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WO2022169184A1 - Nouveau composé et élément électroluminescent organique le comprenant - Google Patents

Nouveau composé et élément électroluminescent organique le comprenant Download PDF

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Publication number
WO2022169184A1
WO2022169184A1 PCT/KR2022/001394 KR2022001394W WO2022169184A1 WO 2022169184 A1 WO2022169184 A1 WO 2022169184A1 KR 2022001394 W KR2022001394 W KR 2022001394W WO 2022169184 A1 WO2022169184 A1 WO 2022169184A1
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group
light emitting
independently
organic light
layer
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PCT/KR2022/001394
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English (en)
Korean (ko)
Inventor
정은빈
이남걸
장유정
김문배
유승일
한용규
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JINWOONG INDUSTRIAL Co Ltd
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JINWOONG INDUSTRIAL Co Ltd
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Priority claimed from KR1020220007266A external-priority patent/KR102702819B1/ko
Application filed by JINWOONG INDUSTRIAL Co Ltd filed Critical JINWOONG INDUSTRIAL Co Ltd
Publication of WO2022169184A1 publication Critical patent/WO2022169184A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Definitions

  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • An organic light emitting device is a device for converting electrical energy into light energy using an organic material, and includes a structure in which a light emitting organic material layer is formed between an anode and a cathode.
  • the organic light emitting device can be formed in various structures, and among them, a tandem type organic light emitting device in which a plurality of light emitting units are stacked is being studied.
  • a tandem type organic light emitting device a plurality of light emitting units including a light emitting layer are stacked between an anode and a cathode.
  • a charge generating layer for generating and moving charges is positioned between adjacent light emitting units.
  • the charge generation layer requires a low driving voltage and high efficiency.
  • the object of the present invention is achieved by a compound for an organic light emitting device represented by the following formula (1).
  • Formula A is selected from Formula A-1 or B-1,
  • X1 to X3 two are nitrogen atoms, the rest are CR1,
  • one of X4 to X11 is a carbon atom bonded to Formula 1 by a single bond, and the rest are each independently a nitrogen atom or CR2,
  • one of X12 to X16 is a carbon atom bonded to Formula 1 by a single bond, and the rest are each independently a nitrogen atom or CR2,
  • Formulas A-1 and B-1 each contain at least two heteroatoms
  • Y1 is N or CR3
  • Y2 is NR, O, S or C(R')(R''),
  • R1-R3 are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; a phosphine oxide group; C1 ⁇ C20 alkyl group; C2 ⁇ C20 alkenyl group; C2 ⁇ C20 alkynyl group; C1-C20 alkoxyl group; C1-C20 silyl group; C6 ⁇ C30 aryloxy group; C6 ⁇ C30 arylthio group; C3-C30 aliphatic ring; C6 ⁇ C30 aryl group; C2 ⁇ C30 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; selected from the group consisting of
  • a plurality of R2 may combine with each other to form a ring
  • R, R', R'' are each independently a C1-C20 alkyl group; C6 ⁇ C30 aryl group; C2 ⁇ C30 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; selected from the group consisting of
  • L1 and L2 are independently a C6 ⁇ C30 arylene group or a C3 ⁇ C30 heterocyclic group
  • Ar1 and Ar2 are independently a C6 ⁇ C30 aryl group or a C3 ⁇ C30 heteroaryl group,
  • a and b are independently integers from 0 to 3;
  • R1 to R3, R, R', R'', L1, L2, Ar1 and Ar2 are independently deuterium; halogen; C1 ⁇ C20 alkyl group; C6 ⁇ C20 aryl group; C2 ⁇ C20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; It may be further substituted with one or more substituents selected from the group consisting of.
  • a of Formula 1 may be selected from the group of Formulas a-1 to a-4 and b-1 to b-3 below.
  • R4 is deuterium; halogen; C1 ⁇ C20 alkyl group; C6 ⁇ C20 aryl group; C2 ⁇ C20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; may be further substituted with one or more substituents selected from the group consisting of
  • a is an integer from 0 to 5
  • b is an integer from 0 to 4
  • c is an integer from 0 to 4.
  • L1 and L2 may be independently selected from the group represented by the following Chemical Formulas L-1 to L-15.
  • R5 is hydrogen; heavy hydrogen; halogen; cyano group; nitro group; a phosphine oxide group; C1 ⁇ C20 alkyl group; C2 ⁇ C20 alkenyl group; C2 ⁇ C20 alkynyl group; C1-C20 alkoxyl group; C1-C20 silyl group; C6 ⁇ C30 aryloxy group; C6 ⁇ C30 arylthio group; C3-C30 aliphatic ring; C6 ⁇ C30 aryl group; C2 ⁇ C30 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; selected from the group consisting of
  • R5 is deuterium; halogen; C1 ⁇ C20 alkyl group; C6 ⁇ C20 aryl group; C2 ⁇ C20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; may be further substituted with one or more substituents selected from the group consisting of
  • d may be an integer from 0 to 4
  • e may be an integer from 0 to 6
  • f may be an integer from 0 to 8
  • g, h, and i may be independently integers from 0 to 2.
  • the compound may be selected from the group represented by the following Chemical Formulas 1-1 to 1-10.
  • At least one of Ar1 and Ar2 may be of the following formula (C).
  • a and B rings are independently a C6 ⁇ C14 aryl group or a C3 ⁇ C13 heterocyclic group
  • Z1 and Z2 are independently selected from the group consisting of a single bond, CR8R9, NR10, O, S, and when one of them is a single bond, the other is selected from NR10, O, S,
  • R8 to R10 are independently a C1-C20 alkyl group; C6 ⁇ C20 aryl group; It is a C2-C20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P.
  • An object of the present invention is a first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode and emitting light, wherein the organic material layer is formed of a plurality of layers and at least one layer is achieved by an organic light emitting device including the compound.
  • the at least one layer may include a charge generation layer (CGL).
  • CGL charge generation layer
  • the charge generation layer (CGL) may be an n-type.
  • the at least one layer may include an electron transport layer.
  • An object of the present invention is a first electrode; a second electrode; and a first light emitting part positioned between the first electrode and the second electrode and including a first light emitting layer; a second light emitting unit positioned between the second electrode and the first light emitting unit and including a second light emitting layer; and a charge generation layer positioned between the first light emitting unit and the second light emitting unit, wherein the charge generation layer is achieved by the organic light emitting device including the compound.
  • a compound capable of improving the driving voltage and efficiency by minimizing the energy level difference between the n-type charge generating layer and the p-type charge generating layer to improve the electron injection amount in the light emitting part, and an organic light emitting device including the same do.
  • the alkali metal is tightly coordinated with the new compound as a host material to minimize the diffusion of the alkali metal into the p-type charge generating layer, thereby reducing the lifetime of the organic light emitting diode.
  • a novel compound capable of improving the , and an organic light emitting device comprising the same are provided.
  • the novel compound according to the present invention may be included in an organic film, preferably a hole injection layer or a hole transport layer, of an organic light emitting device to lower the driving voltage of the device and improve luminous efficiency.
  • the lifetime of the organic light emitting device can be improved by the thermal stability of the novel compound according to the present invention.
  • FIG. 1 is a cross-sectional view of an organic light emitting device according to an embodiment of the present invention.
  • the compound according to the present invention is represented by the following formula (1).
  • Formula A is selected from Formula A-1 or B-1,
  • X1 to X3 two are nitrogen atoms, the rest are CR1,
  • one of X4 to X11 is a carbon atom bonded to Formula 1 by a single bond, and the rest are each independently a nitrogen atom or CR2,
  • one of X12 to X16 is a carbon atom bonded to Formula 1 by a single bond, and the rest are each independently a nitrogen atom or CR2,
  • Formulas A-1 and B-1 each contain at least two heteroatoms
  • Y1 is N or CR3
  • Y2 is NR, O, S or C(R')(R''),
  • R1-R3 are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; a phosphine oxide group; C1 ⁇ C20 alkyl group; C2 ⁇ C20 alkenyl group; C2 ⁇ C20 alkynyl group; C1-C20 alkoxyl group; C1-C20 silyl group; C6 ⁇ C30 aryloxy group; C6 ⁇ C30 arylthio group; C3-C30 aliphatic ring; C6 ⁇ C30 aryl group; C2 ⁇ C30 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; selected from the group consisting of
  • a plurality of R2 may combine with each other to form a ring
  • R, R', R'' are each independently a C1-C20 alkyl group; C6 ⁇ C30 aryl group; C2 ⁇ C30 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; selected from the group consisting of
  • L1 and L2 are independently a C6 ⁇ C30 arylene group or a C3 ⁇ C30 heterocyclic group
  • Ar1 and Ar2 are independently a C6 ⁇ C30 aryl group or a C3 ⁇ C30 heteroaryl group,
  • a and b are independently integers from 0 to 3;
  • R1 to R3, R, R', R'', L1, L2, Ar1 and Ar2 are independently deuterium; halogen; C1 ⁇ C20 alkyl group; C6 ⁇ C20 aryl group; C2 ⁇ C20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; It may be further substituted with one or more substituents selected from the group consisting of.
  • a in Formula 1 may be selected from the group of Formulas a-1 to a-4 and b-1 to b-3 below.
  • R4 is deuterium; halogen; C1 ⁇ C20 alkyl group; C6 ⁇ C20 aryl group; C2 ⁇ C20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; may be further substituted with one or more substituents selected from the group consisting of
  • a is an integer from 0 to 5
  • b is an integer from 0 to 4
  • c is an integer from 0 to 4.
  • L1 and L2 may be independently selected from the group represented by the following Chemical Formulas L-1 to L-15.
  • R5 is hydrogen; heavy hydrogen; halogen; cyano group; nitro group; a phosphine oxide group; C1 ⁇ C20 alkyl group; C2 ⁇ C20 alkenyl group; C2 ⁇ C20 alkynyl group; C1-C20 alkoxyl group; C1-C20 silyl group; C6 ⁇ C30 aryloxy group; C6 ⁇ C30 arylthio group; C3-C30 aliphatic ring; C6 ⁇ C30 aryl group; C2 ⁇ C30 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; selected from the group consisting of
  • R5 is deuterium; halogen; C1 ⁇ C20 alkyl group; C6 ⁇ C20 aryl group; C2 ⁇ C20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; may be further substituted with one or more substituents selected from the group consisting of
  • d may be an integer from 0 to 4
  • e may be an integer from 0 to 6
  • f may be an integer from 0 to 8
  • g, h, and i may be independently integers from 0 to 2.
  • the compound may be selected from the group represented by the following Chemical Formulas 1-1 to 1-10.
  • At least one of Ar1 and Ar2 may be of the following formula (C).
  • a and B rings are independently a C6 ⁇ C14 aryl group or a C3 ⁇ C13 heterocyclic group
  • Z1 and Z2 are independently selected from the group consisting of a single bond, CR8R9, NR10, O, S, and when one of them is a single bond, the other is selected from NR10, O, S,
  • R8 to R10 are independently a C1-C20 alkyl group; C6 ⁇ C20 aryl group; It is a C2-C20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P.
  • the organic light emitting device 1 has a tandem structure with a first electrode (anode, 110), a second electrode (cathode, 120), a first light emitting unit 210, and a second light emitting unit 220. and a charge generation layer 230 .
  • the first light-emitting unit 210 , the second light-emitting unit 220 , and the charge generation layer 230 are organic layers and are positioned between the first electrode 110 and the second electrode 120 , and the charge generation layer 230 includes: It is positioned between the first light emitting unit 210 and the second light emitting unit 220 .
  • the first light emitting unit 210 includes a hole injection layer 211 , a first hole transport layer 212 , a first light emitting layer 213 , and a first electron transport layer 214
  • the second light emitting unit 220 is a second light emitting unit 220 . It consists of a 2 hole transport layer 221 , a second light emitting layer 222 , a second electron transport layer 223 , and an electron injection layer 224 .
  • the light emitting layers 213 and 222 may have a single stack structure of RGB or a multi-stack structure in which RGB is repeatedly formed a plurality of times.
  • the charge generation layer 230 includes an n-type charge generation layer 231 and a p-type charge generation layer 232 .
  • the n-type charge generation layer 231 may be doped with an alkali metal.
  • the novel compound according to the present invention may be included in the first electron transport layer 212 , the second electron transport layer 223 and the charge generation layer 230 , and in particular may be used in the n-type charge generation layer 231 .
  • the described organic light emitting device 1 can be variously modified. Some organic layers may be omitted or added, may not be in a tandem form, and may be in a tandem form having three or more light emitting layers.
  • Table 1 below shows 1H NMR and MASS/FAB of the synthesized materials.
  • s denotes singlet
  • d denotes doublet
  • t denotes triplet
  • g denotes quartet
  • m denotes multiplet.
  • the ITO substrate After patterning the ITO substrate so that the emission area was 2 mm ⁇ 2 mm in size, washing was performed with isopropyl alcohol and UV ozone, respectively. Then, the ITO substrate was mounted on the substrate holder of the vacuum deposition apparatus, and the pressure was applied so that the degree of vacuum was 1 ⁇ 10 -7 torr.
  • the HAT-CN compound was vacuum-deposited to form a thickness of 5 nm. This compound acts as the first hole injection layer.
  • an NPB material was formed to a thickness of 30 nm as a first hole transport layer.
  • an HT-1 material was formed to a thickness of 10 nm as a first electron blocking layer.
  • the YGH-1 material as a host and the YGD-1 material as a dopant were co-deposited to a thickness of 30 nm in a mass ratio of about 10% to form a yellow first light emitting layer.
  • a TmPyPB compound was formed on the light emitting layer to have a thickness of 25 nm and a first electron transport layer. Thereafter, an N-type charge generation layer was formed by co-depositing a Li material to a thickness of 10 nm in a 2% mass ratio on the BPhen material. Thereafter, the HAT-CN compound was vacuum-deposited to a thickness of 5 nm as a P-type charge generation layer. The foreign material is also used as the second hole injection layer. On this, an NPB material was formed to a thickness of 60 nm as a second hole transport layer. Then, an HT-1 material was formed to a thickness of 10 nm as a second electron blocking layer.
  • the CPB material as a host and the Ir compound as a dopant were co-deposited to a thickness of 30 nm in a mass ratio of about 10% to form a yellow second light emitting layer.
  • a TmPyPB compound was formed on the light emitting layer to have a thickness of 25 nm and a second electron transport layer.
  • the LiF material was vacuum-deposited to a thickness of 1 nm as an electron injection layer.
  • Al was deposited to a thickness of 100 nm to form a cathode to fabricate an organic EL device.
  • An organic light emitting diode was manufactured by changing the N-type charge generation layer material to the comparative compound 1 or the comparative compound 2, except that it was configured in the same manner as in the comparative example described above.
  • An organic light emitting device was manufactured by changing the N-type charge generation layer material to the compound shown in Table 2 below, except that it was configured in the same manner as in the above-described Comparative Example.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique comprenant le nouveau composé dans une ou plusieurs couches organiques pour ainsi être hautement efficace.
PCT/KR2022/001394 2021-02-04 2022-01-26 Nouveau composé et élément électroluminescent organique le comprenant Ceased WO2022169184A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2021-0016131 2021-02-04
KR20210016131 2021-02-04
KR10-2022-0007266 2022-01-18
KR1020220007266A KR102702819B1 (ko) 2021-02-04 2022-01-18 신규 화합물 및 이를 포함하는 유기발광소자

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023112915A1 (fr) * 2021-12-14 2023-06-22 出光興産株式会社 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190053579A (ko) * 2017-11-10 2019-05-20 주식회사 진웅산업 퀴놀린 화합물 및 이를 포함하는 유기발광소자
WO2020012685A1 (fr) * 2018-07-09 2020-01-16 コニカミノルタ株式会社 Film mince, dispositif électronique, élément électroluminescent organique, matériau pour électroluminescence organique, dispositif d'affichage et équipement d'éclairage
US20200095224A1 (en) * 2018-09-25 2020-03-26 Wuhan Tianma Micro-Electronics Co., Ltd. Nitrogen heterocyclic compound, display panel and display apparatus
CN112079767A (zh) * 2020-09-04 2020-12-15 江苏三月科技股份有限公司 芳胺类化合物及包含其的有机电致发光器件
KR20210010006A (ko) * 2019-07-19 2021-01-27 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190053579A (ko) * 2017-11-10 2019-05-20 주식회사 진웅산업 퀴놀린 화합물 및 이를 포함하는 유기발광소자
WO2020012685A1 (fr) * 2018-07-09 2020-01-16 コニカミノルタ株式会社 Film mince, dispositif électronique, élément électroluminescent organique, matériau pour électroluminescence organique, dispositif d'affichage et équipement d'éclairage
US20200095224A1 (en) * 2018-09-25 2020-03-26 Wuhan Tianma Micro-Electronics Co., Ltd. Nitrogen heterocyclic compound, display panel and display apparatus
KR20210010006A (ko) * 2019-07-19 2021-01-27 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN112079767A (zh) * 2020-09-04 2020-12-15 江苏三月科技股份有限公司 芳胺类化合物及包含其的有机电致发光器件

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023112915A1 (fr) * 2021-12-14 2023-06-22 出光興産株式会社 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique

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