a result of the experiment, it was found that the values of 1-4, 1-7, 1-8, 1-9, 1-16, 1-19, 1-20, 1-21, 1-28, 1-31, 1-32 , 1-33, 1-40, 1-43, 1-44, 1-45, 1-52, 1-55, 1-56, 1-57, 1-64, 1-67, 1-68, 1 -72 was used as a host material of the light emitting layer, the red organic EL devices of Examples 1 to 24 of Experimental Example 4 were superior to the red organic EL devices of Comparative Example 1 using CBP in terms of current efficiency, driving voltage and lifetime And it is confirmed that it shows excellent performance in terms of surface area. It can be seen that the above compounds having triazines and quinazolines as substituents are suitable as red light emitting organic devices.

 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: Electron transport layer

Claims (18)

A compound represented by the following formula (3):
(3)

In Formula 3,
Ar 1 to Ar 3 are the same or different and each independently represents an aryl group substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group, an aryl group, an arylamine group and a heterocyclic group; A carbazole group substituted with an aryl group; A pyridyl group substituted with an aryl group; A pyrimidyl group substituted with an aryl group; A triazine group substituted with an aryl group; A quinazoline group substituted with an aryl group; A dibenzofurane group; Or a dibenzothiophene group,
R3 to R5 are hydrogen,
X is O, S, SO, SO ₂ , C (R 6) (R 7) or Si (R 8)
R 6 to R 9 are the same or different and each independently represents an alkyl group having 1 to 6 carbon atoms,
c to e are the same as or different from each other, and each independently an integer of 0 to 4; delete The compound according to claim 1, wherein the formula (3) is represented by any one of the following formulas (5) to (15):
[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In Formulas 5 to 10,
The definitions of Ar1 to Ar3, R3 to R9, c, d and e are as shown in general formula (3). delete The compound according to claim 1, wherein at least one of Ar1 to Ar3 is represented by the following formula (1-1):
[Formula 1-1]

In Formula 1-1,
X 1 to X 3 are the same or different and each independently N or CR,
R is hydrogen,
Ar4 and Ar5 are the same or different and are each independently an aryl group,
L3 is a direct bond,
p is an integer of 0 to 5; delete delete delete delete delete delete delete delete The compound according to claim 1, wherein the compound of formula (3) 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 disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers is a compound according to any one of claims 1, 3, 5, and 14 And the organic light emitting device. 16. The organic light emitting device according to claim 15, wherein the organic compound layer containing the compound is a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting holes and transporting holes. 16. The organic light emitting device according to claim 15, wherein the organic compound layer containing the compound is an electron injection layer, an electron transport layer, or a layer simultaneously performing electron injection and electron transport. 16. The organic light emitting device according to claim 15, wherein the organic compound layer containing the compound is a light emitting layer.

Images