KR101907739B1 - 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]

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2015-0084492 filed with the Korean Intellectual Property Office on June 15, 2015, 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 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,

L1 and L2 are the same or different from each other and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

R1 to R3 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring,

R4 and 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,

a is an integer of 0 to 3,

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

c is an integer of 0 to 8,

d is an integer of 0 to 6,

0? E + d? 9,

p and q are the same or different and each independently represents an integer of 0 to 5,

When a, b, c, d, e, p and q are each 2 or more, the structures in parentheses are the same or different.

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

The compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can improve the efficiency, lower driving voltage and / or lifetime characteristics in the organic light emitting device. In particular, the compounds described herein can be used as hole injecting, hole transporting, hole injecting and hole transporting, light emitting, electron transporting, or electron injecting materials. In addition, the compounds described in the present specification can be preferably used as a light emitting layer, an electron transporting or electron injecting material. 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 3, an electron transporting layer 7 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; Or a heterocyclic group, or a substituted or unsubstituted one in which at least two of the above-exemplified substituents are connected to each other. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

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

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

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

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

In the present specification, the boron group may be represented by the formula of -BRR ", 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 methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert- 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, 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 triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazoline 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 the arylene group is a divalent group.

In the present specification, the explanation on the above-mentioned heterocyclic group can be applied except that the heteroarylene group is divalent.

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 benzene ring, naphthalene ring, anthracene ring, and the like, 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 any one of the following formulas 1-1 and 2-5.

[Formula 1-1]

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In Formula 1-1,

The definitions of L1, L2, p, q, R1 to R5, a, b, d and e are as shown in formula (1)

c is an integer of 0 to 7, and when c is 2 or more, the structures in parentheses are the same or different,

R6 is hydrogen.

In the above formulas 2 to 5,

The definitions of L1, L2, p, q, 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 (6) to (9).

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the general formulas (6) to (9)

The definitions of L1, L2, p, q, 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 (10) to (15).

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

In the general formulas (10) to (15)

The definitions of L1, L2, p, q, 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 the following formula (16) or (17).

[Chemical Formula 16]

[Chemical Formula 17]

In the above formulas (16) and (17)

R11 to R13 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,

r11 to r13 each independently represent an integer of 0 to 4,

0? R12 + r13? 6,

When r11 to r13 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, the formula (1) may be represented by the following formula (18) or (19).

[Chemical Formula 18]

[Chemical Formula 19]

In Formulas 18 and 19,

R21 to R23 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,

r21 to r23 each independently represents an integer of 0 to 4,

0? R22 + r23? 6,

When each of r21 to r23 is 2 or more, the structures in parentheses are the same or different from each other.

According to an embodiment of the present invention, L1 and L2 may be the same or different from each other, and each may be a direct bond or 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; And a heterocyclic group, which may be substituted or unsubstituted.

According to one embodiment of the present disclosure, L1 and L2 are the same or different and are each independently a direct bond; Or a substituted or unsubstituted monocyclic or tricyclic arylene group.

According to one embodiment of the present disclosure, L1 and L2 are the same or different and are each independently a direct bond; Substituted or unsubstituted phenylene; Or substituted or unsubstituted naphthylene.

According to one embodiment of the present disclosure, L1 and L2 are the same or different and are each independently a direct bond; Phenylene; Or naphthylene.

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

According to one embodiment of the present disclosure, L2 is a direct bond; Phenylene; Or naphthylene.

According to one embodiment of the present disclosure, L1 is a direct bond, L2 is a direct bond; Phenylene; Or naphthylene.

According to one embodiment of the present disclosure, L2 is a direct bond and L1 is a direct bond; Phenylene; Or naphthylene.

According to one embodiment of the present disclosure, L1 is phenylene; Or naphthylene, L2 is a direct bond; Phenylene; Or naphthylene.

According to one embodiment of the present disclosure, L2 is selected from the group consisting of phenylene; Or naphthylene, and L1 is a direct bond; Phenylene; Or naphthylene.

According to one embodiment of the present disclosure, L1 is phenylene, L2 is a direct bond; Phenylene; Or naphthylene.

According to one embodiment of the present disclosure, L2 is phenylene, L1 is a direct bond; Phenylene; Or naphthylene.

According to one embodiment of the present disclosure, L1 is naphthylene, L2 is a direct bond; Phenylene; Or naphthylene.

According to one embodiment of the present disclosure, L2 is naphthylene, and L1 is a direct bond; Phenylene; Or naphthylene.

According to one embodiment of the present disclosure, L1 is substituted or unsubstituted phenylene.

According to one embodiment of the present disclosure, L1 is substituted or unsubstituted naphthylene.

According to one embodiment of the present disclosure, L1 is phenylene.

According to one embodiment of the present disclosure, L1 is naphthylene.

According to one embodiment of the present disclosure, L2 is substituted or unsubstituted phenylene.

According to one embodiment of the present disclosure, L2 is substituted or unsubstituted naphthylene.

According to one embodiment of the present disclosure, L2 is phenylene.

According to one embodiment of the present disclosure, L2 is naphthylene.

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

According to one embodiment of the present disclosure, L2 is a direct bond.

According to one embodiment of the present disclosure, R1 to R5 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present disclosure, R1 to R5 are the same or different from each other, and each independently hydrogen; An alkyl group; An aryl group; Or a heteroaryl group.

According to one embodiment of the present disclosure, R1 to R5 are hydrogen.

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

According to one embodiment of the present disclosure, R2 is hydrogen.

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

According to one embodiment of the present disclosure, R4 is hydrogen.

According to one embodiment of the present disclosure, R5 is hydrogen.

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

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 3, an electron transporting layer 7 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, 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 layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting 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 may be 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 heterocyclic compound 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 with a low work function followed by an aluminum layer or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

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

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

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

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

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

< Manufacturing example >

< Of naphthobenzofuran  Synthesis>

In the above Reaction Scheme 1, X ₁ and X ₂ are the same or different and each independently represents a general substituent.

Synthesis of Compound A

With a 1-bromo-2-naphthol (1 eq) and the fluoroboric substituted with X ₂ substituted by X ₁ is dissolved Nick acid (1.1 eq.) In THF solvent by dissolving potassium carbonate (3 eq) in water, heating and stirring Respectively. The catalyst used was tetrakistriphenylphosphine palladium (0.03 eq.). After the completion of the reaction, the organic layer and the aqueous layer were separated, and the solvent was removed by evaporation, followed by purification using a column.

Halogen substitution Of naphthobenzofuran  synthesis

Compound A (1 eq.) And potassium carbonate (2 eq.) Were added to NMP solvent and heated and stirred. After the reaction was completed, water was added to remove the salt, and the organic layer was extracted and the solvent was evaporated off. The reaction was purified through a column.

< Manufacturing example  1> Synthesis of Compound 21

compound 21a  synthesis

2-Bromonaphthobenzofuran (13 g, 1 equivalent) synthesized by the above method and Compound A (13.3 g, 1.2 equivalent) were placed in 1,4-dioxane and the mixture was heated and stirred. The catalyst used was bisdibipiperadium (750 mg, 0.03 eq.), Ligand rottric cyclohexanephosphine (740 mg, 0.06 eq.) And potassium acetate (10.7 g, 3 eq.) As the base. After the reaction was completed, water was added to remove the base, and the organic solvent was extracted. The extracted organic solvent was dried over anhydrous magnesium sulfate and the solvent was evaporated off. The residue was purified through a column to obtain 21a (14.8 g, yield 98%).

compound 21b  synthesis

9-Bromoanthracene (10 g, 1 equivalent) and 21a (14.7 g, 1.1 eq.) Were dissolved in THF solvent and potassium carbonate (13.4 g, 2.5 eq.) In water. After about 4 hours, the reaction mixture was cooled to room temperature and the organic layer was extracted. The extracted organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation, dissolved in chloroform, and the remaining catalyst was removed through flash column. Using an ethanol as an anti-solvent, it was dropped into a solid, filtered and dried to obtain 21b (14.1 g, yield 91%).

compound 21c  synthesis

Compound 21b (14.1 g, 1 eq.) Was added to a solvent mixture of chloroform and DMF in a ratio of 5: 1 and kept at 0 캜 using an ice bath. NBS (6.6 g, 1.05 eq.) Is slowly added to the flour over a period of about 30 minutes. After completion of the reaction, saturated sodium thiosulfate is added and stirred for about 2 hours to remove the remaining NBS. The organic layer was extracted separately, and water was removed using anhydrous magnesium sulfate, and the solvent was removed by evaporation. Ethyl acetate and ethanol were used to drop into a solid, followed by filtration and drying to obtain 21c (14.6 g, yield 87%).

compound 21  synthesis

In the synthesis of compound 21b, compound 21c (14.6 g, 1 eq.) Was used in place of 9-bromoanthracene, and the same procedure was followed except that 1-boronic acid dibenzofurane (7.2 g, 1.1 eq.) Was used in place of compound 21a Respectively. After column purification, Compound 21 (15.7 g, yield 91%) was obtained. The NMR data of Compound 21 was the same as ¹ H-NMR (CDCl ₃ ) 7.32-7.34 (m, 9H), 7.5-7.75 (m, 7H), 7.89-7.91 (m, 7H), 8.34 .

< Manufacturing example  2> Synthesis of Compound 167

compound 167a  synthesis

The same procedure was followed except that 10-bromonaphthobenzofuran (15 g, 1 eq.) Was used in the synthesis of 21a instead of 2-bromonaphthobenzofuran. A column was then used to obtain Compound 167a (16.5 g, yield 95%).

compound 167b  synthesis

Except that in the synthesis of compound 21b 9-bromo-10- (4-chlorophenyl) -anthracene (15 g, 1 eq.) Was used instead of 9-bromoanthracene and 167a (14.8 g, 1.05 eq. . After purification, 167b (18.3 g, yield 89%) was obtained.

compound 167c  synthesis

The same procedure was followed except that 167b (18 g, 1 equivalent) was used in the synthesis of 21a instead of 2-bromonaphthobenzofuran. After purification, 167c (19.6 g, yield 92%) was obtained.

compound 167  synthesis

The same procedure was followed except that in the synthesis of compound 21b 1-bromodibenzofuran (7 g, 1 eq.) Was used instead of 9-bromoanthracene and 167c (18.6 g, 1.1 eq.) Was used instead of 21a. After purification, 167 (15 g, yield 83%) was obtained. The NMR data of the compound 167 was ¹ H-NMR (CDCl ₃ ) 7.25-7.44 (m, 11H), 7.59-7.81 (m, 10H), 7.89-7.91 (d, 1H).

< Manufacturing example  3> Synthesis of Compound 230

compound 230a  synthesis

The same procedure was followed except that 4-boronic acid dibenzofurane (10.4 g, 1.2 eq.) Was used in the synthesis of compound 167b instead of 167a. After purification, compound 230a (16 g, yield 86%) was obtained.

compound 230b  synthesis

The same procedure was followed except that 230a (15.5 g, 1 equivalent) was used instead of 2-bromonaphthobenzofuran in the synthesis of compound 21a. After purification, compound 230b (16.8 g, yield 90%) was obtained.

Synthesis of Compound 230

The same procedure was followed except that 2-bromonaphthobenzofuran (8.2 g, 1 eq.) Was used instead of 9-bromoanthracene in the synthesis of compound 21b and 230b (16.6 g, 1.1 eq.) Instead of 21a. After purification, compound 230 (15.3 g, yield 87%) was obtained. NMR data of the above compound 230 was confirmed by ¹ H-NMR (CDCl ₃ ) 7.25 (d, 4H), 7.32-7.39 (m, 9H), 7.59-7.73 (m, 5H), 7.81-7.92 (s, 1H).

< Manufacturing example  4> Synthesis of Compound 650

Synthesis of Compound 652a

The same procedure was followed except that 7-bromonaphthalene-2-ol (15 g, 1 equivalent) was used in the synthesis of 21a instead of 2-bromonaphthobenzofuran. After purification, Compound 652a (15.3 g, yield 83%) was obtained.

Synthesis of Compound 652b

The same procedure was followed except that 9-bromo-10- (4-chlorophenyl) anthracene (15 g, 1 equivalent) was used instead of 9-bromoanthracene and 652a (11.6 g, 1.05 eq. . Compound 652b (15.5 g, yield 88%) was obtained through purification.

Synthesis of Compound 652c

The same procedure was followed except that 652b (15.5 g, 1 equivalent) was used instead of 2-bromonaphthobenzofuran in the synthesis of compound 21a. After purification, compound 652c (14.3 g, yield 76%) was obtained.

Synthesis of Compound 652d

The same procedure was followed except that in the synthesis of compound 21b, 1-bromodibenzofuran (8 g, 1 eq.) Was used instead of 9-bromoanthracene and compound 652c (18.6 g, 1.1 eq.) Was used instead of 21a. Compound 652d (16.6 g, yield 91%) was obtained after purification.

Synthesis of Compound 652e

Compound 652d (15 g, 1 eq.) And potassium carbonate (11.1 g, 3 eq.) Were added to an acetonitrile solvent and the mixture was stirred at 60 占 폚. Compound B (9.7 g, 1.2 equivalents) was added while maintaining the temperature, and when the reaction was completed, the reaction mixture was cooled to room temperature. After the temperature dropped, the resulting solid was filtered immediately after adding water and stirring. Recrystallization was performed using chloroform and ethanol to obtain Compound 652e (21.4 g, yield 95%).

Synthesis of Compound 652f

The same procedure was followed except that 3-bromonaphthobenzofuran (10 g, 1 eq.) Was used in the synthesis of 21a instead of 2-bromonaphthobenzofuran. After purification, Compound 652f (10.8 g, yield 93%) was obtained.

compound 650's  synthesis

The same procedure was followed except for the use of compound 652e (20 g, 1 eq.) Instead of 9-bromoanthracene and 652f (9 g, 1.1 eq.) Instead of 21a in the synthesis of compound 21b. Compound 65 (15.5 g, yield 86%) was obtained after purification. The NMR data of the above compound 650 was confirmed by NMR data of ¹ H-NMR (CDCl ₃ ) 7.25 (d, 4H), 7.32 (t, 2H), 7.38-7.39 (m, 6H), 7.44 (t, 1H), 7.58-7.59 , 4H), 7.62 (d, 1H), 7.66 (d, 3H), 7.73-7.75 (m, 4H), 7.89-7.91 (m, 8H), 8.06

Example

< Experimental Example 1 >

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to 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, N-bis- (1-naphthalenyl) -N, N-bis-phenyl- (1,1- biphenyl) -4,4-diamine) compound of the following structure A thick hole transport layer was formed by thermal vacuum deposition.

[NPB]

Subsequently, a dopant D1 (4 wt%) having the following structure was vacuum deposited on the hole transporting layer together with the compound 21 to form a light emitting layer at 300 ANGSTROM.

[D1]

The following electron transporting material was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injecting and transporting layer.

[Electron transport material]

Aluminum was sequentially deposited on the electron injecting and transporting layer to a thickness of 12 Å and a thickness of 2000 Å to form a cathode.

< Experimental Example  2>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 28 was used instead of Compound 21 in Experimental Example 1.

< Experimental Example  3>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 52 was used instead of Compound 21 in Experimental Example 1.

< Experimental Example  4>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 167 was used instead of Compound 21 in Experimental Example 1.

< Experimental Example  5>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 227 was used instead of Compound 21 in Experimental Example 1.

< Experimental Example  6>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 230 was used instead of Compound 21 in Experimental Example 1.

< Experimental Example  7>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 318 was used instead of Compound 21 in Experimental Example 1.

< Experimental Example  8>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 427 was used instead of Compound 21 in Experimental Example 1.

< Experimental Example  9>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 586 was used instead of Compound 21 in Experimental Example 1.

< Experimental Example  10>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 650 was used instead of Compound 21 in Experimental Example 1.

< Comparative Example  1>

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

< Comparative Example  2>

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

< Comparative Example  3>

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

Table 1 shows the device results of the compounds prepared in Experimental Examples 1 to 10 and Comparative Examples 1 to 3 as a light emitting layer.

Host The driving voltage (V) Current efficiency (cd / A) Power Efficiency (lm / W) Experimental Example 1 Compound 21 6. 2 43.5 22. 0 Experimental Example 2 Compound 28 5. 0 42. 5 26. 7 Experimental Example 3 Compound 52 4.9 45. 6 29. 3 Experimental Example 4 Compound 167 5. 2 43. 7 26. 4 Experimental Example 5 Compound 227 4.8 45. 8 30. 0 Experimental Example 6 Compound 230 4. 3 43. 3 31.6 Experimental Example 7 Compound 318 5. 3 42.9 25. 4 Experimental Example 8 Compound 427 5.6 47.8 26. 8 Experimental Example 9 Compound 586 5.7 42. 6 23. 5 Experimental Example 10 Compound 650 5. 4 49. 0 28.5 Comparative Example 1 Compound A 7.1 42 18. 6 Comparative Example 2 Compound B 6. 4 41.2 20. 2 Comparative Example 3 Compound C 6. 3 42.2 20. 8

As can be seen from Table 1, the luminescent characteristics of the hosts prepared in Experimental Examples 1 to 10 are significantly lower than those of the compounds of Comparative Examples 1 to 3, and the power efficiency is higher.

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art.

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

Claims (16)

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

In Formula 1,
L1 and L2 are the same or different from each other and are each independently a direct bond; A phenylene group; Or a naphthylene group,
R <1> to R <5> are hydrogen,
a is an integer of 0 to 3,
b and e are the same or different and each independently an integer of 0 to 4,
c is an integer of 0 to 8,
d is an integer of 0 to 6,
0? E + d? 9,
p and q are the same as or different from each other, and are each independently an integer of 0 to 5; The compound according to claim 1, wherein the formula (1) is represented by the following formula (1-1).

In Formula 1-1,
The definitions of L1, L2, p, q, R1 to R5, a, b, d and e are as shown in Formula 1,
c is an integer of 0 to 7,
R6 is hydrogen. The compound according to claim 1, wherein the compound represented by formula (1) is represented by any one of the following formulas (2) to (5)
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,
The definitions of L1, L2, p, q, R1 to R5, a, b, c, d and e are as shown in the above formula (1). The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (6) to (9):
[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the general formulas (6) to (9)
The definitions of L1, L2, p, q, R1 to R5, a, b, c, d and e are as shown in the above formula (1). The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (10) to (15):
[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

In the general formulas (10) to (15)
The definitions of L1, L2, p, q, R1 to R5, a, b, c, d and e are as shown in the above formula (1). The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 16 or 17:
[Chemical Formula 16]

[Chemical Formula 17]

In the above formulas (16) and (17)
R11 to R13 are hydrogen,
r11 to r13 each independently represent an integer of 0 to 4,
0? R12 + r13? 6. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 18 or 19:
[Chemical Formula 18]

[Chemical Formula 19]

In Formulas 18 and 19,
R21 to R23 are hydrogen,
r21 to r23 each independently represents an integer of 0 to 4,
0? R22 + r23? 6. delete The compound according to claim 1, wherein L 1 and L 2 are the same or different and are each independently a direct bond or any one selected from the following structures:

delete delete 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 7, 9 and 12, And the organic light emitting device. [Claim 14] The organic light emitting device according to claim 13, 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. [14] The organic light emitting device according to claim 13, wherein the organic compound layer containing the compound is an electron injecting layer, an electron transporting layer, or a layer simultaneously performing electron injection and electron transporting. 14. The organic light emitting device according to claim 13, wherein the organic compound layer including the compound is a light emitting layer.

Images