KR101961346B1 - Organic light emitting device - Google Patents

Abstract

The present disclosure includes a cathode; Anode; A light emitting layer provided between the cathode and the anode; A hole transport layer provided between the anode and the light emitting layer, the hole transport layer comprising a compound represented by the following formula (1); And at least one hole-transporting layer provided between the anode and the light-emitting layer and including at least one of a compound represented by the following formula (2), a compound represented by the following formula (3), and a compound represented by the following formula will be.

Description

ORGANIC LIGHT EMITTING DEVICE

The present invention claims the benefit of Korean Patent Application No. 10-2016-0065969, filed on May 27, 2016, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

The present disclosure relates to an organic light emitting device.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected into the anode, electrons are injected into the organic layer from 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.

U.S. Patent Application Publication No. 2004-0251816

The present invention provides an organic light emitting device using specific materials.

An embodiment of the present disclosure includes a cathode; Anode; A light emitting layer provided between the cathode and the anode; A hole transport layer provided between the anode and the light emitting layer, the hole transport layer comprising a compound represented by the following formula (1); And at least one hole-transporting layer provided between the anode and the light-emitting layer and including at least one of a compound represented by the following formula (2), a compound represented by the following formula (3), and a compound represented by the following formula do:

 [Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

In formulas (1) to (4)

La to Lg and L1 to L9 are the same or different from each other and each independently represents a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted carbazolylene group; Or a substituted or unsubstituted heteroarylene group, and a1, b1, c1, d1, e1, f1, g1, c, d, e, f, l, r, s, w and v are each an integer of 0 to 3 , When they are two or more, the structures in parentheses are the same or different from each other,

Ara to Are and Ar1 to Ar6 are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group, or Arb and Are; Arc and Ard; Ar1 and Ar2; Ar3 and Ar4; Ar5 and Ar6; Arc and Lg; Arb and Lb; Ar2 and L9; Ar5 and L5; Or Ar4 and L8 are bonded to each other to form a monocyclic or polycyclic aromatic or aliphatic substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring,

R21, R22, and R1 to R13 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight or branched chain alkyl group, a substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group Or adjacent groups may combine with each other to form a monocyclic or polycyclic aromatic or aliphatic substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring, and at least one of the above-mentioned alkyl, alkoxy or thioalkyl groups The adjacent CH ₂ groups may be replaced by SiRR ', C═NR ₂ , P (═O) R, SO, SO ₂ , NR, O, S or CONR, g is an integer from 0 to 5, a, h, i, j, m, n and o are 0 A1, k1, a, h, i, j, m, n, o, b1 and k2 are integers of 0 to 3, When b, p and k are each 2 or more, the structures in parentheses are equal to or different from each other,

R, R 'and R "are the same or different and each independently hydrogen, deuterium, halogen, nitrile, substituted or unsubstituted straight-chain alkyl, alkoxy or thioalkyl, substituted or unsubstituted branched or A substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted aralkyl group, Or adjacent groups are bonded to each other to form a monocyclic or polycyclic aromatic or aliphatic hydrocarbon ring or a heterocyclic ring.

In the organic light emitting device according to one embodiment of the present invention, since the first organic material layer and the second organic material layer are disposed in the anode and the light emitting layer, it is possible to improve the efficiency, the low driving voltage and / or the lifetime characteristic in the organic light emitting device .

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a view illustrating a laminated structure of an organic light emitting device according to an embodiment of the present invention.
2 illustrates a laminated structure of an organic light emitting device according to another embodiment of the present invention.

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

An organic light emitting device according to an embodiment of the present invention includes a cathode; Anode; A light emitting layer provided between the cathode and the anode; A hole transport layer provided between the anode and the light emitting layer, the hole transport layer comprising a compound represented by the following formula (1); And at least one hole-transporting layer provided between the anode and the light-emitting layer, the hole-transporting layer including at least one of a compound represented by Chemical Formula 2, a compound represented by Chemical Formula 3 and a compound represented by Chemical Formula 4 below.

An organic light-emitting device having an anode and a cathode, an organic material layer formed therebetween, and an organic material layer containing a material according to an embodiment state described in this specification has a low driving voltage and a long lifetime. Conventionally, aromatic diamine derivatives and aromatic condensed ring diamine derivatives have been known as hole transporting materials used in organic light emitting devices. However, in this case, since the applied voltage is mostly high, there is a problem such that the lifetime of the device is shortened and the power consumption is increased. As a solution to the above problem, there has been proposed a method in which an electron-accepting compound such as Lewis acid is doped or used alone in the hole injection layer of an organic light emitting element. However, the above method has limitations in the injection and transport of holes. Accordingly, in the present invention, the combination of the material between the hole transport layer and the hole control layer, or the combination of the hole transport layer and the hole control layer in multiple layers, has resulted in the effect of low voltage, high efficiency, and long life. In general, the hole transport layer material is a tertiary amine substituted with an aromatic group, and the device characteristics that can be found in the combination group of these materials show various results. According to the embodiment of the present invention, when a substance having a structure in which a fluorene unit is substituted in the structure of a tertiary amine is introduced as a hole control layer material, improvement in device characteristics due to hole transport and carrier control can be achieved. Particularly, the combination with the carbazole unit as the hole transport layer material exhibited the most excellent characteristics in terms of the voltage. In particular, when the hole-regulating layer is formed in a multi-layer structure, the result is improved due to a more refined energy level.

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

In this specification, when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.

Examples of 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 substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted aryloxy group, A substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted arylalkenyl group, An unsubstituted carbazolyl group, and a substituted or unsubstituted fluorenyl group, or two or more of the above-exemplified substituents are substituted with a substituted or unsubstituted substituent, For example, the "substituent group to which at least two substituents are connected" means an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, an aryl group substituted with an aryl group Heterocyclic group, may be an aryl group substituted with an alkyl group.

In the present specification, the halogen group is F, Cl, Br, I, or the like.

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. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, 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.

In the present specification, the cyclic alkyl group is not particularly limited, but preferably has 3 to 40 carbon atoms, and specifically includes 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 and the like. 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 is preferably 1 to 40 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In this specification, the amine group is -NH ₂ ; An alkylamine group; N-alkylarylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1 to 40. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenylamine group; And an N-biphenylfluorenylamine group, but are not limited thereto.

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

In the present specification, the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.

In the present specification, the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroarylamine group.

In the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine group is the same as the alkyl group described above.

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. 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 the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 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 is preferably 6 to 60 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 60 carbon atoms. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a perylenyl group and a klycenyl group.

In the present specification, the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.

,

,

,

,

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, 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 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. 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 aryl group in the aryloxy group, the N-arylalkylamine group, and the N-arylheteroarylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- 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, 9-phenanthryloxy group and the like.

In the present specification, the heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, , An isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, But are not limited to, phenanthroline, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazyl and dibenzofurane 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 heteroarylamine group having 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 above-mentioned heteroaryl group.

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

In the specification, the description of the aryl group described above can be applied except that the arylene group is a divalent group.

In this specification, the description of the above-mentioned heterocyclic group can be applied, except that the heteroarylene group is divalent.

In the present specification, the description of the above-mentioned aryl group can be applied to the aryl group of the aralkyl group, the arylalkenyl group and the aryloxy group.

In the present specification, the alkyl group of the aralkyl group can be applied to the alkyl group described above.

In the present specification, the alkenyl group of the arylalkenyl group can be applied to the description of the alkenyl group described above.

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

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

In the present specification, the hetero ring includes one or more non-carbon atoms and hetero atoms. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples thereof may be selected from the examples of the heterocyclic group except that the heterocyclic group is not monovalent.

)은 코어 구조 또는 다른 치환기에 결합되는 부위를 의미한다. In this specification, the dotted line (

) Refers to a site that is bonded to a core structure or other substituent.

According to another embodiment of the present specification, Ara to Are and Ar1 to Ar6 are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted fluorenyl group.

According to another embodiment of the present specification, Ara to Are and Ar1 to Ar6 are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted fluorenyl group.

According to another embodiment of the present invention, Ara to Are and Ar1 to Ar6 are the same or different from each other and each independently represents a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, Which may be one or a combination of two or more selected from the group consisting of a triphenylenyl group, a triphenylenyl group, a pyrenyl group, a klycenyl group, a carbazolyl group, a dibenzofurane group, a dibenzothiophene group, a fluorenyl group, ≪ / RTI >

According to another embodiment of the present invention, Ara to Are and Ar1 to Ar6 are the same or different from each other and each independently represents a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, Which may be a combination of one or two or more selected from the group consisting of an alkyl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a heterocyclic group, Or a heterocyclic group.

According to another embodiment of the present invention, Ara to Are and Ar1 to Ar6 are the same or different from each other and each independently represents a phenyl group, a biphenyl group, a terphenyl group, a quarter phenyl group, a naphthyl group, a dibenzofurane group, And a fluorenyl group, which may be substituted or unsubstituted with an additional alkyl group, aryl group, or heterocyclic group.

According to another embodiment of the present invention, Ara to Are and Ar1 to Ar6 are the same or different from each other and each independently represents a phenyl group, a biphenyl group, a terphenyl group, a quarter phenyl group, a naphthyl group, a dibenzofurane group, And a fluorenyl group, which may be substituted or unsubstituted with an additional alkyl group, aryl group or heterocyclic group. Here, the heterocyclic group may be a dibenzofurane group or a dibenzothiophene group.

According to another embodiment of the present disclosure, Ara to Are and Ar1 to Ar6 are the same or different from each other and can be selected from the following structural formulas.

In the above structural formulas, R, R 'and R "represent hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted branched or cyclic alkyl group , A substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group. Preferably, R, R 'and R " are hydrogen; heavy hydrogen; A straight chain alkyl group; An aryl group; Or a heterocyclic group.

According to one embodiment of the present disclosure, at least one of -NArbAre, -NArcArd, -NAr1Ar2, -NAr3Ar4, and -NAr5Ar6 can be represented by Structural Formula A below.

[Structural Formula A]

In the above formula,

Xa is CRbRd; NRc; O; Or S, y is 0 or 1, and when y is 0, the two carbons bound to Xa are directly bonded,

Ra to Rd are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight or branched chain alkyl group, a substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group, and x is an integer of 0 to 8 And when x is 2 or more, R a are the same or different from each other, and R, R 'and R "are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present disclosure, the structural formula A may be represented by the following structural formulas.

In the above structural formulas, R 101 to R 110 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight or branched chain alkyl group, a substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group, and R, R 'and R " Are the same or different and are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present disclosure, at least one of - (Lg) g1-NArcArd, (Lb) b1-NArbAre, - (L9) v-NAr1Ar2, One can be represented by the following structural formula B.

[Structural formula B]

In the above formula,

Xb is CRbRd; NRc; O; Or S, y is 0 or 1, and when y is 0, the two carbons bound to Xa are directly bonded,

L11 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, z is an integer of 0 to 3, and when z is 2 or more, L11 is the same or different,

Ar9 represents a substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group,

Rb to Re are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight or branched chain alkyl group, a substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group, z 'is 0 to 7 R < e > and R " are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present disclosure, the structural formula B may be represented by the following structural formulas.

In the above structural formulas, R101, R102 and R104 to R110 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight or branched chain alkyl group, a substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group, and R, R 'and R " Are the same or different and are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group,

Ar101 is a substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group.

According to another embodiment of the present disclosure, La to Lg and L1 to L9 are the same or different from each other, and each independently represents a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted fluorenylene group; Or a substituted or unsubstituted carbazolylene group.

According to another embodiment of the present disclosure, La to Lg and L1 to L9 are the same or different from each other, and each independently represents a direct bond; Or a substituted or unsubstituted arylene group.

According to another embodiment of the present invention, La to Lg and L1 to L9 are the same or different and each independently represents a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, A substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenylene group, or a substituted or unsubstituted spirobifluorenylene group.

According to another embodiment of the present invention, La to Lg and L1 to L9 are the same or different and each independently represents a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, A substituted or unsubstituted phenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenylene group, or a substituted or unsubstituted spirobifluorenylene group, which may be substituted or unsubstituted with an alkyl group, an aryl group or a heterocyclic group .

According to another embodiment of the present invention, La to Lg and L1 to L9 are the same or different and each independently represents a direct bond, a substituted or unsubstituted phenylene group, a biphenyllylene group, a methyl group, A phenanthrenylene group, or a spirobifluorenylene group.

According to another embodiment of the present disclosure, La to Lg and L1 to L9 are the same or different from each other, and each independently represents a direct bond; Or may be selected from among the following structural formulas.

In the above structural formulas, R111 to R122 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight or branched chain alkyl group, a substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group, and R, R 'and R " Are the same or different and are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, the formula (1) is represented by the following formula (1-1).

According to another embodiment of the present disclosure, k1 is 0 or 1.

According to another embodiment of the present disclosure, a is 0 or 1, and when a is 1, R3 is hydrogen; An alkyl group or an aryl group.

According to one embodiment of the present disclosure, Formula 1 may be selected from the following embodiments.

According to one embodiment of the present disclosure, Formula 2 may be selected from the following embodiments.

According to one embodiment of the present disclosure, Formula 3 may be selected from the following embodiments.

According to one embodiment of the present disclosure, Formula 4 may be selected from the following embodiments.

According to one embodiment of the present invention, the compounds of Formulas 1 to 4 may be prepared using starting materials and reaction conditions known in the art. The kind and number of substituents can be determined by appropriately selecting starting materials known to a person skilled in the art. The compounds of the above formulas (1) to (4) are commercially available.

According to one embodiment of the present invention, the organic light emitting device may include only the hole transport layer, the hole control layer, and the light emitting layer described above as the organic material layer, but may further include an additional organic material layer. For example, it may further include a hole injection layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer.

According to an embodiment of the present invention, the hole transport layer and the hole control layer are provided in contact with each other.

According to one embodiment of the present invention, the hole adjusting layer is provided in contact with the first electrode.

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

1 illustrates a structure of an organic light emitting device in which an anode 101, a hole transport layer 201, a hole control layer 202, a light emitting layer 401, and a cathode 401 are sequentially stacked on a substrate 100. 1 is an exemplary structure of an organic light emitting diode according to an embodiment of the present invention, and may further include another organic layer. Further, a cathode, a light emitting layer, a hole adjusting layer, a hole transporting layer, and an anode may be sequentially stacked on the substrate.

2, an electron transport layer 501 and an electron injection layer 502 are additionally provided between the light emitting layer 401 and the cathode 401, as compared with the device of FIG. 2 is an exemplary structure according to the embodiment of the present invention, and may further include another organic layer, and the electron transporting layer or the electron injecting layer may be omitted. Further, a cathode, an electron injecting layer, an electron transporting layer, a light emitting layer, a hole adjusting layer, a hole transporting layer and an anode may be sequentially stacked on a substrate.

1 and 2 illustrate a structure in which the hole-regulating layer is one layer, but the present invention is not limited thereto, and the hole-regulating layer may be composed of two or more layers. When the hole-regulating layer is formed in a multi-layer structure, an improved result can be obtained due to a more refined energy level.

According to one embodiment of the present invention, the hole-transporting layer may include at least one of a first hole-transporting layer containing at least one of the compounds represented by Formulas 2 to 4 and a compound represented by Formulas 2 to 4 And a second hole-regulating layer. According to one example, the first hole-regulating layer and the second hole-regulating layer are in contact with each other. According to another example, the second hole-regulating layer contacts the light-emitting layer.

According to an example, the composition of the first hole-regulating layer and the second hole-regulating layer is different. According to another example, the first hole-regulating layer and the second hole-regulating layer include compounds different from each other.

According to an example, the first hole-regulating layer includes a compound of Formula 2, and the second hole-regulating layer comprises a compound of Formula 2. [

According to one example, the first hole-regulating layer includes a compound of Formula 2, and the second hole-regulating layer includes a compound of Formula 3. [

According to one example, the first hole-regulating layer includes a compound of Formula 2 and the second hole-controlling layer comprises a compound of Formula 4. [

According to an example, the first hole-regulating layer includes a compound of Formula 3, and the second hole-regulating layer includes a compound of Formula 2. [

According to an example, the first hole-regulating layer includes a compound of Formula 3 and the second hole-regulating layer comprises a compound of Formula 3. [

According to an embodiment, the first hole-regulating layer includes the compound of Formula 3, and the second hole-regulating layer includes the compound of Formula 4. [

According to an example, the first hole-regulating layer includes a compound of Formula 4 and the second hole-regulating layer comprises a compound of Formula 2. [

According to an example, the first hole-regulating layer includes the compound of Formula 4 and the second hole-regulating layer includes the compound of Formula 3. [

According to an example, the first hole-regulating layer includes the compound of Formula 4 and the second hole-regulating layer includes the compound of Formula 4. [

According to an embodiment of the present invention, the first hole adjusting layer is thicker than the second hole adjusting layer.

According to one embodiment of the present invention, the hole transport layer is thicker than the hole regulating layer.

According to an embodiment of the present invention, the sum of the thicknesses of the first hole-regulating layer and the second hole-regulating layer is smaller than the thickness of the hole-transporting layer.

According to one embodiment of the present invention, the thickness of the hole transport layer, the first hole regulating layer and the second hole regulating layer may be selected from the group consisting of thickness of the hole transporting layer, thickness of the first hole regulating layer, Satisfies.

The combination according to the claims of the present invention can balance the HOMO between the respective layers and balance the proper hole inflow in the light emitting layer of the red light emitting device through the effective movement of the hole of the chemical structure mentioned, thereby positively effecting the low voltage, high efficiency red light emission Lt; / RTI >

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

For example, the organic light emitting device of the present invention can be manufactured using materials and methods known in the art. For example, a metal or a metal oxide having conductivity or an alloy thereof is deposited on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming an anode, forming an organic layer thereon, and then 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 an anode material on a substrate. In addition, the compound represented by Formula 1 or 2 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

As the anode material, a material having a large work function is preferably used so that injection of holes into the organic material layer is smooth. Specific examples of the anode 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 cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode 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, LiO ₂ / Al, and Mg / Ag, but are not limited thereto.

The hole injecting layer is a layer for injecting holes from the electrode. The hole injecting layer has a hole injecting effect for hole injecting effect on the anode, a hole injecting effect for the light emitting layer or the light emitting material due to its ability to transport holes to the hole injecting 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. If necessary, the hole-injecting layer may be doped with an electron-accepting compound.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer as the hole transport material. 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 of the light emitting layer 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 high 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; Benzoxazole, benzothiazole and benzimidazole compounds; 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 an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting material of the electron transporting layer is a layer that transports electrons from the electron injection layer to the electron transport layer and transports electrons from the cathode to the light emitting layer. This large material is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer may be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer. Optionally, the electron transporting layer can be doped with an n-type dopant such as Liq.

An electron control layer may be additionally provided between the light emitting layer and the electron transporting layer.

The electron injection layer is a layer for injecting electrons from an electrode and has an ability to transport electrons and has an electron injection effect from the cathode, an excellent electron injection effect on 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, magnesium, lithium fluoride, and the like, 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.

Hereinafter, the present invention will be illustrated by way of examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the invention.

≪ Example 1 > Manufacture of OLED

The substrate on which ITO / Ag / ITO was deposited as an anode of 70/1000/70Å was cut into a size of 50 mm x 50 mm x 0.5 mm, and the dispersant was dissolved in distilled water and ultrasonically washed. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

HIL1 of the following Table 1 was thermally vacuum deposited on the prepared anode to form a hole injection layer < HIL > , and HTM3, which is a hole transport material, was vacuum deposited on the hole transport layer < HTL1 &gt; . Next, using the HTM6 (950Å) layer control hole -1 <HTL2 - 1> to form a. Subsequently, host H1 and dopant D1 (2 wt%) were vacuum-deposited to a thickness of 360 Å to form a light emitting layer <EML> . Then, ETM1 was deposited to a thickness of 50 Å to form an electron control layer <ETL1> , and the compound ETM2 and Liq were mixed in a ratio of 7: 3 to form an electron transport layer <ETL2> having a thickness of 250 Å. A 50 Å thick layer of magnesium and lithium fluoride (LiF) was deposited as an electron injection layer (EIL ), followed by 200 Å of magnesium and silver (1: 4) as a cathode, followed by deposition of 600 Å of CPL1. The deposition rate of the organic material was maintained at 1 Å / sec.

< Example  2>

The same experiment was performed except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 1.

< Example  3>

The same experiment was conducted except that HTM8 was used instead of HTM6 as the hole-regulating layer-1 in Example 1.

< Example  4>

The same experiment was performed except that HTM4 was used instead of HTM3 as the hole transporting layer in Example 1 above.

< Example  5>

The same experiment was performed except that HTM7 was used instead of HTM6 as the hole-regulating layer-1 in Example 4 above.

< Example  6>

The same experiment was carried out except that HTM8 was used instead of HTM6 as the hole control layer-1 in Example 4 above.

< Example  7>

The same experiment was carried out except that HTM5 was used instead of HTM3 as the hole transport layer in Example 1 above.

< Example  8>

Except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 7.

< Example  9>

The same experiment was carried out except that HTM8 was used instead of HTM6 as the hole control layer-1 in Example 7.

< Example  10>

Example 1 and by thermal vacuum deposition to a thickness of 50Å of the foregoing HIL1 hole injection layer <HIL> formation, vacuum-deposited material is HTM3 transporting a thickness 1150Å a hole thereon the above prepared positive electrode as the hole transport layer <HTL1 > was formed. Next, forming an HTM6 (800Å) layer of a hole adjustment -1 <HTL2-1>, then the HTM9 (150Å) of the hole control layer -2 <HTL2-2> thereon. Subsequently, host H1 and dopant D1 (2 wt%) were vacuum-deposited to a thickness of 360 Å to form a light emitting layer <EML> . ETM1 was then deposited as electron control layer < ETL1 > at 50 ANGSTROM to form electron transport layer < ETL2 > with compound ETM2 and Liq and 7: 3 (250 ANGSTROM). A 50 Å thick layer of magnesium and lithium fluoride (LiF) was deposited as an electron injection layer (EIL ), followed by 200 Å of magnesium and silver (1: 4) as a cathode, followed by deposition of 600 Å of CPL1. .

< Example  11>

The same experiment was conducted except that HTM7 was used instead of HTM6 as the hole-regulating layer-1 in Example 10.

< Example  12>

The same experiment was performed except that HTM8 was used instead of HTM6 as the hole control layer-1 in Example 10.

< Example  13>

The same experiment was performed except that HTM4 was used instead of HTM3 as the hole transporting layer in Example 10.

< Example  14>

The same experiment was carried out except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 13.

< Example  15>

The same experiment was carried out except that HTM8 was used instead of HTM6 as the hole control layer-1 in Example 13.

< Example  16>

The same experiment was conducted except that HTM5 was used instead of HTM3 as the hole transporting layer in Example 10.

< Example  17>

The same experiment was carried out except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 13.

< Example  18>

The same experiment was carried out except that HTM8 was used instead of HTM6 as the hole control layer-1 in Example 13.

< Example  19>

The same experiment was carried out except that HTM10 was used instead of HTM9 as the hole control layer-2 in Example 10.

< Example  20>

Except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 19.

< Example  21>

Except that HTM8 was used instead of HTM6 as the hole control layer-1 in Example 19.

< Example  22>

The same experiment was performed except that HTM4 was used instead of HTM3 as the hole transporting layer in Example 19.

< Example  23>

The same experiment was conducted except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 22.

< Example  24>

Except that HTM8 was used instead of HTM6 as the hole-regulating layer-1 in Example 22.

< Example  25>

The same experiment was conducted except that HTM5 was used instead of HTM3 as the hole transporting layer in Example 19.

< Example  26>

The same experiment was conducted except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 25.

< Example  27>

Except that HTM8 was used instead of HTM6 as the hole control layer-1 in Example 25.

< Comparative Example  1>

The same experiment was conducted except that HTM1 was used instead of HTM3 as the hole transport layer in Example 1, and HTM2 was used in place of HTM6 as the hole control layer-1

< Comparative Example  2>

In the same manner as in Comparative Example 1 except that HTM9 was formed between the hole-transporting layer-1 and the light-emitting layer as the hole-transporting layer-2

The thicknesses of the organic layers of the devices of Examples 1 to 27 and Comparative Examples 1 and 2 are shown in Table 2 below.

HIL
(Thick) HTL1
(Thick) HTL2
(Thick) EML
(Thick) ETL1
(Thick) ETL2
(Thick) HTL2 -One HTL2 -2 Example 1 HIL1
(5 nm) HTM3
(115 nm) HTM6
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 2 HIL1
(5 nm) HTM3
(115 nm) HTM7
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 3 HIL1
(5 nm) HTM3
(115 nm) HTM8
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 4 HIL1
(5 nm) HTM4
(115 nm) HTM6
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 5 HIL1
(5 nm) HTM4
(115 nm) HTM7
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 6 HIL1
(5 nm) HTM4
(115 nm) HTM8
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 7 HIL1
(5 nm) HTM5
(115 nm) HTM6
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 8 HIL1
(5 nm) HTM5
(115 nm) HTM7
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 9 HIL1
(5 nm) HTM5
(115 nm) HTM8
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 10 HIL1
(5 nm) HTM3
(115 nm) HTM6
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 11 HIL1
(5 nm) HTM3
(115 nm) HTM7
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 12 HIL1
(5 nm) HTM3
(115 nm) HTM8
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 13 HIL1
(5 nm) HTM4
(115 nm) HTM6
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 14 HIL1
(5 nm) HTM4
(115 nm) HTM7
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 15 HIL1
(5 nm) HTM4
(115 nm) HTM8
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 16 HIL1
(5 nm) HTM5
(115 nm) HTM6
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 17 HIL1
(5 nm) HTM5
(115 nm) HTM7
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 18 HIL1
(5 nm) HTM5
(115 nm) HTM8
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 19 HIL1
(5 nm) HTM3
(115 nm) HTM6
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 20 HIL1
(5 nm) HTM3
(115 nm) HTM7
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 21 HIL1
(5 nm) HTM3
(115 nm) HTM8
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 22 HIL1
(5 nm) HTM4
(115 nm) HTM6
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 23 HIL1
(5 nm) HTM4
(115 nm) HTM7
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 24 HIL1
(5 nm) HTM4
(115 nm) HTM8
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 25 HIL1
(5 nm) HTM5
(115 nm) HTM6
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 26 HIL1
(5 nm) HTM5
(115 nm) HTM7
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 27 HIL1
(5 nm) HTM5
(115 nm) HTM8
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Comparative Example 1 HIL1
(5 nm) HTM1
(115 nm) HTM2
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Comparative Example 2 HIL1
(5 nm) HTM1
(115 nm) HTM2
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm)

Table 3 shows the driving voltage, efficiency, quantum efficiency, and color coordinates when the applied currents of the devices of Examples 1 to 27 and Comparative Examples 1 and 2 were 20 mA .

j0 = 20mA Voltage (V) Cd / A QE CIE_x CIE_y Example 1 4.42 60.1 46.5 0.680 0.315 Example 2 4.43 59.2 47.6 0.682 0.311 Example 3 4.41 60.8 46.8 0.681 0.316 Example 4 4.4 59.8 47.1 0.680 0.315 Example 5 4.52 61.1 46.9 0.680 0.315 Example 6 4.51 60.8 47.2 0.682 0.315 Example 7 4.43 58.9 46.2 0.680 0.317 Example 8 4.45 59.9 47.2 0.680 0.315 Example 9 4.5 60.3 48.2 0.680 0.315 Example 10 4.33 64.2 49.2 0.680 0.315 Example 11 4.32 65.5 53.6 0.680 0.315 Example 12 4.35 63.5 51.2 0.680 0.315 Example 13 4.31 62.8 50.9 0.681 0.314 Example 14 4.29 63.8 52.8 0.680 0.315 Example 15 4.33 62.8 51.9 0.680 0.315 Example 16 4.32 62.8 50.8 0.680 0.315 Example 17 4.32 63.1 53.1 0.682 0.313 Example 18 4.38 62.5 52.7 0.680 0.315 Example 19 4.31 63.5 50.9 0.680 0.315 Example 20 4.29 63.4 54.2 0.680 0.315 Example 21 4.35 63.8 52.1 0.683 0.317 Example 22 4.33 62.8 53.5 0.682 0.315 Example 23 4.33 63.8 53.4 0.680 0.315 Example 24 4.32 62.8 52.9 0.680 0.316 Example 25 4.34 62.9 53.1 0.680 0.315 Example 26 4.31 62.5 54.1 0.680 0.315 Example 27 4.3 63 54.2 0.681 0.316 Comparative Example 1 4.62 56.5 42.2 0.680 0.315 Comparative Example 2 4.59 57.3 43.5 0.680 0.315

&Lt; Example 28 >

HTM3 was thermally vacuum deposited on the anode prepared as in Example 1 to a thickness of 100 Å to form a hole injection layer <HIL> , but the compound HIL2 was doped with a doping concentration of 5%. That was formed on the material of HTM3 of transporting holes and then the hole-controlling layer -1 <HTL2 -1> to HTM6 (950Å) was vacuum-deposited to form a hole transport layer <HTL1> 1150Å in thickness. Subsequently, host H1 and dopant D1 (2 wt%) were vacuum-deposited to a thickness of 360 Å to form a light emitting layer <EML> . ETM1 was then deposited as electron control layer < ETL1 > to form electron transport layer < ETL2 > with compounds ETM2 and Liq and 7: 3 (250 ANGSTROM). Subsequently the 50Å magnesium and lithium fluoride (LiF) having a thickness of the cathode after forming the film by an electron injection layer <EIL> magnesium and silver (1: 4) was formed to a 200Å CPL1 thus completing an element by depositing 600 Å.

&Lt; Example 29 >

The same experiment was conducted except that HTM7 was used instead of HTM6 as the hole-regulating layer-1 in Example 28. [

&Lt; Example 30 >

The same experiment was conducted except that HTM8 was used instead of HTM6 as the hole control layer-1 in Example 28. [

&Lt; Example 31 >

In Example 28, HTM4 was used instead of HTM3 as the hole injecting layer and the hole transporting layer.

&Lt; Example 32 >

The same experiment was carried out except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 31.

&Lt; Example 33 >

The same experiment was conducted except that HTM8 was used instead of HTM6 as the hole control layer-1 in Example 31. [

&Lt; Example 34 >

The same experiment was performed as in Example 28 except that HTM5 was used instead of HTM3 as the hole injecting layer and the hole transporting layer.

&Lt; Example 35 >

The same experiment was conducted except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 34. [

&Lt; Example 36 >

The same experiment was carried out except that HTM8 was used instead of HTM6 as the hole control layer-1 in Example 34.

&Lt; Example 37 >

HIL3 was doped with a doping concentration of 5% to form a hole injection layer < HIL & gt; by thermally vacuum depositing HTM3 to a thickness of 100 ANGSTROM on the prepared anode as in Example 1, and HTM3, which is a hole transporting material, HTM9 the vacuum-deposited to form a hole transport layer was 1150Å <HTL1> hole adjustment in the following layers -1 <HTL2 -1> to HTM6 (800Å), on the hole in the control layer -2 <HTL2 -2> (150Å) Respectively. Subsequently, host H1 and dopant D1 (2 wt%) were vacuum-deposited to a thickness of 360 Å to form a light emitting layer <EML> . ETM1 was then deposited as electron control layer < ETL1 > to form electron transport layer < ETL2 > with compounds ETM2 and Liq and 7: 3 (250 ANGSTROM). A 50 Å thick layer of magnesium and lithium fluoride (LiF) was deposited as an electron injection layer (EIL ), followed by 200 Å of magnesium and silver (1: 4) as a cathode, followed by deposition of 600 Å of CPL1. .

&Lt; Example 38 >

The same experiment was conducted except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 37. [

&Lt; Example 39 >

The same experiment was conducted except that HTM8 was used instead of HTM6 as the hole control layer-1 in Example 37.

&Lt; Example 40 >

The same experiment was conducted as in Example 37 except that HTM4 was used instead of HTM3 as the hole injecting layer and the hole transporting layer.

&Lt; Example 41 >

The same experiment was carried out except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 40. [

&Lt; Example 42 >

The same experiment was conducted except that HTM8 was used instead of HTM6 as the hole-regulating layer-1 in Example 40. [

&Lt; Example 43 >

The same experiment was performed as in Example 37 except that HTM5 was used instead of HTM3 as the hole injecting layer and the hole transporting layer.

&Lt; Example 44 >

The same experiment was conducted except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 43.

&Lt; Example 45 >

The same experiment was conducted except that HTM8 was used instead of HTM6 as the hole control layer-1 in Example 43.

&Lt; Example 46 >

The same experiment was conducted except that HTM10 was used instead of HTM9 as the hole control layer-2 in Example 37.

&Lt; Example 47 >

The same experiment was carried out except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 46.

&Lt; Example 48 >

Except that HTM8 was used instead of HTM6 as the hole-regulating layer-1 in Example 46. [

&Lt; Example 49 >

In Example 46, HTM4 was used instead of HTM3 as the hole injecting layer and the hole transporting layer.

&Lt; Example 50 >

The same experiment was carried out except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 49.

&Lt; Example 51 >

The same experiment was conducted except that HTM8 was used instead of HTM6 as the hole-regulating layer-1 in Example 49.

< Example  52>

Except that HTM5 was used instead of HTM3 as the hole injecting layer and the hole transporting layer in Example 46. [

< Example  53>

The same experiment was conducted except that HTM7 was used instead of HTM6 as the hole control layer-1 in Example 52. [

< Example  54>

The same experiment was conducted except that HTM8 was used instead of HTM6 as the hole-regulating layer-1 in Example 52. [

< Comparative Example  3>

Except that HTM1 was used instead of HTM3 as the hole transport layer in Example 28 and HTM2 was used in place of HTM6 as the hole control layer-1

< Comparative Example  4>

The same experiment was conducted except that HTM9 was formed as the hole-adjusting layer-2 between the hole-adjusting layer-1 and the light-emitting layer in Comparative Example 3

The thicknesses of the organic layers of the devices of Examples 28 to 54 and Comparative Examples 3 and 4 are shown in Table 4 below.

HIL
(Thick) HTL1
(Thick) HTL2
(Thick) EML
(Thick) ETL1
(Thick) ETL2
(Thick) HTL2-1 HTL2-2 Example 28 HTM3: HIL2 (3%)
(10 nm) HTM3
(115 nm) HTM6
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 29 HTM3: HIL2 (3%)
(10 nm) HTM3
(115 nm) HTM7
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 30 HTM3: HIL2 (3%)
(10 nm) HTM3
(115 nm) HTM8
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 31 HTM4: HIL2 (3%)
(10 nm) HTM4
(115 nm) HTM6
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 32 HTM4: HIL2 (3%)
(10 nm) HTM4
(115 nm) HTM7
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 33 HTM4: HIL2 (3%)
(10 nm) HTM4
(115 nm) HTM8
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 34 HTM5: HIL2 (3%)
(10 nm) HTM5
(115 nm) HTM6
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 35 HTM5: HIL2 (3%)
(10 nm) HTM5
(115 nm) HTM7
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 36 HTM5: HIL2 (3%)
(10 nm) HTM5
(115 nm) HTM8
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 37 HTM3: HIL2 (3%)
(10 nm) HTM3
(115 nm) HTM6
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 38 HTM3: HIL2 (3%)
(10 nm) HTM3
(115 nm) HTM7
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 39 HTM3: HIL2 (3%)
(10 nm) HTM3
(115 nm) HTM8
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 40 HTM4: HIL2 (3%)
(10 nm) HTM4
(115 nm) HTM6
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 41 HTM4: HIL2 (3%)
(10 nm) HTM4
(115 nm) HTM7
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 42 HTM4: HIL2 (3%)
(10 nm) HTM4
(115 nm) HTM8
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 43 HTM5: HIL2 (3%)
(10 nm) HTM5
(115 nm) HTM6
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 44 HTM5: HIL2 (3%)
(10 nm) HTM5
(115 nm) HTM7
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 45 HTM5: HIL2 (3%)
(10 nm) HTM5
(115 nm) HTM8
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 46 HTM3: HIL2 (3%)
(10 nm) HTM3
(115 nm) HTM6
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 47 HTM3: HIL2 (3%)
(10 nm) HTM3
(115 nm) HTM7
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 48 HTM3: HIL2 (3%)
(10 nm) HTM3
(115 nm) HTM8
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 49 HTM4: HIL2 (3%)
(10 nm) HTM4
(115 nm) HTM6
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 50 HTM4: HIL2 (3%)
(10 nm) HTM4
(115 nm) HTM7
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 51 HTM4: HIL2 (3%)
(10 nm) HTM4
(115 nm) HTM8
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 52 HTM5: HIL2 (3%)
(10 nm) HTM5
(115 nm) HTM6
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 53 HTM5: HIL2 (3%)
(10 nm) HTM5
(115 nm) HTM7
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Example 54 HTM5: HIL2 (3%)
(10 nm) HTM5
(115 nm) HTM8
(80 nm) HTM10
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Comparative Example 3 HTM1: HIL2 (3%)
(10 nm) HTM1
(115 nm) HTM2
(95 nm) - H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm) Comparative Example 4 HTM1: HIL2 (3%)
(10 nm) HTM1
(115 nm) HTM2
(80 nm) HTM9
(15 nm) H1 (98%): D1 (2%)
(36 nm) ETM1
(5 nm) ETM2 (70%): Liq (30%)
(25 nm)

The driving voltage, efficiency, quantum efficiency and color coordinates when the applied currents of the devices of Examples 28 to 54 and Comparative Examples 3 and 4 were 20 mA are shown in Table 5 below.

j0 = 20mA Voltage (V) Cd / A QE CIE_x CIE_y Example 28 4.41 61.1 47.5 0.680 0.315 Example 29 4.39 60.2 48.2 0.682 0.311 Example 30 4.38 60.1 48.3 0.681 0.316 Example 31 4.4 59.8 48.2 0.680 0.315 Example 32 4.39 60.5 48.1 0.680 0.315 Example 33 4.42 59.8 47.9 0.682 0.315 Example 34 4.44 59.9 48.3 0.680 0.317 Example 35 4.35 60.1 48.3 0.680 0.315 Example 36 4.37 61.3 49.2 0.680 0.315 Example 37 4.31 62 50.1 0.680 0.315 Example 38 4.29 62.2 54.3 0.680 0.315 Example 39 4.33 61.8 52.3 0.680 0.315 Example 40 4.28 62.9 51.2 0.681 0.314 Example 41 4.21 63 51.1 0.680 0.315 Example 42 4.39 62.8 53.2 0.680 0.315 Example 43 4.27 63.8 51.3 0.680 0.315 Example 44 4.28 62.4 52.8 0.682 0.313 Example 45 4.31 63.1 53 0.680 0.315 Example 46 4.35 62.9 52.3 0.680 0.315 Example 47 4.28 63.8 55.4 0.680 0.315 Example 48 4.21 63.8 53.5 0.683 0.317 Example 49 4.2 62.7 54 0.682 0.315 Example 50 4.39 63.8 54.2 0.680 0.315 Example 51 4.18 63.7 53.8 0.680 0.316 Example 52 4.28 62.7 54.7 0.680 0.315 Example 53 4.33 63.8 55.1 0.680 0.315 Example 54 4.28 63.7 55.3 0.681 0.316 Comparative Example 3 4.61 57.2 43.3 0.680 0.315 Comparative Example 4 4.57 58.2 45.4 0.680 0.315

Through the examples and the comparative examples, it has been found that the combination described in the claims of the present invention has a strong point in driving devices particularly in the red organic light emitting device.

100: substrate
101: anode
201: first organic layer
202: second organic layer
401: light emitting layer
401: cathode
501: electron transport layer
502: electron injection layer

Claims (12)

Cathode; Anode; A light emitting layer provided between the cathode and the anode; A hole transport layer provided between the anode and the light emitting layer, the hole transport layer comprising a compound represented by the following formula (1); And at least one hole-transporting layer provided between the hole transporting layer and the light-emitting layer and in contact with the hole transporting layer, the hole-transporting layer including at least one of a compound represented by the following Chemical Formula 2, a compound represented by the following Chemical Formula 3, An organic light emitting device comprising:
[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

In formulas (1) to (4)
La to Lg and L1 to L9 are the same or different from each other and each independently represents a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted carbazolylene group; D1, e1, f1, g1, h1, i1, c, d, e, f, l, r, s, w and v are each independently an integer of 0 to 3, or a substituted or unsubstituted heteroarylene group, And when they are each 2 or more, the structures in parentheses are the same or different from each other,
Ar 3 and Ar 4 are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group, or Ar3 and Ar4 are bonded to each other to form a monocyclic or polycyclic aromatic or aliphatic substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring,
Ar 1 and Ar 1, Ar 2, Ar 5 and Ar 6 are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group, or Arb and Are; Arc and Ard; Ar1 and Ar2; Ar5 and Ar6; Arb and Lb; Ar2 and L9; Ar5 and L5; Or Ar4 and L8 are bonded to each other to form a monocyclic or polycyclic aromatic or aliphatic substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring,
Arb and Are; And Ar and Ard are bonded to each other to form a monocyclic or polycyclic aromatic or aliphatic substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle, the Lb and Lg are not a direct bond,
R21 is hydrogen,
R22, and R1 to R13 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight or branched chain alkyl group, a substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group Or adjacent groups may combine with each other to form a monocyclic or polycyclic aromatic or aliphatic substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring, and at least one of the above-mentioned alkyl, alkoxy or thioalkyl groups An adjacent CH ₂ group may be replaced by SiRR ', C═NR ₂ , P (═O) R, SO, SO ₂ , NR, O, S or CONR, g is an integer from 0 to 5, h, i, j, m, n and o are 0 to 4 It is an integer, b1, b, p, and k is an integer of 0 to 3,
k1 is 0,
a1 + k1 is 4 or less and the structures in parentheses are the same or different when g, a1, a, h, i, j, m, n, o, b1, b, p,
R, R 'and R "are the same or different and each independently hydrogen, deuterium, halogen, nitrile, substituted or unsubstituted straight-chain alkyl, alkoxy or thioalkyl, substituted or unsubstituted branched or A substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted aralkyl group, Or adjacent groups are bonded to each other to form a monocyclic or polycyclic aromatic or aliphatic hydrocarbon ring or a heterocyclic ring. delete The organic light emitting diode according to claim 1, wherein the hole adjusting layer and the light emitting layer are in contact with each other. The organic light emitting diode according to claim 1, wherein the hole adjusting layer comprises a first hole adjusting layer and a second hole adjusting layer. The organic electroluminescent device according to claim 1, wherein Arb to Are and Ar1 to Ar6 are the same or different from each other and are selected from the following structural formulas:

In the above structural formulas, R, R 'and R "represent hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted branched or cyclic alkyl group , A substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group. An organic light-emitting device according to claim 1, wherein at least one of -NArbAre, -NArcArd, -NAr1Ar2, -NAr3Ar4, and -NAr5Ar6 is represented by the following structural formula A:
[Structural Formula A]

In the above formula,
Xa is CRbRd; NRc; O; Or S, y is 0 or 1, and when y is 0, the two carbons bound to Xa are directly bonded,
Ra to Rd are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight or branched chain alkyl group, a substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group, and x is an integer of 0 to 8 And when x is 2 or more, R a are the same or different from each other, and R, R 'and R "are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group. The organic electroluminescent device according to claim 1, wherein at least one of - (L9) v-NAr1Ar2, - (L5) 1-NAr5Ar6, and - (L8) w-
[Structural formula B]

In the above formula,
Xb is CRbRd; NRc; O; Or S, y is 0 or 1, and when y is 0, two carbons bonded to Xb are directly bonded,
L11 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, z is an integer of 0 to 3, and when z is 2 or more, L11 is the same or different,
Ar9 represents a substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group,
Rb to Re are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight or branched chain alkyl group, a substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group, z 'is 0 to 7 R &lt; e &gt; and R &quot; are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group. The compound according to claim 1, wherein La to Lg and L1 to L9 are the same or different from each other, and are each independently a direct bond; Or an organic electroluminescent element selected from the following structural formulas:

In the above structural formulas, R111 to R118 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight or branched chain alkyl group, a substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group, and R, R 'and R " Are the same or different and are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted straight-chain alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted branched or cyclic alkyl group, an alkoxy group or a thioalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted fluorenyl group. The organic electroluminescent device according to claim 1, wherein the formula (1) is selected from the following specific examples:

The organic electroluminescent device according to claim 1, wherein the formula (2) is selected from the following specific examples:

The organic electroluminescent device according to claim 1, wherein the formula (3) is selected from the following specific examples:

The organic electroluminescent device according to claim 1, wherein the formula (4) is selected from the following specific examples:

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