KR102148056B1 - Organic light emitting device - Google Patents

Abstract

The present specification provides an organic light emitting device.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

The present specification relates to an organic light emitting device.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.

Development of a new material for the organic light emitting device as described above is continuously required.

Korean Patent Publication 2000-0051826

In the present specification, an organic light emitting device is provided.

According to an exemplary embodiment of the present specification, the anode; A cathode provided to face the anode; A light emitting layer provided between the anode and the cathode; A first organic material layer provided between the anode and the emission layer; And a second organic material layer provided between the cathode and the emission layer, wherein the first organic material layer includes a compound represented by Formula 1 below, and the second organic material layer is represented by Formula 2 or 3 below. It provides an organic light-emitting device comprising a compound.

[Formula 1]

[Formula 2]

[Formula 3]

In Formulas 1 to 3,

At least one of X1 to X3 is N, the rest are CH,

At least one of X4 to X6 is N, the rest are CH,

X7 is N or CH, X8 is N or CH, X9 is N or CH,

When X7 to X9 are CH, adjacent groups combine with each other to form a substituted or unsubstituted ring,

L1 to L8 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

L9 is a substituted or unsubstituted arylene group,

Ar1 and Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar2 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 5-cyclic aryl group; A substituted or unsubstituted 7 ring or more aryl group; Or a substituted or unsubstituted heteroaryl group,

R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide 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 alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine 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 heteroaryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

l9, r6 and r7 are each an integer of 1 to 3,

r5 and r8 are each an integer of 1 to 4,

When l9, r5 to r8 are each 2 or more, the structures in the two or more parentheses are the same as or different from each other.

The organic light emitting device according to the exemplary embodiment of the present specification may improve lifespan characteristics and/or efficiency characteristics of the device.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 having excellent hole transport and/or electron blocking ability, contains a monocyclic heteroaryl group having very excellent ability as electron transport and/or electron injection, or When the compound of 3 is used as an electron injection layer and/or an electron transport layer provided between the cathode and the emission layer (A) excellent hole injection properties; (B) high hole mobility; (C) excellent electron blocking power; (D) stable thin film state; And/or (E) has excellent heat resistance and thus exhibits characteristics of low voltage, high efficiency, and long life.

1 illustrates an organic light-emitting device 10 according to an exemplary embodiment of the present specification.
2 shows an organic light-emitting device 11 according to another exemplary embodiment of the present specification.

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

Examples of the substituents in the present specification are described below, but are not limited thereto.

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxy 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 alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or no substituent. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification,

Means a site bonded to another substituent or a bonding portion.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the nitrogen of the amide group may be substituted with hydrogen, a straight-chain, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. 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 carbonyl group is not particularly limited, but it is preferably 1 to 30 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 C1-C25 linear, branched or cyclic alkyl group or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are limited thereto. It is not.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. May be, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-arylalkylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, and the like, but are not limited thereto.

In the present specification, the N-alkylarylamine amine group means an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroarylamine group are substituted with N of the amine group.

In the present specification, the alkyl group in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is the same as the example of the aforementioned alkyl group. Specifically, the alkyl thioxy group includes methyl thioxy group, ethyl thioxy group, tert-butyl thioxy group, hexyl thioxy group, octyl thioxy group, and the like. And the like, but are not limited thereto.

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ R ₁₀₂ , wherein R ₁₀₀ , R ₁₀₁ and R ₁₀₂ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

And

Etc. However, it is not limited thereto.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the aryl group among the aryloxy group, arylthioxy group, arylsulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group is the same as the example of the aryl group described above. Specifically, the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, and 9-phenanthryloxy group, and the arylthioxy group includes a phenylthioxy group, 2- There are a methylphenyl thioxy group, a 4-tert-butylphenyl thioxy group, and the like, and the aryl sulfoxy group includes a benzene sulfoxy group and a p-toluene sulfoxy group, but is 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 include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group includes one or more atoms and heteroatoms other than carbon, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, p Nanthrolinyl group (phenanthroline), thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are not limited thereto.

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 heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as those of the aforementioned heteroaryl group.

In the present specification, the heterocyclic group may be monocyclic or polycyclic, may be aromatic, aliphatic, or condensed rings of aromatic and aliphatic, and may be selected from examples of the heteroaryl group.

In the present specification, an arylene group means that the aryl group has two bonding positions, that is, a divalent group. The description of the aryl group described above may be applied except that each of these is a divalent group.

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.

In the present specification, the ring is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or the aryl group, except for the non-monovalent one.

In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.

In the present specification, the heterocycle includes one or more atoms and heteroatoms other than carbon, and specifically, the heterocycle may include one or more atoms selected from the group consisting of O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group or heterocyclic group except that it is not monovalent.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formula 1-1 below.

[Formula 1-1]

In Formula 1-1,

The definitions of L1, Ar1, and R1 to R4 are the same as in Chemical Formula 1.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formula 1-2 below.

[Formula 1-2]

In Formula 1-2,

The definitions of L1, Ar1, and R1 to R4 are the same as in Chemical Formula 1.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formula 1-2 below.

According to an exemplary embodiment of the present specification, Formula 2 is represented by any one of the following Formulas 2-1 to 2-7.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

In Formulas 2-1 to 2-7,

The definitions of L2 to L4 and Ar2 to Ar4 are the same as in Chemical Formula 2.

According to an exemplary embodiment of the present specification, Formula 3 is represented by any one of the following Formulas 3-1 to 3-9.

[Formula 3-1]

[Chemical Formula 3-2]

[Chemical Formula 3-3]

[Formula 3-4]

[Formula 3-5]

[Formula 3-6]

[Formula 3-7]

[Formula 3-8]

[Chemical Formula 3-9]

In Formulas 3-1 to 3-9,

The definitions of L5 to L9, Ar5 to Ar8, and L9 are the same as in Chemical Formula 3.

According to an exemplary embodiment of the present specification, L1 to L8 are the same as or different from each other, and each independently a direct bond; An arylene group unsubstituted or substituted with an alkyl group; Or a heteroarylene group.

According to an exemplary embodiment of the present specification, L1 to L8 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Naphthylene group; A fluorenylene group substituted with a methyl group; Or it is a carbazolylene group.

According to an exemplary embodiment of the present specification, in Formula 1, L1 is a direct bond; An arylene group unsubstituted or substituted with an alkyl group; Or a heteroarylene group.

According to an exemplary embodiment of the present specification, in Formula 1, L1 is a direct bond; Phenylene group; Biphenylylene group; Naphthylene group; A fluorenylene group substituted with a methyl group; Or it is a carbazolylene group.

According to an exemplary embodiment of the present specification, in Formula 2, L2 to L4 are the same as or different from each other, and each independently a direct bond; Arylene group; Or a heteroarylene group.

According to an exemplary embodiment of the present specification, in Formula 2, L2 to L4 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Or it is a carbazolylene group.

According to an exemplary embodiment of the present specification, in Formula 3, L5 to L8 are the same as or different from each other, and each independently a direct bond; Or an arylene group.

According to an exemplary embodiment of the present specification, in Formula 3, L5 to L8 are the same as or different from each other, and each independently a direct bond; Or a phenylene group.

According to an exemplary embodiment of the present specification, in Formula 3, L9 is an arylene group.

According to an exemplary embodiment of the present specification, in Formula 3, L9 is a phenylene group; Or it is a naphthylene group.

According to an exemplary embodiment of the present specification, Ar1 and Ar5 to Ar8 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar5 to Ar8 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; A fluorenyl group unsubstituted or substituted with an alkyl group; Triphenylenyl group; Dibenzofuranyl group; Dibenzothiophene group; A carbazolyl group unsubstituted or substituted with an aryl group; A benzocarbazolyl group unsubstituted or substituted with an aryl group; Or a pyridyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar5 to Ar8 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group; A biphenyl group unsubstituted or substituted with a phenyl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; A fluorenyl group unsubstituted or substituted with a methyl group; Triphenylenyl group; Dibenzofuranyl group; Dibenzothiophene group; A carbazolyl group unsubstituted or substituted with a phenyl group, a biphenyl group, or a naphthyl group; A benzocarbazolyl group unsubstituted or substituted with a phenyl group; Or a pyridyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is an aryl group unsubstituted or substituted with an alkyl group or an aryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is a phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; A substituted or unsubstituted fluorenyl group selected from the group consisting of an alkyl group and an aryl group; Triphenylenyl group; Dibenzofuranyl group; Dibenzothiophene group; A carbazolyl group unsubstituted or substituted with an aryl group; Or a benzocarbazolyl group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is a phenyl group unsubstituted or substituted with a phenyl group; A biphenyl group unsubstituted or substituted with a phenyl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; A substituted or unsubstituted fluorenyl group selected from the group consisting of a methyl group and a phenyl group; Triphenylenyl group; Dibenzofuranyl group; Dibenzothiophene group; A carbazolyl group unsubstituted or substituted with a phenyl group, a biphenyl group, or a naphthyl group; Or a benzocarbazolyl group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, in Formula 2, Ar2 to Ar4 are the same as or different from each other, and each independently a monocyclic to 5-cyclic aryl group unsubstituted or substituted with an alkyl group or an aryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, in Formula 2, Ar2 to Ar4 are the same as or different from each other, and each independently a phenyl group substituted or unsubstituted with an aryl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; A fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; Triphenylenyl group; Pyridyl group; Dibenzofuranyl group; A carbazolyl group unsubstituted or substituted with an aryl group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, in Formula 2, Ar2 to Ar4 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Triphenylenyl group; Pyridyl group; Dibenzofuranyl group; A carbazolyl group unsubstituted or substituted with a phenyl group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, in Chemical Formula 3, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Aryl group; Or a heteroaryl group.

According to an exemplary embodiment of the present specification, in Chemical Formula 3, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; Or a pyridyl group.

According to an exemplary embodiment of the present specification, in Formula 3, when X7 to X9 are CH, adjacent groups combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, in Formula 3, when X7 to X9 are CH, adjacent groups combine with each other to form a substituted or unsubstituted heterocycle.

According to an exemplary embodiment of the present specification, in Formula 3, when X7 to X9 are CH, adjacent groups combine with each other to form a substituted or unsubstituted pyridine ring.

According to an exemplary embodiment of the present specification, in Formula 3, when X7 to X9 are CH, adjacent groups combine with each other to form a pyridine ring.

According to an exemplary embodiment of the present specification, in Formula 1, R1 to R4 are the same as or different from each other, and each independently an alkyl group; Or an aryl group.

According to an exemplary embodiment of the present specification, in Formula 1, R1 to R4 are the same as or different from each other, and each independently a methyl group; Or a phenyl group.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are bonded to each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are bonded to each other to form a substituted or unsubstituted aromatic ring.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are bonded to each other to form a substituted or unsubstituted fluorene ring.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are bonded to each other to form a fluorene ring.

According to an exemplary embodiment of the present specification, in Formula 1, R3 and R4 are bonded to each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, in Formula 1, R3 and R4 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, R3 and R4 are bonded to each other to form a substituted or unsubstituted aromatic ring.

According to an exemplary embodiment of the present specification, in Formula 1, R3 and R4 are bonded to each other to form a substituted or unsubstituted fluorene ring.

According to an exemplary embodiment of the present specification, in Formula 1, R3 and R4 are bonded to each other to form a fluorene ring.

According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 1-3 to 1-8.

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Formulas 1-3 to 1-8,

The definition of L1 and Ar1 is the same as in Chemical Formula 1.

According to an exemplary embodiment of the present specification, Chemical Formula 3 is represented by Chemical Formula 3-10 below.

[Chemical Formula 3-10]

In Formula 3-10,

The definitions of X4 to X9, L5 to L8, and Ar5 to Ar8 are the same as in Chemical Formula 3,

L10 and L11 are the same as or different from each other, and each independently, a direct bond; Or an arylene group.

According to another exemplary embodiment of the present specification, in Formula 3-10, L10 and L11 are the same as or different from each other, and each independently a direct bond; Or a phenylene group.

According to an exemplary embodiment of the present specification, Formula 1 is selected from the following compounds.

According to an exemplary embodiment of the present specification, Chemical Formula 2 is selected from the following structures.

According to an exemplary embodiment of the present specification, Formula 3 is selected from the following compounds.

According to an exemplary embodiment of the present specification, the glass transition temperature (Tg) of the compound represented by Formulas 2 and 3 is 120°C or higher.

It can be seen that this is significantly higher than that of the conventional NPB (Tg: 96℃). This increase in thermal stability becomes an important factor providing driving stability to the device.

The organic material layer of the organic light emitting device of the present specification 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 injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like 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.

For example, the structure of the organic light-emitting device of the present specification may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

1 illustrates a structure of an organic light emitting diode 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. 1 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.

2 shows a first electrode 30, a hole injection layer 60, a hole transport layer 70, an electron blocking layer 80, a light emitting layer 40, an electron transport layer 90, and an electron injection layer on the substrate 20. 100) and the second electrode 50 are sequentially stacked on the structure of an organic light-emitting device. 2 is an exemplary structure according to the exemplary embodiment of the present specification, and may further include another organic material layer.

In the exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes.

In one embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons.

According to an exemplary embodiment of the present specification, the first organic material layer includes a hole transport layer, and the hole transport layer includes the compound represented by Formula 1 above.

According to the exemplary embodiment of the present specification, the second organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound represented by Formula 2 above.

According to an exemplary embodiment of the present specification, the second organic material layer includes an electron transport layer and an electron injection layer, and the electron transport layer includes the compound represented by Chemical Formula 2.

According to an exemplary embodiment of the present specification, the second organic material layer includes an electron transport layer and an electron injection layer, and the electron injection layer includes the compound represented by Chemical Formula 2.

In another exemplary embodiment, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, 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, one or more organic material layers, and an anode are sequentially stacked on a substrate.

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

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating an anode, an organic material layer, and a cathode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate. It can be prepared by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

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

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected 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); A combination of a metal and an oxide such as ZnO:Al or SnO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is 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; There are a multilayered material such as LiF/Al or LiO ₂ /Al, and Mg/Ag, but are not limited thereto.

The hole injection layer is a layer that injects holes from an electrode as a hole injection material, and has an ability to transport holes as a hole injection material, and thus has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material. , A compound that prevents the movement of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer, and the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

The electron blocking layer is a layer capable of improving the life and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer, and when necessary, a light emitting layer and a hole are used. It may be formed in an appropriate portion between the injection layer.

As the light-emitting material of the light-emitting layer, a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency against fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzothiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or hetero ring-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compound is substituted or unsubstituted A compound in which at least one arylvinyl group is substituted on the arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The hole blocking layer is a layer capable of improving the life and efficiency of the device by preventing holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer, and when necessary, a light emitting layer and an electron It may be formed in an appropriate portion between the injection layer.

The electron transport material of the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. The electron transport material is a material that can receive electrons from the cathode and transfer them to the emission layer. This large material is suitable. Specific examples include the 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 transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or light emitting material, and injects holes of excitons generated from the light emitting layer. A compound that prevents migration to the layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

The hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but are not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

The structure according to the exemplary embodiment of the present specification may act on a principle similar to that applied to an organic light-emitting device in organic electronic devices including organic solar cells, organic photoreceptors, and organic transistors.

The organic light-emitting device of the present specification includes materials known in the art, except that the first organic material layer includes the compound represented by Formula 1, and the second organic material layer includes the compound represented by Formula 2 It can be manufactured by the method.

The fabrication of the organic light emitting device will be described in detail in the following examples. However, the following examples are for illustrative purposes only, and the scope of the present specification is not limited thereto.

< Example >

< Comparative example 1-1>

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500Å to form a hole injection layer.

A hole transport layer was formed by vacuum depositing the following compound 4-4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (300Å), which is a material that transports holes on the hole injection layer. I did.

Then, the following compound N-([1,1'-bisphenyl]-4-yl)-N-(4-(11-([1,1'-biphenyl]-4) with a film thickness of 100Å on the hole transport layer -yl)-11H-benzo[a]carbazole-5-yl)phenyl)-[1,1'-biphenyl]-4-amine (100Å) was vacuum deposited to form an electron blocking layer.

Subsequently, on the electron blocking layer, a light emitting layer was formed by vacuum depositing the following BH and BD at a weight ratio of 25:1 with a film thickness of 300Å.

The compound ET1 and the compound LiQ (Lithium Quinolate) were vacuum-deposited at a weight ratio of 1:1 on the emission layer to form an electron injection and transport layer with a thickness of 300Å. Lithium fluoride (LiF) at a thickness of 12Å and aluminum at a thickness of 2,000Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

In the above process, the deposition rate of organic matter was maintained at 0.4 ~ 0.7Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3Å/sec, and the deposition rate of aluminum was 2Å/sec, and the vacuum degree during deposition was 2×10 ⁻ Maintaining ⁷ ~ 5 × 10 ^-6 torr, an organic light emitting device was manufactured.

< Experimental example 1-1>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-31 was used instead of EB-1 in Comparative Example 1-1.

< Experimental example 1-2>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-32 was used instead of EB-1 in Comparative Example 1-1.

< Experimental example 1-3>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-33 was used instead of Compound EB-1 in Comparative Example 1-1.

< Experimental example 1-4>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-34 was used instead of Compound EB-1 in Comparative Example 1-1.

< Experimental example 1-5>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-81 was used instead of Compound EB-1 in Comparative Example 1-1.

< Experimental example 1-6>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-97 was used instead of Compound EB-1 in Comparative Example 1-1.

< Experimental example 1-7>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-122 was used instead of Compound EB-1 in Comparative Example 1-1.

< Experimental example 1-8>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-140 was used instead of Compound EB-1 in Comparative Example 1-1.

< Experimental example 1-9>

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

< Experimental example 1-10>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 2-51 was used instead of Compound ET-1 in Comparative Example 1-1.

< Experimental example 1-11>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 2-64 was used instead of Compound ET-1 in Comparative Example 1-1.

< Experimental example 1-12>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 2-74 was used instead of Compound ET-1 in Comparative Example 1-1.

< Experimental example 1-13>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 2-87 was used instead of Compound ET-1 in Comparative Example 1-1.

< Experimental example 1-14>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 2-88 was used instead of Compound ET-1 in Comparative Example 1-1.

< Experimental example 1-15>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 2-102 was used instead of Compound ET-1 in Comparative Example 1-1.

< Experimental example 1-16>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 2-108 was used instead of Compound ET-1 in Comparative Example 1-1.

< Experimental example 1-17>

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

< Experimental example 1-18>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 3-13 was used instead of Compound ET-1 in Comparative Example 1-1.

< Experimental example 1-19>

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

< Experimental example 1-20>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 3-27 was used instead of Compound ET-1 in Comparative Example 1-1.

< Experimental example 1-21>

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

< Experimental example 1-22>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 3-30 was used instead of Compound ET-1 in Comparative Example 1-1.

< Experimental example 1-23>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-33 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 2-9 was used instead of Compound ET-1. Was produced.

< Experimental example 1-24>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-33 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 2-108 was used instead of Compound ET-1. Was produced.

< Experimental example 1-25>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-33 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 3-1 was used instead of Compound ET-1. Was produced.

< Experimental example 1-26>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-33 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 3-27 was used instead of Compound ET-1. Was produced.

< Experimental example 1-27>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-81 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 2-9 was used instead of Compound ET-1. Was produced.

< Experimental example 1-28>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-81 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 2-108 was used instead of Compound ET-1. Was produced.

< Experimental example 1-29>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-81 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 3-1 was used instead of Compound ET-1. Was produced.

< Experimental example 1-30>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-81 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 3-27 was used instead of Compound ET-1. Was produced.

< Experimental example 1-31>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-122 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 2-9 was used instead of Compound ET-1. Was produced.

< Experimental example 1-32>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-122 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 2-108 was used instead of Compound ET-1. Was produced.

< Experimental example 1-33>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-122 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 3-1 was used instead of Compound ET-1. Was produced.

< Experimental example 1-34>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-122 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 3-27 was used instead of Compound ET-1. Was produced.

< Experimental example 1-35>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-140 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 2-9 was used instead of Compound ET-1. Was produced.

< Experimental example 1-36>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-140 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 2-108 was used instead of Compound ET-1. Was produced.

< Experimental example 1-37>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-140 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 3-1 was used instead of Compound ET-1. Was produced.

< Experimental example 1-38>

An organic light-emitting device in the same manner as in Comparative Example 1-1, except that Compound 1-140 was used instead of Compound EB-1 in Comparative Example 1-1, and Compound 3-27 was used instead of Compound ET-1. Was produced.

Table 1 shows the results of applying a current to the organic light-emitting devices manufactured according to Comparative Example 1-1 and Experimental Examples 1-1 to 1-38.

Electron transport layer Electron blocking layer Voltage(eV) Luminance (V) T95(hr) Comparative Example 1-1 ET-1 EB-1 4.42 5.95 285 Experimental Example 1-1 ET-1 Compound 1-31 4.02 6.19 285 Experimental Example 1-2 ET-1 Compound 1-32 4.23 6.23 285 Experimental Example 1-3 ET-1 Compound 1-33 4.15 6.18 290 Experimental Example 1-4 ET-1 Compound 1-34 4.36 6.22 285 Experimental Example 1-5 ET-1 Compound 1-81 4.07 6.28 285 Experimental Example 1-6 ET-1 Compound 1-97 4.29 6.18 270 Experimental Example 1-7 ET-1 Compound 1-122 4.35 6.23 285 Experimental Example 1-8 ET-1 Compound 1-140 4.37 6.12 280 Experimental Example 1-9 Compound 2-9 EB-1 4.24 6.24 275 Experimental Example 1-10 Compound 2-51 EB-1 4.16 6.25 290 Experimental Example 1-11 Compound 2-64 EB-1 4.31 6.26 285 Experimental Example 1-12 Compound 2-74 EB-1 4.29 6.19 275 Experimental Example 1-13 Compound 2-87 EB-1 4.17 6.28 290 Experimental Example 1-14 Compound 2-88 EB-1 4.34 6.18 285 Experimental Example 1-15 Compound 2-102 EB-1 4.06 6.23 275 Experimental Example 1-16 Compound 2-108 EB-1 4.25 6.12 270 Experimental Example 1-17 Compound 3-1 EB-1 4.28 6.32 285 Experimental Example 1-18 Compound 3-13 EB-1 4.29 6.19 275 Experimental Example 1-19 Compound 3-16 EB-1 4.34 6.28 285 Experimental Example 1-20 Compound 3-27 EB-1 4.05 6.31 285 Experimental Example 1-21 Compound 3-29 EB-1 4.19 6.25 270 Experimental Example 1-22 Compound 3-30 EB-1 4.25 6.36 295 Experimental Example 1-23 Compound 2-9 Compound 1-33 3.74 6.64 330 Experimental Example 1-24 Compound 2-108 Compound 1-33 3.76 6.60 345 Experimental Example 1-25 Compound 3-1 Compound 1-33 3.77 6.64 365 Experimental Example 1-26 Compound 3-27 Compound 1-33 3.72 6.65 355 Experimental Example 1-27 Compound 2-9 Compound 1-81 3.65 6.75 340 Experimental Example 1-28 Compound 2-108 Compound 1-81 3.62 6.79 350 Experimental Example 1-29 Compound 3-1 Compound 1-81 3.63 6.76 375 Experimental Example 1-30 Compound 3-27 Compound 1-81 3.64 6.71 350 Experimental Example 1-31 Compound 2-9 Compound 1-122 3.65 6.52 335 Experimental Example 1-32 Compound 2-108 Compound 1-122 3.66 6.53 325 Experimental Example 1-33 Compound 3-1 Compound 1-122 3.90 6.57 380 Experimental Example 1-34 Compound 3-27 Compound 1-122 3.91 6.52 350 Experimental Example 1-35 Compound 2-9 Compound 1-140 3.93 6.60 345 Experimental Example 1-36 Compound 2-108 Compound 1-140 3.79 6.59 345 Experimental Example 1-37 Compound 3-1 Compound 1-140 3.88 6.49 370 Experimental Example 1-38 Compound 3-27 Compound 1-140 3.86 6.52 355

Comparative Example 1-1 of the present specification uses materials widely used in conventional blue organic light-emitting devices as a reference, and has a structure using compound EB-1 as an electron blocking layer and compound ET-1 as an electron transport layer.

According to Table 1, in Experimental Examples 1-1 to 1-8, the compound of Formula 1 according to an exemplary embodiment of the present specification was used as an electron blocking layer material instead of compound EB-1, and Experimental Examples 1-9 to 1- 22 is an organic light-emitting device manufactured by using the compound of Formula 2 or Formula 3 according to an exemplary embodiment of the present specification as an electron transport layer material instead of compound ET-1, and Formula 1, Formula 2 and 3 were applied to each organic material layer. Shows basic device characteristics.

Experimental Examples 1-23 to 1-38 use the compound of Formula 1 according to an exemplary embodiment of the present specification as an electron blocking layer material instead of compound EB-1, and the compound of Formula 2 or 3 according to an exemplary embodiment of the present specification ET It is used as an electron transfer layer instead of -1 and shows the characteristics of a device when applied to one device. Compared to those applied to each layer, overall luminous efficiency is similar, but the voltage is lowered by 7 to 10% and the lifespan is measured to be longer than 10%.

In particular, in Experimental Examples 1-27 to 1-30, when compound 1-81 was used as the electron blocking layer material, and the compounds of Formula 2 or 3 according to an exemplary embodiment of the present specification were used as the electron transport layer material, the voltage It can be seen that this is low and the luminous efficiency is high. In addition, in Experimental Examples 1-25, 1-29, 1-33 and 1-37, the compound of Formula 1 according to an exemplary embodiment of the present specification was used as an electron blocking layer material, and compound 3-1 was used as an electron transport layer material. The longest life was measured when used.

Through this, the formula 1 (structure in which an amine group is directly connected to a fluorene-type core or a linker is connected) according to an exemplary embodiment of the present specification is used as an electron blocking layer material, and one or two triazines having very excellent ability as electron injection are used. It can be seen that the driving voltage and lifetime characteristics of a blue organic light emitting diode made by combining the compound of Formula 2 or 3 consisting of dogs with an electron transport layer material provided between the cathode and the emission layer can be improved.

<Experimental Examples 2-1 to 2-8>

In Comparative Example 1-1, except for using compounds 1-31, 1-32, 1-33, 1-34, 1-81, 1-97, 1-122 or 1-140 instead of the compound NPB, the above An organic light emitting device was manufactured in the same manner as in Comparative Example 1-1.

<Experimental Examples 2-9 to 2-22>

Instead of compound ET-1 in Comparative Example 1-1, compounds 2-9, 2-51, 2-64, 2-74, 2-87, 2-88, 2-102, 2-108, 3-1, An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that 3-13, 3-16, 3-27, 3-29, or 3-30 was used.

<Experimental Example 2-23>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-31 was used instead of Compound NPB in Comparative Example 1-1, and Compound 2-64 was used instead of Compound ET-1. I did.

<Experimental Example 2-24>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-31 was used instead of Compound NPB in Comparative Example 1-1, and Compound 3-13 was used instead of Compound ET-1. I did.

<Experimental Example 2-25>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-31 was used instead of Compound NPB in Comparative Example 1-1, and Compound 3-29 was used instead of Compound ET-1. I did.

<Experimental Example 2-26>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-33 was used instead of Compound NPB in Comparative Example 1-1, and Compound 2-64 was used instead of Compound ET-1. I did.

<Experimental Example 2-27>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-33 was used instead of Compound NPB in Comparative Example 1-1, and Compound 3-13 was used instead of Compound ET-1. I did.

<Experimental Example 2-28>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-33 was used instead of Compound NPB in Comparative Example 1-1, and Compound 3-29 was used instead of Compound ET-1. I did.

<Experimental Example 2-29>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-34 was used instead of Compound NPB in Comparative Example 1-1, and Compound 2-64 was used instead of Compound ET-1. I did.

<Experimental Example 2-30>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-34 was used instead of Compound NPB in Comparative Example 1-1, and Compound 3-13 was used instead of Compound ET-1. I did.

<Experimental Example 2-31>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that the compound 1-34 was used instead of the compound NPB in Comparative Example 1-1, and the compound 3-29 was used instead of the compound ET-1. I did.

Table 2 below shows the results of applying a current to the organic light emitting device manufactured according to Comparative Example 1-1 and Experimental Examples 2-1 to 2-31.

Electron transport layer Hole transport layer Voltage(eV) Luminance (V) T95(hr) Comparative Example 1-1 ET-1 NPB 4.42 5.95 285 Experimental Example 2-1 ET-1 Compound 1-31 4.07 6.15 275 Experimental Example 2-2 ET-1 Compound 1-32 4.25 6.24 275 Experimental Example 2-3 ET-1 Compound 1-33 4.14 6.17 280 Experimental Example 2-4 ET-1 Compound 1-34 4.38 6.23 275 Experimental Example 2-5 ET-1 Compound 1-81 4.11 6.26 275 Experimental Example 2-6 ET-1 Compound 1-97 4.25 6.14 260 Experimental Example 2-7 ET-1 Compound 1-122 4.36 6.25 275 Experimental Example 2-8 ET-1 Compound 1-140 4.38 6.11 270 Experimental Example 2-9 Compound 2-9 NPB 4.22 6.22 265 Experimental Example 2-10 Compound 2-51 NPB 4.18 6.25 280 Experimental Example 2-11 Compound 2-64 NPB 4.33 6.27 275 Experimental Example 2-12 Compound 2-74 NPB 4.25 6.19 265 Experimental Example 2-13 Compound 2-87 NPB 4.14 6.26 280 Experimental Example 2-14 Compound 2-88 NPB 4.33 6.14 275 Experimental Example 2-15 Compound 2-102 NPB 4.05 6.25 265 Experimental Example 2-16 Compound 2-108 NPB 4.24 6.15 260 Experimental Example 2-17 Compound 3-1 NPB 4.22 6.39 275 Experimental Example 2-18 Compound 3-13 NPB 4.21 6.17 265 Experimental Example 2-19 Compound 3-16 NPB 4.36 6.24 275 Experimental Example 2-20 Compound 3-27 NPB 4.03 6.31 275 Experimental Example 2-21 Compound 3-29 NPB 4.17 6.20 260 Experimental Example 2-22 Compound 3-30 NPB 4.28 6.35 285 Experimental Example 2-23 Compound 2-64 Compound 1-31 3.79 6.64 320 Experimental Example 2-24 Compound 3-13 Compound 1-31 3.71 6.63 335 Experimental Example 2-25 Compound 3-29 Compound 1-31 3.75 6.60 365 Experimental Example 2-26 Compound 2-64 Compound 1-33 3.63 6.77 330 Experimental Example 2-27 Compound 3-13 Compound 1-33 3.65 6.78 340 Experimental Example 2-28 Compound 3-29 Compound 1-33 3.64 6.70 365 Experimental Example 2-29 Compound 2-64 Compound 1-34 3.87 6.50 325 Experimental Example 2-30 Compound 3-13 Compound 1-34 3.89 6.51 315 Experimental Example 2-31 Compound 3-29 Compound 1-34 3.88 6.56 370

Comparative Example 1-1 of the present specification uses materials widely used in the conventional blue organic light-emitting device as a reference, and has a structure using compound NPB as a hole transport layer and compound ET-1 as an electron transport layer.

According to Table 2, in Experimental Examples 2-1 to 2-8, the compound of Formula 1 according to an exemplary embodiment of the present specification was used as a hole transport layer material instead of the compound NPB, and Experimental Examples 2-9 to 2-22 were An organic light emitting device manufactured by using a compound of Formula 2 or Formula 3 according to an exemplary embodiment of the specification as an electron transport layer material instead of compound ET-1, and a basic device when Formula 1, Formula 2, and 3 are applied to each organic material layer It shows the characteristics of.

The organic light-emitting devices manufactured according to Experimental Examples 2-1 to 2-31 were measured to have a driving voltage of 5 to 10% lower as compared to the organic light-emitting device of Comparative Example 1-1.

Experimental Examples 2-23 to 2-31 use the compound of Formula 1 according to an exemplary embodiment of the present specification as a hole transport layer material instead of the compound NPB, and instead of the compound ET-1 of Formula 2 or 3 according to an exemplary embodiment of the present specification When it was used as an electron transfer layer and applied to one device, the voltage was the lowest and the luminous efficiency was high. In addition, in Experimental Examples 2-25, 2-28, and 2-31, when the compound of Formula 1 according to an exemplary embodiment of the present specification was used as the hole transport layer material, and the compound 3-19 was used as the electron transport layer material, the life span was most It was measured long.

Through this, formula 1 (a structure in which an amine group is directly connected to a fluorene-type core or a linker is included) according to an exemplary embodiment of the present specification is used as a material for a hole transport layer, and one or two triazines having very excellent ability as electron injection are used. It can be seen that the driving voltage and lifespan characteristics of a blue organic light-emitting device made by combining the formed compound of Formula 2 or 3 with an electron transport layer material provided between the cathode and the emission layer can be improved.

10, 11: organic light emitting device
20: substrate
30: first electrode
40: light emitting layer
50: second electrode
60: hole injection layer
70: hole transport layer
80: electron blocking layer
90: electron transport layer
100: electron injection layer

Claims (17)

anode;
A cathode provided to face the anode;
A light emitting layer provided between the anode and the cathode;
A first organic material layer provided between the anode and the emission layer; And
An organic light-emitting device comprising a second organic material layer provided between the cathode and the emission layer,
The first organic material layer includes a compound represented by the following Formula 1-1,
The second organic material layer is an organic light emitting device including a compound represented by Formula 3-10:
[Formula 1-1]

[Chemical Formula 3-10]

In Formulas 1-1 and 3-10,
At least one of X4 to X6 is N, the rest are CH,
X7 is N or CH, X8 is N or CH, X9 is N or CH,
When X7 to X9 are CH, adjacent groups among X7 to X9, -L7-Ar7 and -L8-Ar8 combine with each other to form a pyridine ring,
L1 is a direct bond; Phenylene group; Biphenylylene group; Naphthylene group; Or a fluorenylene group substituted with a methyl group,
L5 to L8 are the same as or different from each other, and each independently a direct bond; Or a phenylene group,
L10 and L11 are the same as or different from each other, and each independently a direct bond; Or a phenylene group,
Ar1 is a phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; A substituted or unsubstituted fluorenyl group selected from the group consisting of an alkyl group and an aryl group; Triphenylenyl group; Dibenzofuranyl group; Or a dibenzothiophene group,
Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; Or a pyridyl group,
R1 and R2 are a phenyl group, or combine with each other to form a fluorene ring,
R3 and R4 are the same as or different from each other, and each independently a methyl group; Or a phenyl group, or combine with each other to form a fluorene ring. delete delete delete delete delete delete delete The organic light-emitting device of claim 1, wherein Formula 1-1 is selected from the following compounds:

. delete The organic light-emitting device of claim 1, wherein Formula 3-10 is selected from the following compounds:

The organic light-emitting device of claim 1, wherein the glass transition temperature (Tg) of the compound represented by Chemical Formula 3-10 is 120°C or higher. The organic light-emitting device of claim 1, wherein the first organic material layer includes a hole transport layer, and the hole transport layer includes a compound represented by Formula 1-1. The organic light-emitting device of claim 1, wherein the first organic material layer includes an electron blocking layer, and the electron blocking layer includes a compound represented by Formula 1-1. The organic light-emitting device of claim 1, wherein the second organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a compound represented by Formula 3-10. The organic light-emitting device of claim 1, wherein the second organic material layer includes an electron transport layer and an electron injection layer, and the electron transport layer includes a compound represented by Formula 3-10. The organic light-emitting device of claim 1, wherein the second organic material layer includes an electron transport layer and an electron injection layer, and the electron injection layer includes a compound represented by Formula 3-10.

Images