KR101920141B1 - 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]

The present application claims the benefit of Korean Patent Application No. 10-2016-0015663 filed on February 11, 2016, filed with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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 enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

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,

X is C or Si,

R1 to R5 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to adjacent groups to form a substituted or unsubstituted ring,

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

d is an integer of 0 to 3,

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

At least one of R 1 to R 5 is represented by the following formula (2)

(2)

In Formula 2,

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

Ar1 and Ar2 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 a phosphine group to form a substituted or unsubstituted ring,

m is an integer of 0 to 10,

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

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. Still more preferably, according to one embodiment of the present disclosure, the compound can be used as a blue light emitting dopant. In addition, according to one embodiment of the present invention, the compound can be used as an electron transporting layer and can realize an organic light emitting device having a long life compared to a conventional electron transporting material group.

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.

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

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

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

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

According to one embodiment of the present disclosure, the term " substituted or unsubstituted " preferably means deuterium; A halogen group; A nitrile group; An alkyl group; An aryl group; And a heterocyclic group, which is substituted or unsubstituted.

Alternatively, according to one embodiment of the present disclosure, the term " substituted or unsubstituted " preferably includes deuterium; A halogen group; A nitrile group; An alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 30 carbon atoms; And a heterocyclic group having 2 to 30 carbon atoms. The term " substituted or unsubstituted "

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

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

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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

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

In the present specification, the boron group may be represented by the formula of -BRR ', wherein 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 and a fluorenyl group.

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

,

,

, 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 furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, A benzothiazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, a thiazolyl group, a thiazolyl group, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is 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 R1 to R5, a, b, 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 (8).

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above formulas 5 to 8,

The definition of R2 to R5, a, b, c, d, e, Ar1, Ar2,

The definition of R6 is the same as that of R2 to R5,

f is an integer of 0 to 3, and when f is 2 or more, R6 are the same or different from each other.

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (9) to (12).

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

In the general formulas (9) to (12)

The definition of R1 to R4, a, b, c, d, e, Ar1, Ar2,

The definition of R7 is the same as that of R1 to R4,

g is an integer of 0 to 3, and when g is 2 or more, R < 7 >

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (13) to (16).

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

In Formulas 13 to 16 above,

The definition of R1, R3, R4, R5, a, b, c, d, e, Ar1, Ar2,

The definition of R8 is the same as that of R1, R3, R4 and R5,

h is an integer of 0 to 3, and when h is 2 or more, R8 are the same or different from each other.

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

According to one embodiment of the present disclosure, L is a direct bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted biphenylene; Substituted or unsubstituted terphenylene; Substituted or unsubstituted quaterphenylene; Substituted or unsubstituted naphthylene; Substituted or unsubstituted anthracenylene; Substituted or unsubstituted fluorenylenes; Substituted or unsubstituted phenanthrylene; Substituted or unsubstituted pyrenylene; Substituted or unsubstituted chlorenylene; A substituted or unsubstituted divalent thiophene group; A substituted or unsubstituted divalent furanyl group; A substituted or unsubstituted divalent quinoline group; Or a substituted or unsubstituted divalent quinazoline group.

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

In the above structures,

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 amine 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,

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

According to one embodiment of the present disclosure, L is a direct bond; Phenylene; Biphenyllylene; Terphenylene; Quaterphenylene; Naphthylene; Anthracenylene; Fluorenylene; Phenanthrylene; Pyrenylene; Chlorenilen; A divalent thiophene group; A divalent furanyl group; A divalent quinoline group; Or a divalent quinazoline group.

According to one embodiment of the present disclosure, L is a direct bond; Arylene having 6 to 30 carbon atoms which is substituted or unsubstituted with a nitrile group; Or heteroarylene having 2 to 30 carbon atoms.

According to one embodiment of the present disclosure, L is a direct bond; Arylene substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, halogen and nitrile groups; Or monocyclic heteroarylene containing N or more.

According to one embodiment of the present disclosure, L is a direct bond; Phenylene substituted or unsubstituted with a nitrile group; Naphthylene; Or monocyclic heteroarylene containing N or more.

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

According to one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represents an aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 2 to 30 carbon atoms.

According to one embodiment of the present invention, Ar 1 and Ar 2 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted quaterphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furanyl group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted pyrimidyl; A substituted or unsubstituted triazine group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted benzocarbazole group, or may be bonded to a phosphine group to form a ring.

According to one embodiment of the present invention, Ar1 and Ar2 are the same or different and are each independently a phenyl group substituted or unsubstituted with a nitrile group; A biphenyl group; A terphenyl group; A quaterphenyl group; Naphthyl group; A fluorenyl group; A phenanthryl group; Thiophene group; A furanyl group; A pyridyl group; Pyrimidyl; Triazine; A dibenzothiophene group; A dibenzofuranyl group; Carbazole group; Or a benzocarbazole group, or may be bonded to a phosphine group to form a ring.

According to one embodiment of the present invention, Ar 1 and Ar 2 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted quaterphenyl group; A substituted or unsubstituted 1-naphthyl group; A substituted or unsubstituted 2-naphthyl group; A substituted or unsubstituted 2-fluorenyl group; A substituted or unsubstituted 3-fluorenyl group; A substituted or unsubstituted 4-fluorenyl group; A substituted or unsubstituted 2-phenanthryl group; A substituted or unsubstituted 3-phenanthryl group; A substituted or unsubstituted 9-phenanthryl group; A substituted or unsubstituted 2-thiophene group; A substituted or unsubstituted 3-thiophene group; A substituted or unsubstituted 2-furanyl group; A substituted or unsubstituted 3-furanyl group; A substituted or unsubstituted 2-dibenzothiophene group; A substituted or unsubstituted 2-dibenzofuranyl group; A substituted or unsubstituted 4-dibenzofuranyl group; A substituted or unsubstituted 4-dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted 1-carbazole group; A substituted or unsubstituted 2-carbazole group; A substituted or unsubstituted 3-carbazole group; A substituted or unsubstituted a-benzocarbazole group; Or a substituted or unsubstituted c-benzocarbazole group, or may be bonded to a phosphine group to form a ring.

According to one embodiment of the present disclosure, Ar1 and Ar2 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; A phosphine oxide group; an alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; An arylheteroarylamine group; Arylphosphine groups; And a heterocyclic group, which may be substituted or unsubstituted.

According to one embodiment of the present invention, 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, the halogenated fused carbazole (1 eq) is dissolved in a solvent mixture of dioxane: DMAC in the ratio of x: y or tetrahydrofuran and placed in a round bottom flask, do. Subsequently, a base and a nickel catalyst are sequentially added and refluxed. When the solution boils, the diarylphosphine oxide is dissolved in a solvent and slowly poured. Then, the reaction is refluxed and reacted until the halogenated fused carbazole material disappears. When the reaction is carried out, The compound to be displayed can be produced.

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 one embodiment of the present invention, the electron transporting layer, the electron injecting layer, or the layer that simultaneously injects electrons and transports electrons may further include an n-type dopant in addition to the compound of Formula 1.

In one embodiment of the present invention, when the electron transporting layer, the electron injection layer, or the layer simultaneously injecting electrons and electrons further contains an n-type dopant in addition to the compound of Formula 1, the compound of Formula 1 and the n- The weight ratio of the dopant may be from 1: 100 to 100: 1. Specifically 1:10 to 10: 1. More specifically, it may be 1: 1.

In one embodiment of the present invention, the n-type dopant may be a metal complex or the like and may be an alkali metal such as Li, Na, K, Rb, Cs or Fr; Alkaline earth metals such as Be, Mg, Ca, Sr, Ba or Ra; Rare earth metals such as La, Ce, Pr, Nd, Sm, Eu, Tb, Th, Dy, Ho, Er, Em, Gd, Yb, Lu, Y or Mn; Or a metal compound containing at least one of the above-mentioned metals may be used, but not limited thereto, and those known in the art can be used. According to an example, the electron transport layer, the electron injection layer, or the layer that simultaneously injects electrons and transports electrons including the compound of Formula 1 may further include LiQ.

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. The organic light emitting device of claim 1, wherein the organic compound layer comprises a compound represented by Formula (1). 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 included 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, a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a metal oxide having conductivity or an alloy thereof on a 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 layer is a layer for injecting holes from an electrode. The hole injecting layer has a hole injecting effect, a hole injecting effect for the light emitting layer or a light emitting material, a thin film forming ability Good compounds are preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

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

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

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

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

The electron transporting layer is a layer that receives electrons from the electron 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. 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 transporting layer may further include an n-type dopant. The n-type dopant may be an alkali metal such as Li, Na, K, Rb, Cs or Fr; Alkaline earth metals such as Be, Mg, Ca, Sr, Ba or Ra; Rare earth metals such as La, Ce, Pr, Nd, Sm, Eu, Tb, Th, Dy, Ho, Er, Em, Gd, Yb, Lu, Y or Mn; Or a metal compound containing at least one of the above-mentioned metals may be used, but not limited thereto, and those known in the art can be used. According to an example, the electron transport layer containing the compound of Formula 1 may further include LiQ.

The electron injection layer is a layer for injecting electrons from an electrode and has an ability to transport electrons, an electron injection effect from the cathode, an electron injection effect to the light emitting layer or a light emitting material, Do. 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.

<Production Example>

PREPARATION EXAMPLE 1 Synthesis of Compound A1

(20 g, 41.3 mmol) was dissolved in tetrahydrofuran (200 mL) and heated. Then, cesium (2-bromoethyl) ([Ni (dppp) Cl ₂ ]] was added to a solution of [nickel (1,3-bis (diphenylphosphino) propane) chloride] (40 mg, 123.9 mmol) (1.12 g, 2.1 mmol). When the solution was boiled, structural diphenylphosphine oxide (12.5 g, 61.9 mmol) was added and stirred for 8 hours. After cooling to room temperature, the resulting solid was filtered to obtain Compound A1 (17.8 g, yield 71%).

MS: [M + H] &lt; ⁺ &gt; = 606

PREPARATION EXAMPLE 2 Synthesis of Compound A2

Compound A2 was obtained in the same manner as in the production of Compound A1, except that the structural formula naphthalene-2-yl (phenyl) phosphine oxide was used in place of the structural diphenylphosphine oxide.

MS: [M + H] &lt; ⁺ &gt; = 656

PREPARATION EXAMPLE 3 Synthesis of Compound A8

Instead of the structural formula 2-bromopyrro [fluorene-9,8'-indolo [3,2,1-de] acridine], A8-1 was used instead of the structural diphenylphosphine oxide and di (naphthalene- Yl) phosphine oxide, Compound A8 was obtained in the same manner as in the production of Compound A1.

MS: [M + H] &lt; ⁺ &gt; = 782

PREPARATION EXAMPLE 4 Synthesis of Compound A9

Acylidine] -2-ylboronic acid (20 g, 44.5 mmol) and 5- (4-bromophenyl) benzo [b] thiophene [b] Phosphine indole 5-oxide (15.8 g, 44.51 mmol) was dissolved in tetrahydrofuran (200 mL) and heated. A solution of potassium carbonate (18.5 g, 133.54 mmol) in water (80 mL) was added. If solution boils formula tetrakis palladium _{(Pd (PPh 3) 4)} (1.54g, 1.34mmol) to insert after stirring for 8 hours and then cooled to room temperature and filtered and the resulting solid compound A9 (20.3g, yield: 67% ).

MS: [M + H] &lt; ⁺ &gt; = 680

Production Example 5 Synthesis of the following compounds A22-1 and A22

Compound A22-1 Synthesis

Compound A22-1 was obtained in the same manner as in the preparation of Compound A9, except that diphenylphosphine oxide was used in place of the structural 5- (4-bromophenyl) benzo [b] phosphine indole 5-oxide.

MS: [M + H] &lt; ⁺ &gt; = 671

Compound A22 Synthesis

Except that the compound A22-1 was used instead of the structural formula 2-bromopyrola [fluorene-9,8'-indolo [3,2,1-de] acridine] Compound A22 was obtained.

MS: [M + H] &lt; ⁺ &gt; = 837

PREPARATION EXAMPLE 6 Synthesis of Compound B3

Bromo-pyrrolo [9,2'-indolo [3,2,1-de] acridine] in place of the structural formula 2-bromopyrro [fluorene- 2-yl] phosphine oxide was used instead of diphenylphosphine oxide and di (pyridin-2-yl) phosphine oxide was used in place of diphenylphosphine oxide, compound B3 was obtained.

MS: [M + H] &lt; ⁺ &gt; = 608

PREPARATION EXAMPLE 7 Synthesis of the following compound D1

Instead of the structural formula 2-bromopyrro [fluorene-9,8'-indolo [3,2,1-de] acridine], 2,7-dibromospyro [fluorene- [3,2,1-de] acridine] was used in place of the compound [X].

MS: [M + H] &lt; ⁺ &gt; = 806

PREPARATION EXAMPLE 8 Synthesis of the following compound D3

Using 2-chloro-4,6-diphenyl-1,3,5-triazine instead of the structural formula 5- (4-bromophenyl) benzo [b] phosphine indole 5-oxide, spiro [fluorene- (Diphenylphosphoryl) spiro [fluorene-9,8'-indolo [3,2,1-de] acridine] -2-ylboronic acid was used in place of 8'- 2,1-de] acridine] -7-yl) boronic acid was used in place of acetic anhydride, the compound D3 was obtained in the same manner as the compound A9.

MS: [M + H] &lt; ⁺ &gt; = 837

Production Example 9 Synthesis of the following compounds C15-1 and C15

Compound C15-1 Synthesis

Substituted spiro [fluorene-9,8'-indolo [3,2,1-de] acridine] -2-ylboronic acid instead of spiro [fluorene- , 3-bromo-5-chlorobenzonitrile was used instead of 5- (4-bromophenyl) benzo [b] phosphine indole 5-oxide Compound C15-1 was obtained in the same manner as in the preparation of Compound A9, except for using.

MS: [M + H] &lt; ⁺ &gt; = 541

Compound C15 Synthesis

Was obtained in the same manner as in the production of Compound A1, except that C15-1 was used in place of the structural formula 2-bromopyrro [fluorene-9,8'-indolo [3,2,1-de] acridine] C15.

MS: [M + H] &lt; ⁺ &gt; = 707

PREPARATION EXAMPLE 10 Synthesis of the following compound E11

Instead of 4- (diphenylphosphoryl) naphthalen-1-yl 1,1,2,2,3,3,4,4, -tetrahydropyran in place of the structural formula 5- (4-bromophenyl) benzo [ Instead of spiro [fluorene-9,8'-indolo [3,2,1-de] acridine] -2-ylboronic acid using 2-chloro-4- - (diphenylphosphoryl) spiro [fluorene-9,8'-indolo [3,2,1-de] acridine] -7-yl) boronic acid was used in the preparation of Compound A9 Compound E11 was obtained in the same manner as in the above method.

MS: [M + H] &lt; ⁺ &gt; = 732

PREPARATION EXAMPLE 11 Synthesis of the following compound E12

(5-chloropyridin-3-yl) diphenylphosphine oxide was used instead of the structural formula 5- (4-bromophenyl) benzo [b] phosphine indole 5-oxide and spiro [fluorene-9,8'-indole (Diphenylphosphoryl) spiro [fluorene-9,8'-indolo [3,2,1-a] pyridine] instead of [ de] acridine] -7-yl) boronic acid was used in place of acetic anhydride, the compound E12 was obtained in the same manner as the compound A9.

MS: [M + H] &lt; ⁺ &gt; = 683

PREPARATION EXAMPLE 12 Synthesis of Compound A7

Instead of 2- (4-chlorophenyl) spiro [fluorene-9,8'-indole [3,2,1-de] [3,2,1-de] acridine] was used in place of the compound [A].

MS: [M + H] &lt; ⁺ &gt; = 682

PREPARATION EXAMPLE 13 Synthesis of the following compound G4

Bromoaspiro [fluoro-9,8'-indolo [3,2,1-de] acridine] instead of the structural formula 2-bromopyrro [fluorene- room Reno [3,2,1- jk] carbazol-5,5'-dibenzo using [b, d] silole] and di benil phosphine oxide instead of di (naphthalene-2-yl) with phosphine oxide , Compound G4 was obtained in the same manner as in the preparation of Compound A1.

MS: [M + H] &lt; ⁺ &gt; = 722

PREPARATION EXAMPLE 14 Synthesis of the following compound G7

(4-chlorophenyl) spiro [benzo [5, &lt; RTI ID = 0.0 &gt; 6] [1,4] azacilino [3,2,1- jk ] carbazole-5,5'-dibenzo [ b, d ] To give compound G7.

MS: [M + H] &lt; ⁺ &gt; = 698

PREPARATION EXAMPLE 15 Synthesis of Compound A24

The compound represented by the above formula (A24) was prepared in the same manner as in Preparation Example 1, except that each starting material was changed to the above reaction scheme.

MS [M + H] &lt; ⁺ &gt; = 682

PREPARATION EXAMPLE 16 Synthesis of Compound F2

A compound represented by the above formula (F2) was prepared in the same manner as in Preparation Example 1, except that each starting material was changed to the above reaction scheme.

MS [M + H] &lt; ⁺ &gt; = 656

Production Example 17 Synthesis of the following compound F3

The compound represented by the above formula (F3) was prepared in the same manner as in Preparation Example 1, except that each starting material was changed to the above reaction scheme.

MS [M + H] &lt; ⁺ &gt; = 608

Production Example 18 Synthesis of Compound F8 shown below

The compound represented by the above formula (F8) was prepared in the same manner as in Preparation Example 1, except that each starting material was changed to the above reaction scheme.

MS [M + H] &lt; ⁺ &gt; = 782

Production Example 19 Synthesis of Compound F5 shown below

A compound represented by the above formula (F5) was prepared in the same manner as in Preparation Example 1, except that each starting material was changed to the above reaction scheme.

MS [M + H] &lt; ⁺ &gt; = 604

PREPARATION EXAMPLE 20 Synthesis of the following compound H10

The compound represented by the above formula H10 was prepared in the same manner as in Preparation Example 1, except that each starting material was changed to the above reaction scheme.

MS [M + H] &lt; ⁺ &gt; = 606

PREPARATION EXAMPLE 21 Synthesis of the following compound E7

The compound represented by the above formula (E7) was prepared in the same manner as in Preparation Example 1, except that each starting material was changed to the above reaction scheme.

MS [M + H] &lt; ⁺ &gt; = 682

Production Example 22 Synthesis of the following compound H11

A compound represented by the above formula H11 was prepared in the same manner as in Preparation Example 1 except that each starting material was changed to the above reaction formula.

MS [M + H] &lt; ⁺ &gt; = 606

Production Example 23 Synthesis of the following compound H1

A compound represented by the formula H1 was prepared in the same manner as in Preparation Example 1, except that the starting materials were the same as in the above reaction scheme.

MS [M + H] &lt; ⁺ &gt; = 606

<Experimental Example 1-1>

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

The following compound [HI-A] was thermally vacuum-deposited on the thus-prepared ITO transparent electrode to a thickness of 600 Å to form a hole injection layer. A hole transport layer was formed on the hole injection layer by sequentially vacuum-depositing hexa-nitrile hexaazatriphenylene (HAT) of the following formula and 50 Å of the following compound [HT-A] (600 Å).

Subsequently, the following compounds [BH] and [BD] were vacuum deposited on the hole transport layer at a weight ratio of 25: 1 at a thickness of 200 ANGSTROM to form a light emitting layer.

The compound of A1 and the compound [LiQ] (Lithiumquinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injecting and transporting layer having a thickness of 350 Å. Lithium fluoride (LiF) and aluminum having a thickness of 1,000 Å were sequentially deposited on the electron injecting and transporting layer to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 ~ 5 × 10 ^- to maintain the ⁸ torr, it was produced in the organic light emitting device.

[LINE]

[HI-A]

[HT-A]

[BH] [BD]

[LiQ]

[ET-1-A] [ET-1-B]

[ET-1-C]

<Experimental Example 1-2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of Formula A2 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-3>

An organic light emitting device was prepared in the same manner as in Experimental Example 1-1 except that the compound of Formula A8 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that the compound of Formula A9 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-5>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that the compound of Formula A22 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-6>

An organic light emitting device was prepared in the same manner as in Experimental Example 1-1 except that the compound of Formula B3 was used in place of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-7>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that the compound of Formula D1 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-8>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that the compound of Formula D3 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-9>

An organic light emitting device was prepared in the same manner as in Experimental Example 1-1 except that the compound of Formula C15 was used in place of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-10>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of Formula E11 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-11>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that the compound of Formula E12 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-12>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that the compound of Formula A7 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-13>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of Formula G4 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-14>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that the compound of Formula G7 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-15>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of Formula A24 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-16>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of Formula F2 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-17>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that the compound of Formula F3 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-18>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of Formula F8 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-19>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that the compound of Formula F5 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-20>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that the compound of Formula H10 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-21>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of Formula E7 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-22>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that the compound of Formula H11 was used instead of the compound of Formula A1 in Experimental Example 1-1.

<Experimental Example 1-23>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that the compound of Formula H1 was used instead of the compound of Formula A1 in Experimental Example 1-1.

&Lt; Comparative Example 1-1 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of the formula (ET-1-A) was used instead of the compound of the formula (A1).

&Lt; Comparative Example 1-2 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of the formula (ET-1-B) was used instead of the compound of the formula (A1).

&Lt; Comparative Example 1-3 >

An organic light emitting device was prepared in the same manner as in Experimental Example 1-1, except that the compound of the formula (ET-1-C) was used instead of the compound of the formula (A1).

The driving voltage and the luminous efficiency were measured at a current density of 10 mA / cm ² and the time (T ₉₀ ), which is 90% of the initial luminance at a current density of 20 mA / cm ² , was measured Respectively. The results are shown in Table 1 below.

The Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Life span (h)
T ₉₀ at 20 mA / cm ² Experimental Example 1-1 A1 4.30 4.90 (0.142, 0.097) 184 Experimental Example 1-2 A2 4.41 5.20 (0.142, 0.096) 180 Experimental Example 1-3 A8 4.36 5.28 (0.142, 0.096) 161 Experimental Examples 1-4 A9 4.53 4.99 (0.142, 0.096) 211 Experimental Examples 1-5 A22 4.32 5.31 (0.142, 0.096) 159 Experimental Example 1-6 B3 4.41 5.24 (0.142, 0.097) 163 Experimental Example 1-7 D1 4.32 5.32 (0.142, 0.096) 150 Experimental Examples 1-8 D3 4.21 4.99 (0.142, 0.099) 145 Experimental Examples 1-9 C15 4.27 5.03 (0.142, 0.096) 158 Experimental Example 1-10 E11 4.29 5.34 (0.142, 0.098) 169 Experimental Example 1-11 E12 4.50 4.89 (0.142, 0.096) 167 Experimental Example 1-12 A7 4.21 5.32 (0.142, 0.097) 171 Experimental Example 1-13 G4 4.22 5.33 (0.142, 0.096) 181 Experimental Example 1-14 G7 4.52 4.91 (0.142, 0.097) 176 Experimental Example 1-15 A24 4.48 4.95 (0.142, 0.097) 162 Experimental Example 1-16 F2 4.53 4.90 (0.142, 0.096) 178 Experimental Example 1-17 F3 4.54 4.90 (0.142, 0.097) 200 Experimental Example 1-18 F8 4.39 5.00 (0.142, 0.097) 160 Experimental Example 1-19 F5 4.42 5.01 (0.142, 0.096) 165 Experimental Example 1-20 H10 4.43 4.99 (0.142, 0.096) 181 Experimental Example 1-21 E7 4.44 5.11 (0.142, 0.097) 177 Experimental Example 1-22 H11 4.46 5.10 (0.142, 0.097) 167 Experimental Example 1-23 H1 4.40 5.27 (0.142, 0.097) 180 Comparative Example 1-1 ET-1-A 4.82 3.92 (0.142, 0.098) 90 Comparative Example 1-2 ET-1-B 4.94 4.03 (0.142, 0.102) 101 Comparative Example 1-3 ET-1-C 4.98 3.98 (0.142, 0.096) 103

From the results of Table 1, it can be seen that the compound represented by Chemical Formula 1 according to one embodiment of the present invention can be used for an organic layer capable of simultaneously injecting electrons and transporting electrons of an organic light emitting device.

Also, it can be seen from the above Experimental Examples and Comparative Examples that it is possible to provide a long-lived organic light-emitting device when phosphine oxide is included as in the present embodiment.

The compound represented by Formula 1 according to one embodiment of the present invention has excellent thermal stability and can exhibit excellent characteristics due to a deep HOMO level of 5.7 eV or more, high triplet energy (ET), and hole stability.

In one embodiment of the present specification, n-type dopants can be mixed when used for an organic material layer capable of electron injection and electron transport at the same time. The compound represented by Formula 1 has low driving voltage and high efficiency, and can improve the stability of the device by hole stability of the compound.

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

Claims (15)

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

In Formula 1,
X is C or Si,
R1 to R5 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Or a heterocyclic group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms,
a to e are the same or different and each independently represents an integer of 0 or 1,
At least one of R 1 to R 3 and R 5 is represented by the following formula (2)
(2)

In Formula 2,
L is a direct bond; Arylene having 1 to 4 carbon atoms which is substituted or unsubstituted with a nitrile group; Or a monocyclic or bicyclic heteroarylene which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms,
Ar 1 and Ar 2 are the same or different and each independently represent an aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with a nitrile group; Or a heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms or may form a ring by bonding with a phosphine group,
m is an integer of 0 to 2,
When m is 2 or more, the structures in parentheses are the same or different from each other. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 3 or 4:
(3)

[Chemical Formula 4]

In the above formulas (3) and (4)
The definitions of R1 to R5, a, b, c, d and e are as shown in formula (1). The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (5) to (8)
[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above formulas 5 to 8,
The definition of R2 to R5, b, c, d, e, Ar1, Ar2, L and m is as shown in formula (1)
The definition of R6 is the same as that of R2 to R5,
f is an integer of 0 or 1. The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (9) to (12)
[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

In the general formulas (9) to (12)
R 1 to R 4, a, b, c, d, Ar 1, Ar 2, L and m are as defined in the formula (1)
The definition of R7 is the same as that of R1 to R4,
g is an integer of 0 or 1; The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (13) to (16):
[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

In Formulas 13 to 16 above,
The definition of R1, R3, R4, R5, a, c, d, e, Ar1, Ar2,
The definition of R8 is the same as that of R1, R3, R4 and R5,
h is an integer of 0 or 1. 2. The compound according to claim 1, wherein L is any one selected from the following structures:

In the above structures,
A1 and A2 are the same or different from each other, and each independently hydrogen; Or a nitrile group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring,
The structures include nitrile groups; Or an aryl group having 6 to 30 carbon atoms. 2. The compound of claim 1, wherein L is a direct bond; Arylene substituted or unsubstituted with a nitrile group; Or monocyclic heteroarylene containing at least one N atom. 2. The compound of claim 1, wherein L is a direct bond; Phenylene substituted or unsubstituted with a nitrile group; Naphthylene; Or monocyclic heteroarylene containing at least one N atom. delete [2] The compound according to claim 1, wherein Ar1 and Ar2 are the same or different and are each independently a phenyl group substituted or unsubstituted with a nitrile group; Naphthyl group; A pyridyl group; Or a thiophene group, or combine with the phosphine group to form a ring. The compound according to claim 1, wherein the compound of formula (1) is any one selected from the following compounds:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers is a compound according to any one of claims 1 to 8 and claims 10 to 11 And an organic light emitting layer. The organic electroluminescent device according to claim 12, wherein the organic compound layer containing the compound is a hole injection layer; A hole transport layer; Or a layer which simultaneously injects holes and transports holes. 14. The organic electroluminescent device according to claim 12, wherein the organic compound layer comprising the compound comprises an electron injecting layer; An electron transport layer; Or an electron injection and electron transporting layer simultaneously. 13. The organic light emitting device according to claim 12, wherein the organic compound layer containing the compound is a light emitting layer.

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