WO2018038401A1 - Composé organique et dispositif à électroluminescence organique comprenant un tel composé - Google Patents

Composé organique et dispositif à électroluminescence organique comprenant un tel composé Download PDF

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WO2018038401A1
WO2018038401A1 PCT/KR2017/007718 KR2017007718W WO2018038401A1 WO 2018038401 A1 WO2018038401 A1 WO 2018038401A1 KR 2017007718 W KR2017007718 W KR 2017007718W WO 2018038401 A1 WO2018038401 A1 WO 2018038401A1
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aryl
alkyl
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boron
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심재의
이용환
박우재
한송이
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주식회사 두산
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    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors.
  • a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB, BCP, Alq 3 and the like are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layer materials, and anthracene derivatives have been reported as emission layer materials.
  • metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.
  • the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, the development of the organic material layer material which is excellent in performance is calculated
  • an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.
  • the present invention provides a compound represented by the following formula (1):
  • X is O or N (R 5 );
  • Rings Q 1 to Q 3 are each independently selected from the group consisting of C 6 ⁇ C 30 arene and 5 to 30 heteroarylene atoms;
  • l, m and n are each independently an integer from 0 to 4.
  • p and q are each independently integers of 0 to 3;
  • R 1 to R 4 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and R
  • R 5 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha A aryl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
  • Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 5 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
  • Ar 1 is a substituent represented by any one of the following Formulas 2 to 4;
  • Z 1 to Z 5 are each independently N or C (R 6 );
  • R 6 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha Or a C 6 to C 60 mono or diarylphosphinyl group and a C 6 to C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and when there are a plurality of R 6 s , Same
  • the present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers provides an organic electroluminescent device comprising the compound of Formula 1. .
  • Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
  • Alkenyl in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
  • Alkynyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon triple bonds, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
  • monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom for example, may have 8 to 60 carbon atoms
  • the whole molecule has non-aromacity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity).
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycides such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl Click ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms.
  • R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1-40 alkyl, and is linear, branched or cyclic structure.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • cycloalkyl in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms.
  • examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 5 to 60 carbon atoms.
  • Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the compound of the present invention has excellent thermal stability, carrier transporting ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic EL device.
  • the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel since the aspects such as light emission performance, driving voltage, lifespan, and efficiency are greatly improved.
  • FIG. 1 illustrates a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • FIG. 2 illustrates a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • organic layer 31 hole transport layer
  • X is O or N (R 5 );
  • Ring Q 1 to Q 3 are each independently selected from the group consisting of a C 6 ⁇ C 30 of the arene and the nuclear atoms of 5 to 30 hetero arene;
  • l, m and n are each independently an integer from 0 to 4.
  • p and q are each independently integers of 0 to 3;
  • R 1 to R 4 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and R
  • R 5 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha A aryl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
  • Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 5 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
  • Ar 1 is a substituent represented by any one of the following Formulas 2 to 4;
  • Z 1 to Z 5 are each independently N or C (R 6 );
  • R 6 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha Or a C 6 to C 60 mono or diarylphosphinyl group and a C 6 to C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and when there are a plurality of R 6 s , Same
  • novel compounds of the present invention can be represented by the following formula (1):
  • X is O or N (R 5 );
  • Rings Q 1 to Q 3 are each independently selected from the group consisting of C 6 ⁇ C 30 arene and 5 to 30 heteroarylene atoms;
  • l, m and n are each independently an integer from 0 to 4.
  • p and q are each independently integers of 0 to 3;
  • R 1 to R 4 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and R
  • R 5 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha A aryl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
  • Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 5 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
  • Ar 1 is a substituent represented by any one of the following Formulas 2 to 4;
  • Z 1 to Z 5 are each independently N or C (R 6 );
  • R 6 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha Or a C 6 to C 60 mono or diarylphosphinyl group and a C 6 to C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and when there are a plurality of R 6 s , Same
  • the novel organic compound represented by Formula 1 of the present invention is an electron withdrawing electron with high electron absorption such as a nitrogen-containing heterocyclic ring (e.g. pyrimidine, triazine, quinazoline, quinoline, triazolopyridinyl, etc.) in the spiro moiety
  • a nitrogen-containing heterocyclic ring e.g. pyrimidine, triazine, quinazoline, quinoline, triazolopyridinyl, etc.
  • the groups (EWG) form the basic backbone connected by various linkers (phenyl, biphenyl, naphthalene, fluorene, carbazolyl, phenanthrene, etc.).
  • the spiro moiety has very good electrochemical stability, high glass transition temperature and carrier transport ability, and in particular, has excellent electron mobility and thus an electron transport layer or an electron transport auxiliary layer.
  • the structure in which the benzene ring is condensed to the spiro moiety increases conjuagation length while maintaining the properties of the material, thereby enhancing thermal stability of the device, and thus it is expected to be a long-life material.
  • At least two of Z 1 to Z 5 in the formula (2) is N, and at least two of Z 1 to Z 3 in the formula (3) and 4 is N it is organic electroluminescence When applied to the device can ensure a low driving voltage and high luminous efficiency.
  • the rings Q 1 to Q 3 may be each independently represented by any one of the following Formulas 5 to 8:
  • the dotted line means the part where condensation takes place
  • r is an integer from 0 to 4.
  • R 7 is each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group , 3 to 40 heterocycloalkyl groups, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl groups, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryl jade group, C group 3 ⁇ C 40 alkylsilyl, C 6 ⁇ C aryl silyl group of 60, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ aryl phosphine of C 60 wave group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ , or selected from the group consisting of an aryl amine of the C 60, the combined group adjacent to
  • the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group of R 7 is heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group
  • the compound may be a compound represented by any one of the following formulas 9 to 14:
  • X, R 1 to R 4 , 1, m, n, p, q and Ar 1 are each as defined in Chemical Formula 1.
  • the compound may be a compound represented by the formula (13).
  • the substituent represented by Formula 2 may be a substituent represented by the following Formula 15:
  • Z 1 , Z 3 and Z 5 are each independently N or C (R 6 );
  • R 6 , R 8 and R 9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 arylphosphanyl group, C 6 ⁇ C 60 Mono or diaryl phosphinyl group and C 6 ⁇ C 60 An arylamine group or selected from the group consisting of a con
  • Ar 1 may be a substituent represented by any one of the following Formulas A-1 to A-5:
  • R 8 and R 9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphazene group, selected from the group consisting of an arylamine C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of, or by combining the adjacent tile to form
  • R 8 and R 9 are each independently composed of hydrogen, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms Can be selected from the group.
  • R 8 and R 9 may be each independently selected from the group consisting of hydrogen, phenyl group, biphenyl group and naphthalenyl group.
  • Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
  • organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1).
  • the compound may be used alone or mixed two or more.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by 1.
  • the structure of the organic EL device according to the present invention described above is not particularly limited, but referring to FIG. 1 as an example, for example, the anode 10 and the cathode 20 facing each other, and the anode 10 and the cathode ( 20) and an organic layer 30 positioned between them.
  • the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34.
  • a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32
  • an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.
  • the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, the electron transport layer 34 and the cathode
  • the electron injection layer 36 may be further included between the 20.
  • the hole injection layer 37 stacked between the hole transport layer 31 and the anode 10 may not only improve the interface property between the ITO used as the anode and the organic material used as the hole transport layer 31.
  • the surface is applied to the upper surface of the uneven ITO to soften the surface of the ITO, a layer that can be used without particular limitation as long as it is commonly used in the art, for example, may be used an amine compound It is not limited to this.
  • the electron injection layer 36 is a layer that is stacked on top of the electron transport layer 34 to facilitate the injection of electrons from the cathode to ultimately improve the power efficiency, commonly used in the art.
  • materials such as LiF, Liq, NaCl, CsF, Li 2 O, BaO and the like can be used.
  • a light emitting auxiliary layer may be further included between the hole transport auxiliary layer 33 and the light emitting layer 32.
  • the emission auxiliary layer may serve to transport holes to the emission layer 32 and to adjust the thickness of the organic layer 30.
  • the emission auxiliary layer may include a hole transport material, and may be made of the same material as the hole transport layer 31.
  • a life improvement layer may be further included between the electron transport auxiliary layer 35 and the light emitting layer 32. Holes traveling through the ionization potential level in the organic light emitting device to the light emitting layer 32 are blocked by the high energy barrier of the lifespan improvement layer, and thus do not diffuse or move to the electron transport layer, and consequently, the holes are limited to the light emitting layer. .
  • Such a function of limiting holes to the light emitting layer prevents holes from diffusing into the electron transporting layer that moves electrons by reduction, thereby suppressing the lifespan phenomenon through irreversible decomposition reaction by oxidation and contributing to improving the life of the organic light emitting device. Can be.
  • the spiro moiety has excellent electrochemical stability, high glass transition temperature and carrier transporting ability, and particularly excellent electron mobility to increase blue emission efficiency. Indicates.
  • the benzene ring is condensed on the spiro moiety to increase the conjugation length while maintaining the properties of the material, it is expected to be a long-life material by enhancing the thermal stability of the device.
  • the above-mentioned moiety is connected to a nitrogen-containing heterocyclic ring having high electron absorption (e.g., pyrimidine, triazine, quinazoline, quinoline, triazolopyridinyl, etc.) to provide particularly high electron mobility and high glass transition temperature.
  • thermal stability is excellent. Therefore, the organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer, an electron transporting layer, or an electron transporting auxiliary layer, and more preferably, an electron transporting layer or an electron transporting auxiliary layer.
  • the organic electroluminescent device may not only sequentially stack an anode, at least one organic material layer, and a cathode as described above, but may further include an insulating layer or an adhesive layer at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic material layers (for example, an electron transport auxiliary layer) is formed to include the compound represented by Chemical Formula 1. It can be prepared by forming other organic material layer and electrode using.
  • the organic material layers for example, an electron transport auxiliary layer
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
  • the positive electrode material may be made of a high work function conductor, for example, to facilitate hole injection, and may include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • the cathode material may be made of a low work function conductor, for example, to facilitate electron injection, and may include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. The same metal or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • Compound (2) as the electron transporting the secondary layer material, and has, in the same way as in example 1 except that for depositing the Alq 3 electron transporting material to 30 nm instead of 25 nm to prepare a blue organic light emitting element .
  • Example 1 Compound 2 4.0 456 7.8 Example 2 Compound 7 3.9 452 7.9 Example 3 Compound 15 4.1 450 7.8 Example 4 Compound 24 4.1 452 7.8 Example 5 Compound 26 4.2 455 7.8 Example 6 Compound 38 3.9 452 7.7 Example 7 Compound 47 3.8 455 7.7 Example 8 Compound 51 3.7 455 8.2 Example 9 Compound 53 3.7 452 8.3 Example 10 Compound 57 4.0 455 8.1 Example 11 Compound 72 4.0 455 8.1 Example 12 Compound 78 4.2 458 7.8 Example 13 Compound 87 4.2 455 7.8 Example 14 Compound 96 3.9 456 7.7 Example 15 Compound 108 4.1 455 7.6 Example 16 Compound 117 4.1 458 8.2 Example 17 Compound 123 3.7 455 8.2 Example 18 Compound 140 4.0 456 8.0 Example 19 Compound 142 4.0 455 8.0 Example 20 Compound 156 3.9 4
  • the blue organic electroluminescent devices (Examples 1 to 58) using the compound of the present invention in the electron transport auxiliary layer were compared to the blue organic electroluminescent devices (Comparative Example 1) without the electron transport auxiliary layer. It was found to exhibit excellent performance in terms of current efficiency, light emission peak, and driving voltage.
  • a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • DS-205 Doosan Electronics, 80 nm
  • NPB 15 nm
  • DS-405 Doosan Electronics, 30nm
  • Compound 2 to Compound 531 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked to fabricate an organic EL device.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 59, except that Alq 3 was used instead of the compound 2 as the electron transporting layer material.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 59, except that Compound 2 was not used as the electron transporting material.
  • the blue organic electroluminescent devices (Examples 59 to 76) using the compound of the present invention in the electron transporting layer are blue organic electroluminescent devices (Comparative Example 2) using Alq 3 as the electron transporting layer and Compared with the blue organic electroluminescent device (Comparative Example 3) without an electron transporting layer, it was found to exhibit excellent performance in terms of driving voltage, light emission peak, and current efficiency.
  • the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.

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  • Physics & Mathematics (AREA)
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  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un dispositif à électroluminescence organique le contenant. Le composé, selon la présente invention, est destiné à une couche de matériau organique d'un dispositif à électroluminescence organique, de préférence une couche électroluminescente, une couche de transport d'électrons ou une couche de transport d'électrons auxiliaire, et permet ainsi d'améliorer l'efficacité lumineuse, la tension de commande et la durée de vie du dispositif à électroluminescence organique.
PCT/KR2017/007718 2016-08-23 2017-07-18 Composé organique et dispositif à électroluminescence organique comprenant un tel composé WO2018038401A1 (fr)

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CN110835328A (zh) * 2019-11-18 2020-02-25 苏州久显新材料有限公司 螺苯并芴酮类衍生物和电子器件
WO2020122384A1 (fr) * 2018-12-14 2020-06-18 주식회사 엘지화학 Composé cyclique condensé et dispositif électroluminescent organique le comprenant
CN111344285A (zh) * 2018-10-19 2020-06-26 株式会社Lg化学 新型杂环化合物及利用其的有机发光器件
KR20200090674A (ko) * 2017-06-30 2020-07-29 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
CN113130799A (zh) * 2019-12-31 2021-07-16 乐金显示有限公司 有机电子元件、包括其的显示面板和包括其的显示装置
US20210280794A1 (en) * 2018-11-13 2021-09-09 Lg Chem, Ltd. Novel compound and organic light emitting device comprising the same
WO2021246698A1 (fr) * 2020-06-05 2021-12-09 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé
WO2024014303A1 (fr) * 2022-07-13 2024-01-18 出光興産株式会社 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique

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KR102280260B1 (ko) * 2018-10-16 2021-07-20 주식회사 엘지화학 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
WO2020162703A1 (fr) * 2019-02-08 2020-08-13 주식회사 엘지화학 Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant
KR102360902B1 (ko) * 2019-02-08 2022-02-09 주식회사 엘지화학 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR20210129524A (ko) * 2020-04-20 2021-10-28 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR20220090265A (ko) * 2020-12-22 2022-06-29 솔루스첨단소재 주식회사 유기 화합물 및 이를 이용한 유기 전계 발광 소자

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KR20200090674A (ko) * 2017-06-30 2020-07-29 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR102202886B1 (ko) 2017-06-30 2021-01-14 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
CN111344285A (zh) * 2018-10-19 2020-06-26 株式会社Lg化学 新型杂环化合物及利用其的有机发光器件
CN111344285B (zh) * 2018-10-19 2023-06-30 株式会社Lg化学 杂环化合物及利用其的有机发光器件
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WO2020122384A1 (fr) * 2018-12-14 2020-06-18 주식회사 엘지화학 Composé cyclique condensé et dispositif électroluminescent organique le comprenant
CN112654613A (zh) * 2018-12-14 2021-04-13 株式会社Lg化学 稠环化合物和包含其的有机发光器件
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CN110835328A (zh) * 2019-11-18 2020-02-25 苏州久显新材料有限公司 螺苯并芴酮类衍生物和电子器件
CN113130799A (zh) * 2019-12-31 2021-07-16 乐金显示有限公司 有机电子元件、包括其的显示面板和包括其的显示装置
WO2021246698A1 (fr) * 2020-06-05 2021-12-09 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé
WO2024014303A1 (fr) * 2022-07-13 2024-01-18 出光興産株式会社 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique

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