WO2019235857A1 - Composé pour élément optoélectronique organique, composition pour élément optoélectronique organique, élément optoélectronique organique et dispositif d'affichage - Google Patents

Composé pour élément optoélectronique organique, composition pour élément optoélectronique organique, élément optoélectronique organique et dispositif d'affichage Download PDF

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WO2019235857A1
WO2019235857A1 PCT/KR2019/006821 KR2019006821W WO2019235857A1 WO 2019235857 A1 WO2019235857 A1 WO 2019235857A1 KR 2019006821 W KR2019006821 W KR 2019006821W WO 2019235857 A1 WO2019235857 A1 WO 2019235857A1
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group
unsubstituted
substituted
organic optoelectronic
compound
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PCT/KR2019/006821
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English (en)
Korean (ko)
Inventor
조영경
김형선
장기포
양용탁
정호국
허달호
고종훈
류진현
이미진
정성현
조평석
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삼성에스디아이 주식회사
삼성전자주식회사
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Priority claimed from KR1020190066084A external-priority patent/KR102430047B1/ko
Application filed by 삼성에스디아이 주식회사, 삼성전자주식회사 filed Critical 삼성에스디아이 주식회사
Priority to US16/972,688 priority Critical patent/US20210273179A1/en
Priority to CN201980044872.9A priority patent/CN112368853A/zh
Publication of WO2019235857A1 publication Critical patent/WO2019235857A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • a compound for organic optoelectronic devices a composition for organic optoelectronic devices, an organic optoelectronic device, and a display device.
  • Organic optoelectronic diodes are devices that can switch electrical energy and light energy.
  • Organic optoelectronic devices can be divided into two types according to the principle of operation.
  • One is an optoelectronic device in which excitons formed by light energy are separated into electrons and holes, and electrons and holes are transferred to different electrodes to generate electrical energy, and the other is electrical energy by supplying voltage or current to the electrodes.
  • It is a light emitting element which generates light energy from the.
  • Examples of the organic optoelectronic device may be an organic photoelectric device, an organic light emitting device, an organic solar cell and an organic photo conductor drum.
  • organic light emitting diodes have recently attracted much attention as demand for flat panel displays increases.
  • An organic light emitting device is a device that converts electrical energy into light, and the performance of the organic light emitting device is greatly influenced by the organic material located between the electrodes.
  • One embodiment provides a compound for an organic optoelectronic device capable of implementing high efficiency and long life organic optoelectronic devices.
  • Another embodiment provides an organic optoelectronic device composition comprising the compound for an organic optoelectronic device.
  • Yet another embodiment provides an organic optoelectronic device including the compound for an organic optoelectronic device or a composition for an organic optoelectronic device.
  • Another embodiment provides a display device including the organic optoelectronic device. 2019/235857 1 »(: 1 ⁇ 1 ⁇ 2019/006821
  • a compound for an organic optoelectronic device represented by Chemical Formula 1 is provided.
  • Seedlings 1 to 3 seedlings are each independently hydrogen, deuterium, a cyano group or a substituted or unsubstituted (alkyl group that 1 to 010,
  • compositions for an organic optoelectronic device including the above-described compound for an organic optoelectronic device (hereinafter, "a compound for a first organic optoelectronic device) and a compound for a second organic optoelectronic device represented by the following formula (2). .
  • ⁇ And Figures 4 to II 7 are each independently hydrogen, deuterium, cyano group, substituted or 2019/235857 1 »(: 1 ⁇ 1 ⁇ 2019/006821 unsubstituted 01 to 010 alkyl group, substituted or unsubstituted 06 to 020 aryl group, or substituted or unsubstituted 02 to 030 heterocyclic group,
  • 111 is an integer from 0 to 2.
  • an anode and a cathode facing each other including at least one organic layer positioned between the anode and the cathode, the organic layer comprises the compound for the organic optoelectronic device or the composition for organic optoelectronic devices
  • An organic optoelectronic device is provided.
  • a display device including the organic optoelectronic device is provided.
  • 1 and 2 are cross-sectional views illustrating organic light emitting diodes according to one embodiment, respectively.
  • substituted means at least one hydrogenated hydrogen, halogen group, hydroxyl group, amino group, substituted or unsubstituted (the 1 to 030 amine group, nitro group, Substituted or unsubstituted 01 to 040 silyl group, (the 1 to 030 alkyl group, (the 1 to 010 alkylsilyl group, 06 to 030 arylsilyl group, 03 to 030 cycloalkyl group, 03 to 030 heterocycloalkyl group, 06 to 030) Aryl group, 02 to 030 heteroaryl group, (1 to 020 alkoxy group, (: 1 to 010 trifluoroalkyl group, cyano group, Or a combination thereof.
  • substituted means at least one of hydrogen substituted hydrogen, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30
  • substituted means substituted with at least one hydrogen deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group in the substituent or compound.
  • substituted means substituted with at least one hydrogen deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, a cyano group in a substituent or a compound.
  • substituted means a substituent substituted with at least one of hydrogen deuterium, cyano group, methyl group, ethyl group, propaneyl group, butyl group, phenyl group, biphenyl group, terphenyl group or naphthyl group.
  • hetero means one to three heteroatoms selected from the group consisting of N, 0, S, P, and Si in one functional group, and the remainder is carbon unless otherwise defined.
  • aryl group refers to a group having one or more hydrocarbon aromatic moieties, wherein all p-orbitals are conjugated (conjugation) while all elements of the hydrocarbon aromatic moiety have p-orbitals.
  • Forms such as phenyl group, naphthyl group, etc., and two or more hydrocarbon aromatic moieties are connected via a sigma bond, such as biphenyl group, terphenyl group, quarterphenyl group, etc., two or more hydrocarbon aromatic moieties
  • non-aromatic fused rings such as fluorenyl groups, to which they are directly or indirectly fused.
  • Aryl groups are monocyclic, polycyclic or fused ring polycyclic (i.e.
  • Ring groups that share adjacent pairs of carbon atoms that share adjacent pairs of carbon atoms.
  • a “heterocyclic group” is a higher concept that includes a heteroaryl group, and replaces N, O, S, P instead of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. And it means containing at least one hetero atom selected from the group consisting of Si.
  • the heterocyclic group may include one or more heteroatoms in all or each ring. 2019/235857 1 »(: 1 ⁇ 1 ⁇ 2019/006821
  • a "heteroaryl (10-> 4) group” means that the aryl group contains at least one hetero atom selected from the group consisting of X and V. Two or more heteroaryl groups are directly linked through a sigma bond. When the heteroaryl group includes two or more rings, the two or more rings may be fused to each other.
  • each ring may contain 1 to 3 heteroatoms.
  • the substituted or unsubstituted 06 to 030 aryl group is substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or Unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted!)-terphenyl group, substituted or unsubstituted 111-terphenyl group, substituted or unsubstituted 0 Terphenyl groups, substitutions or
  • Unsubstituted chrysenyl group substituted or unsubstituted triphenylene group, substituted or unsubstituted perenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted indenyl group, or a combination thereof, It is not limited to this.
  • the substituted or unsubstituted 02-030 heterocyclic group is substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted pyrazolyl group, substituted Or an unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted
  • Thiadiazolyl group substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted Or unsubstituted benzothiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted Quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazinyl group, substituted or unsubstitute
  • Acridinyl group substituted or unsubstituted phenazineyl group, substituted or unsubstituted phenthiazineyl group, substituted or unsubstituted phenoxazineyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group Or a substituted or unsubstituted dibenzothiophenyl group, or 2019/235857 1 »(: 1 ⁇ 1 ⁇ 2019/006821 combination, but is not limited thereto.
  • the hole characteristic is an electric field When it is applied, it is a characteristic that can form a hole by donating electrons.It has a conduction characteristic along the level of 0, and it is injected into the light emitting layer of the hole formed in the anode, the movement of the hole formed in the light emitting layer to the anode and in the light emitting layer It means a property that facilitates movement.
  • the electron characteristic is a characteristic which can receive an electron when an electric field is applied, and has electroconductivity along 1; 0 level, and it injected
  • a compound for an organic optoelectronic device according to one embodiment is described.
  • the compound for an organic optoelectronic device is represented by the following formula (1). [Formula 1]
  • II 1 to II 3 are each independently hydrogen, deuterium, cyano group or substituted or unsubstituted 01 to 010 alkyl group,
  • 1 and 2 each independently represent a substituted or unsubstituted 06 to 030 aryl group, except when 1 and 2 are simultaneously unsubstituted phenyl groups when II is 0.
  • a 9-carbazole group is directly or indirectly connected to triazine through phenylene, the 9-carbazole group includes a phenyl substituent at position 3, and the triazine group It has a structure containing an aryl substituent.
  • the 9-carbazole group is linked to triazine via phenylene, the LUMO electron cloud is expanded, thereby lowering the LUMO energy level, resulting in electron injection and electron transport.
  • 2019/235857 1 »(: 1 ⁇ 1 ⁇ 2019/006821 capability is further enhanced, which can lower the driving voltage of the device to which it is applied.
  • the hole injection and hole transporting ability is also enhanced, so that an appropriate charge balance is achieved in the light emitting layer, and thus the efficiency and life of the device to which the same is applied. Properties can be improved.
  • II may be an integer of 0 or 1
  • Chemical Formula 1 may be represented by the following Chemical Formula 1 show or Chemical Formula 1. [Chemical formula 1 taste]
  • any one of 1 and 1 of Formula 1 shows an unsubstituted phenyl group, and the other is a substituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group.
  • Anthracenyl group substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenyltene group, or substituted or unsubstituted fluorenyl group.
  • 1 and 2 in the formula are each independently substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl Group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylene group, or substituted or unsubstituted fluorenyl group.
  • 1 and 2 may be independently selected from the groups listed in Group I below. 2019/235857 1 »(: 1/10 ⁇ 019/006821
  • the yarns 1 and 2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, but is not limited thereto.
  • any one of 1 and the show may be an unsubstituted phenyl group, and the other one may be a substituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group. have.
  • 11 1, 1 and may be independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
  • the aforementioned compound for organic optoelectronic devices may be one selected from the compounds listed in Group 1 below, but is not limited thereto.
  • composition for an organic optoelectronic device includes the aforementioned compound for an organic optoelectronic device (hereinafter, referred to as a ⁇ first organic optoelectronic device ''), and a compound for a second organic optoelectronic device represented by Chemical Formula 2 below. .
  • Ne 2 are each independently a single bond or a substituted or unsubstituted 06 to 2019/235857 1 »(: 1 ⁇ 1 ⁇ 2019/006821
  • ⁇ And ⁇ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted 01 to 010 alkyl group, substituted or unsubstituted 06 to 020 aryl group, or substituted or unsubstituted 02 to 030 heterocyclic group,
  • III is an integer from 0 to 2.
  • the second organic optoelectronic device compound may be used in the light emitting layer together with the first organic optoelectronic device compound to improve charge mobility and stability, thereby improving luminous efficiency and lifetime characteristics.
  • V 1 and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted Anthracenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted
  • It may be a dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted pyridinyl group.
  • and of Formula 2 may each independently be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, but is not limited thereto.
  • I; and I? Of Formula 2 are each independently a single bond, a substituted or unsubstituted phenylene group, and Figures 4 to II 7 of Formula 2 are each hydrogen, and the wave may be 0, It is not limited to this.
  • substituted of Formula 2
  • at least one hydrogen-weighted hydrogen at least one hydrogen-weighted hydrogen
  • Formula 2 may be represented by the following Formula 2. 2019/235857 1 »(: 1/10 ⁇ 019/006821
  • Formula 2 may be one of the structures listed in Group II below, and * -1 and * 2 -may be one of the substituents listed in Group III below.
  • Formula 2 is represented by Formula 0-8 or Formula 0-17 of Group II, and the * -1 person and * ⁇ 2 -may be selected from the group.
  • V 1 and are each independently substituted or
  • the *--and * -1 may be selected from 6-1, 6-2, and 3 of the above group, but is not limited thereto. It is not.
  • the compound for the first organic optoelectronic device is represented by the formula (1) or in the formula, for the second organic optoelectronic device
  • the compound may be represented by the formula (2).
  • the formulas 1 show and II 1 to II 3 in the formula are each hydrogen, 1 and 2 of the formula 1 show are each independently substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group or substituted or unsubstituted Terphenyl group, show! ⁇ 1 and show! 2 is not an unsubstituted phenyl group at the time of operation,
  • Show] ⁇ 1 and Show of the formula (18) may be each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group or a substituted or unsubstituted terphenyl group.
  • the second organic optoelectronic device may be one selected from the compounds listed in Group 2, but is not limited thereto.
  • the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device may be included, for example, in a weight ratio of 1:99 to 99: 1.
  • the electron transport capacity and the second capacity of the compound for the first organic optoelectronic device may be included.
  • the hole transporting ability of the compound for organic optoelectronic devices it is possible to improve the efficiency and lifespan by implementing the bipolar property by matching the appropriate weight ratio.
  • the weight ratio may be included in a weight ratio of 20:80 to 40:60.
  • the weight ratio may be included in a weight ratio of 30:70, 40:60, or 50:50.
  • the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device described above may further include one or more compounds.
  • organic optoelectronic device or composition for organic optoelectronic devices may be a composition further comprising a dopant.
  • the dopant may be, for example, a phosphorescent dopant, for example red, green or blue
  • Correction Paper (Article 91) / It may be a phosphorescent dopant, for example it may be a green or red phosphorescent dopant.
  • the dopant is a substance mixed with the organic optoelectronic device or the composition for the organic optoelectronic device and emits light.
  • the dopant is composed of a metal complex that emits light by multiple excitation which excites above a triplet state.
  • the same material may be used.
  • the dopant may be, for example, an inorganic, organic, or organic compound, and may be included in one kind or two or more kinds.
  • An example of a dopant may be a phosphorescent dopant, and an example of a phosphorescent dopant may be Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof.
  • An organic metal compound containing it is mentioned.
  • the phosphorescent dopant may be, for example, a compound represented by the following formula, but is not limited thereto.
  • M is a metal
  • ! / And X are the same or different and are ligands that form a complex with M.
  • the above-mentioned compound for organic optoelectronic devices or the composition for organic optoelectronic devices can be formed by a dry film forming method such as chemical vapor deposition.
  • the organic optoelectronic device is not particularly limited as long as it is a device capable of mutually converting electrical energy and light energy, and examples thereof include organic photoelectric devices, organic light emitting devices, organic solar cells, and organic photosensitive drums.
  • the organic light emitting device 100 includes an anode 120 and a cathode 110 facing each other, and an organic layer 10 ⁇ positioned between the anode 120 and the cathode 110. Include.
  • the anode 120 has a high work function conductor, for example, to facilitate hole injection. 2019/235857 1 »(: 1 ⁇ 1 ⁇ 2019/006821 and may be made of metal, metal oxide and / or conductive polymer, for example.
  • the anode 120 is, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold or an alloy thereof; Zinc oxide, indium oxide, indium tin oxide (110),
  • Metal oxides such as indium zinc oxide (10); Metal and oxide combinations such as 3 ⁇ 40 and 3 ⁇ 40 2 and 3 ⁇ 4; Poly (3-methylthiophene), poly (3,4- (ethylene- 1,2- Conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode 110 may be made of a low work function conductor, for example, to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer.
  • the cathode 110 is, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; Substances, but are not limited thereto.
  • the organic layer 105 may include the aforementioned compound for organic optoelectronic devices or the composition for organic optoelectronic devices. '
  • the organic layer 105 may include a light emitting layer 130, and the light emitting layer 130 may include the aforementioned compound for an organic optoelectronic device or a composition for an organic optoelectronic device.
  • the organic optoelectronic device composition further comprising a dopant may be, for example, a green or red light emitting composition.
  • the light emitting layer 130 may include, for example, a compound for a first organic optoelectronic device and a compound for a second organic optoelectronic device as the phosphorescent host.
  • the organic layer may further include an auxiliary layer in addition to the light emitting layer.
  • the auxiliary layer may be, for example, a hole auxiliary layer 140.
  • the organic light emitting device 200 further includes a hole auxiliary layer 140 in addition to the light emitting layer 130.
  • the hole auxiliary layer 140 may further increase hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.
  • the hole auxiliary layer 140 may include, for example, at least one of the compounds listed in Group I).
  • (1) in the hole auxiliary layer comprise a hole transport layer between the auxiliary anode (20 1) and a light emitting layer (1) between the hole transport layer, and the light-emitting layer 130 and the hole transport layer 2019/235857 1 »(: 1/10 ⁇ 019/006821, and at least one of the compounds listed in Group I below) may be included in the hole transport assistance.
  • the hole transport auxiliary layer may be a compound known in the art and similar structures as described in 1185061569 Human 1993- 009471 ⁇ 01995-009147 Show 1, ⁇ 1995-126615 ⁇ ⁇ 1998-095973, and the like.
  • an organic light emitting device further comprising an electron transport layer, an electron injection layer, a hole injection layer, etc. as the organic layer 105 in FIG.
  • the organic light emitting diodes 100 and 200 form an anode or a cathode on a substrate
  • the organic light emitting device described above may be applied to an organic light emitting display device.
  • Compound 11-1 was synthesized in the same manner as in Synthesis Example 1 using 2-chloro-4,6-diphenyl-1,3,5-triazine.
  • Compound 11-2 was synthesized in the same manner as in Synthesis Example 1 using (3-chlorophenyl) boronic acid instead of (4-chlorophenyl) boronic acid.
  • Tetrahydrofuran 80 11 dl, distilled water 40 11 dl was added, 1 equivalent of the above-mentioned intermediate 11-4-3, 0.03 equivalent of tetrakistriphenylphosphine palladium and 2 equivalents of potassium carbonate were added under heating under nitrogen atmosphere. After 18 hours, the reaction solution was cooled, and the precipitated solid was filtered and washed with 500 11 Pa of water. The solid was recrystallized from monochlorobenzene 500 11 kPa to give compound mo-4rul (70% yield).
  • Compound 99 was synthesized in the same manner as the method known in Show 1. (Production of organic light emitting device)
  • the thin film-coated glass substrate was washed with distilled water ultrasonic waves. 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, and then washed the substrate using an oxygen plasma for 10 minutes and then transferred to a vacuum evaporator.
  • a compound show was vacuum deposited on the 110 substrate to form a hole injection layer having a thickness of 700 ⁇ , and Compound 8 was deposited to a thickness of 50 persons on the injection layer.
  • the hole transport layer was formed by depositing at a thickness of 1020 particles.
  • Use as compound show-2 rule host of Synthesis Example 1 on the hole transport layer A light emitting layer having a thickness of 400 particles was formed by vacuum deposition. Subsequently, the compound I) and 0 (1 were simultaneously vacuum deposited on the light emitting layer in a 1: 1 ratio to form an electron transport layer having a thickness of 300 persons, and vacuum deposition of 1 ⁇ 3 ⁇ 4 15 persons and Show 1 1200 sets was sequentially performed on the electron transport layer.
  • An organic light emitting device was manufactured by forming a cathode.
  • the organic light emitting device has a structure having five organic thin film layers, specifically as follows.
  • Example 5 Except for changing the host and its ratio and changing the dopant ratio as described in Tables 1 to 4 below, Examples 2 to 5 and Comparative Examples 1 to 1 were compared in the same manner as in Example 1. The device of Example 5 and the reference example was produced. Evaluation: Improvement of driving voltage, confirmation of light emission efficiency and lifetime increase
  • the driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting diode according to Examples 1 to 5, Comparative Examples 1 to 5, and Reference Examples were evaluated.
  • the specific measuring method is as follows, and the result is as Tables 1-4.
  • the current value flowing through the unit device was measured by using a current-voltmeter ((2400) while increasing the voltage from 0 to 10 ⁇ , and the result was divided by the area.
  • the voltage The result was obtained by measuring the luminance at that time using a luminance meter (1 11 ( & 08-1000 hours) while increasing from 10 to 10.
  • the current efficiency / hour of the same current density (10111 011 2 ) was calculated using the brightness, current density and voltage measured from (1) and (2).
  • 190 life ratio (%) ⁇ [190 (11) / [Comparative Example (Comparative or Reference Example) of Example (Applying Compound for First Organic Optoelectronic Device as a Single or Mixed Host) Applying a Compound as a Single or Mixed Host 190 ( ⁇ ) ⁇ X 100
  • Evaluation of a single host or a mixed host embodiment using the same second host (the first organic optoelectronic compound is applied as the first host) and the mixed host comparative example (comparative or reference compound is applied as the first host) Indicates a comparison value.
  • Drive voltage ratio (%) ⁇ [drive voltage (V) of the example (compound for the first organic optoelectronic device alone or mixed host)] / [comparative example (comparative example or reference example) Compound alone or mixed host Drive voltage) ⁇ 100
  • Luminous Efficiency Ratio (%) ⁇ [Luminous Efficiency of Example (Applying First Compound for Organic Optoelectronic Devices as a Single or Mixed Host) (1 / show)] / [Comparative Example (Comparative or Reference Example) Luminous efficiency of mixed host) (1 / hour) ⁇ X 100 2019/235857 1 »(: 1 ⁇ 1 ⁇ 2019/006821
  • the compound for an organic optoelectronic device according to the present invention has a lower driving voltage and improved lifespan and luminous efficiency than the compound for an organic optoelectronic device according to a comparative example. 2019/235857 1 »(: 1 ⁇ 1 ⁇ 2019/006821

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Abstract

La présente invention concerne un composé représenté par la formule chimique 1 pour un élément optoélectronique organique, une composition comprenant le composé représenté par la formule chimique 1 pour un élément optoélectronique organique, un élément optoélectronique organique et un dispositif d'affichage. La description de la formule chimique 1 est telle que définie dans la partie descriptive.
PCT/KR2019/006821 2018-06-08 2019-06-05 Composé pour élément optoélectronique organique, composition pour élément optoélectronique organique, élément optoélectronique organique et dispositif d'affichage WO2019235857A1 (fr)

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US16/972,688 US20210273179A1 (en) 2018-06-08 2019-06-05 Compound for organic optoelectronic element, composition for organic optoelectronic element, organic optoelectronic element, and display device
CN201980044872.9A CN112368853A (zh) 2018-06-08 2019-06-05 用于有机光电元件的化合物、用于有机光电元件的组合物、有机光电元件及显示装置

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KR20180066252 2018-06-08
KR10-2018-0066252 2018-06-08
KR1020190066084A KR102430047B1 (ko) 2018-06-08 2019-06-04 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111233832A (zh) * 2020-01-08 2020-06-05 上海传勤新材料有限公司 一种含有芴和三嗪的有机电子材料及其应用
CN114685464A (zh) * 2020-12-29 2022-07-01 江苏三月科技股份有限公司 一种含三嗪类结构的化合物及其应用
CN114685464B (zh) * 2020-12-29 2024-06-11 江苏三月科技股份有限公司 一种含三嗪类结构的化合物及其应用

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