WO2016024728A1 - Élément luminescent organique - Google Patents

Élément luminescent organique Download PDF

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Publication number
WO2016024728A1
WO2016024728A1 PCT/KR2015/007418 KR2015007418W WO2016024728A1 WO 2016024728 A1 WO2016024728 A1 WO 2016024728A1 KR 2015007418 W KR2015007418 W KR 2015007418W WO 2016024728 A1 WO2016024728 A1 WO 2016024728A1
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Prior art keywords
group
substituted
organic light
unsubstituted
light emitting
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PCT/KR2015/007418
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English (en)
Korean (ko)
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허정오
이동훈
천민승
장분재
정원익
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주식회사 엘지화학
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Priority claimed from KR1020150028550A external-priority patent/KR101772746B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to US14/912,537 priority Critical patent/US9502669B2/en
Priority to EP15831494.8A priority patent/EP3181657B1/fr
Priority to CN201580029639.5A priority patent/CN106459745B/zh
Priority to JP2016569452A priority patent/JP6332885B2/ja
Publication of WO2016024728A1 publication Critical patent/WO2016024728A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K99/00—Subject matter not provided for in other groups of this subclass
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present specification relates to an organic light emitting device.
  • the organic light emitting phenomenon is an example of converting an electric current into visible light by an internal process of a specific organic molecule.
  • the principle of the organic light emitting phenomenon is as follows.
  • An organic light emitting device using this principle may generally be composed of an organic material layer including a cathode and an anode, and an organic material layer disposed therebetween, such as a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.
  • the materials used in the organic light emitting device are pure organic materials or complex compounds in which organic materials and metals are complexed, and depending on the purpose, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. It can be divided into.
  • the hole injection material or the hole transport material an organic material having a p-type property, that is, an organic material which is easily oxidized and has an electrochemically stable state during oxidation, is mainly used.
  • organic materials having n-type properties that is, organic materials that are easily reduced and have an electrochemically stable state at the time of reduction are mainly used.
  • the light emitting layer material a material having a p-type property and an n-type property at the same time, that is, a material having a stable form in both oxidation and reduction states, and a material having high luminous efficiency that converts it to light when excitons are formed desirable.
  • An object of the present specification is to provide an organic light emitting device having a high luminous efficiency.
  • the present specification is a cathode; An anode provided opposite the cathode; A light emitting layer provided between the cathode and the anode; An electron transport layer provided between the cathode and the light emitting layer; And an electron adjusting layer provided between the light emitting layer and the electron transport layer.
  • the electron transport layer includes an organic compound containing an aromatic hetero ring,
  • the electron control layer comprises a heterocyclic compound represented by the formula (1),
  • the ionization potential Ip m of the electron transport layer is larger than the ionization potential Ip a of the electron control layer.
  • X1 is CR1 or N
  • X2 is CR2 or N
  • Y1 is CR5 or N
  • Y2 is CR6 or N
  • Y3 is CR7 or N
  • Y4 is CR8 or N
  • Z1 is CR9 or N
  • Z2 is CR10 or N
  • Z3 is CR11 or N
  • Z4 is CR12 or N
  • X1, X2, Y1 to Y4 and Z1 to Z4 are not N at the same time
  • R1, R2 and R5 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or a substituted or unsubstituted phosphine oxide group, or adjacent substituents of R1, R2, and R5 to R12 combine with each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring.
  • the organic light emitting diode according to the exemplary embodiment of the present specification provides a low driving voltage and / or high efficiency.
  • FIG. 1 illustrates an example of an organic light emitting diode according to an exemplary embodiment of the present specification.
  • the present specification is a cathode; An anode provided opposite the cathode; A light emitting layer provided between the cathode and the anode; An electron transport layer provided between the cathode and the light emitting layer; And an electron control layer provided between the emission layer and the electron transport layer, wherein the transport layer includes an organic compound containing an aromatic hetero ring, and the electron control layer comprises a heterocyclic compound represented by Formula 1 above. It provides an organic light emitting device.
  • the electron control layer refers to a layer that controls the mobility of electrons according to the energy level of the light emitting layer in the organic light emitting device.
  • the ionization potential Ip m of the electron transport layer is larger than the ionization potential Ip a of the electron control layer.
  • the hole supplied from the anode may serve as a hole barrier so as not to fall toward the cathode, and the ability to adjust the electron mobility of the electron adjusting layer may be maximized.
  • the electron control layer is provided in contact with the light emitting layer.
  • the electron adjusting layer may simultaneously play a role of controlling electron mobility and a factory wall to prevent holes from being supplied from the anode to the cathode, in particular, the electron transport layer.
  • the thickness of the electron transport layer is thicker than the thickness of the electron control layer.
  • the thickness of the electron control layer that controls the movement of electrons is thicker than the thickness of the electron transport layer, the amount of electrons that can move to the light emitting layer per unit time is reduced, so that holes from the anode are supplied excessively to the cathode, thereby decreasing the efficiency of the device. have. Therefore, when the thickness of the electron transport layer is greater than the thickness of the electron control layer, the amount of electrons that can move to the light emitting layer per unit time can be properly adjusted to balance the amount of holes supplied from the anode to maximize the exciton formation of the light emitting layer and High device efficiency can be expected.
  • the light emitting layer includes a host and a dopant.
  • the dopant is a fluorescent dopant.
  • the dopant is a blue fluorescent dopant.
  • the organic light emitting device emits blue fluorescent light.
  • Organic light emitting devices currently used in the art are used in a combination of blue fluorescence, green and red phosphorescence or blue fluorescence and green fluorescence and red phosphorescence.
  • an organic light emitting device that emits blue fluorescent light having a high exciton energy
  • there is a problem in that the life of the device is considerably shorter than that of green or red. That is, since the high exciton energy of the blue fluorescence is concentrated in a local region called a narrow light emitting region, the energy stress applied to the material increases, resulting in a low lifetime. Therefore, in order to overcome the above problems, a separate electron control layer may be provided in the light emitting layer and the electron transport layer in addition to the electron transport layer to artificially adjust the amount of electrons to improve the efficiency and lifespan of the organic light emitting device.
  • the electron transport layer includes an organic compound containing an aromatic heterocycle.
  • containing an aromatic heterocycle herein may mean that the compound included in the electron transport layer includes an aromatic heterocycle as a core, or at least one of the substituents of the compound included in the electron transport layer is an aromatic heterocycle.
  • the electron transport layer includes an organic compound containing a nitrogen-containing monocyclic ring or a nitrogen-containing polycyclic ring.
  • the nitrogen-containing monocyclic ring means a ring in which at least one nitrogen atom is substituted in the ring member of a monocyclic hydrocarbon, for example, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a tetrazine group, Pentazine groups, pyrrole groups, thiazole groups, imidazole groups, and oxazole groups, but are not limited thereto.
  • a monocyclic hydrocarbon for example, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a tetrazine group, Pentazine groups, pyrrole groups, thiazole groups, imidazole groups, and oxazole groups, but are not limited thereto.
  • the nitrogen-containing polycyclic ring means a ring in which at least one nitrogen atom is substituted in the ring member of the polycyclic hydrocarbon, and a quinoline group, a cynoline group, a quinazoline group, a quinoxaline group, a pyridopyrazine group, and a pyrazinopyrazine Groups, pyrazinoquinoxaline groups, acridine groups, phenanthroline groups, benzimidazole groups, benzimidazophenanthridine groups, benzobenzimidazopefentridine groups and the like, but are not limited thereto.
  • the electron transport layer includes an organic compound containing a nitrogen-containing monocyclic ring.
  • the organic compound containing the aromatic hetero ring includes an aromatic hetero ring as a core.
  • X1 and X2 are CR1 and CR2, respectively, and R1 and R2 combine with each other to form a substituted or unsubstituted hydrocarbon ring.
  • R1 and R2 combine with each other to form a substituted or unsubstituted benzene ring.
  • R1 and R2 combine with each other to form a benzene ring.
  • X1 is N.
  • X2 is CR2.
  • R7 and R8 combine with each other to form a hydrocarbon ring.
  • R7 and R8 combine with each other to form a benzene ring.
  • R5 and R6 combine with each other to form a hydrocarbon ring.
  • R5 and R6 combine with each other to form a benzene ring.
  • the benzene ring or hydrocarbon ring may be substituted or unsubstituted.
  • the heterocyclic compound represented by Formula 1 is represented by the following Formula 1A or Formula 1B.
  • Y1 to Y4, Z1 to Z4 and R2 are the same as defined in Formula 1,
  • X3 to X6 are the same as or different from each other, and each independently CR3 or N,
  • Each R 3 is independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or a substituted or unsubstituted phosphine oxide group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring.
  • Y1 is CR5.
  • Y2 is CR6
  • Y3 is CR7.
  • Y4 is CR8.
  • Z1 is CR9.
  • Z2 is CR10.
  • Z3 is CR11.
  • Z4 is CR12.
  • X3 to X6 are each CR3.
  • each CR3 of the X3 to X6 may be the same or different from each other.
  • the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.
  • a, b and c are each an integer of 1 to 4,
  • d and e are each an integer of 1 to 6,
  • A1 to A5 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or a substituted or unsubstituted phosphine oxide group.
  • At least one of R1, R2, and R5 to R12 is substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group or Unsubstituted aryl group; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group, or adjacent substituents are bonded to each other to form a cyano group, an aryl A hydrocarbon ring substituted or unsubstituted with one or two or more substituents selected from the group consisting of a group, a heterocyclic group and a phosphine oxide group is formed.
  • At least one of R1 to R3 and R5 to R12 is substituted or unsubstituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group Ring aryl group; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group, or adjacent substituents are bonded to each other to form a cyano group, an aryl A benzene ring unsubstituted or substituted with one or two or more substituents selected from the group consisting of a group, a heterocyclic group and a phosphine oxide group is formed.
  • R1 to R3 and R5 to R12 are the same as or different from each other, and each independently hydrogen; An aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group, or adjacent substituents are bonded to each other to form a cyano group, an aryl A benzene ring unsubstituted or substituted with one or two or more substituents selected from the group consisting of a group, a heterocyclic group and a phosphine oxide group is formed.
  • R1 to R3 and R5 to R12 are the same as or different from each other, and each independently hydrogen; A phenyl group substituted with a pyridine group; A phenyl group substituted with a quinoline group; Phenyl group substituted with pyrene group; A naphthyl group substituted with a phenyl group substituted with a naphthyl group; Naphthyl group substituted with phenanthrenyl group; A fluorenyl group substituted with one or two or more substituents selected from the group consisting of Formula 1B and a phenyl group; A naphthyl group substituted with a phenyl group substituted with a cyano group; A phenyl group substituted with an anthracene group substituted with a naphthyl group; A naphthyl group substituted with a phosphine oxide group substituted with an aryl group; Phosphine oxide groups substituted
  • R1 is hydrogen
  • R2 is hydrogen
  • R2 is a substituted or unsubstituted aryl group.
  • R2 is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
  • R2 is an aryl group which is substituted with a substituted or unsubstituted aryl group.
  • R2 is an aryl group which is substituted with a pyrene group.
  • R2 is a phenyl group substituted with a substituted or unsubstituted aryl group.
  • R2 is a phenyl group substituted with a pyrene group.
  • R2 is a phenyl group substituted with a substituted or unsubstituted anthracene group.
  • R2 is a phenyl group substituted with an anthracene group substituted with a naphthyl group.
  • R2 is a naphthyl group which is substituted with a substituted or unsubstituted aryl group.
  • R2 is a naphthyl group substituted with a phenanthrenyl group.
  • R2 is a naphthyl group which is substituted with a substituted or unsubstituted phenyl group.
  • R2 is a naphthyl group substituted with a phenyl group substituted with a cyano group.
  • R2 is a naphthyl group substituted with a phenyl group substituted with a naphthyl group.
  • R2 is a fluorenyl group which is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted Formula 1B and a phenyl group.
  • R2 is a fluorenyl group substituted with Formula 1B and a naphthyl group.
  • R3 is hydrogen
  • R3 is a substituted or unsubstituted aryl group.
  • R3 is a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
  • R3 is an aryl group which is substituted with an aryl group.
  • R3 is an aryl group which is substituted with a naphthyl group.
  • R3 is a phenyl group substituted with a naphthyl group.
  • R3 is an aryl group which is substituted with a phenyl group.
  • R3 is a phenyl group substituted with an aryl group.
  • R3 is a naphthyl group which is substituted with an aryl group.
  • R3 is a phenyl group substituted with a phenyl group.
  • R3 is a naphthyl group which is substituted with a phenyl group.
  • R3 is an unsubstituted aryl group.
  • R3 is a naphthyl group.
  • R3 is a phenanthrenyl group.
  • R3 is a terphenyl group.
  • R3 is a triphenylene group.
  • R3 is a biphenyl group.
  • R3 is an aryl group substituted with a heterocyclic group.
  • R3 is an aryl group which is substituted with a pyridine group.
  • R3 is a phenyl group substituted with a pyridine group.
  • R3 is an aryl group substituted with a phosphine oxide group.
  • R3 is a naphthyl group substituted with a phosphine oxide group.
  • R3 is a naphthyl group substituted with a phosphine oxide group substituted with an aryl group.
  • R3 is a naphthyl group substituted with a phosphine oxide group substituted with a phenyl group.
  • R3 is a phosphine oxide group substituted with an aryl group.
  • R3 is a phosphine oxide group substituted with a naphthyl group.
  • R5 is hydrogen
  • R6 is hydrogen
  • R6 is a substituted or unsubstituted aryl group.
  • R6 is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
  • R6 is an aryl group substituted with a heterocyclic group.
  • R6 is an aryl group which is substituted with a pyridine group.
  • R6 is a phenyl group substituted with a pyridine group.
  • R7 is hydrogen
  • R7 is an aryl group substituted with a phosphine oxide group.
  • R7 is a naphthyl group substituted with a phosphine oxide group.
  • R7 is a naphthyl group substituted with a phosphine oxide group substituted with an aryl group.
  • R7 is a naphthyl group substituted with a phosphine oxide group substituted with a phenyl group.
  • R7 is a substituted or unsubstituted aryl group.
  • R7 is an aryl group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
  • R7 is an aryl group substituted with a heterocyclic group.
  • R7 is an aryl group which is substituted with a quinoline group.
  • R7 is a phenyl group substituted with a quinoline group.
  • R8 is hydrogen
  • R9 is hydrogen
  • R10 is hydrogen
  • R10 is a substituted or unsubstituted aryl group.
  • R10 is an aryl group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
  • R10 is an aryl group substituted with a heterocyclic group.
  • R10 is an aryl group which is substituted with a quinoline group.
  • R10 is a phenyl group substituted with a quinoline group.
  • R11 is hydrogen
  • R12 is hydrogen
  • At least one of A1 to A3 is an aryl group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group ; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
  • A1 to A5 are the same as or different from each other, and each independently hydrogen; An aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
  • A1 to A5 are the same as or different from each other, and each independently hydrogen; A phenyl group substituted with a pyridine group; A phenyl group substituted with a quinoline group; Phenyl group substituted with pyrene group; A naphthyl group substituted with a phenyl group substituted with a naphthyl group; Naphthyl group substituted with phenanthrenyl group; A fluorenyl group substituted with one or two or more substituents selected from the group consisting of Formula 1B and a phenyl group; A naphthyl group substituted with a phenyl group substituted with a cyano group; A phenyl group substituted with an anthracene group substituted with a naphthyl group; A naphthyl group substituted with a phosphine oxide group substituted with an aryl group; Phosphine oxide groups substituted with naphthyl
  • At least one of the R1 to R3 and R5 to R12 is selected from the following structure.
  • At least one of A1 to A5 may be selected from the structures.
  • the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1-1 to 1-1-7.
  • the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-2-1 to 1-2-10.
  • the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-3-1 to 1-3-5.
  • the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-4-1 to 1-4-7.
  • the electron transport layer includes an organic compound containing an aromatic hetero ring represented by the following formula (2).
  • X5 and X6 are the same as or different from each other, and each independently N or CH,
  • Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • At least one of Ar1 to Ar3 is represented by the following formula (3).
  • o, p and q are 0 or 1
  • r 1 or 2
  • L1 to L3 are the same as or different from each other, and each independently a phenylene group; Or naphthalene group; Or a fluorenylene group,
  • Ar is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group; Or a heterocyclic group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group.
  • o is 1.
  • o is zero.
  • p 0.
  • p is 1.
  • q is 0.
  • q is one.
  • r is 1.
  • r is two.
  • L1 is a phenylene group.
  • L1 is a naphthalene group.
  • L1 is a fluorenylene group.
  • L2 is a phenylene group.
  • L2 is a naphthalene group.
  • L2 is a fluorenylene group.
  • L3 is a phenylene group.
  • L3 is a naphthalene group.
  • L3 is a fluorenylene group.
  • Ar is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group; Or a heterocyclic group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group.
  • Ar is a heterocyclic group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group.
  • Ar is a quinoline group.
  • Ar is a heterocyclic group unsubstituted or substituted with an aryl group.
  • Ar is a heterocyclic group which is unsubstituted or substituted with a phenyl group.
  • Ar is a pyrimidine group substituted with a phenyl group.
  • Ar is a pyridine group substituted with a phenyl group.
  • Ar is a triazine group substituted with a phenyl group.
  • Ar is a pyridine group.
  • Ar is a carbazole group.
  • Ar is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group.
  • Ar is a phenyl group.
  • Ar is an aryl group which is substituted with an aryl group.
  • Ar is an aryl group which is substituted with a phenyl group.
  • Ar is a fluorenyl group substituted with a phenyl group.
  • Ar1 to Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group.
  • Ar1 to Ar3 are the same as or different from each other, and each independently phenyl; Biphenyl; naphthalene; Phenyl-naphthalene-phenyl-quinoline; Phenyl-naphthalene-phenyl-pyrimidine-phenyl; Phenyl-naphthalene-phenyl-pyridine-phenyl; Phenyl-naphthalene-phenyl-pyrimidine; Fluorene-phenyl; Phenyl-terphenyl; Biphenyl-phenyl; Naphthyl-fluorene-phenyl; Phenyl-fluorene-phenyl; Biphenyl-carbazole; Or phenyl-naphthalene-phenyl-triazine-phenyl.
  • the "-naphthalene-" is 2,7-naphthalene or 1,4-naphthalene.
  • the organic compound containing the aromatic hetero ring represented by Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-13.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents.
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but preferably 6 to 25 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like.
  • carbon number is not specifically limited, It is preferable that it is C2-C60.
  • heterocyclic group examples include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthro
  • the heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic.
  • adjacent means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.
  • the adjacent groups are bonded to each other to form a hydrocarbon ring or a hetero ring, in which the adjacent substituents form a bond, a 5- to 7-membered monocyclic or polycyclic hydrocarbon ring or a 5- to 7-membered monocyclic or multi It means forming the heterocyclic group of the ring.
  • the hydrocarbon ring is a cycloalkyl group; Cycloalkenyl group; Aromatic ring groups; Or include all aliphatic ring groups, which may be monocyclic or polycyclic, and include all rings condensed by combining one or two or more.
  • Heterocycle formed herein means that at least one carbon atom of the hydrocarbon ring is substituted with N, O, or S atoms, may be an aliphatic ring or an aromatic ring, it may be monocyclic or polycyclic.
  • the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except for including an electron transport layer and an electron control layer.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate.
  • the anode is formed by depositing a metal or conductive metal oxide or an alloy thereof on the substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, an electron adjusting layer, and an electron transporting layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer of the organic light emitting device of the present specification may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device further includes one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer. can do.
  • the structure of the organic light emitting device of the present specification may have a structure as shown in FIG. 1, but is not limited thereto.
  • 1 illustrates a structure of an organic light emitting device in which an anode 201, a light emitting layer 301, an electron control layer 401, an electron transport layer 501, and a cathode 601 are sequentially stacked on a substrate 101.
  • 1 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.
  • the organic material layers may be formed of the same material or different materials.
  • the anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • the positive electrode 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), indium zinc oxide (IZO); ZnO: Al or SNO 2 : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is generally a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer.
  • the compound which prevents the movement of the excited excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
  • the material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Dopant materials include organic compounds, metals or metal compounds.
  • Organic compounds as dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds and the like.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like but is not limited thereto.
  • a metal complex may be used as the metal or the metal compound.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, 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-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the hole blocking layer is a layer for blocking the arrival of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • the organic light emitting diode according to the present disclosure may be a normal type in which the lower electrode is an anode and the upper electrode is a cathode, or may be an inverted type in which the lower electrode is a cathode and the upper electrode is an anode.
  • the structure according to the exemplary embodiment of the present specification may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoconductor, an organic transistor, and the like.
  • a glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. was used as a detergent and Millipore Co. was used as distilled water. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried and then transferred to a plasma cleaner. In addition, the substrate was dry-cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • ITO indium tin oxide
  • Hexanitrilehexaazatriphenylene (hereinafter referred to as HAT), a compound of the following formula, was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a thin film.
  • HAT Hexanitrilehexaazatriphenylene
  • a hole transport layer was formed by depositing a compound of Formula HT-1 at a thickness of 400 kPa on the thin film, and an electron blocking layer was formed by depositing a compound of EB-1 at a thickness of 250 kPa thereon.
  • the compound of the following H1 and the following D1 as a host of a light emitting layer was vacuum-deposited at 200 microsecond thickness on it.
  • Compound 1-1-1 was deposited to a thickness of 100 ⁇ on the emission layer to form an electron control layer, and the electron transport layer material of the compound 2-1 and lithium quinolate (LiQ, Lithium Quinolate) were added in a weight ratio of 1: 1. Vacuum deposition was carried out to form an electron injection and transport layer having a thickness of 300 kPa. A cathode was formed by sequentially depositing 12 ⁇ thick lithium fluoride (LiF) and 2,000 ⁇ thick aluminum on the electron transport layer.
  • LiQ lithium quinolate
  • the deposition rate of the organic material was maintained at 0.3 ⁇ 0.8 ⁇ / sec.
  • the lithium fluoride of the negative electrode maintained a deposition rate of 0.3 kPa / sec and aluminum of 1.5 to 2.5 kPa / sec.
  • the degree of vacuum was maintained at 1 to 3 ⁇ 10 ⁇ 7 .
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-3 was used instead of Compound 2-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-4 was used instead of Compound 2-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-7 was used instead of Compound 2-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-8 was used instead of Compound 2-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-13 was used instead of Compound 2-1 in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 2 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 2.
  • An organic light-emitting device was manufactured in the same manner as in Example 2, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 2.
  • An organic light-emitting device was manufactured in the same manner as in Example 2, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 2.
  • An organic light-emitting device was manufactured in the same manner as in Example 2, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Example 2.
  • An organic light-emitting device was manufactured in the same manner as in Example 2, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 2.
  • An organic light emitting diode was manufactured according to the same method as Example 3 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 3.
  • An organic light-emitting device was manufactured in the same manner as in Example 3, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 3.
  • An organic light-emitting device was manufactured in the same manner as in Example 3, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 3.
  • An organic light emitting diode was manufactured according to the same method as Example 3 except for using the compound 1-3-2 instead of the compound 1-1-1 in Example 3.
  • An organic light emitting diode was manufactured according to the same method as Example 3 except for using the compound 1-4-1 instead of the compound 1-1-1 in Example 3.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 4.
  • An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 4.
  • An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 4.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound 1-3-2 instead of the compound 1-1-1 in Example 4.
  • An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 4.
  • An organic light emitting diode was manufactured according to the same method as Example 5 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 5.
  • An organic light emitting diode was manufactured according to the same method as Example 5 except for using the compound 1-2-10 instead of the compound 1-1-1 in Example 5.
  • An organic light-emitting device was manufactured in the same manner as in Example 5, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 5.
  • An organic light-emitting device was manufactured in the same manner as in Example 5, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Example 5.
  • An organic light-emitting device was manufactured in the same manner as in Example 5, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 5.
  • An organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 6.
  • An organic light-emitting device was manufactured in the same manner as in Example 6, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 6.
  • An organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound 1-3-1 instead of the compound 1-1-1 in Example 6.
  • An organic light-emitting device was manufactured in the same manner as in Example 6, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Example 6.
  • An organic light-emitting device was manufactured in the same manner as in Example 6, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 6.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 2 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 2.
  • An organic light emitting diode was manufactured according to the same method as Example 3 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 3.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 4.
  • An organic light emitting diode was manufactured according to the same method as Example 5 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 5.
  • An organic light emitting diode was manufactured according to the same method as Example 6 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 6.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 2 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 2.
  • An organic light emitting diode was manufactured according to the same method as Example 3 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 3.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 4.
  • An organic light emitting diode was manufactured according to the same method as Example 5 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 5.
  • An organic light emitting diode was manufactured according to the same method as Example 6 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 6.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 2 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 2.
  • An organic light emitting diode was manufactured according to the same method as Example 3 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 3.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 4.
  • An organic light emitting diode was manufactured according to the same method as Example 5 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 5.
  • An organic light emitting diode was manufactured according to the same method as Example 6 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 6.
  • Example 1 the electron transporting layer material of the compound 2-1 and lithium quinolate (LiQ, Lithium Quinolate) were vacuum-deposited at a weight ratio of 1 to 1 to form an electron injection and transport layer at a thickness of 400 Pa.
  • LiQ lithium quinolate
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-3 was used instead of Compound 2-1 in Comparative Example 19.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-4 was used instead of Compound 2-1 in Comparative Example 19.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-7 was used instead of Compound 2-1 in Comparative Example 19.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-8 was used instead of Compound 2-1 in Comparative Example 19.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-13 was used instead of Compound 2-1 in Comparative Example 19.
  • Example 1 the electron control layer was formed by depositing the compound 1-1-1 to a thickness of 300 ⁇ on the light emitting layer, and the electron transport layer material of the compound 2-1 and lithium quinolate (LiQ, Lithium Quinolate) 1 Vacuum deposition was carried out at a weight ratio of 1 to form an electron injection and transport layer at a thickness of 100 kPa.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-3 was used instead of Compound 2-1 in Comparative Example 25.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-4 was used instead of Compound 2-1 in Comparative Example 25.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-7 was used instead of Compound 2-1 in Comparative Example 25.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-8 was used instead of Compound 2-1 in Comparative Example 25.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-13 was used instead of Compound 2-1 in Comparative Example 25.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 25.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 25.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 25.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 25.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 25.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 26.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 26.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 26.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 26.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 26.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 27, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 27.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 27, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 27.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 27, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 27.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 27, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 27.
  • An organic light emitting diode was manufactured according to the same method as Comparative Example except for using Compound 1-4-1 instead of Compound 1-1-1 in Comparative Example 27.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 28.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 28.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 28.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 28.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 28.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 29.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 29.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 29.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 29.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 29.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 30.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 30.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 30.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 30.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 30.
  • the driving voltage and the luminous efficiency of the organic light emitting device manufactured by the above-described method were measured at a current density of 10 mA / cm 2 , and the time (LT98) of 98% of the initial luminance at a current density of 20 mA / cm 2 was measured. .
  • the results are shown in Table 1 below.
  • an organic light emitting device having high efficiency and / or long life may be provided.

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Abstract

La présente invention concerne un élément luminescent organique, qui comprend : une cathode ; une anode formée à l'opposé de la cathode ; une couche luminescente formée entre la cathode et l'anode ; et une couche de transport d'électrons formée entre la cathode et la couche luminescente ; et une couche d'ajustement d'électrons formée entre la couche luminescente et la couche de transport d'électrons, la couche de transport d'électrons comprenant un composé organique contenant un hétérocycle aromatique, la couche d'ajustement d'électrons comprenant un composé hétérocyclique représenté par la formule chimique 1, et le potentiel d'ionisation (Ipm) de la couche de transport d'électrons étant supérieur au potentiel d'ionisation (Ipa) de la couche d'ajustement d'électrons.
PCT/KR2015/007418 2014-08-12 2015-07-16 Élément luminescent organique WO2016024728A1 (fr)

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US14/912,537 US9502669B2 (en) 2014-08-12 2015-07-16 Organic light emitting diode
EP15831494.8A EP3181657B1 (fr) 2014-08-12 2015-07-16 Élément luminescent organique
CN201580029639.5A CN106459745B (zh) 2014-08-12 2015-07-16 有机发光二极管
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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016140549A3 (fr) * 2015-03-05 2016-10-27 주식회사 엘지화학 Composé hétérocyclique et élément électroluminescent organique le comprenant
WO2016140551A3 (fr) * 2015-03-05 2016-11-03 주식회사 엘지화학 Composé hétérocyclique et élément électroluminescent organique le comprenant
US20170098777A1 (en) * 2014-04-04 2017-04-06 Lg Chem, Ltd. Heterocyclic compound and organic light-emitting device comprising same
CN107848989A (zh) * 2016-07-20 2018-03-27 株式会社Lg化学 新杂环化合物和包含其的有机发光器件
JP2019503078A (ja) * 2016-04-28 2019-01-31 エルジー・ケム・リミテッド 有機発光素子
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US11877510B2 (en) 2014-04-04 2024-01-16 Lg Chem, Ltd. Heterocyclic compound and organic light-emitting element comprising same
US20170098777A1 (en) * 2014-04-04 2017-04-06 Lg Chem, Ltd. Heterocyclic compound and organic light-emitting device comprising same
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CN107406471B (zh) * 2015-03-05 2020-06-02 株式会社Lg化学 杂环化合物和包含其的有机发光元件
US10355225B2 (en) 2015-03-05 2019-07-16 Lg Chem, Ltd. Heterocyclic compound and organic light emitting element comprising same
WO2016140551A3 (fr) * 2015-03-05 2016-11-03 주식회사 엘지화학 Composé hétérocyclique et élément électroluminescent organique le comprenant
WO2016140549A3 (fr) * 2015-03-05 2016-10-27 주식회사 엘지화학 Composé hétérocyclique et élément électroluminescent organique le comprenant
US10700289B2 (en) 2015-03-05 2020-06-30 Lg Chem, Ltd. Heterocyclic compound and organic light emitting element comprising same
CN107406471A (zh) * 2015-03-05 2017-11-28 株式会社Lg化学 杂环化合物和包含其的有机发光元件
JP2019505091A (ja) * 2016-04-28 2019-02-21 エルジー・ケム・リミテッド 有機発光素子
JP2019503078A (ja) * 2016-04-28 2019-01-31 エルジー・ケム・リミテッド 有機発光素子
US11723268B2 (en) 2016-04-28 2023-08-08 Lg Chem, Ltd. Organic light-emitting element
CN107848989B (zh) * 2016-07-20 2021-06-11 株式会社Lg化学 新杂环化合物和包含其的有机发光器件
CN107848989A (zh) * 2016-07-20 2018-03-27 株式会社Lg化学 新杂环化合物和包含其的有机发光器件
JP2020516068A (ja) * 2017-05-29 2020-05-28 エルジー・ケム・リミテッド 有機発光素子
WO2019151615A1 (fr) * 2018-02-02 2019-08-08 주식회사 엘지화학 Composé hétérocyclique et élément électroluminescent organique le comprenant
CN111406060A (zh) * 2018-02-02 2020-07-10 株式会社Lg化学 杂环化合物和包含其的有机发光元件
CN111406060B (zh) * 2018-02-02 2023-02-03 株式会社Lg化学 杂环化合物和包含其的有机发光元件
US11997926B2 (en) 2018-02-02 2024-05-28 Lg Chem, Ltd. Heterocyclic compound and organic light emitting element comprising same

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