WO2015099507A1 - Nouveau composé organique électroluminescent, matériau hôte à plusieurs constituants et dispositif organique électroluminescent le comprenant - Google Patents

Nouveau composé organique électroluminescent, matériau hôte à plusieurs constituants et dispositif organique électroluminescent le comprenant Download PDF

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WO2015099507A1
WO2015099507A1 PCT/KR2014/012933 KR2014012933W WO2015099507A1 WO 2015099507 A1 WO2015099507 A1 WO 2015099507A1 KR 2014012933 W KR2014012933 W KR 2014012933W WO 2015099507 A1 WO2015099507 A1 WO 2015099507A1
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substituted
unsubstituted
compound
organic electroluminescent
membered
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PCT/KR2014/012933
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Hee-Ryong Kang
Mi-Ja Lee
Hyun-Ju Kang
Young-Gil Kim
Young-Mook Lim
Nam-Kyun Kim
Bitnari Kim
Chi-Sik Kim
Young-Jun Cho
Kyung-Joo Lee
Hong-Yoep NA
Tae-Jin Lee
Jae-Hoon Shim
Kyung-Hoon Choi
Hee-Choon Ahn
Ji-Song JUN
Young-Kwang Kim
Jin-Ri HONG
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020130165394A external-priority patent/KR101478990B1/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to CN201910202934.6A priority Critical patent/CN110078742B/zh
Priority to JP2016538577A priority patent/JP6592439B2/ja
Priority to CN201480069533.3A priority patent/CN105829320A/zh
Publication of WO2015099507A1 publication Critical patent/WO2015099507A1/fr

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Definitions

  • the present disclosure relates to a novel organic electroluminescent compound, and a multi-component host material and an organic electroluminescent device comprising the same.
  • An electroluminescent (EL) device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials to form a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • an organic EL device has a structure comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode. Holes and electrons are injected from an anode and a cathode, respectively, to the organic layer; the compound is in an excited state by recombinations between the holes and the electrons, and the decay of the excited state results in a relaxation of the energy into a ground state, accompanied by light-emission.
  • the organic layer of the organic EL device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
  • a material for preparing the organic layers includes a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • the most important factor determining luminous efficiency in the organic EL device is light-emitting materials.
  • the light-emitting material needs to have high quantum efficiency, high electron mobility, and high hole mobility.
  • the light-emitting layer formed by the light-emitting material needs to be uniform and stable.
  • the light-emitting materials can be classified as a blue-, green-, or red-emitting material, and a yellow- or orange-emitting material can be additionally included therein.
  • the light-emitting material can be classified as fluorescent materials (singlet state) and phosphorescent materials (triplet state). Fluorescent materials have been widely used for the organic EL device. However, since phosphorescent materials enhance luminous efficiency for converting electricity to light by four (4) times compared to fluorescent materials and can reduce power consumption to have longer lifespan, development of phosphorescent light-emitting materials are widely being researched.
  • Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red-, green- and blue-emitting materials, respectively.
  • the light-emitting material can be prepared by combining a host material with a dopant to improve color purity, luminous efficiency, and stability.
  • the host materials greatly influence the efficiency and performance of the EL device when using a host material/dopant system as the light emitting material, and thus their selection is important.
  • 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known host material for phosphorescent materials.
  • Pioneer (Japan) et al. developed a high performance organic EL device using bathocuproine (BCP) and aluminum(III) bis(2-methyl-8-quinolinate)(4-phenylphenolate) (BAlq) etc., as host materials, which were known as hole blocking materials.
  • materials for preparing an organic layer in an organic EL device in particular, a host or a dopant for preparing a light-emitting layer, need to be properly selected.
  • Korean Patent Appln. Laying-Open No. 10-2010-0105099 discloses, as a host material for a light-emitting layer, a heterocyclic compound having condensed 5 rings.
  • a heterocyclic compound having condensed 5 rings discloses, as a host material for a light-emitting layer, a heterocyclic compound having condensed 5 rings.
  • an organic electroluminescent device using a compound of said reference is not satisfactory in power efficiency, luminous efficiency, lifespan, and color purity.
  • the objective of the present disclosure is to provide an organic electroluminescent compound, which can provide an organic electroluminescent device showing low driving voltage, long lifespan, high color purity, and good current and power efficiencies, and a multi-component host material and an organic electroluminescent device comprising the same.
  • Ar 1 represents a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C6-C30)aryl;
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
  • Y represents O, S, N(R 6 ) or C(R 4 )(R 5 );
  • X represents O, S, N(R 6 ) or C(R 7 )(R 8 ); provided that both X and Y cannot be simultaneously N(R 6 );
  • R 1 to R 3 each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxy, a nitro, a hydroxy, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, -NR 9 R 10 or -SiR 11 R 12 R 13 , or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30), mono- or polycyclic, alicyclic or aromatic a
  • R 4 to R 13 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted(C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (5- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR 14 R 15 , -SiR 16 R 17 R 18 , a cyano, a nitro, or a hydroxy, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30), mono- or polycyclic, alicyclic,
  • R 14 to R 18 have the same definition as R 4 to R 13 ;
  • a carbon atom(s) of the alicyclic or aromatic ring may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
  • a, b and c each independently, represent an integer of 1 to 4; where a, b, or c represents an integer of 2 or more, each of R 1 , R 2 , or R 3 may be the same or different;
  • a ring which may be formed between any one of R 1 to R 3 and an adjacent substituent(s) is not a substituted naphthalene ring.
  • An organic electroluminescent compound of the present disclosure can provide higher color purity, longer lifespan, and better luminous efficiency than conventional compounds. Accordingly, an organic electroluminescent device using the compound of the present disclosure as a host material for a light-emitting layer can show higher color purity, lower driving voltage, longer lifespan, better luminous efficiency, in particular, better current efficiency, and improved power consumption.
  • the present disclosure provides the organic electroluminescent compound of formula 1 above, an organic electroluminescent material comprising the same, and an organic electroluminescent device comprising the material.
  • (C1-C30)alkyl(ene) indicates a linear or branched alkyl(ene) having 1 to 30, preferably 1 to 20, and more preferably 1 to 10 carbon atoms, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • “(C2-C30) alkenyl” indicates a linear or branched alkenyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl indicates a linear or branched alkynyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • “(C3-C30)cycloalkyl” indicates a mono- or polycyclic hydrocarbon having 3 to 30, preferably 3 to 20, and more preferably 3 to 7 carbon atoms and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (C6-C30)aryl(ene) indicates a monocyclic or fused ring derived from an aromatic hydrocarbon and having 6 to 30, preferably 6 to 20, and more preferably 6 to 15 ring backbone carbon atoms, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
  • substituted in the expression, “substituted or unsubstituted,” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e. a substituent.
  • the compound of formula 1 may be represented by any one of the following formulae 2 to 5:
  • Ar 1 , L 1 , X, Y, R 1 to R 3 , a, b, and c are as defined in formula 1 above.
  • Ar 1 may represent preferably, a substituted or unsubstituted (5- to 20-membered)heteroaryl, or a substituted or unsubstituted (C6-C20)aryl.
  • the substituent for the substituted group of Ar 1 may be a (C6-C20)aryl, a (6- to 20-membered)heteroaryl or a mono- or di-(C6-C20)arylamino.
  • Ar 1 may represent a substituted or unsubstituted, nitrogen-containing (5- to 20-membered) heteroaryl; and specifically, may be selected from the group consisting of a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted naphthyridinyl, and a substituted or unsubstituted quinoxalinyl.
  • the substituent for the substituted group of Ar 1 may be preferably, a (C6-C20)aryl or a (5- to 20-membered)heteroaryl, and specifically, may be at least one selected from phenyl, naphthyl, biphenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, and dibenzothiophenyl.
  • L 1 may represent preferably, a single bond, a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted (5- to 20-membered)heteroarylene; and more preferably, a single bond, or a substituted or unsubstituted (C6-C20)arylene.
  • L 1 may represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted naphthylene.
  • X and Y each independently, may be selected from O, S, and N(R 6 ); provided that both X and Y cannot be simultaneously N(R 6 ).
  • X and Y each independently, may be selected from O and S.
  • X and Y each independently, may be selected from O and S, and at least one of X and Y may be S.
  • R 6 may represent preferably, a substituted or unsubstituted (C6-C30)aryl, and specifically a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted biphenyl.
  • R 1 to R 3 each independently, may represent preferably, hydrogen, deuterium, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C3-C20)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, -NR 9 R 10 or -SiR 11 R 12 R 13 , or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30), mono- or polycyclic, alicyclic or aromatic ring.
  • the mono- or polycyclic aromatic ring in the definition of R 1 to R 3 is not naphthalene ring and phenanthrene ring.
  • R 9 to R 13 may represent preferably, a substituted or unsubstituted (C6-C30)aryl.
  • R 1 to R 3 may represent hydrogen.
  • Ar 1 represents a substituted or unsubstituted (5- to 20-membered)heteroaryl, or a substituted or unsubstituted (C6-C20)aryl
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted (5- to 20-membered)heteroarylene
  • R 1 to R 3 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C3-C20)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, -NR 9 R 10 or -SiR 11 R 12 R 13 , or may be linked to an adjacent substituent(s
  • the compound represented by formula 1 includes the following, but is not limited thereto.
  • the organic electroluminescent compound of the present disclosure can be prepared by a synthetic method known to one skilled in the art, e.g., bromination, Suzuki reaction, Buchwald-Hartwig reaction, Ullmann reaction, etc.
  • the compound of formula 1 can be prepared as follows: After preparing a five(5) ring-condensed compound represented by formula A, the compound of formula A is subjected to bromination to obtain a compound represented by formula B; the compound of formula B is fused with an indene ring, an indole ring, a benzofuran ring, or a benzothiophene ring to obtain a mother nucleus structure of formula 1; and *-L 1 -Ar 1 is then connected to the prepared mother nucleus structure, thereby the compound of formula 1 is obtained.
  • X and Y each independently, may be selected from O, S, N(R 6 ), C(R 4 )(R 5 ), and C(R 7 )(R 8 ).
  • X can be selected from O, S, N(R 6 ), and C(R 7 )(R 8 ).
  • an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material are provided.
  • the material may comprise one or more compounds selected from the organic electroluminescent compound of formula 1.
  • the material may further comprise a conventional compound(s) which has been comprised for an organic electroluminescent material.
  • the organic electroluminescent material may be preferably a host material. When the organic electroluminescent material is used as a host material, it may further comprise a second host material other than the compound of formula 1 of the present disclosure, whose details are provided below.
  • the organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes, wherein the organic layer may comprise at least one compound of formula 1.
  • the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer, an interlayer, an electron buffer layer, and a hole blocking layer.
  • the organic electroluminescent compound of formula 1 of the present disclosure may be comprised as a host material in the light-emitting layer.
  • the light-emitting layer may further comprise at least one dopant.
  • the light-emitting layer may comprise, in addition to an organic electroluminescent compound of formula 1 of the present disclosure (a first host material), a second host material.
  • the weight ratio between the first host material and the second host material is in the range of 1:99 to 99:1, and preferably 30:70 to 70:30 in view of driving voltage, lifespan, and luminous efficiency.
  • a material for preparing an organic electroluminescent device comprises the compound of the present disclosure.
  • the material may be a material for preparing a light-emitting layer of an organic electroluminescent device.
  • the compound of the present disclosure may be comprised as a host material.
  • the material may further comprise a second host material.
  • the weight ratio between the compound of the present disclosure and the second host material is in the range of 1:99 to 99:1, and preferably 30:70 to 70:30 in view of driving voltage, lifespan, and luminous efficiency.
  • the material may be a composition or a mixture.
  • a phosphorescent host material known in the art may be used as the second host material.
  • the compound selected from the group consisting of the compounds of formulae 6 to 10 below is preferable as the second host material in view of driving voltage, lifespan, and luminous efficiency.
  • L 4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene;
  • M represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • Y 1 and Y 2 each independently, represent -O-, -S-, -N(R 31 )- or -C(R 32 )(R 33 )-, provided that both Y 1 and Y 2 cannot be simultaneously present;
  • X represents O or S;
  • R 21 to R 24 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl,
  • M may represent a substituted or unsubstituted nitrogen-containing (6- to 20-membered) heteroaryl.
  • the substituent for the substituted group of M may be a (C1-C20)alkyl; a (C6-C24)aryl unsubstituted or substituted with a (C1-C10)alkyl, a tri(C6-C13)arylsilyl, or a (6- to 13-membered)heteroaryl; or a (6- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C10)alkyl, a tri(C6-C13)arylsilyl, or a (C6-C24)aryl; or a tri(C6-C20)arylsilyl.
  • M may represent a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridinyl, or a substituted or unsubstituted phenanthrolinyl.
  • At least one of R 23 and R 24 of formulae 6 and 7, or at least one of R 21 and R 22 of formulae 8 to 10 may represent a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzocarbazolyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthothiophenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzonaphthofuranyl, a (C6-C18)aryl substituted with a substituted or unsubstituted carbazolyl, a (C6-C18)aryl substituted with a substituted or unsubstituted benzocarbazolyl, a (C6-C18)aryl substituted with a substituted or unsubstituted dibenzothiophenyl,
  • At least one of R 23 and R 24 , or at least one of R 21 and R 22 may represent a substituted or unsubstituted nitrogen-containing (6- to 20-membered)heteroaryl; or may have, as a substituent, a substituted or unsubstituted nitrogen-containing (6- to 20-membered)heteroaryl.
  • the substituted or unsubstituted nitrogen-containing heteroaryl may represent a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridinyl, or a substituted or unsubstituted phenanthrolinyl.
  • the second host material may be represented by formula 6 above, and more specifically, the following formula 11.
  • a 1 and A 2 each independently, represent a substituted or unsubstituted (C6-C30)aryl; provided that the substituent of the substituted group of A 1 and A 2 is not a nitrogen-containing heteroaryl;
  • L 2 represents a single bond or a substituted or unsubstituted (C6-C30)arylene
  • Z 1 to Z 16 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted
  • the compound of formula 11 may be represented by any one of the following formulae 12, 13, 14, and 15.
  • a 1 , A 2 , L 2 , and Z 1 to Z 16 are as defined in formula 11 above.
  • a 1 and A 2 each independently, represent preferably, a substituted or unsubstituted (C6-C18)aryl, and more preferably, a (C6-C18)aryl unsubstituted or substituted with a cyano, a halogen, a (C1-C6)alkyl, a (C6-C12)aryl or tri(C6-C12)arylsilyl.
  • a 1 and A 2 may be selected from the group consisting of a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted indenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted tetracenyl, a substituted or unsubstituted perylenyl, a substituted or unsubstituted, a
  • the substituent of the substituted group such as the substituted phenyl of A 1 and A 2 may be a cyano, a halogen, a (C1-C6)alkyl, a (C6-C12)aryl, or tri(C6-C12)arylsilyl.
  • Z 1 to Z 16 each independently, represent preferably, hydrogen, a cyano, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted (5- to 20-membered)heteroaryl, or a substituted or unsubstituted tri(C6-C12)arylsilyl.
  • Z 1 to Z 16 each independently, represent more preferably, hydrogen; a cyano; a (C1-C10)alkyl; a (C6-C20)aryl unsubstituted or substituted with a cyano, a (C1-C10)alkyl or tri(C6-C12)arylsilyl; a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C10)alkyl, a (C6-C15)aryl or tri(C6-C12)arylsilyl; or tri(C6-C12)arylsilyl unsubstituted or substituted with a (C1-C10)alkyl.
  • Z 1 to Z 16 may represent hydrogen; a cyano; a (C1-C6)alkyl; phenyl, biphenyl, terphenyl, or naphthyl, unsubstituted or substituted with a cyano, a (C1-C6)alkyl or triphenylsilyl; dibenzothiophenyl or dibenzofuranyl, unsubstituted or substituted with a (C1-C6)alkyl, phenyl, biphenyl, naphthyl, or triphenylsilyl; or triphenylsilyl unsubstituted or substituted with a (C1-C6)alkyl.
  • L 2 represents preferably, a single bond, or a substituted or unsubstituted (C6-C15)arylene. Specifically, L 2 may represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene.
  • a 1 and A 2 each independently, may represent a substituted or unsubstituted (C6-C18)aryl
  • Z 1 to Z 16 each independently, may represent hydrogen, a cyano, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted (5- to 20-membered)heteroaryl, or a substituted or unsubstituted tri(C6-C12)arylsilyl
  • L 2 may represent a single bond, or a substituted or unsubstituted (C6-C15)arylene.
  • the preferable example of the second host material represented by formulae 6 to 10 includes the following, but is not limited thereto:
  • TPS represents triphenylsilyl
  • the dopant is preferably at least one phosphorescent dopant.
  • the phosphorescent dopant material for the organic electroluminescent device of the present disclosure is not limited, but may be preferably selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
  • the dopant to be comprised in the organic electroluminescent device of the present disclosure may be selected from the group consisting of compounds represented by the following formulae 16 to 18.
  • L is selected from the following structures:
  • R 100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl
  • R 101 to R 109 , and R 111 to R 123 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, a cyano, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (C1-C30)alkoxy;
  • R 106 to R 109 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a substituted or unsubstituted fluorene, a substituted or unsubstitute
  • the phosphorescent dopant material includes the following:
  • an organic electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and cathode, wherein the organic layer comprises one or more light-emitting layers; at least one light-emitting layer comprises one or more dopant compounds and two or more host compounds; and a first host compound of the two or more host compounds is the organic electroluminescent compound represented by formula 1 is provided.
  • the weight ratio between the first host material and the second host material is in the range of 1:99 to 99:1, and preferably 30:70 to 70:30 in view of driving voltage, lifespan, and luminous efficiency.
  • a first host compound of the two or more host compounds may be the organic electroluminescent compound represented by formula 1, and a second host compound may be selected from the compound represented by formulae 6 to 10.
  • a first host compound of the two or more host compounds may be the organic electroluminescent compound represented by formula 1, and a second host compound may be the compound represented by formula 11.
  • the one or more dopant compounds may be selected from the compound represented by formulae 12 to 15.
  • the organic electroluminescent device of the present disclosure comprises the compound of formula 1 in the organic layer.
  • the organic electroluminescent device of the present disclosure may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • the organic layer may further comprise, in addition to the compound of formula 1, at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
  • the organic electroluminescent device of the present disclosure may emit white light by further comprising at least one light-emitting layer, which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the field, besides the compound of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
  • at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the field, besides the compound of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
  • a surface layer may be placed on an inner surface(s) of one or both electrode(s), selected from a chalcogenide layer, a metal halide layer and a metal oxide layer.
  • a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
  • the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds
  • the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more light-emitting layers and emitting white light.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods can be used.
  • a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • two or more host compounds for a light-emitting layer may be co-evaporated or mixture-evaporated.
  • a co-evaporation indicates a process for two or more materials to be deposited as a mixture, by introducing each of the two or more materials into respective crucible cells, and applying electric current to the cells for each of the materials to be evaporated.
  • a mixture-evaporation indicates a process for two or more materials to be deposited as a mixture, by mixing the two or more materials in one crucible cell before the deposition, and applying electric current to the cell for the mixture to be evaporated.
  • a display system or a lighting system can be produced.
  • organic electroluminescent compound of the present disclosure the preparation method of the compound, and the luminescent properties of the device will be explained in detail with reference to the following examples.
  • OLED was produced using the organic electroluminescent compound of the present disclosure as follows.
  • a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) (Geomatec) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water sequentially, and was then stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • N 1 ,N 1' -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -(naphthalene-1-yl)-N 4 ,N 4 -diphenylbenzene-1,4-diamine) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was then introduced into another cell of said vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound C-1 was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-87 was introduced into another cell as a dopant.
  • the two materials were evaporated at different rates, so that the dopant was deposited in a doping amount of 4 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
  • 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was then introduced into one cell, and lithium quinolate was introduced into another cell.
  • the two materials were evaporated at the same rate, so that they were respectively deposited in a doping amount of 50 wt% to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
  • an Al cathode having a thickness of 150 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer. Accordingly, an OLED was produced. All the materials used for producing the OLED were those purified by vacuum sublimation at 10 -6 torr.
  • the produced OLED showed a red emission having a luminance of 1,050 cd/m 2 and a current density of 8.1 mA/cm 2 at a driving voltage of 3.6 V.
  • the minimum time taken to be reduced to 90% of the luminance at 5,000 nit was 200 hours.
  • OLED was produced in the same manner as in Device Example 1, except that compound A-1 shown below and compound D-88 were used as a host and a dopant.
  • the produced OLED showed a red emission having a luminance of 980 cd/m 2 and a current density of 16.4 mA/cm 2 at a driving voltage of 3.8 V.
  • the minimum time taken to be reduced to 90% of the luminance at 5,000 nit was 12 hours.
  • OLED was produced in the same manner as in Device Example 1, except that compound A-2 shown below and compound D-88 were used as a host and a dopant.
  • the produced OLED showed a red emission having a luminance of 1,020 cd/m 2 and a current density of 13.1 mA/cm 2 at a driving voltage of 4.1 V.
  • the minimum time taken to be reduced to 90% of the luminance at 5,000 nit was 10 hours.
  • OLED was produced in the same manner as in Device Example 1, except that compound A-3 shown below and compound D-87 were used as a host and a dopant.
  • the produced OLED showed a red emission having a luminance of 1,110 cd/m 2 and a current density of 9.8 mA/cm 2 at a driving voltage of 4.2 V.
  • the minimum time taken to be reduced to 90% of the luminance at 5,000 nit was 10 hours.
  • the organic electroluminescent compounds of the present disclosure provide lower driving voltage, longer lifespan, and better current efficiency than conventional organic electroluminescent compounds.
  • the organic electroluminescent device using the organic electroluminescent compounds of the present disclosure shows excellence in driving voltage, lifespan, and luminous characteristics, in particular, current and power efficiencies.
  • OLED was produced using the light-emitting material of the present disclosure as follows.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) (Geomatec) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water sequentially, and was then stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • N 4 ,N 4' -diphenyl-N 4 ,N 4' -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine ( HI-1 ) was introduced into a cell of the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate.
  • 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile ( HI-2 ) was then introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine ( HT-1 ) was introduced into one cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
  • N,N-di([1,1'-biphenyl]-4-yl)-4'-(9H- carbazol-9-yl)-[1,1'-biphenyl]-4-amine ( HT-2 ) was then introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
  • the two compounds shown in Table 1 below were introduced into two cells of the vacuum vapor depositing apparatus, respectively, as a first host compound and a second host compound.
  • a dopant compound shown in Table 1 was introduced into another cell.
  • the two host compounds were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host compounds, so that the dopant was deposited in a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the hole transport layer.
  • OLED was produced in the same manner as in Device Examples 1-1 to 1-7, except that only a second host compound shown in Table 1 below was used as a host for a light-emitting layer.
  • OLED was produced in the same manner as in Device Examples 1-1 to 1-7, except that only a first host compound shown in Table 1 below was used as a host for a light-emitting layer.
  • the organic electroluminescent device using one organic electroluminescent compound of the present disclosure as a host material showed improvement in driving voltage, current efficiency, color purity, and lifespan.
  • the organic electroluminescent device showed remarkability in the performance, in particular, lifespan of the organic electroluminescent device, by using a multi-component host material comprising the organic electroluminescent compound of the present disclosure. That is, the organic electroluminescent device using a multi-component host material can show longer lifespan than one using one host compound.

Abstract

La présente invention concerne un composé organique électroluminescent, un matériau hôte à plusieurs constituants et un dispositif organique électroluminescent le comprenant. Le composé organique électroluminescent selon la présente invention a une bonne efficacité lumineuse et peut être utilisé comme hôte pour une couche électroluminescente. Grâce à l'utilisation du composé organique électroluminescent selon la présente invention, un dispositif organique électroluminescent peut avoir une grande pureté de couleur, une faible tension d'excitation, une longue durée de vie, ainsi qu'un rendement en courant et un rendement énergétique améliorés.
PCT/KR2014/012933 2013-12-27 2014-12-26 Nouveau composé organique électroluminescent, matériau hôte à plusieurs constituants et dispositif organique électroluminescent le comprenant WO2015099507A1 (fr)

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JP2016538577A JP6592439B2 (ja) 2013-12-27 2014-12-26 新規有機エレクトロルミネッセンス化合物、ならびにそれを含む多成分ホスト材料及び有機エレクトロルミネッセンス素子
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Cited By (37)

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WO2018050583A1 (fr) * 2016-09-14 2018-03-22 Merck Patent Gmbh Composés à structures carbazole
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US10392387B2 (en) 2017-05-19 2019-08-27 Arizona Board Of Regents On Behalf Of Arizona State University Substituted benzo[4,5]imidazo[1,2-a]phenanthro[9,10-c][1,8]naphthyridines, benzo[4,5]imidazo[1,2-a]phenanthro[9,10-c][1,5]naphthyridines and dibenzo[f,h]benzo[4,5]imidazo[2,1-a]pyrazino[2,3-c]isoquinolines as thermally assisted delayed fluorescent materials
US10547014B2 (en) 2017-06-23 2020-01-28 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
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US10644249B2 (en) 2017-12-22 2020-05-05 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US10892425B1 (en) 2017-03-03 2021-01-12 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US10957861B2 (en) 2015-12-29 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
US11069860B2 (en) 2017-08-21 2021-07-20 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11104669B2 (en) 2018-02-02 2021-08-31 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11130747B2 (en) 2014-11-11 2021-09-28 Rohm And Haas Electronic Materials Korea Ltd Plurality of host materials and an organic electroluminescence device comprising the same
US11283027B1 (en) 2017-03-03 2022-03-22 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11444250B2 (en) 2017-12-05 2022-09-13 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11495749B2 (en) 2015-04-06 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11498914B2 (en) 2018-03-30 2022-11-15 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11542260B2 (en) 2018-01-31 2023-01-03 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11575088B2 (en) 2017-12-22 2023-02-07 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11608333B2 (en) 2018-03-20 2023-03-21 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11778904B2 (en) 2018-05-09 2023-10-03 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11800796B2 (en) 2015-07-20 2023-10-24 Rohm And Haas Electronic Materials Korea Ltd. Luminescent material for delayed fluorescence and organic electroluminescent device comprising the same
US11818949B2 (en) 2015-04-06 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11834459B2 (en) 2018-12-12 2023-12-05 Universal Display Corporation Host materials for electroluminescent devices
WO2024062997A1 (fr) * 2022-09-22 2024-03-28 保土谷化学工業株式会社 Composé, film mince organique et élément de conversion photoélectrique

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102054397B1 (ko) * 2016-10-24 2019-12-10 주식회사 엘지화학 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자
KR102037816B1 (ko) * 2016-11-16 2019-10-29 삼성에스디아이 주식회사 유기 광전자 소자 및 표시 장치
KR102550843B1 (ko) * 2017-03-16 2023-07-05 롬엔드하스전자재료코리아유한회사 유기 전계 발광 소자
KR20180111530A (ko) * 2017-03-31 2018-10-11 롬엔드하스전자재료코리아유한회사 유기 전계 발광 소자
KR102427493B1 (ko) * 2017-11-14 2022-08-01 덕산네오룩스 주식회사 유기전기소자용 화합물을 이용한 유기전기소자 및 그 전자 장치
CN113444100A (zh) * 2020-03-27 2021-09-28 苏州深通新材料有限公司 新型杂环化合物及包含该化合物的有机电子元件
CN115181095B (zh) * 2022-07-06 2024-03-22 天津大学 具有荧光-延迟荧光-室温磷光三重发射特性的嘧啶基发光体及其制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010151011A1 (fr) * 2009-06-22 2010-12-29 Dow Advanced Display Materials, Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
KR20140000611A (ko) * 2012-06-22 2014-01-03 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
KR20140039622A (ko) * 2012-09-24 2014-04-02 주식회사 두산 신규 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2014157708A1 (fr) * 2013-03-29 2014-10-02 出光興産株式会社 Composé hétérocyclique, matière pour des éléments électroluminescents organiques l'utilisant, élément électroluminescent organique l'utilisant et dispositif électronique
US20140353640A1 (en) * 2013-05-29 2014-12-04 Idemitsu Kosan Co., Ltd. Organic electroluminescence device

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4747558B2 (ja) * 2004-11-08 2011-08-17 ソニー株式会社 表示素子用有機材料および表示素子
JP4819181B2 (ja) * 2008-05-08 2011-11-24 新日鐵化学株式会社 有機電界発光素子用化合物及び有機電界発光素子
KR101511072B1 (ko) * 2009-03-20 2015-04-10 롬엔드하스전자재료코리아유한회사 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광소자
KR101815909B1 (ko) * 2009-07-27 2018-01-09 에스에프씨 주식회사 인돌로카바졸 유도체 및 이를 이용한 유기전계발광소자
JP6118036B2 (ja) * 2011-04-12 2017-04-19 ユー・ディー・シー アイルランド リミテッド 有機電界発光素子、有機電界発光素子用材料、膜、発光層、及び有機電界発光素子の作製方法
JP5922380B2 (ja) * 2011-11-28 2016-05-24 松沢　庄次 建築物の床下構造
WO2013145923A1 (fr) * 2012-03-30 2013-10-03 出光興産株式会社 Élément électroluminescent organique

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010151011A1 (fr) * 2009-06-22 2010-12-29 Dow Advanced Display Materials, Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
KR20140000611A (ko) * 2012-06-22 2014-01-03 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
KR20140039622A (ko) * 2012-09-24 2014-04-02 주식회사 두산 신규 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2014157708A1 (fr) * 2013-03-29 2014-10-02 出光興産株式会社 Composé hétérocyclique, matière pour des éléments électroluminescents organiques l'utilisant, élément électroluminescent organique l'utilisant et dispositif électronique
US20140353640A1 (en) * 2013-05-29 2014-12-04 Idemitsu Kosan Co., Ltd. Organic electroluminescence device

Cited By (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016036207A1 (fr) * 2014-09-05 2016-03-10 Rohm And Haas Electronic Materials Korea Ltd. Matériau de transport de trous et dispositif électroluminescent organique comprenant celui-ci
WO2016052835A1 (fr) * 2014-09-29 2016-04-07 Rohm And Haas Electronic Materials Korea Ltd. Matières hôtes multiples et dispositif électroluminescent organique comprenant celles-ci
US10633583B2 (en) 2014-10-23 2020-04-28 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compounds and an organic electroluminescent device comprising the same
WO2016064227A1 (fr) 2014-10-23 2016-04-28 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
EP3209643A4 (fr) * 2014-10-23 2018-07-04 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
WO2016076629A1 (fr) * 2014-11-11 2016-05-19 Rohm And Haas Electronic Materials Korea Ltd. Pluralité de matériaux hôtes et dispositif électroluminescent organique comprenant ces matériaux
US11130747B2 (en) 2014-11-11 2021-09-28 Rohm And Haas Electronic Materials Korea Ltd Plurality of host materials and an organic electroluminescence device comprising the same
WO2016093584A1 (fr) * 2014-12-10 2016-06-16 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
US10593890B2 (en) 2015-04-06 2020-03-17 Universal Display Corporation Organic electroluminescent materials and devices
US11818949B2 (en) 2015-04-06 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US10693082B2 (en) 2015-04-06 2020-06-23 Universal Display Corporation Organic electroluminescent materials and devices
US11672175B2 (en) 2015-04-06 2023-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US11495749B2 (en) 2015-04-06 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11245080B2 (en) 2015-04-06 2022-02-08 Universal Display Corporation Organic electroluminescent materials and devices
WO2017014546A1 (fr) * 2015-07-20 2017-01-26 Rohm And Haas Electronic Materials Korea Ltd. Matériau luminescent pour fluorescence retardée et dispositif électroluminescent organique comprenant ce dernier
US11800796B2 (en) 2015-07-20 2023-10-24 Rohm And Haas Electronic Materials Korea Ltd. Luminescent material for delayed fluorescence and organic electroluminescent device comprising the same
US11245078B2 (en) 2015-08-25 2022-02-08 Arizona Board Of Regents On Behalf Of Arizona State University Thermally activated delayed fluorescent material based on 9,10-dihydro-9,9-dimethylacridine analogues for prolonging device longevity
US10211411B2 (en) * 2015-08-25 2019-02-19 Arizona Board Of Regents On Behalf Of Arizona State University Thermally activated delayed fluorescent material based on 9,10-dihydro-9,9-dimethylacridine analogues for prolonging device longevity
JP2020021946A (ja) * 2015-08-28 2020-02-06 株式会社半導体エネルギー研究所 発光素子用材料および発光素子
CN111116454A (zh) * 2015-08-28 2020-05-08 株式会社半导体能源研究所 发光元件、发光装置、电子设备及照明装置
US10957861B2 (en) 2015-12-29 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
JP2017141167A (ja) * 2016-02-08 2017-08-17 出光興産株式会社 化合物、これを用いた有機エレクトロルミネッセンス素子用材料、及びこれを用いた有機エレクトロルミネッセンス素子、照明装置並びに表示装置
KR102459000B1 (ko) * 2016-09-14 2022-10-26 메르크 파텐트 게엠베하 카르바졸 구조를 갖는 화합물
WO2018050583A1 (fr) * 2016-09-14 2018-03-22 Merck Patent Gmbh Composés à structures carbazole
JP2019530676A (ja) * 2016-09-14 2019-10-24 メルク パテント ゲーエムベーハー カルバゾール構造を有する化合物
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US20190214574A1 (en) * 2016-09-14 2019-07-11 Merck Patent Gmbh Compounds with carbazole structures
US11011709B2 (en) * 2016-10-07 2021-05-18 Universal Display Corporation Organic electroluminescent materials and devices
US20180102487A1 (en) * 2016-10-07 2018-04-12 Universal Display Corporation Organic electroluminescent materials and devices
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JP2020505755A (ja) * 2017-01-10 2020-02-20 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機エレクトロルミネセントデバイス
US10892425B1 (en) 2017-03-03 2021-01-12 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11283027B1 (en) 2017-03-03 2022-03-22 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US10615349B2 (en) 2017-05-19 2020-04-07 Arizona Board Of Regents On Behalf Of Arizona State University Donor-acceptor type thermally activated delayed fluorescent materials based on imidazo[1,2-F]phenanthridine and analogues
US10851106B2 (en) 2017-05-19 2020-12-01 Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University Substituted benzo[4,5]imidazo[1,2-F]phenanthridines, dibenzo[I.K]benzo[4,5]imidazo[1,2-F]benzofurophenanthridines and dibenzo[I.K]benzo[4,5]imidazo[1,2-F]benzo[4,5]thienophenanthridines as thermally assisted delayed fluorescent materials
US11450816B2 (en) 2017-05-19 2022-09-20 Arizona Board Of Regents On Behalf Of Arizona State University Donor-acceptor type thermally activated delayed fluorescent materials based on imidazo[1,2-f]phenanthridine and analogues
US11603370B2 (en) 2017-05-19 2023-03-14 Arizona Board Of Regents On Behalf Of Arizona State University Substituted heteroaryls as thermally assisted delayed fluorescent materials
US10392387B2 (en) 2017-05-19 2019-08-27 Arizona Board Of Regents On Behalf Of Arizona State University Substituted benzo[4,5]imidazo[1,2-a]phenanthro[9,10-c][1,8]naphthyridines, benzo[4,5]imidazo[1,2-a]phenanthro[9,10-c][1,5]naphthyridines and dibenzo[f,h]benzo[4,5]imidazo[2,1-a]pyrazino[2,3-c]isoquinolines as thermally assisted delayed fluorescent materials
US10547014B2 (en) 2017-06-23 2020-01-28 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
WO2018237389A1 (fr) * 2017-06-23 2018-12-27 Kyulux Inc. Composition de matière destinée à être utilisée dans des diodes électroluminescentes organiques
US11638390B2 (en) 2017-06-23 2023-04-25 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11069860B2 (en) 2017-08-21 2021-07-20 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11444250B2 (en) 2017-12-05 2022-09-13 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US10672989B2 (en) 2017-12-06 2020-06-02 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and novel compound
US10680181B2 (en) 2017-12-06 2020-06-09 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and novel compound
US10249832B1 (en) 2017-12-06 2019-04-02 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and novel compound
US10658594B2 (en) 2017-12-06 2020-05-19 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and novel compound
US11557730B2 (en) 2017-12-06 2023-01-17 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and novel compound
US11569449B2 (en) 2017-12-06 2023-01-31 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and novel compound
US11575088B2 (en) 2017-12-22 2023-02-07 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US10644249B2 (en) 2017-12-22 2020-05-05 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11542260B2 (en) 2018-01-31 2023-01-03 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11104669B2 (en) 2018-02-02 2021-08-31 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11608333B2 (en) 2018-03-20 2023-03-21 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11498914B2 (en) 2018-03-30 2022-11-15 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US11778904B2 (en) 2018-05-09 2023-10-03 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
US10593889B1 (en) 2018-09-26 2020-03-17 Idemitsu Kosan Co., Ltd. Compound and organic electroluminescence device
US11834459B2 (en) 2018-12-12 2023-12-05 Universal Display Corporation Host materials for electroluminescent devices
WO2024062997A1 (fr) * 2022-09-22 2024-03-28 保土谷化学工業株式会社 Composé, film mince organique et élément de conversion photoélectrique

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