WO2020091446A1 - Composé électroluminescent organique et dispositif électroluminescent organique le comprenant - Google Patents

Composé électroluminescent organique et dispositif électroluminescent organique le comprenant Download PDF

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WO2020091446A1
WO2020091446A1 PCT/KR2019/014568 KR2019014568W WO2020091446A1 WO 2020091446 A1 WO2020091446 A1 WO 2020091446A1 KR 2019014568 W KR2019014568 W KR 2019014568W WO 2020091446 A1 WO2020091446 A1 WO 2020091446A1
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substituted
unsubstituted
organic electroluminescent
alkyl
ring
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PCT/KR2019/014568
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English (en)
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Jin-Ri HONG
Hyo-Soon Park
Hyo-Jung Lee
Hyun-Ju Kang
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020190135292A external-priority patent/KR20200049635A/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to CN201980071338.7A priority Critical patent/CN113015777A/zh
Priority to US17/290,181 priority patent/US20220045281A1/en
Publication of WO2020091446A1 publication Critical patent/WO2020091446A1/fr

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    • 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
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Definitions

  • the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
  • An electroluminescent device is a self-light-emitting display device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • the first organic EL device was developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [ see Appl. Phys. Lett. 51, 913, 1987].
  • An organic EL device changes electric energy into light by applying electricity to an organic electroluminescent material, and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes.
  • the organic layer of the organic EL device may comprise a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer (containing host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
  • the materials used in the organic layer can be classified into a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc., depending on their functions.
  • a hole injection material a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • holes from the anode and electrons from the cathode are injected into a light-emitting layer by the application of electric voltage, and excitons having high energy are produced by the recombination of the holes and electrons.
  • the organic light-emitting compound moves into an excited state by the energy and emits light from the energy when the organic light-emitting compound returns to the ground state from the excited state
  • the important factor determining luminous efficiency in an organic EL device is light-emitting materials.
  • the light-emitting materials are required to have the following features: high quantum efficiency, high movement degree of an electron and a hole, and uniformity and stability of the formed light-emitting material layer.
  • the light-emitting materials are classified into blue, green, and red light-emitting materials according to the light-emitting color, and further include yellow or orange light-emitting materials.
  • the light-emitting materials are classified into a host material and a dopant material in a functional aspect. Recently, an urgent task is the development of an organic EL device having high efficiency and long lifespan.
  • the desirable properties of the host material which acts as a solvent and the sole energy transporter in the solid state, should be high purity and have a suitable molecular weight to enable vacuum deposition.
  • a host material is required to have high glass transition temperature and pyrolysis temperature to achieve thermal stability, high electrochemical stability to achieve long lifespan, easy formability of an amorphous thin film, good adhesion with adjacent layers, and no movement between layers.
  • the object of the present disclosure is to provide an organic electroluminescent compound capable of firstly producing an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long lifespan, and secondly, to provide the organic electroluminescent device comprising the organic electroluminescent compound.
  • B 1 to B 6 are each independently absent or each independently represent a substituted or unsubstituted (C5-C10)aromatic ring, whose at least one carbon atom in the aromatic ring may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; provided that at least five of B 1 to B 6 are present and adjacent rings of B 1 to B 6 may be fused to each other;
  • X represents C or N
  • Y represents -N-L 1 -Ar 1 , -O-, -S-, or -CR 1 R 2 ;
  • L 1 represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or -NR 3 R 4 ;
  • R 1 to R 4 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a substituted or unsubstituted ring.
  • the organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long lifespan can be prepared, by comprising an organic electroluminescent compound according to the present disclosure.
  • the present disclosure relates to an organic electroluminescent compound represented by formula 1, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the organic electroluminescent compound.
  • an organic electroluminescent compound in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised in any layers constituting an organic electroluminescent device, if necessary.
  • an organic electroluminescent material in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound. If necessary, the organic electroluminescent material may be comprised in any layers constituting an organic electroluminescent device.
  • the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material (containing host and dopant materials), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10.
  • the above alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert -butyl, etc.
  • “(C3-C30)cycloalkyl” is a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7.
  • cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (C6-C30)aryl(ene) is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, may be partially saturated, and may comprise a spiro structure.
  • aryl specifically include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, toyly, xylyl, me
  • the aryl may be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, p-terphenyl-4-
  • (3- to 30-membered)heteroaryl(ene) is an aryl group having at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, and Ge and 3 to 30 ring backbone atoms, in which the number of ring backbone atoms is preferably 5 to 25; having preferably 1 to 4 heteroatoms, and may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated.
  • the heteroatom may be linked to at least one substituents selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstit
  • the heteroaryl may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s);
  • examples of the heteroaryl specifically include a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl,
  • the heteroaryl may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridiny
  • Ortho position is a compound with substituents, which are adjacent between each other, e.g., at the 1 and 2 positions on benzene.
  • Meta position is the next substitution position of the immediately adjacent substitution position, e.g., a compound with substituents at the 1 and 3 positions on benzene.
  • Para position is the next substitution position of the meta position, e.g., a compound with substituents at the 1 and 4 positions on benzene.
  • aromatic ring is meant to be a mono- or polycyclic, unsaturated hydrocarbon, and any cyclic moiety exhibiting some aromatic characters or ⁇ -bond, wherein at least one carbon atom in the aromatic ring may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
  • the aromatic ring contains (C5-C30)aryl, (5- to 30-membered)heteroaryl, or the ring(s) in which they are fused.
  • the aromatic ring according to the embodiment may be (C5-C25)aryl or (5- to 25-membered)heteroaryl, e.g., (C5-C18)aryl, (5- to 18-membered)heteroaryl, or the combination thereof.
  • a substituted or unsubstituted ring formed in linking to an adjacent substituent means a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof, formed by linking or fusing two or more adjacent substituents; preferably, may be a substituted or unsubstituted (3- to 26-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof.
  • the formed ring may contain at least a heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably, N, O, and S.
  • the formed ring has (5- to 20-membered) ring backbone atoms, and according to another embodiment, the formed ring has (5- to 15-membered) ring backbone atoms.
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or functional group, i.e., a substituent.
  • the substituents may be a substituted or unsubstituted methyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted pyridinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted benzoxazolyl, etc.
  • the organic electroluminescent compound according to one embodiment is represented by the following formula 1.
  • B 1 to B 6 are each independently absent or each independently represent a substituted or unsubstituted (C5-C10) aromatic ring, whose at least one carbon atom in the aromatic ring may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; provided that at least five of B 1 to B 6 are present and adjacent rings of B 1 to B 6 may be fused to each other;
  • X represents C or N
  • Y represents -N-L 1 -Ar 1 , -O-, -S-, or -CR 1 R 2 ;
  • L 1 represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or -NR 3 R 4 ;
  • R 1 to R 4 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a substituted or unsubstituted ring.
  • B 1 to B 6 are each independently absent, or each independently represent a substituted or unsubstituted (C5-C10) aromatic ring, whose at least one carbon atom in the aromatic ring may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; provided that at least five of B 1 to B 6 are present, and adjacent rings of B 1 to B 6 may be present in fusion with each other.
  • the fusing of each other with adjacent rings of B 1 to B 6 means that B 1 ring and B 2 ring, B 2 ring and B 3 ring, B 3 ring and B 4 ring, B 4 ring and B 5 ring, or B 5 ring and B 6 ring are fused with each other.
  • B 1 to B 6 each independently represent a substituted or unsubstituted (C5-C10) aromatic ring, e.g., a substituted or unsubstituted (C5-C10)aryl, or a substituted or unsubstituted (C5-C10)heteroaryl.
  • Y represents -N-L 1 -Ar 1 , -O-, -S-, or -CR 1 R 2 .
  • L 1 represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene, preferably, may be a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene, more preferably, may be a single bond, a substituted or unsubstituted (C6-C25)arylarylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene.
  • L 1 may be a single bond or a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted pyridinylene, a substituted or unsubstituted isoquinolinylene, a substituted or unsubstituted quinoxalinylene, a substituted or unsubstituted benzoquinoxalinylene, a substituted or unsubstituted quinazolinylene, a substituted or unsubstituted benzoquinazolinylene, a substituted or unsubstituted benzofuropyrimidinylene, or a substituted or unsubstituted naphthyridinylene.
  • Ar 1 presents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or -NR 3 R 4 , preferably, may be a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or -NR 3 R 4 , more preferably, may be a substituted or unsubstituted (C6-C18)aryl, a substituted or unsubstituted (5- to 18-membered)heteroaryl, or -NR 3 R 4 .
  • R 3 and R 4 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a substituted or unsubstituted ring, preferably, may be a substituted or unsubstituted (C6-C25)aryl, more preferably, may be a substituted or unsubstituted (C6-C18)aryl.
  • Ar 1 may be a substituted or unsubstituted phenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted isoquinolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted naphthyridinyl, a substituted or un
  • R 1 and R 2 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a substituted or unsubstituted ring, preferably, may be a substituted or unsubstituted (C1-C30)alkyl or a substituted or unsubstituted (C6-C30)aryl, more preferably, may be a substituted or unsubstituted (C1-C10)alkyl or a substituted or unsubstituted (C6-C18)aryl.
  • R 1 and R 2 each independently may be methyl or
  • X may be C or N, preferably, when X is C, the formula 1 may be represented by the following formula 1-1, and when X is N, the formula 1 may be represented by the following formula 1-2.
  • B 1 to B 6 and Y are as defined in formula 1.
  • the organic electroluminescent compound of formula 1 according to one embodiment in which X represents C; B 1 to B 6 are each independently absent, or each independently represent a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted furan ring, or a substituted or unsubstituted thiophene ring.
  • the organic electroluminescent compound of formula 1 according to one embodiment in which X represents N; B 2 or B 3 is absent, or may be fused with X to form a substituted or unsubstituted pyridine ring or a substituted or unsubstituted indole ring.
  • the formula 1 may be the organic electroluminescent compound in which X represents N; B 2 is absent; and B 3 is fused with X to form a substituted or unsubstituted pyridine ring or a substituted or unsubstituted indole ring.
  • the formula 1 may be the organic electroluminescent compound in which X represents N; B 3 is absent; and B 2 is fused with X to form a substituted or unsubstituted pyridine ring or a substituted or unsubstituted indole ring.
  • the organic electroluminescent compound of formula 1 may be represented by any one of the following formulae 2 to 7.
  • Y 1 is as defined as Y
  • Z 1 to Z 13 each independently represent N or CR a ;
  • R a each independently represent hydrogen, deuterium, halogen, cyano, 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 (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsily
  • R a each independently may be a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino, preferably, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted di(C6-C25)arylamino, a substituted or unsubstituted (C6-C25)aryl(5- to 25-membered)heteroarylamino, more preferably, a substituted or unsubstituted (C6-C18)aryl, a substituted or unsubstituted di(C6-C18)arylamino, or a substituted or unsubstituted (C6-C18)aryl(5
  • Ar 1 , R 1 to R 4 , and R a each independently may be selected from any of the substituents listed in Group 1 below.
  • D1 and D2 each independently represent a benzene ring or a naphthalene ring;
  • X 11 represents O, S, NR 11 , or CR 12 R 13 ;
  • X 12 each independently represent CR 31 or N; provided that at least one X 12 is N;
  • X 13 each independently represent CR 32 or N;
  • L 11 to L 18 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
  • R 11 to R 22 , R 31 , and R 32 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a substituted or unsubstituted ring;
  • aa, ff, and gg each independently represent an integer of 1 to 5
  • bb represents an integer of 1 to 7
  • cc to ee each independently represent an integer of 1 to 4;
  • each of R 11 to R 17 may be the same or different.
  • Ar 1 , R 1 to R 4 , and R a each independently may be selected from any of the substituents listed in Group 2 below.
  • L is as defined as L 1 in formula 1;
  • a 1 to A 3 each independently represent a substituted or unsubstituted (C1-C30)alkyl or a substituted or unsubstituted (C6-C30)aryl.
  • Ar 1 , R 1 to R 4 , and R a each independently may be selected from any of the substituents listed in Group 3 below.
  • the substituents may be (C1-C30)alkyl, (C6-C30)aryl, or (3- to 30-membered)heteroaryl, more preferably (C1-C10)alkyl, (C6-C25)aryl, or (5- to 25-membered)heteroaryl.
  • the substituents may be methyl, phenyl, m-biphenyl, p-biphenyl, naphthyl, fluorenyl, pyridinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or benzoxazolyl, etc.
  • the organic electroluminescent compound represented by the formula 1 may be illustrated by the following compounds, but is not limited thereto.
  • the compound of formula 1 according to the present disclosure may be produced as represented by the following reaction schemes 1 to 6, but is not limited thereto and by a synthetic method known to a person skilled in the art.
  • exemplary synthesis examples of the compounds represented by formulae 2 to 7 are described, but they are based on Wittig reaction, Suzuki cross-coupling reaction, Ullmann-coupling reaction, Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, Intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, Cyclic Dehydration reaction, SN 1 substitution reaction, SN 2 substitution reaction, Phosphine-mediated reductive cyclization reaction, etc. It will be understood by one skilled in the art that the above reaction proceeds even if other substituents defined in the formulae 2 to 7 other than the substituents described in the specific synthesis examples are bonded.
  • the present disclosure may provide an organic electroluminescent material comprising the organic electroluminescent compound of the formula 1, and an organic electroluminescent device comprising the organic electroluminescent material.
  • the organic electroluminescent material may be comprised solely of the organic electroluminescent compound of the present disclosure, or may further comprise conventional materials included in the organic electroluminescent material.
  • An organic electroluminescent material may be used as light-emitting materials for a white organic light-emitting device.
  • the white organic light-emitting device has suggested various structures such as a parallel side-by-side arrangement method, a stacking arrangement method, or CCM (color conversion material) method, etc., according to the arrangement of R (Red), G (Green), B (blue), or YG (yellowish green) light-emitting units.
  • the organic electroluminescent material according to one embodiment may also be applied to the organic electroluminescent device comprising a QD (quantum dot).
  • An organic electroluminescent material may comprise at least one compound represented by the formula 1.
  • the compound of the formula 1 may be contained in a light-emitting layer, and when contained in the light emitting layer, the compound of formula 1 may be contained as a host.
  • the organic electroluminescent device includes a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode.
  • the organic layer includes the light-emitting layer containing the organic electroluminescent compound according to the present disclosure.
  • the light-emitting layer is comprised solely of the organic electroluminescent compound of the present disclosure or at least two species of the organic electroluminescent compound of the present disclosure, and may further comprise conventional materials included in the organic electroluminescent material.
  • the organic layer may further comprise at least one compound selected from the group consisting of an arylamine-based compound and a styryl arylamine-based compound, and may further comprise 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 such a metal.
  • One of the first electrode and the second electrode may be an anode and the other may be a cathode, wherein the first electrode and the second electrode may each be formed as a transmissive conductive material, a transflective conductive material, or a reflective conductive material.
  • the organic electroluminescent device may be a top emission type, a bottom emission type, or a both-sides emission type according to the kinds of the material forming the first electrode and the second electrode.
  • the organic layer may comprise at least one light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron blocking layer, and an electron buffer layer.
  • a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer.
  • the hole injection layer may be multi-layers in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multi-layers may use two compounds simultaneously.
  • the hole injection layer may be doped as a p-dopant.
  • the electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can confine the excitons within the light-emitting layer by blocking the overflow of electrons from the light-emitting layer to prevent a light-emitting leakage.
  • the hole transport layer or the electron blocking layer may be multi-layers, and wherein each layer may use a plurality of compounds.
  • An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode.
  • the electron buffer layer may be multi-layers in order to control the injection of the electron and improve the interfacial properties between the light-emitting layer and the electron injection layer, wherein each of the multi-layers may use two compounds simultaneously.
  • the hole blocking layer or the electron transport layer may also be multi-layers, wherein each layer may use a plurality of compounds.
  • the electron injection layer may be doped as an n-dopant.
  • the light-emitting auxiliary layer may be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer.
  • the light-emitting auxiliary layer When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used for promoting the hole injection and/or the hole transport, or for preventing the overflow of electrons.
  • the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it can be used for promoting the electron injection and/or the electron transport, or for preventing the overflow of holes.
  • the hole auxiliary layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may be effective to promote or block the hole transport rate (or the hole injection rate), thereby enabling the charge balance to be controlled.
  • the hole transport layer which is further included, may be used as the hole auxiliary layer or the electron blocking layer.
  • the light-emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have an effect of improving the efficiency and/or the lifespan of the organic electroluminescent device.
  • a surface layer selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer
  • a surface layer selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer
  • a chalcogenide (including oxides) layer of silicon and aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a halogenated metal layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • the operation stability for the organic electroluminescent device may be obtained by the surface layer.
  • the chalcogenide include SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
  • the halogenated metal include LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide include 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 include various Lewis acids and acceptor compounds
  • the reductive dopant include 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 organic electroluminescent device having two or more light-emitting layers and emitting white light.
  • An organic electroluminescent device of the present disclosure may comprise at least one host compound other than the organic electroluminescent compound of the formula 1, preferably, the light-emitting layer may further comprise at least one dopant.
  • the dopant comprised in the organic electroluminescent material of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant.
  • the phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particulary limited, but may be preferably a metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably an ortho-metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compound(s).
  • the dopant comprised in the organic electroluminescent device may use the compound represented by the following formula 101, but is not limited thereto:
  • L is selected from the following structure 1 or 2;
  • R 100 to R 103 each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, cyano, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C1-C30)alkoxy; or R 100 to R 103 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, e.g., a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indenopyridine,
  • R 104 to R 107 each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, cyano, or a substituted or unsubstituted (C1-C30)alkoxy; or R 104 to R 107 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, e.g., a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofur
  • R 201 to R 211 each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring; and
  • s represents an integer of 1 to 3.
  • the specific examples of the dopant compound include the following, but are not limited thereto.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc.
  • wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc.
  • a thin film may be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent may be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • An OLED device comprising the compound according to the present disclosure was produced.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED device (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus.
  • Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6 torr.
  • compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
  • Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
  • a light-emitting layer was formed thereon as follows: Compound 4 was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-39 was introduced into another cell as a dopant. The two materials were evaporated at a different rate and deposited in a doping amount of 3 wt%, to form a light-emitting layer having a thickness of 40 nm on the hole transport layer.
  • compounds ET-1 and EI-1 were evaporated at a rate of 1:1, and were deposited to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus.
  • an OLED was produced.
  • An OLED was produced in the same manner as in Device Example 1, except that compound CBP was used as the host of the light-emitting layer.
  • the organic electroluminescent device comprising the organic electroluminescent compound according to one embodiment as a host material can significantly reduce the driving voltage and improve the efficiency and lifespan compared to the organic electroluminescent device comprising a conventional host material.

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Abstract

La présente invention concerne un composé électroluminescent organique et un dispositif électroluminescent organique le comprenant. En incluant le composé électroluminescent organique selon la présente invention, un dispositif électroluminescent organique ayant une faible tension de commande et/ou un rendement lumineux élevé et/ou une longue durée de vie peut être fourni.
PCT/KR2019/014568 2018-10-31 2019-10-31 Composé électroluminescent organique et dispositif électroluminescent organique le comprenant WO2020091446A1 (fr)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111995637A (zh) * 2020-09-09 2020-11-27 浙江华显光电科技有限公司 一种有机化合物及其有机电致发光器件
WO2021033970A1 (fr) * 2019-08-20 2021-02-25 덕산네오룩스 주식회사 Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique associé
CN112574109A (zh) * 2020-12-25 2021-03-30 苏州驳凡熹科技有限公司 一种有机电致发光化合物及其应用
CN113121544A (zh) * 2021-04-01 2021-07-16 吉林奥来德光电材料股份有限公司 一种有机电致发光化合物及其制备方法和应用
CN113402503A (zh) * 2021-06-18 2021-09-17 吉林奥来德光电材料股份有限公司 一种有机电致发光化合物及制备方法和应用
CN114256430A (zh) * 2020-06-05 2022-03-29 北京夏禾科技有限公司 一种电致发光器件

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WO2021033970A1 (fr) * 2019-08-20 2021-02-25 덕산네오룩스 주식회사 Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique associé
CN114256430A (zh) * 2020-06-05 2022-03-29 北京夏禾科技有限公司 一种电致发光器件
CN114256430B (zh) * 2020-06-05 2023-10-03 北京夏禾科技有限公司 一种电致发光器件
CN111995637A (zh) * 2020-09-09 2020-11-27 浙江华显光电科技有限公司 一种有机化合物及其有机电致发光器件
CN111995637B (zh) * 2020-09-09 2023-06-27 浙江华显光电科技有限公司 一种有机化合物及其有机电致发光器件
CN112574109A (zh) * 2020-12-25 2021-03-30 苏州驳凡熹科技有限公司 一种有机电致发光化合物及其应用
CN113121544A (zh) * 2021-04-01 2021-07-16 吉林奥来德光电材料股份有限公司 一种有机电致发光化合物及其制备方法和应用
CN113402503A (zh) * 2021-06-18 2021-09-17 吉林奥来德光电材料股份有限公司 一种有机电致发光化合物及制备方法和应用
CN113402503B (zh) * 2021-06-18 2024-05-31 吉林奥来德光电材料股份有限公司 一种有机电致发光化合物及制备方法和应用

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