WO2020130660A1 - Composé organique et dispositif électroluminescent organique l'utilisant - Google Patents

Composé organique et dispositif électroluminescent organique l'utilisant Download PDF

Info

Publication number
WO2020130660A1
WO2020130660A1 PCT/KR2019/018070 KR2019018070W WO2020130660A1 WO 2020130660 A1 WO2020130660 A1 WO 2020130660A1 KR 2019018070 W KR2019018070 W KR 2019018070W WO 2020130660 A1 WO2020130660 A1 WO 2020130660A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
formula
compound
aryl
nuclear atoms
Prior art date
Application number
PCT/KR2019/018070
Other languages
English (en)
Korean (ko)
Inventor
신환규
Original Assignee
두산솔루스 주식회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 두산솔루스 주식회사 filed Critical 두산솔루스 주식회사
Publication of WO2020130660A1 publication Critical patent/WO2020130660A1/fr

Links

Images

Classifications

    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • 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
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present invention relates to a novel organic light-emitting compound and an organic electroluminescent device using the same, and more specifically, a compound having excellent thermal stability, electrochemical stability, light-emitting ability, hole/electron transport ability, and one or more organic material layers to emit light-emitting efficiency , It is related to an organic electroluminescent device having improved characteristics such as driving voltage and life.
  • an organic electroluminescent device In an organic electroluminescent device (hereinafter referred to as an'organic EL device'), when current or voltage is applied to two electrodes, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer at the cathode. When the injected hole meets the electron, an exciton is formed, and the exciton falls to the ground state to emit light.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to its function.
  • the light emitting material of the organic EL device may be divided into blue, green, and red light emitting materials according to the light emission color. In addition, it can be divided into yellow and orange light-emitting materials necessary for realizing a better natural color.
  • a host/dopant system may be used as a light emitting material to increase color purity and increase light emission efficiency through energy transfer.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times that of the fluorescence, attention is focused on phosphorescent host materials as well as phosphorescent dopants.
  • NPB hole blocking layer
  • BCP hole blocking layer
  • Alq 3 and the like represented by the following formula
  • anthracene derivatives are reported as fluorescent dopant/host materials in light emitting materials.
  • metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2, etc., which have great advantages in terms of efficiency improvement, are blue, green, and red dopant materials.
  • CBP has shown excellent properties as a phosphorescent host material.
  • the existing materials have an advantage in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, which is not a satisfactory level in terms of life in the organic EL device. Therefore, development of an organic material layer material having excellent performance is required.
  • An object of the present invention is to provide a novel organic compound that can be applied to an organic electroluminescent device, and can be used as a light emitting layer material having excellent thermal stability, electrochemical stability, light emitting ability, and hole/electron transporting ability.
  • Another object of the present invention is to provide an organic electroluminescent device that exhibits low driving voltage and high luminous efficiency and improves life, including the novel organic compound.
  • a is an integer of 2 or 3
  • b 0 or 1
  • a plurality of A rings are the same as or different from each other, and each independently a C 6 ⁇ C 60 polycyclic aromatic ring,
  • a plurality of X is the same or different from each other, each independently selected from the group consisting of C (R 2 ) (R 3 ), N (R 4 ), O and S,
  • a plurality of L 1 are the same as or different from each other, and each independently a single bond or an arylene group of C 6 to C 60 ,
  • Y 1 to Y 3 are the same as or different from each other, and each independently N or CR 5 , provided that at least one of Y 1 to Y 3 is N, and when CR 5 is plural, a plurality of R 5 s are the same or different from each other Different,
  • Ar 1 is selected from the group consisting of C 6 ⁇ C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms,
  • c is an integer from 0 to 4,
  • the plurality of R 1, and R 2 to R 5 are the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 Alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 nuclear atoms heteroaryl Group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, is selected from the group consisting of C 6 ⁇ C 60 aryl group of boron, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group
  • a group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphine group, an arylphosphine oxide group and an arylamine group are each independently hydrogen, deuterium, halogen, cyano group , Nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalky
  • the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode, at least among the one or more organic material layers
  • an organic electroluminescent device comprising the compound represented by Chemical Formula 1.
  • the compound of the present invention has excellent thermal stability, electrochemical stability, luminescence ability, hole transport ability, and electron transport ability, it can be usefully applied as an organic material layer material of an organic electroluminescent device.
  • the organic electroluminescent device including the compound of the present invention in the organic material layer has significantly improved aspects such as luminescence performance, driving voltage, life, efficiency, and can be effectively applied to a full color display panel.
  • FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to an example of the present invention.
  • FIG. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to another example of the present invention.
  • the present invention provides a novel organic compound that can be used as a high-efficiency light-emitting layer material, specifically a host or a dopant, having excellent electrochemical stability, thermal stability, hole/electron transport ability, and luminescence ability.
  • the compound of Formula 1 according to the present invention includes a core structure composed of 2 to 3 N-containing condensed heteroaromatic ring moieties bonded to each other through an N-containing 6-membered heterocycle as a linker.
  • the N-containing condensed heteroaromatic ring moiety is a group such as a benzene ring, a naphthalene ring, anthracene ring, pyrene ring, etc., on one side of a phenoxazine moiety having a P-type characteristic. It is obtained by condensing a monocyclic or polycyclic aromatic ring, and has a rigid structure. Therefore, the compound of the present invention has a high glass transition temperature, and thus not only has excellent thermal stability, but also excellent electrochemical stability.
  • the N-containing condensed heteroaromatic ring moiety is an electron donating group (EDG) having a large electron donor
  • EDG electron donating group
  • the N-containing 6-membered heterocyclic ring is a pyridine ring, a pyrimidine ring, a triazine ring, and electron absorbency.
  • This is a large electron withdrawing group (EWG). Therefore, the compound of the present invention has not only a high binding force between holes and electrons, but also excellent hole/electron transportability and high triplet energy because the entire molecule has bipolar properties.
  • the compound of the present invention is excellent in luminescence ability and hole/electron transport ability, and thus can exhibit low voltage, high efficiency, and long life characteristics when applied as a light emitting layer material of OLED, especially phosphorescent, fluorescent host, or dopant.
  • the compound of the present invention has a high triplet energy and a small singlet and triplet energy difference ( ⁇ EST).
  • the compound of the present invention when used as a light emitting layer material of an organic electroluminescent device, the compound of the present invention can prevent the exciton generated in the light emitting layer from diffusing into the electron transport layer or the hole transport layer adjacent to the light emitting layer, which in the end
  • the number of excitons contributing to the light emission in the light emitting layer is substantially increased to improve the luminous efficiency and absolute quantum efficiency of the device, and the durability and stability of the device are improved to significantly increase the lifetime characteristics of the device.
  • the compound of the present invention is not only excellent in electrochemical stability due to the strong bond between the N-containing condensed heteroaromatic ring moiety and the N-containing 6-membered heterocyclic ring, but also minimizes the interaction between them, resulting in the structural stability of the molecule. Increased, physical and thermal stability can be significantly increased.
  • the compound of the present invention can control hole/electron transport capacity by specifying a monocyclic or polycyclic aromatic ring condensed on one side of a phenoxazine moiety, and maintains the molecule while maintaining the HOMO level of the molecule. You can tune.
  • the compound of the present invention can control the energy level, the steric effect, and the thin film properties of the compound by controlling the type and position of the substituent introduced into the core structure.
  • the compound represented by Formula 1 according to the present invention has excellent thermal stability, electrochemical stability, hole/electron transportability, and luminescence ability.
  • the compound of the present invention can prevent the movement (diffusion) of the exciton generated in the light emitting layer to the adjacent layer, thereby increasing the number of excitons in the light emitting layer.
  • the compound represented by Formula 1 of the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material, specifically, a green, red, or blue phosphorescent host or dopant, or a green, red, or blue phosphorescent host or dopant. Can be used.
  • the performance of the organic electroluminescent device including the compound of the present invention can be greatly improved, and the performance of a full color organic light emitting panel to which the organic electroluminescent device is applied can be maximized.
  • a is an integer of 2 or 3
  • b is 0 or 1, provided that a+b is 3.
  • a may be 2 and b may be 1.
  • the compound of Formula 1 may be a compound represented by Formula 8, but is not limited thereto.
  • a may be 3 and b may be 0.
  • the compound of Formula 1 may be a compound represented by Formula 9 below, but is not limited thereto.
  • the A ring is a C 6 ⁇ C 60 polycyclic aromatic ring, preferably a C 6 ⁇ C 40 polycyclic aromatic ring, and more preferably a C 6 ⁇ C 40 bicyclic ⁇ It may be an 8-ring aromatic ring.
  • each ring in the polycyclic aromatic ring may be the same as or different from each other.
  • examples of the A ring include a naphthalene ring, anthracene ring, tetracene ring, pyrene ring, phenanthrene ring, phenalene ring, benzoanthracene ring, benzo It may be a pyrene (benzopyrene) ring, a triphenylene ring, a chrysene ring, a pentaphene ring, a pentacene ring, and a condensed ring between the two rings, but is not limited thereto. Does not.
  • the compound represented by Formula 1 may be embodied as a compound represented by Formula 2 below, but is not limited thereto.
  • X, Y 1 to Y 3 , L 1 , Ar 1 , a, b, c and R 1 are each as defined in Formula 1,
  • the plurality of B rings are the same or different from each other, and each independently a C 6 to C 40 monocyclic aromatic ring or a C 6 to C 40 polycyclic aromatic ring, and preferably a benzene ring, a naphthalene ring, anthracene ring, tetracene ( tetracene ring, pyrene ring, phenanthrene ring, phenalene ring, benzoanthracene ring, benzopyrene ring, triphenylene ring, chrysene (chrysene) ring, a pentaphene (pentaphene) ring, a pentacene (pentacene) ring, and may be a condensed ring between the two rings, but is not limited thereto.
  • the compound represented by Formula 1 may be embodied as a compound represented by any one of the following Formulas 3 to 7, but is not limited thereto.
  • X, Y 1 to Y 3 , L 1 , Ar 1 , a, b, c and R 1 are as defined in Formula 1, respectively.
  • c is an integer of 0 to 4.
  • a plurality of R 1 are the same or different from each other, and each independently hydrogen, deuterium, halogen group , Cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms Heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl groups of nuclear atoms, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 ⁇ C 60 boron group, C 6 ⁇ C 60 ⁇ C 60 boron group, C 6 ⁇ C 60 ⁇ C 60
  • R 1 may be selected from the group consisting of hydrogen and the following substituents S1-1 to S1-27.
  • R 6 is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , C 6 to C 60 Aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 Arylphosphine group, C 6 ⁇ C 60 arylphosphine oxide group and C 6 ⁇ C 60 arylamine group, preferably selected from the group consisting of hydrogen, deuterium, hal
  • a plurality of Xs are the same as or different from each other, and each independently selected from the group consisting of C(R 2 )(R 3 ), N(R 4 ), O, and S, Preferably X may be O or S.
  • R 2 to R 4 are the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C Alkynyl group of 2 to C 40 , cycloalkyl group of C 3 to C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ arylboronic group of C 60, C 6 ⁇ C 60 aryl phosphine group, is selected from C 6 ⁇ C 60 aryl phosphine oxide group, and the group consisting
  • R 2 to R 4 are the same or different from each other, and each independently hydrogen, hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alke Nyl group, C 2 ⁇ C 40 alkynyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, and C 6 ⁇ C 60 aryl It may be selected from the group consisting of amine groups.
  • L 1 is a divalent linker group
  • a plurality of L 1 are the same or different from each other, each independently a single bond or C 6 ⁇ C 60 arylene group, preferably a single bond Or it may be a C 6 ⁇ C 40 arylene group.
  • examples of L 1 include a single bond, a phenylene group, a biphenylene group, a terphenylene group, and a divalent naphthalene group, but are not limited thereto.
  • a plurality of L 1 are the same as or different from each other, and may each independently be a single bond or a phenylene group.
  • the N-containing condensed heteroaromatic ring moiety and the N-containing 6-membered heterocyclic ring may be bonded to each other in a para position with respect to L 1 .
  • the compound represented by Formula 1 may be embodied as a compound represented by Formula 8 or 9 below.
  • both of the compound of Formula 8 and the compound of Formula 9 since the bipolar property is increased, the luminous efficiency is high, and injection of electrons/electrons is easy, it can be used as a light emitting layer material of an organic electroluminescent device, specifically a host or dopant At this time, it is possible to increase the current efficiency while lowering the driving voltage of the organic EL device.
  • X, Y 1 to Y 3 , Ar 1 , c and R 1 are each as defined in Formula 1,
  • d 0 or 1
  • the plurality of B rings is as defined in Formula 2.
  • Y 1 to Y 3 are the same as or different from each other, and each independently N or CR 5 , but at least one of Y 1 to Y 3 is N, wherein CR 5 is plural In the case of, a plurality of R 5 are the same or different from each other.
  • Y 1 to Y 3 may all be N.
  • Y 1 to Y 3 are both N a N- containing 6-membered heterocyclic ring (i.e., a triazine ring) is Y 1 to Y 3 in one to two dogs of N- N-containing 6-membered heterocyclic ring (i.e., pyridine ring or Compared to the pyrimidine ring), since the EWG property is stronger, the bipolar property of the compound may be further increased.
  • R 5 is the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 the arylboronic group, C 6 ⁇ C 60 aryl phosphine group, is selected from C 6 ⁇ C 60 aryl phosphine oxide group, and the group consisting of C 6 ⁇ C 60
  • R 5 is hydrogen, hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, nucleus It may be selected from the group consisting of a heterocycloalkyl group having 3 to 40 atoms, an aryl group having C 6 to C 60 , a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group having C 6 to C 60 .
  • Ar 1 is selected from the group consisting of C 6 ⁇ C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms, preferably C 6 ⁇ C 40 aryl group and It may be selected from the group consisting of a heteroaryl group having 5 to 40 nuclear atoms.
  • Ar 1 may be a substituent selected from the group consisting of the following substituents S2-1 to S2-26.
  • R 6 is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , C 6 to C 60 Aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 Arylphosphine group, C 6 ⁇ C 60 arylphosphine oxide group and C 6 ⁇ C 60 arylamine group, preferably selected from the group consisting of hydrogen, deuterium, hal
  • the polycyclic aromatic ring of the A ring, the arylene group of L 1, the aryl group of Ar 1, the heteroaryl group, the alkyl group of R 1 to R 5 , alkenyl group, alkynyl group, cycloalkyl group, heterocyclo Alkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently deuterium , Halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms Heterocycloalkyl group, C 6 ⁇ C 60 ary
  • the compound represented by Formula 1 may be embodied as a compound represented by Formula 10 or 11 below, but is not limited thereto.
  • a plurality of B rings are as defined in Formula 2 above,
  • d 0 or 1
  • e 0 or 1
  • R 7 is C 1 ⁇ C 40 alkylene group, C 2 ⁇ C 40 alkenylene group, C 2 Alkynylene group of ⁇ C 40 , cycloalkylene group of C 3 ⁇ C 40 , heterocycloalkylene group of 3 to 40 nuclear atoms, arylene group of C 6 ⁇ C 60 , and heteroarylene of 5 to 60 nuclear atoms It is selected from the group consisting of groups, specifically, may be selected from the group consisting of a phenylene group, biphenylene group, divalent dibenzothiophene group, divalent dibenzofuran, divalent carbazole group, and divalent fluorene group,
  • f 0 or 1
  • R 8 and R 9 are the same or different from each other, respectively independently C 6 ⁇ C 60-C 6 ⁇ C 60 aryl group and a nuclear atoms are selected from the group consisting of 5 to 60 groups heteroarylene, preferably from C 6 ⁇ C 40 aryl group and the number 5 to the nucleus of atoms of It may be selected from the group consisting of 40 heteroarylene groups, specifically, a group consisting of a phenyl group, a biphenyl group, a monovalent dibenzothiophene group, a monovalent dibenzofuran, a monovalent carbazole group, and a monovalent fluorene group.
  • the alkylene group, alkenylene group, alkynylene group, cycloalkylene group, heterocycloalkylene group, arylene group and heteroarylene group of R 7 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nucleus Heteroaryl group having 5 to 60 atoms, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C group of 1 to alkylboronic of C 40, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine
  • the compound represented by Formula 1 may be embodied as a compound represented by any one of the following Formulas 12 to 21, but is not limited thereto.
  • Compound represented by the formula (1) according to the present invention described above may be more specific to the following exemplary compounds, such as compounds A-1-1 to C-5-28, but is not limited thereto.
  • alkyl means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of this include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
  • alkenyl (alkenyl) means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond.
  • vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like but is not limited thereto.
  • alkynyl (alkynyl) means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds. Examples of this include ethynyl, 2-propynyl, and the like, but are not limited thereto.
  • Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • heterocycloalkyl refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S Or a hetero atom such as Se.
  • heterocycloalkyl include morpholine, piperazine, and the like, but are not limited thereto.
  • aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
  • two or more rings may be simply attached to each other (pendant) or a condensed form. Examples of such aryl include phenyl, naphthyl, phenanthryl, and anthryl, but are not limited thereto.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are simply attached to each other or condensed may be included, and condensed form with an aryl group may also be included.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole
  • alkyloxy refers to a monovalent substituent represented by R'O-, wherein R'refers to alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. It may include. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms.
  • R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like, but are not limited thereto.
  • Alkylsilyl in the present invention means a silyl substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-, tri-alkylsilyl.
  • arylsilyl means silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as di- and tri-arylsilyl as well as mono-.
  • alkyl boron group means a boron group substituted with alkyl having 1 to 40 carbon atoms
  • aryl boron group means a boron group substituted with aryl having 6 to 60 carbon atoms.
  • alkylphosphinyl group means a phosphine group substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups.
  • arylphosphinyl group means a phosphine group substituted with monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphinyl groups.
  • arylamine means an amine substituted with aryl having 6 to 40 carbon atoms, and includes mono- as well as di-arylamine.
  • an organic electroluminescent device (hereinafter referred to as'organic EL device') comprising the compound represented by Chemical Formula 1 described above.
  • the organic electroluminescent device includes an anode (anode), a cathode (cathode) and at least one organic material layer interposed between the anode and the cathode ( ⁇ ), at least one of the one or more organic material layers It includes a compound represented by the formula (1). At this time, the compound may be used alone, or may be used by mixing two or more.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and at least one organic material layer includes a compound represented by Formula 1 above.
  • the organic material layer including the compound of Formula 1 may be a light emitting layer.
  • the organic material layer of the one or more layers includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer
  • the light emitting layer includes a host and a dopant
  • the dopant is a compound represented by Formula 1 Can be
  • the organic material layer of the one or more layers includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer
  • the light emitting layer includes a host and a dopant
  • the host is represented by Formula 1 It can be a compound.
  • the light emitting layer of the present invention may include a compound known in the art as a second host other than the compound of Formula 1 above.
  • the content of the host may be about 70 to 99.9% by weight based on the total amount of the light emitting layer, and the content of the dopant may be about 0.1 to 30% by weight based on the total amount of the light emitting layer.
  • the compound represented by Chemical Formula 1 may be included in the organic electroluminescent device as a light emitting layer material, preferably green, blue and red phosphorescence, a fluorescent host, or a dopant.
  • a light emitting layer material preferably green, blue and red phosphorescence, a fluorescent host, or a dopant.
  • the structure of the organic electroluminescent device of the present invention is not particularly limited, for example, on the substrate, the anode 100, one or more organic material layers 300 and the cathode 200 may be sequentially stacked (FIGS. 1 and 2). Reference).
  • an insulating layer or an adhesive layer may be inserted at the interface between the electrode and the organic material layer.
  • the organic electroluminescent device as shown in Figure 1, on the substrate, the anode 100, the hole injection layer 310, the hole transport layer 320, the light emitting layer 330, the electron transport layer 340 and The cathode 200 may have a structure sequentially stacked.
  • an electron injection layer 350 may be positioned between the electron transport layer 340 and the cathode 200.
  • a hole blocking layer (not shown) may be positioned between the light emitting layer 330 and the electron transport layer 340.
  • the organic electroluminescent device of the present invention includes at least one of the organic material layers 300 (eg, the light emitting layer ( 330), a hole blocking layer (not shown) or an electron transport layer 340], except that it contains a compound represented by the formula (1), by forming an organic material layer and an electrode using materials and methods known in the art Can be produced.
  • the organic material layers 300 eg, the light emitting layer ( 330), a hole blocking layer (not shown) or an electron transport layer 340
  • it contains a compound represented by the formula (1), by forming an organic material layer and an electrode using materials and methods known in the art Can be produced.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution application method include spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer, but are not limited thereto.
  • the substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.
  • examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO 2 :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but is not limited thereto.
  • metals such as vanadium, chromium, copper, zinc and gold or alloys thereof
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO 2 :Sb
  • Conductive polymers such as polythiophene, poly(3-methylthiophene),
  • examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; And a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection layer, the hole transport layer, the electron transport layer and the electron injection layer are not particularly limited, and common materials known in the art may be used.
  • the target compound S- was subjected to the same procedure as in Step 1 of [Preparation Example 6], except that Compound S-4 obtained in Preparation Example 2 was used instead of Compound S-2 used in ⁇ Step 1> of Preparation Example 6 13 (10.2 g, Yield: 43%).
  • a target compound was performed by performing the same procedure as in ⁇ Step 1> of [Preparation Example 6], except that Compound S-6 obtained in Preparation Example 3 was used instead of Compound S-2 used in ⁇ Step 1> of Preparation Example 6 S-15 (12.8 g, yield: 62%) was obtained.
  • the target compound S-16 (9.8) was subjected to the same procedure as ⁇ Step 2> of [Preparation Example 6], except that Compound S-15 was used instead of Compound S-11 used in ⁇ Step 2> of Preparation Example 6. g, yield: 90%).
  • the compound A-1-2 synthesized in Synthesis Example 1 was subjected to a high-purity sublimation purification by a commonly known method, and then a blue organic electroluminescent device was manufactured as follows.
  • the glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone or methanol
  • UV ozone cleaner Power sonic 405, Hwashin Tech
  • a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that each of the compounds shown in Table 1 below was used instead of Compound A-1-2 used as the light emitting layer material in Example 1.
  • a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq 3 was used instead of Compound A-1-2 used as the light emitting layer material in Example 1.
  • the structure of Alq 3 used at this time is as follows.
  • a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following compound Com-1 was used instead of the compound A-1-2 used as the light emitting layer material in Example 1.
  • the structure of the compound Com-1 used at this time is as follows.
  • Example 1 A-1-2 3.2 535 40
  • Example 2 A-1-4 4.2 532 41
  • Example 3 A-1-5 4.1 530 40
  • Example 4 A-1-16 4.2 550 50
  • Example 5 A-1-20 4.1 550 53
  • Example 6 A-1-24 4.2 545 46
  • Example 7 A-3-2 4.3 545 45
  • Example 8 A-3-4 4.3 545 44
  • Example 9 A-3-5 4.3 545 43
  • Example 10 A-3-16 4.2 542 44
  • Example 11 A-3-26 4.2 550 46
  • Example 12 A-3-27 4.5 550 40
  • Example 13 A-3-28 4.1 557 45
  • Example 14 A-3-29 4.4 523 36
  • Example 15 A-4-2 4.3 525 37
  • Example 17 B-1-2 4.5 553 39
  • Example 18 B-1-4 4.4 525 40
  • Example 19 B-3-2 4.3 535 40
  • Example 20 B-3-4 4.4 540 41
  • the green organic EL devices of Examples 1 to 24 using Compounds A-1-2 to C-3-4 according to the present invention as a light emitting layer material together with mCBP, conventional mCBP and Alq 3 It was found that the green organic EL device of Comparative Example 1 used was superior in terms of driving voltage, emission peak, and current efficiency.
  • the green organic EL devices of Examples 1 to 24 were superior in current efficiency to the green organic EL devices of Comparative Example 2 using the conventional compound Com-1.
  • the compound A-1-10 synthesized in Synthesis Example 25 was subjected to a high-purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with a thin film of ITO (Indium tin oxide) at a thickness of 1500 ⁇ was washed with distilled water. After washing with distilled water, ultrasonic cleaning is performed with a solvent such as isopropyl alcohol, acetone or methanol, dried and transferred to a UV ozone cleaner (Power sonic 405, Hwashin Tech), and then the substrate is cleaned using UV for 5 minutes and then vacuum-deposited. The substrate was transferred to.
  • ITO Indium tin oxide
  • M-MTDATA 60 nm)/TCTA (80 nm)/90 wt% of Compound A-1-10 + 10 wt% of Ir(ppy) 3 (300 nm)/BCP (10 nm)/Alq 3 on the ITO transparent electrode thus prepared (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in order to prepare an organic EL device.
  • the structures of m-MTDATA, TCTA, Ir(ppy) 3 , and BCP used at this time are as follows.
  • An organic EL device was manufactured in the same manner as in Example 25, except that each of the compounds shown in Table 2 below was used instead of Compound A-1-10 used as a light emitting host material in the formation of the light emitting layer in Example 25.
  • An organic EL device was manufactured in the same manner as in Example 25, except that CBP was used instead of Compound A-1-10 used as a light emitting host material in the formation of the light emitting layer in Example 25.
  • the structure of the CBP used at this time is as follows.
  • An organic EL device was manufactured in the same manner as in Example 25, except that the following compound Com-2 was used instead of Compound A-1-10 used as a light emitting host material in the formation of the light emitting layer in Example 25.
  • the structure of the following compound Com-2 used at this time is as follows.
  • the organic EL devices of Examples 25 to 34 using the compounds A-1-10 to C-1-24 according to the present invention as hosts for the light emitting layer, CBP and Com-2, which are conventional hosts, are used. It was found that the organic EL devices of Comparative Examples 3 to 4, respectively, were superior in terms of driving voltage, emission peak, and current efficiency.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé électroluminescent organique et un dispositif électroluminescent organique l'utilisant, et plus particulièrement un composé ayant une stabilité thermique, une stabilité électrochimique, une luminescence et une capacité de transport de trous/d'électrons excellentes, ainsi qu'un dispositif électroluminescent organique comprenant ce composé dans une ou plusieurs couches de matériau organique de telle sorte que des propriétés telles que le rendement lumineux, la tension de commande et la durée de vie sont améliorées.
PCT/KR2019/018070 2018-12-21 2019-12-19 Composé organique et dispositif électroluminescent organique l'utilisant WO2020130660A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2018-0167199 2018-12-21
KR1020180167199A KR20200077880A (ko) 2018-12-21 2018-12-21 유기 화합물 및 이를 이용한 유기 전계 발광 소자

Publications (1)

Publication Number Publication Date
WO2020130660A1 true WO2020130660A1 (fr) 2020-06-25

Family

ID=71102585

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2019/018070 WO2020130660A1 (fr) 2018-12-21 2019-12-19 Composé organique et dispositif électroluminescent organique l'utilisant

Country Status (2)

Country Link
KR (1) KR20200077880A (fr)
WO (1) WO2020130660A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114621241A (zh) * 2020-12-11 2022-06-14 江苏三月科技股份有限公司 一种以三嗪接苯并呋喃结构为核心骨架的化合物及其应用
CN114685454B (zh) * 2020-12-29 2024-01-12 广州华睿光电材料有限公司 有机化合物、混合物、组合物及有机电子器件

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100171417A1 (en) * 2009-01-06 2010-07-08 Fujifilm Corporation Charge transport material and organic electroluminescence device
US20160028025A1 (en) * 2013-03-18 2016-01-28 Idemitsu Kosan Co., Ltd. Light-emitting device
KR20160055375A (ko) * 2014-11-07 2016-05-18 주식회사 엠비케이 유기 발광 화합물, 잉크 조성물, 유기 발광 소자 및 전자 기기
CN107142103A (zh) * 2017-04-21 2017-09-08 中节能万润股份有限公司 一种以吖啶为骨架的包含tadf单体的共轭聚合物有机电致发光材料及其应用和器件

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100171417A1 (en) * 2009-01-06 2010-07-08 Fujifilm Corporation Charge transport material and organic electroluminescence device
US20160028025A1 (en) * 2013-03-18 2016-01-28 Idemitsu Kosan Co., Ltd. Light-emitting device
KR20160055375A (ko) * 2014-11-07 2016-05-18 주식회사 엠비케이 유기 발광 화합물, 잉크 조성물, 유기 발광 소자 및 전자 기기
CN107142103A (zh) * 2017-04-21 2017-09-08 中节能万润股份有限公司 一种以吖啶为骨架的包含tadf单体的共轭聚合物有机电致发光材料及其应用和器件

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
YOSHIMASA, W.: "Highly efficient electroluminescence from a solution-processable thermally activated delayed fluorescence emitter", APPLIED PHYSICS LETTERS, 2015, pages 183303, XP012201947 *

Also Published As

Publication number Publication date
KR20200077880A (ko) 2020-07-01

Similar Documents

Publication Publication Date Title
WO2017179809A1 (fr) Composé organique électroluminescent et élément électroluminescent organique l'utilisant
WO2016089080A1 (fr) Composé luminescent organique et dispositif électroluminescent organique comprenant un tel composé
WO2015190718A1 (fr) Dispositif électroluminescent organique
WO2020159019A1 (fr) Composé électroluminescent organique, et dispositif électroluminescent organique l'utilisant
WO2016105161A2 (fr) Composé organique et élément électroluminescent organique comprenant ce composé
WO2018038400A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2020209679A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2017111439A1 (fr) Composé organique et dispositif électroluminescent organique comprenant ledit composé
WO2014010810A1 (fr) Nouveau composé et dispositif électroluminescent le comprenant
WO2014142488A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2011081451A2 (fr) Composés triphénylés, et dispositif électroluminescent organique les utilisant
WO2017209488A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2015133804A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2015111943A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2015125986A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2016105123A2 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2020027463A1 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2017111389A1 (fr) Composé organique et diode électroluminescente organique comprenant ledit composé
WO2020218680A1 (fr) Composé organique et diode électroluminescente organique l'utilisant
WO2020130660A1 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2018117493A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2018212463A1 (fr) Composé électroluminescent organique, et élément électroluminescent organique l'utilisant
WO2015133808A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2020130555A1 (fr) Composé luminescent organique, et diode électroluminescente organique l'utilisant
WO2020130725A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19900609

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19900609

Country of ref document: EP

Kind code of ref document: A1