KR101461344B1 - New compound and organic light emitting device using the same - Google Patents

Abstract

The present invention relates to a compound represented by the following formula (1) and an organic light emitting device using the compound. The novel compound of the present invention can greatly improve the lifetime, efficiency, electrochemical stability, and thermal stability of the organic light emitting device.
[Chemical Formula 1]

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a novel organic light emitting diode (OLED)

The present invention relates to a novel compound capable of greatly improving lifetime, efficiency, electrochemical stability and thermal stability of an organic light emitting device, and an organic light emitting device in which the compound is contained in an organic compound layer.

The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is as follows. When an organic layer is positioned between an anode and a cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. Electrons and holes injected into the organic layer are recombined to form an exciton, and the exciton falls back to the ground state to emit light. An organic light emitting device using such a principle may be generally composed of an organic material layer including a cathode, an anode and an organic material layer disposed therebetween, for example, a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer.

As a material used in an organic light emitting device, a pure organic material or a complex in which an organic material and a metal form a complex is mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material that is easily oxidized and electrochemically stable at the time of oxidation is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable form in oxidation and in a reduced state is preferable, and a material having a high luminous efficiency for converting an exciton into light desirable.

In addition to the above, it is preferable that the material used in the organic light emitting device further has the following properties.

In order to obtain a highly efficient organic light emitting device capable of driving at a low voltage, holes or electrons injected into the organic light emitting element must be smoothly transferred to the light emitting layer, and injected holes and electrons should not escape from the light emitting layer. For this purpose, the material used in the organic light emitting device should have an appropriate band gap and a HOMO or LUMO energy level. Alq3, which is mainly used as an electron transport layer material, does not have a sufficiently high HOMO energy level, and it is difficult to manufacture a process and an organic light emitting device because a BAlq layer having a relatively high HOMO energy level should be used.

In addition, materials used in organic light emitting devices should have excellent chemical stability, charge mobility, and interface characteristics with electrodes or adjacent layers. That is, the material used in the organic light emitting device should have little deformation of the material due to moisture or oxygen. In addition, by having appropriate hole or electron mobility, it is necessary to maximize the formation of excitons by balancing the density of holes and electrons in the light emitting layer of the organic light emitting device. And, for the stability of the device, the interface with the electrode including the metal or the metal oxide should be good.

Accordingly, there is a continuing need in the art for the development of organic materials having the above-mentioned requirements.

SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems of the prior art, and it is an object of the present invention to satisfy the conditions required for a material usable in an organic light emitting device, for example, appropriate energy level, electrochemical stability, And a hetero-compound derivative having a chemical structure capable of playing various roles required in an organic light-emitting device according to a substituent, and an organic light-emitting device including the same.

According to one aspect of the present invention, there is provided a compound represented by Formula 1 below.

[Chemical Formula 1]

Wherein at least one of R ₇ and R ₁ , R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₄ and R ₅ , R ₅ and R _6, and R ₆ and R ₇ The paired anion forms an aliphatic or hetero condensation ring.

Also, each of R ₁ to R ₇ , which does not form an aliphatic or heterocyclic ring, is independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl A C _{1 -50} alkyl group substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group and an acetylene group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl an alkoxy group an alkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, and a substituted or unsubstituted C _{1 -40} with at least one substituent selected from the group consisting of an acetylene ring; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted aryl group, A C _2-50 alkenyl group which is substituted or unsubstituted with at least one substituent selected from the group consisting of a substituted heterocyclic group, a nitrile group and an acetylene group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted A substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, a silane group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted bis (spirobifluorenyl) group, hwandoen carbazolyl group, an aryl group, a substituted or unsubstituted germanium group, and a substituted or unsubstituted C _{6 -60} ring with one or more substituents selected from the group consisting of an acetylene ring; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted N, S or P, which is unsubstituted or substituted by one or more substituents selected from the group consisting of a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group and an acetylene group, heterocyclic group having a C _{3 -60;} A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted arylalkyl group, or a substituted or unsubstituted arylalkenyl group An amine group substituted with at least one substituent selected from the group; A halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl A fluorenyl group which is substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group and an alkenyl group; A halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl A bis (spirobifluorenyl) group substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group, and an alkenyl group; A halogen atom, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, A carbazolyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group; A nitrile group; Cyano; A nitro group; Amide group; An ester group; A silane group and a germanium group.

According to another aspect of the present invention, there is provided an organic electronic device including the compound in an organic material layer.

The compound of the present invention can be used as an electron injecting material, an electron transporting material, a light emitting material, a hole injecting material and a hole transporting material in an organic light emitting device. When this compound is used for an organic light emitting device, The light efficiency is improved, and the lifetime characteristics of the device can be improved by the thermal stability of the compound.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.
2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

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

One aspect of the present invention relates to a compound represented by the above formula (1).

The compounds represented by the formula (1) include compounds represented by the following formulas (2) and (3), but are not limited thereto.

       [Chemical Formula 2] < EMI ID =

In Formula 2 or Formula 3, R ₈ to R ₃₁ are each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl A C _{1 -50} alkyl group substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group and an acetylene group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl an alkoxy group an alkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, and a substituted or unsubstituted C _{1 -40} with at least one substituent selected from the group consisting of an acetylene ring; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted aryl group, hwandoen heterocyclic group, an alkenyl group of a nitrile group and a substituted or unsubstituted C _{2 -50} with one or more substituents selected from the group consisting of an acetylene; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted A substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, a silane group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted bis (spirobifluorenyl) group, hwandoen carbazolyl group, an aryl group, a substituted or unsubstituted germanium group, and a substituted or unsubstituted C _{6 -60} ring with one or more substituents selected from the group consisting of an acetylene ring; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted N, S or P, which is unsubstituted or substituted by one or more substituents selected from the group consisting of a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group and an acetylene group, heterocyclic group having a C _{3 -60;} A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted arylalkyl group, or a substituted or unsubstituted arylalkenyl group An amine group substituted with at least one substituent selected from the group; A halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl A fluorenyl group which is substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group and an alkenyl group; A halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl A bis (spirobifluorenyl) group substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group, and an alkenyl group; A halogen atom, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, A carbazolyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group; A nitrile group; Cyano; A nitro group; Amide group; An ester group; A silane group and a germanium group, wherein they may form an aliphatic or hetero condensation ring with adjacent groups.

The present invention also includes, but is not limited to, compounds represented by the following general formula (4).

[Chemical Formula 4]

In Formula 4, n is an integer of 0 to 5,

A ₁ and A ₂ are the same or different and are each independently a substituent represented by one of R ₁ to R ₇ in the above formula (1) as a linking group, and in formula (2), one of R ₈ to R ₁₈ is a linking group And a substituent represented by the formula (3) in which one of R ₁₉ to R ₃₁ is a linking group,

Y is a simple bond; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl alkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, and substituted by one or more substituents selected from the group consisting of an acetylene or unsubstituted alkylene group of C _{1 -50;} A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted aryl group, hwandoen heterocyclic group, a nitrile group, and a substituted or unsubstituted C _{2 -50} with one or more substituents selected from the group consisting of an acetylene alkenylene group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted A C _{6 -60} arylene group which is substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group, an arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group and an acetylene group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted N, S or P, which is unsubstituted or substituted by one or more substituents selected from the group consisting of a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group and an acetylene group, A divalent heterocyclic group of C _{3 - 60} ; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted arylalkyl group, or a substituted or unsubstituted arylalkenyl group A divalent amine group substituted with a substituent selected from the group; A halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl A fluorenylene group substituted or unsubstituted with at least one substituent selected from the group consisting of a halogen atom and an alkenyl group; A halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl A bis (spirobifluorenylene) group substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group and an alkenyl group; A halogen atom, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, A silane group and a germanium group substituted or unsubstituted with at least one substituent selected from the group consisting of a substituted or unsubstituted heterocyclic group, a nitrile group and an acetylene group,

When n is 2 or more, each Y may be the same or different.

The present invention also includes, but is not limited to, compounds represented by the following general formula (5).

[Chemical Formula 5]

In Formula 5, m is an integer of 1 to 5,

B ₁ to B ₃ are the same or different and each independently represents a substituent represented by one of R ₁ to R ₇ in the above formula (1) as a linking group, and one of R ₈ to R ₁₈ in the above formula And a substituent represented by the formula (3) in which one of R ₁₉ to R ₃₁ is a linking group, and X is selected from the group consisting of deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group , A substituted or unsubstituted alkoxy 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 nitrile group and an acetylene group A divalent or trivalent alkyl group of C _{1 -50} substituted or unsubstituted with at least one substituent selected from A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted aryl group, A divalent or trivalent alkenyl group of C _{2 -50} substituted or unsubstituted with at least one substituent selected from the group consisting of a substituted heterocyclic group, a nitrile group and an acetylene group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted A divalent or trivalent C _{6 -60} substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group, an arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group and an acetylene group, An aryl group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted N, S or P, which is unsubstituted or substituted by one or more substituents selected from the group consisting of a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group and an acetylene group, A divalent or trivalent heterocyclic group having _{3 to 60 carbon atoms} ; An amine group; A halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl A divalent or trivalent fluorenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group and an alkenyl group; A halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl A divalent or trivalent bis (spirobifluorenyl) group substituted or unsubstituted with at least one substituent selected from the group consisting of a halogen atom and an alkenyl group; A halogen atom, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, A bivalent or trivalent carbazole group substituted or unsubstituted with at least one substituent selected from the group consisting of a halogen atom, a heterocyclic group, a nitrile group and an acetylene group; A silane group and a germanium group,

When n is 2 or more, each Y may be the same or different.

The substituents of the above formulas 1 to 5 will be described in detail as follows.

The number of carbon atoms of the alkyl group, alkylene group and alkoxy group in the above Chemical Formulas 1 to 5 is not particularly limited, but is preferably 1-50, and more preferably 1-40.

The number of carbon atoms of the alkenyl group, alkenylene group, acetyl group and acetylene group in the above Chemical Formulas 1 to 5 is not particularly limited, but is preferably 2-50, more preferably 2-40.

The number of carbon atoms of the aryl group and the arylene group in the general formulas (1) to (5) is not particularly limited, but is preferably 6-60, more preferably 6-50.

The number of carbon atoms of the heterocyclic group of the above formulas (1) to (5) is not particularly limited, but is preferably 3-60, more preferably 3-50, and O, N, S or P as a heteroatom .

In addition, the number of carbon atoms of the arylalkyl group of the formulas (1) to (5) is not particularly limited, but is preferably 7-50, and more preferably 7-40.

In addition, the number of carbon atoms of the arylalkenyl group of the above general formulas (1) to (5) is not particularly limited, but is preferably 7-50, and more preferably 7-40.

In addition, the number of carbon atoms of the arylamine group of the above formulas (1) to (5) is not particularly limited, but is preferably 6-50, more preferably 6-40.

Unless otherwise specified in the above Chemical Formulas 1 to 5, the term "substituted or unsubstituted" means a group selected from the group consisting of halogen, alkyl, alkenyl, alkoxy, aryl, arylalkyl, arylalkenyl, heterocyclic, , A fluorenyl group, a nitrile group, and an acetylene group, but is not limited thereto.

The length of the alkyl group contained in the compound does not affect the conjugation length of the compound, but may additionally affect the application of the compound to an organic light emitting device, for example, a vacuum deposition method or a solution coating method.

The substituents of the above formulas (1) to (5) will be described in more detail as follows.

In the general formulas (1) to (5), R ₁ to R ₃₁ each independently represent hydrogen; heavy hydrogen; halogen; An alkyl group having _{1 to 50 carbon} atoms; A C _{1 -50} alkoxy group; An alkenyl group having _{2 to 50} carbon atoms; An acetyl group of C _{2 -50} ; Alkyl group of C _{1 -40,} substituted or unsubstituted C _{6 -60} aryl amine group, a substituted or an aryl group, a substituted or unsubstituted C _{6 -60} aryl group, a substituted or unsubstituted C _{7 -50} the ring A heterocyclic group having _{3 to 40} carbon atoms having O, N, S or P as a hetero atom, a nitrile group, a silane group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted bis (spirobifluorenyl) An unsubstituted C ₆ -C ₆₀ aryl group substituted or unsubstituted with at least one substituent selected from the group consisting of unsubstituted carbazolyl groups; An aryl group or a heteroatom in the C _{6 -12} O, N, S or a heterocyclic group of C _{3 -60} having a P and unsubstituted or substituted with a C _{3 -60} with O, N, S or P as heteroatoms A heterocyclic group; An arylalkyl group of C _{7 -50} ; An arylalkenyl group having _{8 to 50} carbon atoms; C _{6 -50} arylamine groups; C _{6 -12} aryl group or a heteroatom group O, N, S, or C _{3 -60} a substituted or unsubstituted heterocyclic group having a carbazolyl of P; Alkyl group of C _{1 -40,} an aryl group or a heteroatom in the C _{6 -12} O, N, S or P _{3 -60} C a substituted or unsubstituted heterocyclic group of the fluorenyl group having; And a nitrile group.

In the above formulas (1) to (5), preferred _examples of the aryl group as R ₁ to R ₃₁ include monocyclic aromatic and naphthyl groups such as phenyl group, biphenyl group, terphenyl group and stilbene group, anthracenyl group, phenanthrene group, A perylene group, a perylene group, a fluorene group, and the like, but is not limited thereto.

In the above formulas (1) to (5), the heterocyclic group represented by R ₁ to R ₃₁ is preferably a thiophene group, furan group, pyrrolyl group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, A furyl group, a furyl group, a quinolinyl group, an isoquitolyl group, an acridyl group, and the like, but are not limited thereto.

R ₁ to R ₃₁ are each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, phenyl, biphenyl, terphenyl, stilbene, naphthyl, anthracenyl, phenanthrene, A thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a pyrazinyl group, a quinolinyl group, an iso An acridinyl group, a methoxy group, an ethoxy group, a carbazolyl group, and the following substituent groups, but is not limited thereto.

The compounds represented by the formulas (1) to (5) are preferably represented by one of the following formulas (1) to (82), but the present invention is not limited thereto.

The general method for preparing the compound represented by the formula (1) is as follows.

Substituted or unsubstituted 2'-iodoacetophenone and substituted or unsubstituted phenylhydrazine to form an imine, and then an iodine-substituted indole derivative is synthesized through a cyclization reaction. The substituent containing acetylene may be introduced through Suzuki reaction and the cyclization reaction may be repeated to synthesize the compound represented by Formula 1 above.

Those skilled in the art will readily prepare the compound represented by Formula 1 with reference to the above general production method and the examples of the present specification.

A second aspect of the present invention is an organic electronic device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, To 5 < RTI ID = 0.0 >. ≪ / RTI >

The compounds of formulas (1) to (5) may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic electroluminescent device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers includes the compound of the present invention, i.e., the compounds of the above formulas 1 to 5.

The organic material layer of the organic electroluminescent device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.

That is, in the organic electric device, the organic material layer includes an electron injection layer and an electron transport layer, and the electron injection layer and the electron transport layer may include the compounds represented by the above Chemical Formulas 1 to 5.

In addition, the organic layer may include a light emitting layer, and the light emitting layer may include the compounds represented by the general formulas (1) to (5).

The organic material layer may include a hole injection layer and a hole transport layer, and the hole injection layer and the hole transport layer may include the compounds represented by the above general formulas (1) to (5).

For example, the organic electroluminescent device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic electric device is not limited thereto and may include a smaller number of organic layers.

The organic electroluminescent device may be selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

In the organic electroluminescent device, the organic material layer may include an electron transporting layer, and the electron transporting layer may include a compound represented by the above Chemical Formulas 1 to 5, or a compound into which a thermosetting or photo-curable functional group is introduced.

In the organic electroluminescent device, the light emitting layer may include a compound represented by the general formulas (1) to (5), or a compound into which a thermosetting or photo-curable functional group is introduced.

The organic electroluminescent device of the present invention can be manufactured, for example, by sequentially laminating a first electrode, an organic material layer and a second electrode on a substrate. In this case, a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation may be used, but the present invention is not limited to these methods.

The preparation of the compounds of the formulas (1) to (5) and the preparation of the organic light emitting device using them will be described in detail in the following Preparation Examples and Examples. However, the following Preparation Examples and Examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Example

PREPARATION EXAMPLE 1 Preparation of the compound represented by formula 3

Preparation of Structural Formula 3A

2'-iodoacetophenone (20 mL, 140.0 mmol) and phenylhydrazine (16.6 g, 153.8 mmol) were added to ethanol (150 mL) and glacial acetic acid (50 mL), and the mixture was heated with stirring for 5 hours. The resulting solid was filtered, washed with ethanol (50 mL), and vacuum dried to obtain the structural formula 3A (41 g, yield 87%).

MS: [M + H] < ⁺ > = 337

Preparation of formula 3B

Phosphorous pentoxide (36.4 g, 256.1 mmol) was added to methanesulfonic acid (500 mL), and the mixture was stirred at 80 째 C until phosphorus pentoxide completely dissolved. The structural formula 3A (41 g, 121.9 mmol) was slowly added, stirred at 90 ° C for 3 hours, and cooled to room temperature. The reaction solution was added to an aqueous sodium hydroxide solution at 0 ° C and stirred for 10 minutes, and the resulting solid was filtered. Washed with distilled water and dried in vacuo to give structural formula 3B (31.4 g, 80% yield).

MS: [M + H] < ⁺ > = 320

Preparation of Structural Formula 3C

PdCl ₂ (PPh ₃ ) ₂ (3.3 g, 4.7 mmol) and copper (I) iodide (895 mg, 4.7 mmol) were dissolved in a mixture of triethylsilyl acetylene (20 mL, 140.1 mmol) Was added to ethylamine (250 mL), and the mixture was stirred at room temperature for 3 hours. The reaction solution was diluted with ethyl acetate, the reaction was terminated with an aqueous ammonium chloride solution, and the water layer was removed. The organic layer was concentrated, and then recrystallized with n-hexane to obtain the structural formula 3C (17.8 g, yield 65%).

MS: [M + H] < ⁺ > = 290

Manufacture of structural formula 3D

The structural formula 3C (17.8 g, 61.5 mmol) was dissolved in methanol, followed by the addition of an excessive amount of potassium carbonate, and the mixture was stirred at room temperature for 3 hours. The reaction solution was extracted with ethyl ether, and the organic layer was collected and washed with water. The water layer was discarded and the organic layer was concentrated and recrystallized with n-hexane to obtain structural formula 3D (13.2 g, yield 99%).

MS: [M + H] < ⁺ > = 218

Preparation of formula 3E

The structural formula 3D (13 g, 60.8 mmol) and platinum chloride (PtCl ₂ ) (809 mg, 3.0 mmol) were added to toluene (150 mL) and the mixture was heated and stirred for 24 hours. The temperature was lowered to room temperature, the solvent of the reaction mixture was concentrated, and 3E (5.1 g, yield 39%) was obtained through column purification.

MS: [M + H] < ⁺ > = 218

Preparation of Structural Formula 3F

The structure 3E (5 g, 23.0 mmol) was completely dissolved in chloroform (250 mL), and the temperature was lowered to 0 째 C and bromine (1.2 mL, 23.0 mmol) was slowly added. After stirring for 20 minutes, the reaction solution was slowly poured into ice water and stirred for 5 minutes. The resulting solid was filtered and purified by column chromatography to obtain the structural formula 3F (5.1 g, yield 75%).

MS: [M +] < ⁺ & gt ^; = 296

Manufacture of structural formula 3G

4-Chlorophenylboronic acid (3.2 g, 20.3 mmol) was heated in tetrahydrofuran (100 ml) to completely dissolve it. Then, 2 ml of an aqueous potassium carbonate solution (100 ml) was added, and Pd PPh _{3) 4} (put ^{195 mg, 1.7 x 10 -1 mmol} ) was stirred under heating for 5 hours. After lowering the temperature to room temperature, the water layer was removed and the resulting solid was filtered. The filtered solid was recrystallized from ethanol to give structural formula 3G (4.7 g, 85% yield).

MS: [M + H] < ⁺ > = 328

Preparation of the formula 3H

Carbazole (10 g, 119.6 mmol), 4-bromoiodobenzene (37.2 g, 131.6 mmol) and potassium carbonate (24.5 g, 179.4 mmol) were placed in toluene (500 mL) and the mixture was heated with stirring for 30 minutes. Copper (I) iodide (1.1 g, 6 mmol) and N, N'-dimethylethylenediamine (1.3 mL, 12.0 mmol) were added and the mixture was heated and stirred for 24 hours. The temperature was lowered to room temperature, and the reaction solution was filtered and concentrated on a celite pad, and then recrystallized with ethanol to obtain a structural formula 3H (31.1 g, yield 81%).

MS: [M < ⁺ >] ⁺ = 322

Preparation of formula III

Dissolving the compound of formula 3H (20 g, 62.1 mmol), bis (pinacolato) diboron (17.3 g, 68.3 mmol) and potassium acetate (18.3 g, 286.3 mmol) in dioxane C, Pd (dppf) Cl ₂ (507 mg, 0.6 mmol) was added, and the mixture was heated and stirred for 12 hours. After cooling the reaction solution to room temperature, distilled water (200 mL) was added and extracted with methylene chloride (200 mL x 3). The organic layer was concentrated and recrystallized from ethanol to give structural formula 3I (18.4 g, 80%).

MS: [M + H] < ⁺ > = 370

Preparation of Structural Formula 3

Structure 3G (4 g, 12.2 mmol), and Structural Formula 3I (5.0 g, 13.4 mmol) the tetrahydrofuran was completely dissolved by heating on (100 ml), 2 M was added to 100 ml aqueous solution of potassium carbonate and Pd (PPh _{3) 4} (141 mg, 1.2 x 10 ^-1 mmol) were added thereto, and the mixture was heated with stirring for 5 hours. After lowering the temperature to room temperature, the water layer was removed and the resulting solid was filtered. The filtered solid was recrystallized from ethyl acetate to give structural formula 3 (4.7 g, yield 72%).

MS: [M + H] < ⁺ > = 535

PREPARATION EXAMPLE 2 Preparation of Compound Represented by Structural Formula 5

Preparation of formula 5A

2,4,6-Trichloro-1,3,5-triazine (15 g, 81.3 mmol) was dissolved in anhydrous tetrahydrofuran (150 mL), the temperature was lowered to -78 ° C and 1 M phenylmagnesium bromide (162.6 mL, 162.6 mmol) was added slowly, and the mixture was stirred at room temperature for 3 hours while slowly warming to room temperature. After adding a 1 N aqueous hydrochloric acid solution (100 mL), the water layer was removed, and the organic layer was concentrated, and then recrystallized with n-hexane to obtain the structural formula 5A (16.9 g, yield 78%).

MS: [M + H] < ⁺ > = 268

Preparation of formula 5B

(10 g, 37.4 mmol) and 4-hydroxyphenylboronic acid pinacol ether (9.9 g, 44.8 mmol) were dissolved in tetrahydrofuran (150 ml) to completely dissolve it. Then, 150 ml of 2M potassium carbonate aqueous solution was added And Pd (PPh ₃ ) ₄ (432 mg, 3.7 x 10 ^-1 mmol) was added thereto, followed by heating and stirring for 5 hours. After the temperature was lowered to room temperature, the water layer was removed, and the organic layer was concentrated, and then recrystallized with n-hexane to obtain the structural formula 5B (9.6 g, yield 79%)

MS: [M + H] < ⁺ > = 326

Preparation of formula 5C

The structure 5B (9.6 g, 29.5 mmol) was dissolved in anhydrous dichloromethane (100 mL), the temperature was lowered to 0 캜, triethylamine (6.1 mL, 43.6 mmol) was added, and the mixture was stirred for 30 minutes. Trifluoromethanesulfonic anhydride (7.3 mL, 43.6 mmol) was added slowly and the temperature was raised to room temperature and stirred for 1 hour. The temperature was lowered to 0 占 폚, aqueous sodium hydrogencarbonate solution (100 mL) was added slowly, and the mixture was extracted with dichloromethane, and the aqueous layer was removed. The organic layer was concentrated and then recrystallized with n-hexane to obtain the structural formula 5C (11.9 g, yield 88%).

MS: [M + H] < ⁺ > = 458

Preparation of formula 5D

Structural formula 5D was obtained in the same manner as the production method of structural formula 3I, except that structural formula 3G was used instead of structural formula 3H.

MS: [M + H] < ⁺ > = 420

Preparation of formula 5

Structural formula 5 was obtained in the same manner as the production method of structural formula 3, except that structural formula 5C was used instead of structural formula 3G and structure 5D was used in place of structural formula 3I.

MS: [M + H] < ⁺ > = 601

PREPARATION EXAMPLE 3 Preparation of Compound Represented by Structural Formula 8

Preparation of formula 8A

Phenylbenzaldehyde (20 g, 108.1 mmol) and N-phenyl-1,2-phenylenediamine (19.9 g, 108.1 mmol) were added to toluene (150 mL) and the mixture was heated with stirring for 2 hours. 100 mL of toluene was distilled off, and then dimethylacetamide (150 mL) was added thereto, and the remaining toluene was distilled off. The reaction solution was heated and stirred for 12 hours, and then cooled to room temperature. The reaction solution was concentrated and then recrystallized with ethanol to obtain the structural formula 8A (31 g, yield 82%).

MS: [M +] < ⁺ & gt ^; = 349

Preparation of Structural Formula 8

A structural formula 8 was obtained in the same manner as in the production method of the structural formula 3, except that the structural formula 8A was used instead of the structural formula 3G and the structural formula 5D was used in place of the structural formula 3I.

MS: [M + H] < ⁺ > = 562

PREPARATION EXAMPLE 4 Preparation of the compound represented by the structural formula 22

Preparation of formula 22A

(4-chlorophenyl) -1,2-phenylenediamine instead of benzaldehyde and N-phenyl-1,2-phenylenediamine in place of bromobenzaldehyde, the same method as the preparation method of the structural formula 8A To give the structural formula 22A.

MS: [M + H] < ⁺ > = 305

Preparation of formula 22B

The structural formula 22B was obtained in the same manner as the production method of the structural formula 3I, except that the structural formula 22A was used instead of the structural formula 3H.

MS: [M + H] < ⁺ > = 397

Preparation of formula 22C

The structural formula 22C was obtained in the same manner as the preparation method of the structural formula 3A, except that 4-bromophenylhydrazine was used instead of phenylhydrazine.

MS: [M < ⁺ >] ⁺ = 415

Preparation of formula 22D

The structural formula 22D was obtained in the same manner as in the production method of the structural formula 3B, except that the structural formula 22C was used instead of the structural formula 3A.

MS: [M +] < ⁺ & gt ^; = 398

Preparation of formula 22E

The structural formula 22E was obtained in the same manner as in the production method of the structural formula 3C, except that the structural formula 22D was used instead of the structural formula 3B.

MS: [M +] < ⁺ & gt ^; = 368

Preparation of formula 22F

A structural formula 22F was obtained in the same manner as in the production method of the structural formula 3D, except that the structural formula 22E was used instead of the structural formula 3C.

MS: [M +] < ⁺ & gt ^; = 296

Preparation of formula 22G

A structural formula 22G was obtained in the same manner as in the production method of the structural formula 3E, except that the structural formula 22F was used in place of the structural formula 3D.

MS: [M +] < ⁺ & gt ^; = 296

Preparation of formula 22H

The structural formula 22H was obtained in the same manner as in the production method of the structural formula 3G, except that the structural formula 22G was used instead of the structural formula 3F.

MS: [M + H] < ⁺ > = 328

Preparation of formula 22I

The structural formula 22I was obtained in the same manner as the production method of the structural formula 3F, except that the structural formula 22H was used instead of the structural formula 3E.

MS: [M +] < ⁺ & gt ^; = 406

Preparation of formula 22J

Structural formula 22J was obtained in the same manner as in the production method of structural formula 3G, except that phenylboronic acid was used instead of 4-chlorophenylboronic acid in the structural formula 22I instead of the structural formula 3F.

MS: [M + H] < ⁺ > = 404

Preparation of Formula 22

The structural formula 22 was obtained in the same manner as in the production method of the structural formula 3, except that the structural formula 22J was used instead of the structural formula 3G, and the structural formula 22B was used in place of the structural formula 3I.

MS: [M + H] < ⁺ > = 638

PREPARATION EXAMPLE 5 Preparation of the compound represented by the structural formula 27

Preparation of Structural Formula 27A

The structural formula 27A was obtained in the same manner as in the production method of the structural formula 3H, except that 4-iodophenol was used instead of phenylamine and 4-bromoiodobenzene in place of the carbazole.

MS: [M +] < ⁺ & gt ^; = 262

Preparation of formula 27B

The structural formula 27B was obtained in the same manner as in the production method of the structural formula 5C, except that the structural formula 27A was used instead of the structural formula 5B.

MS: [M + H] < ⁺ > = 394

Preparation of formula 27C

A structural formula 27C was obtained in the same manner as in the production of the structural formula 3I, except that the structural formula 27B was used instead of the structural formula 3H.

MS: [M +] < ⁺ & gt ^; = 372

Preparation of formula 27D

The structural formula 27D was obtained in the same manner as in the production method of the structural formula 3G, except that 2-naphthalene boronic acid was used instead of the structural formula 22I and 4-chlorophenylboronic acid instead of the structural formula 3F.

MS: [M + H] < ⁺ > = 454

Preparation of Structural Formula 27

The structural formula 27 was obtained in the same manner as in the structural formula 3, except that the structural formula 27D was used instead of the structural formula 3G, and the structural formula 27C was used in place of the structural formula 3I.

MS: [M + H] < ⁺ > = 663

PREPARATION EXAMPLE 6 Preparation of the compound represented by Structural Formula 37

Preparation of Structural Formula 37A

3-Methylindole (7.5 g, 56.8 mmol) was completely dissolved in chloroform (100 mL). N-Bromosuccinimide (11.1 g, 62.5 mmol) was slowly added thereto and stirred at room temperature for 30 minutes. After adding water, the mixture was stirred for 20 minutes. The water layer was removed, and the organic layer was distilled under reduced pressure to completely remove the solvent. Ethanol was added at 0 ° C and stirred for 20 minutes. The resulting precipitate was filtered and vacuum-dried at room temperature to obtain the structural formula 37A (10 g, yield 84%).

MS: [M +] < ⁺ & gt ^; = 210

Preparation of Structural Formula 37B

The structural formula 37A (10 g, 47.6 mmol) was completely dissolved in chloroform (150 mL), followed by the addition of a 1N aqueous sodium hydroxide solution (100 mL) and the mixture was stirred for 10 minutes. The temperature was lowered to 5 ° C, benzyl bromide (5.9 mL, 50.0 mmol) was added slowly, and the mixture was heated and stirred for 1 hour. The temperature was lowered to room temperature, and the water layer was removed. The organic layer was concentrated, and recrystallized with n-hexane to obtain structural formula 37B (10.2 g, yield 71%).

MS: [M +] < ⁺ & gt ^; = 300

Preparation of Structural Formula 37C

Acetylphenylboronic acid (6.0 g, 36.6 mmol) was dissolved in tetrahydrofuran (150 ml) by heating to complete dissolution, 150 ml of 2M potassium carbonate aqueous solution was added, and Pd ( PPh ₃ ) ₄ (385 mg, 3.3 x 10 ^-1 mmol) was added thereto, followed by heating and stirring for 5 hours. After the temperature was lowered to room temperature, the water layer was removed, and the organic layer was concentrated. Then, the resultant was purified by column chromatography to obtain the structural formula 37C (9.5 g, yield 84%).

MS: [M + H] < ⁺ > = 340

Preparation of formula 37D

After dissolving the structural formula 37C (9.5 g, 28.0 mmol) in tetrahydrofuran (150 ml), potassium t-butoxide (12.6 g, 111.9 mmol) was added and the mixture was stirred with heating for 20 minutes. The temperature was lowered to room temperature, water was added to terminate the reaction, and the mixture was extracted with ethyl ether. The organic layer was concentrated and then subjected to column purification to obtain the structural formula 37D (7 g, yield 74%).

MS: [M + H] < ⁺ > = 340

Preparation of Structural Formula 37E

Molecular sieve and p-toluenesulfonic acid (550 mg, 3.1 mmol) were dissolved in dichloromethane (150 ml), and the mixture was stirred at room temperature for 24 hours. The reaction solution was filtered to remove solid impurities, followed by concentration and column purification to obtain the structural formula 37E (5.1 g, yield 77%).

MS: [M + H] < ⁺ > = 322

Preparation of Structural Formula 37F

A structural formula 37F was obtained in the same manner as in the production method of the structural formula 3F, except that the structural formula 37E was used instead of the structural formula 3E.

MS: [M +] < ⁺ & gt ^; = 400

Preparation of Structural Formula 37G

A structural formula 37G was obtained in the same manner as the production method of the structural formula 3I, except that the structural formula 5C was used instead of the structural formula 3H.

MS: [M + H] < ⁺ > = 436

Preparation of Structural Formula 37

A structural formula 37 was obtained in the same manner as in the production method of the structural formula 3, except that the structural formula 37F was used instead of the structural formula 3G and the structural formula 37G was used in place of the structural formula 3I.

MS: [M + H] < ⁺ > = 629

PREPARATION EXAMPLE 7 Preparation of the compound represented by Structural Formula 40

Preparation of structural formula 40A

Structural formula 40A was obtained in the same manner as in the method for producing structural formula 37C, except that 4-aminophenylboronic acid was used instead of 2-acetylphenylboronic acid in the structural formula 37F instead of the structural formula 37B.

MS: [M + H] < ⁺ > = 413

Preparation of structural formula 40

Sodium iodobiphenyl (16.3 g, 58.2 mmol) was dissolved in xylene (150 mL) and sodium-tertiary-butoxide (5.6 g, 58.2 mmol) and Pd [ P (t-Bu) ₃ ] ₂ (62 mg, 0.12 mmol) was added thereto, followed by heating with stirring in a nitrogen stream for 2 hours. The temperature was lowered to room temperature and 100 ml of distilled water was added to the reaction solution. The resulting solid was filtered and recrystallized from ethyl acetate to give structural formula 40 (11.8 g, yield 68%).

MS: [M + H] < ⁺ > = 717

PREPARATION EXAMPLE 8 Preparation of the compound represented by the structural formula 43

Preparation of structural formula 43A

A structural formula 43A was obtained in the same manner as the production method of the structural formula 3I, except that the structural formula 8A was used instead of the structural formula 3H.

MS: [M + H] < ⁺ > = 397

Preparation of structural formula 43B

The structural formula 43B was obtained in the same manner as the production method of the structural formula 3G, except that the structural formula 43A was used instead of the 1-bromo-5-naphthol and 4-chlorophenylboronic acid instead of the structural formula 3F.

MS: [M + H] < ⁺ > = 413

Preparation of structural formula 43C

The structural formula 43C was obtained in the same manner as in the production method of the structural formula 5C, except that the structural formula 43B was used instead of the structural formula 5B.

MS: [M + H] < ⁺ > = 545

Preparation of formula 43D

A structural formula 43D was obtained in the same manner as in the production method of the structural formula 3G, except that the structural formula 43C was used instead of the structural formula 3F.

MS: [M + H] < ⁺ > = 507

Preparation of formula 43E

A structural formula 43E was obtained in the same manner as the production method of the structural formula 3I, except that the structural formula 43D was used instead of the structural formula 3H.

MS: [M + H] < ⁺ > = 599

Preparation of structural formula 43

A structural formula 43 was obtained in the same manner as the production method of the structural formula 3, except that the structural formula 37F was used instead of the structural formula 3G and the structural formula 43E was used in place of the structural formula 3I.

MS: [M + H] < ⁺ > = 792

PREPARATION EXAMPLE 9 Preparation of Compound Represented by Structural Formula 59

Preparation of formula 59A

(32 g, 1902.7 mmol), benzaldehyde (38.7 mL, 380.5 mmol) and ammonium acetate (44 g, 570.8 mmol) were added to acetic acid (1.5 L) Followed by heating and stirring. The temperature was lowered to room temperature, water was added, and the mixture was extracted with chloroform. After concentrating the chloroform in half, the resulting solid was filtered off and discarded. The filtrate was concentrated, and recrystallized from ethyl ether to give structural formula 59A (123 g, yield 72%).

MS: [M + H] < ⁺ > = 451

Preparation of Structural Formula 59B

The structural formula 59B was obtained in the same manner as in the production method of the structural formula 3I, except that the structural formula 59A was used instead of the structural formula 3H.

MS: [M + H] < ⁺ > = 499

Preparation of formula 59C

The structural formula 59C was obtained in the same manner as the production method of the structural formula 3H, except that indole was used in place of carbazole, and 2-bromoiodobenzene was used in place of 4-bromoiodobenzene.

MS: [M +] < ⁺ & gt ^; = 272

Preparation of formula 59D

(130 mg, 1.2 mmol) and dppp (100 mg, 1.5 mmol) were dissolved in acetonitrile (100 mL, 100 mmol) ) And dissolved in toluene (100 mL). O- (trimethylsilyl) phenyltriflate (14.9 g, 50 mmol) dissolved in acetonitrile (20 mL) and toluene (20 mL) was slowly added and the mixture was heated and stirred for 24 hours. After lowering the temperature to room temperature, the solution was filtered through a celite pad, concentrated, and then subjected to column purification to obtain structural formula 59D (8.9 g, 67%).

MS: [M +] < ⁺ & gt ^; = 268

Preparation of formula 59E

The structural formula 59E was obtained in the same manner as in the production method of the structural formula 3F, except that the structural formula 59D was used instead of the structural formula 3E.

MS: [M +] < ⁺ & gt ^; = 346

Preparation of formula 59F

Structural formula 59F was obtained in the same manner as in the method for producing structural formula 3G, except that phenylboronic acid was used in place of structural formula 59E and 4-chlorophenylboronic acid instead of the structural formula 3F.

MS: [M + H] < ⁺ > = 344

Preparation of formula 59G

A structural formula 59G was obtained in the same manner as the production method of the structural formula 3F, except that the structural formula 59F was used instead of the structural formula 3E.

MS: [M +] < ⁺ & gt ^; = 422

Preparation of Structural Formula 59H

The structural formula 59H was obtained in the same manner as in the production method of the structural formula 3G, except that the structural formula 59G was used instead of the structural formula 3F.

MS: [M + H] < ⁺ > = 454

Preparation of Structural Formula 59

Structural formula 59 was obtained in the same manner as in the production method of structural formula 3, except that structural formula 59H was used instead of structural formula 3G and structural formula 59B was used in place of structural formula 3I.

MS: [M + H] < ⁺ > = 790

PREPARATION EXAMPLE 10 Preparation of the compound represented by Structural Formula 64

Preparation of Structure 64

The structural formula 64 was obtained in the same manner as in the production of the structural formula 40, except that the structural formula 59H was used instead of the p-ditolylamine and 4-iodobiphenyl in place of the structural formula 40A.

MS: [M + H] < ⁺ > = 615

Preparation Example 11: Preparation of the compound represented by the structural formula 68

Preparation of formula 68A

Structural formula 68A was obtained in the same manner as in the production of 3H, except that iodobenzene was used instead of 4-bromoiodobenzene.

MS: [M < ⁺ >] ⁺ = 244

Preparation of formula 68B

The structural formula 68B was obtained in the same manner as the production method of the structural formula 37A, except that the structural formula 68A was used instead of 3-methylindole.

MS: [M < ⁺ >] ⁺ = 322

Preparation of Structural Formula 68C

The structure 68B (17.9 g, 55.6 mmol) was dissolved in 200 ml of anhydrous tetrahydrofuran, cooled to -78 ° C and 2.5 M n-butyllithium (24.5 mL, 61.2 mmol) was added slowly and stirred for 1 hour. Trimethylborate (9.4 mL, 83.4 mmol) was added to the reaction solution, and the mixture was stirred for 30 minutes, and 50 mL of 6N HCl was added. The temperature was raised to room temperature and stirred for 1 hour. The organic layer was extracted, concentrated, and then recrystallized with n-hexane to obtain structural formula 68C (11.5 g, yield 72%).

MS: [M + H] < ⁺ > = 288

Preparation of structural formula 68

A structural formula 68 was obtained in the same manner as in the production method of the structural formula 3, except that the structural formula 59H was used instead of the structural formula 3G and the structural formula 68C was used in place of the structural formula 3I.

MS: [M + H] < ⁺ > = 661

PREPARATION EXAMPLE 12 Preparation of the compound represented by Structural Formula 70

Preparation of structural formula 70A

Structural formula 70A was obtained in the same manner as in the production method of structural formula 3G, except that 2-naphthylboronic acid was used instead of 4-chlorophenylboronic acid in the structural formula 59E instead of the structural formula 3F.

MS: [M + H] < ⁺ > = 394

Preparation of Structural Formula 70B

A structural formula 70B was obtained in the same manner as in the production method of the structural formula 3F, except that the structural formula 70A was used in place of the structural formula 3E.

MS: [M +] < ⁺ & gt ^; = 472

Preparation of Structural Formula 70C

Structural formula 70C was obtained in the same manner as in the production method of structural formula 3I, except that structural formula 70B was used instead of structural formula 3H.

MS: [M + H] < ⁺ > = 520

Preparation of structural formula 70

Structural formula 70 was obtained in the same manner as in the production method of structural formula 3, except that 4-iodobiphenyl in place of structural formula 3G and structural formula 70C in place of structural formula 3I were used.

MS: [M + H] < ⁺ > = 546

PREPARATION EXAMPLE 13 Preparation of the compound represented by Structural Formula 76

Preparation of formula 76A

A structural formula 76A was obtained in the same manner as in the production method of the structural formula 3I, except that the structural formula 59E was used instead of the structural formula 3H.

MS: [M + H] < ⁺ > = 394

Preparation of formula 76B

The structural formula 76B was obtained in the same manner as the production method of the structural formula 3G, except that the structural formula 76A was used in place of the 4F bromoiodobenzene and 4-chlorophenylboronic acid instead of the structural formula 3F.

MS: [M +] < ⁺ & gt ^; = 422

Preparation of formula 76C

Structural formula 76C was obtained in the same manner as in the method for the preparation of the structural formula 37C, except that 4-aminophenylboronic acid was used instead of the structural formula 59E and 2-acetylphenylboronic acid instead of the structural formula 37B.

MS: [M + H] < ⁺ > = 359

Preparation of structural formula 76

The structural formula 76 was obtained in the same manner as in the production method of the structural formula 40, except that the structural formula 76C was used in place of the structural formula 40A instead of the structural formula 76C and 4-iodobiphenyl.

MS: [M + H] < ⁺ > = 1040

≪ Example 1 >

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) thin film with a thickness of 1000 Å was immersed in distilled water containing dissolved dispersant and ultrasonically cleaned. 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.

Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. NPB (400 Å), which is a hole transporting material, was vacuum deposited thereon, and host H1 and a dopant D1 compound were vacuum deposited as a light emitting layer to a thickness of 300 Å. Then, the compound of Formula 5 (200 Å) synthesized in Preparation Example 2 was sequentially vacuum-deposited by electron injection and transport layer. A 12 Å thick lithium fluoride (LiF) layer and a 2000 Å thick aluminum layer were successively deposited on the electron transport layer to form a cathode, thereby preparing an organic light emitting device.

E1 was used as a comparative example of the electron transport layer.

In the above procedure, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of lithium fluoride was maintained at 0.2 Å / sec, and the deposition rate of aluminum was maintained at 3 to 7 Å / sec.

≪ Example 2 >

The same experiment was carried out except that the electron transport layer in Example 1 was replaced with the electron transport layer 8, which was synthesized in Production Example 3, instead of the structure 5.

≪ Example 3 >

The same experiment was carried out except that the electron transport layer in Example 1 was replaced by the electron transport layer of Formula 22 synthesized in Production Example 4 instead of the structure 5.

<Example 4>

The same experiment was carried out except that the electron transport layer in Example 1 was replaced with the electron transport layer of Structure 37 synthesized in Production Example 6 instead of the structure 5.

&Lt; Example 5 >

The same experiment was carried out except that the electron transport layer in Example 1 was replaced by the structural formula 43 synthesized in Production Example 8 instead of the structure 5.

&Lt; Example 6 >

The same experiment was conducted except that the electron transport layer in Example 1 was replaced by the structural formula 59 synthesized in Production Example 9 instead of the structure 5.

&Lt; Comparative Example 1 &

Except that E1 was used instead of the structural formula 5 synthesized in Production Example 2 as an electron transporting layer in Example 1 above.

Table 1 shows the results of an experiment on an organic light emitting device manufactured by using each compound as an electron transporting layer material as in the above examples.

[Table 1]

&Lt; Example 7 >

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) thin film with a thickness of 1000 Å was immersed in distilled water containing dissolved dispersant and ultrasonically cleaned. 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.

Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. (400 Å) synthesized in Preparation Example 1, which is a hole transport material, was vacuum deposited on the hole transport layer. Then, a host H1 and a dopant D1 compound were vacuum deposited as a light emitting layer to a thickness of 300 Å. The E1 compound (300 ANGSTROM) was then thermally vacuum deposited sequentially by electron injecting and transporting layers. A 12 Å thick lithium fluoride (LiF) layer and a 2000 Å thick aluminum layer were successively deposited on the electron transport layer to form a cathode, thereby preparing an organic light emitting device.

NPB was used as a comparative example of the hole transport layer.

In the above procedure, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of lithium fluoride was maintained at 0.2 Å / sec, and the deposition rate of aluminum was maintained at 3 to 7 Å / sec.

&Lt; Example 8 >

The same experiment was carried out as in Example 7 except that the hole transport layer was replaced by the structural formula 27 synthesized in Production Example 5 instead of the structural formula 3. [

&Lt; Example 9 >

The same experiment was carried out as in Example 7 except that the hole transport layer was replaced with the structural formula 40 synthesized in Production Example 7 instead of the structure 3.

&Lt; Example 10 >

The same experiment was conducted as in Example 7 except that the hole transport layer was replaced with the structural formula 64 synthesized in Production Example 10 instead of the structure 3.

&Lt; Example 11 >

The same experiment was conducted except that the hole transport layer in Example 7 was replaced by the structural formula 68 synthesized in Production Example 11 instead of the structure 3.

&Lt; Example 12 >

The same experiment was conducted except that the hole transport layer in Example 7 was replaced by the structural formula 70 synthesized in Production Example 12 instead of the structure 3.

&Lt; Example 13 >

The same experiment was carried out as in Example 7 except that the hole transport layer was replaced with the structural formula 76 synthesized in Production Example 13 instead of the structure 3.

&Lt; Comparative Example 2 &

The same experiment was conducted as in Example 7 except that NPB was used instead of the structural formula 3 synthesized in Production Example 1 as a hole transport layer.

Table 2 shows the results of an experiment of an organic light emitting device manufactured by using each compound as a hole transporting layer material as in the above examples.

[Table 2]

The compound represented by the chemical formula according to the present invention can act as an electron injecting, electron transporting, hole injecting and transporting, or light emitting material in an organic electric device including an organic light emitting device. And exhibits excellent properties in terms of surface area.

Claims (15)

delete A compound represented by the following formula (2) or (3):
[Chemical Formula 2] &lt; EMI ID =

In the general formula (2) or (3)
R ₈ is a C _6-50 aryl group is substituted or unsubstituted aryl group of cattle heteroatoms O, N, S or C group of _3-60 heterocycle substituted or unsubstituted C _6-50 having a P; Or a C _1-40 alkyl group,
R ₁₀ is hydrogen; Or a group of C _6-50 aryl and substituted or unsubstituted heteroatom Thoreau O, N, S or a heterocyclic group of C _3-60 having P, or C _6-50 arylamine group unsubstituted or substituted with a C _{6- Lt} ; / RTI &gt;
R ₁₃ is hydrogen; Or a C _6-50 aryl group,
R ₁₄ is hydrogen; Or a C _1-40 alkyl group,
R ₉ , R ₁₁ , R _12, and R ₁₅ to R ₁₈ are hydrogen,
R ₁₉ is a C _6-50 aryl group which is substituted or unsubstituted with a C _6-50 arylamine group substituted with a C _3-60 heterocyclic group having O, N, S or P as a hetero atom,
R ₂₁ is hydrogen; Or a group of C _6-50 aryl and substituted or unsubstituted heteroatom Thoreau O, N, S, or an aryl group of C _3-60 A C _6-50 substituted or unsubstituted heterocyclic group having a P, or C _1-50 Substituted or unsubstituted C _6-50 arylamine group substituted with an alkyl group of 1 to ₆ carbon _atoms ,
R ₂₀ and R ₂₂ to R ₃₁ are hydrogen. delete delete delete delete The compound according to claim 2, wherein the compound is represented by any one of the following structural formulas.

1. An organic electronic device comprising a first electrode, a second electrode, and at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to claim 2 or 7 &Lt; / RTI &gt; The organic electroluminescent device according to claim 8, wherein the organic layer includes an electron injection layer and an electron transport layer, and the electron injection layer and the electron transport layer comprise the compound. 9. The organic electroluminescent device according to claim 8, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. The organic electroluminescent device according to claim 8, wherein the organic material layer includes a hole injection layer and a hole transport layer, and the hole injection layer and the hole transport layer comprise the compound. The organic electroluminescent device according to claim 8, wherein the organic electroluminescent device is selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor. 9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises an electron transporting layer, and the electron transporting layer comprises the compound. delete 9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises a hole transporting layer, and the hole transporting layer comprises the compound.

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