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WO2015034140A1 - Composé polycyclique contenant du pyrazole et dispositif électroluminescent organique l'utilisant - Google Patents

Composé polycyclique contenant du pyrazole et dispositif électroluminescent organique l'utilisant Download PDF

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WO2015034140A1
WO2015034140A1 PCT/KR2013/012050 KR2013012050W WO2015034140A1 WO 2015034140 A1 WO2015034140 A1 WO 2015034140A1 KR 2013012050 W KR2013012050 W KR 2013012050W WO 2015034140 A1 WO2015034140 A1 WO 2015034140A1
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substituted
compound
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monocyclic
formula
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정수진
김기용
홍장미
음성진
이주동
정정한
김미진
노영석
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LT Materials Co Ltd
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Heesung Material Ltd
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Definitions

  • the present invention relates to a novel pyrazole-containing polycyclic compound and an organic light emitting device comprising the same.
  • the electroluminescent device is a kind of self-luminous display device, and has an advantage of having a wide viewing angle, excellent contrast, and fast response speed.
  • the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined in the organic thin film to form a pair, then disappear and emit light.
  • the organic thin film may be composed of a single layer or multiple layers as necessary.
  • the material of the organic thin film may have a light emitting function as necessary.
  • a compound which may itself constitute a light emitting layer may be used, or a compound which may serve as a host or a dopant of a host-dopant-based light emitting layer may be used.
  • a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.
  • the present invention provides a novel pyrazole-containing polycyclic compound and an organic light emitting device comprising the same.
  • the present invention provides a compound of formula
  • R 1 to R 8 are the same as or different from each other, and each independently hydrogen; halogen; C 1 to C 60 straight or branched chain substituted or unsubstituted alkyl; C 2 Through C 60 A straight or branched chain substituted or unsubstituted alkenyl; C 2 to C 60 straight or branched substituted or unsubstituted alkynyl; C 1 to C 60 straight or branched chain substituted or unsubstituted alkoxy; C 6 to C 60 straight or branched chain substituted or unsubstituted aryloxy; C 3 to C 60 of monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl
  • the present invention provides an organic light emitting device comprising an anode, a cathode and at least one organic material layer provided between the anode and the cathode, one or more layers of the organic material layer comprises a compound of the formula (1). .
  • the compound described in this specification can be used as an organic material layer material of an organic light emitting element.
  • the compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material in the organic light emitting device.
  • the compound may be usefully used as a material for the electron injection and / or transport layer of the organic light emitting device.
  • the compound may be used as a light emitting material.
  • the compound can be used as a phosphorescent host material.
  • 1 to 3 illustrate the stacking order of electrodes and organic material layers of organic light emitting diodes according to exemplary embodiments of the present invention.
  • FIG. 11 shows a PL measurement graph for 320 nm of compound 38.
  • FIG. 13 shows a PL measurement graph for 260 nm of Compound 66.
  • FIG. 14 shows a UV measurement graph of compound 76.
  • FIG. 15 shows a PL measurement graph for 303 nm of compound 76.
  • Compounds described herein may be represented by the formula (1). Specifically, the compound of Formula 1 may be used as the organic material layer material of the organic light emitting device by the structural features of the core structure and substituents as described above.
  • the compound of Formula 1 has a HOMO / LUMO value suitable for electron injection or transport of the organic light emitting device, excellent electron transport ability by the N-N bond and excellent thermal stability.
  • the compound of formula 1 is also suitable for use as a light emitting layer material, in particular as a phosphorescent host material of the light emitting layer.
  • a compound having a bipolar structure may be used as a host material of the light emitting layer of the organic light emitting device.
  • the condensed ring group of the N-containing ring and the S-containing ring is substituted in the core of Formula 1, the condensed ring group includes both a donor and an acceptor, and when used as a light emitting layer material, the light emitting layer ( In EML), holes and electrons can be balanced to form excitons.
  • the condensed ring group heterobands N and S affect the band gap when they are in the same direction and in different directions. When N and S are in the same direction, the conjugation length of ⁇ -electrons is short, and when N and S are in different directions, the conjugation length of ⁇ -electrons is long, affecting the T1 value.
  • substituted or unsubstituted is C 1 to C 60 linear or branched alkyl; C 2 Through C 60 Straight or branched alkenyl; C 2 to C 60 straight or branched alkynyl; C 3 to C 60 monocyclic or polycyclic cycloalkyl; C 2 to C 60 monocyclic or polycyclic heterocycloalkyl; C 6 Through C 60 Monocyclic or polycyclic aryl; C 2 Through C 60 Monocyclic or polycyclic heteroaryl; C 10 to C 60 spiro groups; C 1 to C 20 alkylamines; C 6 Through C 60 Monocyclic or polycyclic arylamine; And it means unsubstituted or substituted with one or more substituents selected from the group consisting of C 2 to C 60 monocyclic or polycyclic heteroarylamine. Said additional substituents may be further substituted further.
  • alkyl includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents.
  • the carbon number of the alkyl may be 1 to 60, specifically 1 to 40, more specifically 1 to 20.
  • alkenyl includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • Alkenyl may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more specifically 2 to 20 carbon atoms.
  • alkynyl includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • Alkynyl may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more specifically 2 to 20 carbon atoms.
  • cycloalkyl includes monocyclic or polycyclic having 3 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic means a group in which cycloalkyl is directly connected or condensed with another ring group.
  • the other ring group may be cycloalkyl, but may also be other types of ring groups such as heterocycloalkyl, aryl, heteroaryl, and the like.
  • the cycloalkyl may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, more specifically 5 to 20 carbon atoms.
  • the heterocycloalkyl includes S, O, N or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic means a group in which heterocycloalkyl is directly connected or condensed with another ring group.
  • the other ring group may be heterocycloalkyl, but may also be other types of ring groups such as cycloalkyl, aryl, heteroaryl, and the like.
  • the heterocycloalkyl may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more specifically 3 to 20 carbon atoms.
  • aryl includes monocyclic or polycyclic having 6 to 60 carbon atoms, and may be further substituted with other substituents.
  • polycyclic means a group in which aryl is directly connected or condensed with another ring group.
  • the other ring group may be aryl, but may also be other types of ring groups such as cycloalkyl, heterocycloalkyl, heteroaryl, and the like.
  • the aryl may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, more specifically 6 to 25 carbon atoms.
  • aryl examples include phenyl, biphenyl, triphenyl, naphthyl, anthryl, chrysenyl, phenanthrenyl, peryllenyl, fluoranthenyl, triphenylenyl, penalenyl, pyrenyl, tetrasenyl, pentacenyl, Fluorenyl, indenyl, acenaphthylenyl, and the like, and condensed rings thereof, but are not limited thereto.
  • the heteroaryl includes S, O, N or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic means a group in which heteroaryl is directly connected or condensed with another ring group.
  • the other ring group may be heteroaryl, but may also be other types of ring groups such as cycloalkyl, heterocycloalkyl, aryl, and the like.
  • the heteroaryl may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more specifically 3 to 25 carbon atoms.
  • heteroaryl examples include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, fura Zanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxynyl, triazinyl, tetrazinyl, quinolyl, isoqui Nolyl, quinazolinyl, isoquinazolinyl, acridinyl, phenantridinyl, imidazopyridinyl, diazanaphthalenyl, triazaindene, indolyl, indi
  • the spiro group includes a spiro structure, and may have 15 to 60 carbon atoms.
  • the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro bonded to a fluorene group.
  • the spiro group includes a group of the following structural formula.
  • aryl and heteroaryl are divalent groups.
  • R 1 to R 4 is C 6 Through C 60 Monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or a substituted or unsubstituted C 10 to C 60 spiro group, with the remainder being hydrogen; halogen; C 1 to C 60 straight or branched chain substituted or unsubstituted alkyl; C 2 Through C 60 A straight or branched chain substituted or unsubstituted alkenyl; C 2 to C 60 straight or branched substituted or unsubstituted alkynyl; C 1 to C 60 straight or branched chain substituted or unsubstituted alkoxy; C 6 to C 60 straight or branched chain substituted or unsubstituted aryloxy; C 3 to C 60 of monocyclic or polycyclic substituted or unsubstituted cycloalky
  • At least one of R 1 to R 4 is C 6 Through C 60 Monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or a substituted or unsubstituted C 10 to C 60 spiro group.
  • one of R 1 to R 4 is C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or a substituted or unsubstituted C 10 to C 60 spiro group.
  • At least one of R 1 to R 4 is C 6 Through C 60 Monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or a substituted or unsubstituted C 10 to C 60 spiro group, and the rest of R 1 to R 4 are hydrogen, or combine with an adjacent substituent to form an aromatic hydrocarbon ring or heterocycle.
  • At least one of R 1 to R 4 is C 6 Through C 60 Monocyclic or polycyclic substituted or unsubstituted aryl; Or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl, and the remainder of R 1 to R 4 is hydrogen, or combines with an adjacent substituent to form an aromatic hydrocarbon ring or heterocycle.
  • R 2 is a C 6 Through C 60 Monocyclic or polycyclic substituted or unsubstituted aryl; Or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R 2 is a C 6 Through C 60 Monocyclic or polycyclic substituted or unsubstituted aryl; Or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl, R 1 , R 3 and R 4 are hydrogen.
  • R 2 is a C 6 Through C 60 Monocyclic or polycyclic substituted or unsubstituted aryl; Or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl, R 1 is hydrogen, and R 3 and R 4 combine with each other to form a substituted or unsubstituted benzene ring.
  • R 2 is substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenan Trityl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl group.
  • R 2 is substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenan Triyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl group, which are phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl At least one may be further substituted, and they may further be further substituted with at least one of phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl At least one may be further substituted
  • R 2 is further phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, pyridyl substituted phenyl, pyrimidyl substituted phenyl, triazinyl substituted Phenyl, quinolyl substituted phenyl, isoquinolyl substituted phenyl, naphthyl substituted phenyl, anthryl substituted phenyl, phenanthryl substituted phenyl, phenyl substituted naphthyl, phenyl substituted anthryl, phenyl substituted phenanthryl, naphthyl substituted anthryl, an Triyl substituted naphthyl, phenyl substituted pyridyl, naphthyl substituted pyridyl, anthryl substituted pyridyl or
  • R 4 is C 6 Through C 60 Monocyclic or polycyclic substituted or unsubstituted aryl; Or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R 4 is C 6 Through C 60 Monocyclic or polycyclic substituted or unsubstituted aryl; Or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl, and R 1 to R 3 are hydrogen.
  • R 4 is C 6 Through C 60 Monocyclic or polycyclic substituted or unsubstituted aryl; Or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl, R 3 is hydrogen, and R 1 and R 2 combine with each other to form a substituted or unsubstituted benzene ring.
  • R 4 is substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenan Trityl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl group.
  • R 4 is substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenan Triyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl group, which are phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl At least one may be further substituted, and they may further be further substituted with at least one of phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl At least one may be further substituted
  • R 4 is further phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, pyridyl substituted phenyl, pyrimidyl substituted phenyl, triazinyl substituted Phenyl, quinolyl substituted phenyl, isoquinolyl substituted phenyl, naphthyl substituted phenyl, anthryl substituted phenyl, phenanthryl substituted phenyl, phenyl substituted naphthyl, phenyl substituted anthryl, phenyl substituted phenanthryl, naphthyl substituted anthryl, an Triyl substituted naphthyl, phenyl substituted pyridyl, naphthyl substituted pyridyl, anthryl substituted pyridyl or
  • R 1 is C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; Or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R 1 is C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; Or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl, and R 2 to R 4 are hydrogen.
  • R 1 is C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; Or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl, R 2 is hydrogen, and R 3 and R 4 combine with each other to form a substituted or unsubstituted benzene ring.
  • R 1 is substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenan Trityl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl group.
  • R 1 is substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenan Triyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl group, which are phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl At least one may be further substituted, and they may further be further substituted with at least one of phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl At least one may be further substituted
  • R 1 is further phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, pyridyl substituted phenyl, pyrimidyl substituted phenyl, triazinyl substituted Phenyl, quinolyl substituted phenyl, isoquinolyl substituted phenyl, naphthyl substituted phenyl, anthryl substituted phenyl, phenanthryl substituted phenyl, phenyl substituted naphthyl, phenyl substituted anthryl, phenyl substituted phenanthryl, naphthyl substituted anthryl, an Triyl substituted naphthyl, phenyl substituted pyridyl, naphthyl substituted pyridyl, anthryl substituted pyridyl or
  • R 1 and R 2 combine with each other to form a substituted or unsubstituted benzene ring.
  • R 2 and R 3 combine with each other to form a substituted or unsubstituted benzene ring.
  • R 3 and R 4 combine with each other to form a substituted or unsubstituted benzene ring.
  • R 5 to R 8 are the same as or different from each other, and each independently hydrogen; halogen; C 1 to C 60 straight or branched chain substituted or unsubstituted alkyl; C 2 Through C 60 A straight or branched chain substituted or unsubstituted alkenyl; C 2 to C 60 straight or branched substituted or unsubstituted alkynyl; C 1 to C 60 straight or branched chain substituted or unsubstituted alkoxy; C 6 to C 60 straight or branched chain substituted or unsubstituted aryloxy; C 3 to C 60 of monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted
  • R 5 to R 8 are the same as or different from each other, and each independently hydrogen; C 1 to C 60 straight or branched chain substituted or unsubstituted alkyl; C 2 Through C 60 A straight or branched chain substituted or unsubstituted alkenyl; C 2 to C 60 straight or branched substituted or unsubstituted alkynyl; C 3 to C 60 of monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; And substituted or unsubstituted C 10 to C 60 spiro groups.
  • R 5 to R 8 are the same as or different from each other, and each independently hydrogen; C 1 to C 60 straight or branched chain substituted or unsubstituted alkyl; And C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl.
  • R 5 to R 8 is hydrogen.
  • Chemical Formula 1 may be represented by one of the following Chemical Formulas 2 to 4.
  • R 1 to R 8 are the same as defined in Formula 1,
  • R is as defined in R 1 to R 8 , u is an integer from 1 to 4,
  • R is the same as or different from each other.
  • Chemical Formula 1 may be represented by one of the following Chemical Formulas 5 to 8.
  • R 5 to R 8 are the same as defined in Formula 1,
  • R is as defined in R 1 to R 4 ,
  • n is an integer of 1 to 3
  • v is an integer of 1 to 5
  • R is the same or different from each other
  • L is C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted arylene; Or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroarylene, p and x are each an integer of 0 to 3, when p or x is 2 or more, L is the same as or different from each other,
  • Ar is C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; Or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl, q and y are each an integer of 0 to 3, and when q or y is 2 or more, Ar is the same as or different from each other.
  • L is a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, a substituted or unsubstituted anthracene group , A substituted or unsubstituted phenanthrene group, a substituted or unsubstituted naphthalene group, or a substituted or unsubstituted phenylene group.
  • L is a pyridine group, pyrimidine group, triazine group, anthracene group, phenanthrene group, naphthalene group, or phenylene group.
  • L is a pyridine group, pyrimidine group, triazine group, anthracene group, or phenylene group.
  • p and x are each 0 or 1.
  • Ar is substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted anthryl, Substituted or unsubstituted phenanthryl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl group.
  • Ar is substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted anthryl, Substituted or unsubstituted phenanthryl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl group, which is phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, qui And further substituted with at least one of isnoquinol and isoquinolyl, which are further further substituted with at least one of phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl,
  • q and y are each 1 or 2.
  • q and y are each one.
  • R is hydrogen
  • Chemical Formula 1 may be represented by one of the following Chemical Formulas 9 to 13.
  • R 5 to R 8 are the same as defined in Formula 1,
  • X 1 to X 3 are the same as or different from each other, each independently N or CY 6 , at least one of X 1 to X 3 is N,
  • R, and Y 1 to Y 6 are the same as or different from each other, and each independently, as defined by R 1 to R 4 , at least two adjacent substituents in R, or at least two adjacent ones of Y 1 to Y 6
  • the substituents may be bonded to each other to form an aromatic hydrocarbon ring or heterocycle
  • n is an integer of 1 to 3, when n is 2 or more, R is the same as or different from each other, r is an integer of 1 to 5, when r is 2 or more, Y 3 is the same as or different from each other, s is an integer of 1 to 7, and when s is 2 or more, Y 4 is the same or different from each other, t is an integer of 1 to 9, and t is 2 or more Y 5 is the same as or different from each other,
  • L is C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted arylene; Or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroarylene, p is an integer of 0 to 3, when p is 2 or more, L is the same as or different from each other,
  • Z1 and Z2 are C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aromatic hydrocarbon ring; Or a C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted aromatic hetero ring.
  • the formula (9) May be represented as follows.
  • Y 11 to Y 13 are the same as the definition of Y 6 .
  • Y 11 to Y 13 are each C 6 to C 60 monocyclic or polycyclic aryl or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl C 6 to C of the 60 monocyclic or polycyclic aryl; Or heteroaryl unsubstituted or substituted with C 6 to C 60 monocyclic or polycyclic aryl or C 2 to C 60 monocyclic or polycyclic heteroaryl.
  • T 1 to T 9 are each CRR ', NR, S or O,
  • R and R ' are the same as or different from each other, and each hydrogen; C 1 to C 60 straight or branched chain substituted or unsubstituted alkyl; Or C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl.
  • T 1 , T 2 , T 4 , T 7 , T 8 , T 9 are each independently CRR ', NR, S or O, and T 3 , T 5 and T 6 are each Independently S or O.
  • R and R' are the same as or different from each other, and each independently C 1 to C 6 alkyl; Or C 6 to C 20 aryl.
  • R and R' are the same as or different from each other, and are each independently methyl or phenyl.
  • R is C 6 to C 20 aryl.
  • R is phenyl
  • p is an integer of 0 to 2
  • L is phenylene
  • the compound of Formula 1 may be selected from the following compounds.
  • the compounds described above may be prepared based on the preparation examples described below. In the following production examples, representative examples are described, but if necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, it is possible to change starting materials, reactants, reaction conditions and the like. Changing the type or position of substituents at the remaining positions as needed can be performed by those skilled in the art using techniques known in the art.
  • the organic light emitting device comprises the compound of Formula 1 described above.
  • the organic light emitting device according to the present invention includes one or more organic material layers provided between the anode, the cathode and the anode and the cathode, one or more of the organic material layer comprises a compound of formula (1).
  • FIG. 1 to 3 illustrate the stacking order of electrodes and organic material layers of organic light emitting diodes according to exemplary embodiments of the present invention.
  • these drawings are not intended to limit the scope of the present invention, the structure of the organic light emitting device known in the art can be applied to the present invention.
  • an organic light emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is illustrated.
  • the present invention is not limited thereto, and as shown in FIG. 2, an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.
  • the organic light emitting diode according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, an electron transport layer 304, and an electron injection layer 305.
  • the scope of the present invention is not limited by such a laminated structure, and other layers except for the light emitting layer may be omitted, and other functional layers may be added as needed.
  • the organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that the compound of Formula 1 is included in at least one layer of the organic material layer.
  • the compound of Formula 1 may constitute one or more layers of the organic material layer of the organic light emitting device alone. However, if necessary, the organic material layer may be mixed with other materials.
  • the compound of Formula 1 may be used as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material and the like in the organic light emitting device.
  • the organic material layer including the compound of Formula 1 may be a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer or an electron injection layer.
  • the compound of Formula 1 may be used as the electron injection and / or transport layer material of the organic light emitting device.
  • the organic material layer including the compound of Formula 1 is an electron transport layer.
  • the compound of Formula 1 may be used as a light emitting material of an organic light emitting device.
  • the organic material layer including the compound of Formula 1 may be a light emitting layer of the organic light emitting device.
  • the compound of Formula 1 may be used as a phosphorescent host material.
  • the compound of Formula 1 is used together with a light emitting dopant.
  • the light emitting dopant material those known in the art may be used.
  • phosphorescent dopant materials represented by LL'MX, LL'L''M, LMXX ', L 2 MX, and L 3 M can be used, but the scope of the present invention is not limited to these examples.
  • L, L ', L ", X and X' are bidentate ligands different from each other, and M is a metal which forms an 8-sided complex.
  • M may be iridium, platinum, osmium or the like.
  • L is an anionic bidentate ligand coordinated to M by sp 2 carbon and hetero atom, and X may function to trap electrons or holes.
  • Non-limiting examples of L include 2- (1-naphthyl) benzoxazole, (2-phenylbenzooxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole), (7,8 -Benzoquinoline), (thienylpyridin), phenylpyridine, benzothienylpyridin, 3-methoxy-2-phenylpyridine, thienylpyridin, tolylpyridine and the like.
  • Non-limiting examples of X include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.
  • anode material materials having a relatively large work function may be used, and a transparent conductive oxide, a metal, or a conductive polymer may be used.
  • the cathode material materials having a relatively low work function may be used, and a metal, a metal oxide, or a conductive polymer may be used.
  • hole injection material a well-known hole injection material may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or described in Advanced Material, 6, p.677 (1994).
  • Starburst-type amine derivatives such as TCTA, m-MTDATA, m-MTDAPB, polyaniline / dodecylbenzenesulfonic acid (polyaniline / dodecylbenzenesulfonic acid) or PEDOT / PSS (Poly (3, 4-ethylenedioxythiophene) / Poly (4-styrenesulfonate): poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate)), Pani / CSA (Polyaniline / Camphor sulfonic acid: polyaniline / camphorsulfonic acid) or PANI / PSS (Polyaniline / Poly (4-styrene-sulfonate): polyaniline / poly (4-styrenesulfonate)) and the like can be used.
  • Polyaniline / dodecylbenzenesulfonic acid polyaniline / dode
  • pyrazoline derivatives arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like may be used, and low molecular or polymer materials may be used.
  • Examples of the electron transport material include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinomethane and derivatives thereof, and fluorenone Derivatives, diphenyl dicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like can be used, as well as high molecular weight materials as well as high molecular materials.
  • LiF is representatively used in the art, but the present invention is not limited thereto.
  • a red, green or blue light emitting material may be used, and if necessary, two or more light emitting materials may be mixed.
  • a fluorescent material can be used as a light emitting material, it can also be used as a phosphorescent material.
  • a material which combines holes and electrons injected from the anode and the cathode, respectively, to emit light may be used, but materials in which both the host material and the dopant material are involved in light emission may be used.
  • the compound of formula 1 may be prepared by introducing a substituent in the same manner as in Scheme 2 or 3.
  • R is as defined in R 1 to R 8 of Formula 1 above.
  • a compound 1, a compound 3, a compound 8, a compound 12, a compound 13, a compound 16, a compound 18, a compound 28 was performed in the same manner as in Preparation Example 1, except that the compound of Table 1 was used as the compound Ar 1 . , Compound 35 and compound 38 were prepared.
  • a compound of Chemical Formula 1 may be prepared according to Scheme 4 below.
  • R is as defined in R 1 to R 8 of Formula 1 above. It will be apparent to those skilled in the art that the position of the substituent can be changed depending on the substituted position of Br.
  • a compound of Chemical Formula 1 may be prepared according to Scheme 5 below.
  • R is as defined in R 1 to R 8 of Formula 1 above. It will be apparent to those skilled in the art that the position of the substituents can be varied depending on the substituted position of Br or the position of the condensed ring of the starting material.
  • a compound of Chemical Formula 1 may be prepared according to Scheme 6 below.
  • R is as defined in R 1 to R 8 of Formula 1 above. It will be apparent to those skilled in the art that the position of the substituents can be varied depending on the substituted position of Br or the position of the condensed ring of the starting material.
  • a compound of Chemical Formula 1 may be prepared according to the following Scheme 7.
  • R is as defined in R 1 to R 8 of Formula 1 above. It will be apparent to those skilled in the art that the type and position of the substituent of the compound of Formula 1 can be changed according to the type and position of the substituent of the starting material.
  • Trifluoroacetic acid (46.5 ml, 2.4 eq) was added to an acetic acid (700 ml) mixture containing Compound 250-1 (68.9 g, 1.0 eq) in one neck rbf and stirred at 100 ° C. for 15 hours. The solution cooled to room temperature was washed with acetic acid and hexane and filtered to obtain an ivory solid compound 250-2 (27.3 g, 42%).
  • Synthesis was performed in the same manner as in the preparation of Compound 236, except that Compound a-5 was used instead of Compound a-1.
  • HOMO, LUMO, and BAND GAP of Compound 38, Compound 66, and Compound 76 were measured using a CV measuring instrument (princeton appied research, model name: Parstat2273) using the following method. Are shown in Tables 9 to 11 below.
  • Electrolyte solution 3.3 g of tetrabutylammonium tetrafluoroborate was precisely weighed and placed in a 100 ml volumetric flask, and methylene chloride was added to make 100 ml.
  • Standard solution Approximately 1 mg of NPB was precisely weighed, placed in a 10 ml volumetric flask, and the electrolyte was added to make 10 ml.
  • Sample solution About 1 mg of the compound was accurately weighed and placed in a 10 ml volumetric flask, and the electrolyte solution was added to 10 ml before being used as a sample solution.
  • the y axis represents current (unit: A), and the x axis represents potential (unit: V).
  • Figure 10 shows a UV measurement graph of the compound 38.
  • FIG. 11 shows a PL measurement graph for 320 nm of compound 38.
  • FIG. 13 shows a PL measurement graph for 260 nm of Compound 66.
  • FIG. 14 shows a UV measurement graph of compound 76.
  • FIG. 15 shows a PL measurement graph for 303 nm of compound 76.
  • the y-axis of FIGS. 10 to 15 are intensity, respectively, and the x-axis is wavelength (unit: nm).
  • the transparent electrode ITO thin film obtained from the glass for OLED was subjected to ultrasonic washing using trichloroethylene, acetone, ethanol and distilled water in sequence, and used after washing in isopropyl alcohol.
  • an ITO substrate is placed in the substrate folder of the vacuum deposition equipment, and evacuated until the vacuum degree in the vacuum deposition equipment reaches 10 -7 torr, and then the following 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenyl amine: hereinafter referred to as 2-TNATA) by vapor deposition A 600 ⁇ m thick hole injection layer was deposited on the ITO substrate.
  • NPB N, N'-bis ( ⁇ -naphthyl) -N, N'-diphenyl-4,4'-diamine
  • a light emitting layer was deposited thereon as follows.
  • the following ⁇ -ADN was used as a host as a light emitting material in one cell in the vacuum deposition equipment, and the following BD1 was added as a dopant in the other cell.
  • the following tris (8-hydroxyquinoline) aluminum (III) (hereinafter referred to as Alq 3 ) was deposited to an thickness of 200 kPa as the electron transporting layer.
  • lithium fluoride LiF
  • Al cathode was deposited to a thickness of 1200 ⁇ to produce an OLED.
  • An OLED was manufactured in the same manner as in the comparative example, except that the compound of Table 12 was used instead of the tris (8-hydroxyquinoline) aluminum (III) (Alq 3 ) of the comparative example as the electron transport layer material.
  • the driving voltage (V), power efficiency (cd / A) and driving life of the OLED device fabricated as described above at 1,000 cd / m 2 and the time until the efficiency drops to 50% are described in Table 12 below. It was.
  • the organic light emitting device manufactured by using the compound of Preparation Example of the present invention as an electron transporting material from the results of Table 12 the organic light emitting device using tris (8-hydroxyquinoline) aluminum (III) (Alq 3 ) in the Comparative Example Excellent characteristics in driving voltage, efficiency and lifespan were confirmed. Accordingly, it was confirmed that the pyrazole-containing polycyclic derivative represented by Chemical Formula 1 of the present invention was useful as a material of the electron transport layer when manufacturing an organic light emitting device.
  • the transparent electrode ITO thin film obtained from the glass for OLED was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol, and distilled water in sequence, and then stored in isopropanol and used.
  • substrate was installed in the board
  • a current was applied to the cell to evaporate 2-TNATA to deposit a 600 kW hole injection layer on the ITO substrate.
  • NPB was placed in another cell in the vacuum deposition equipment, and a 300 ⁇ thick hole transport layer was deposited on the hole injection layer by applying an electric current to the cell.
  • the phosphorescent green light emitting material having the following structure was deposited on the light emitting layer.
  • CBP 4,4'-bis (carbazol-9-yl) biphenyl
  • Ir (ppy) 3 green light emitting dopant material
  • Tris (2-phenylpyridine) iridium (III)) was 10% vacuum deposited relative to the host material.
  • BCP 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
  • Alq 3 as an electron transport layer was 200 GPa thick.
  • lithium fluoride was deposited to a thickness of 10 kPa with an electron injection layer.
  • Al cathode was deposited to a thickness of 1000 ⁇ to produce an OLED.
  • Test Example 3 OLED device fabrication
  • a device was fabricated using the same materials as in Comparative Example 2 except for using the materials shown in Table 13 corresponding to the green light emitting layer in Comparative Example instead of CBP.
  • the drive voltage (Op.V) and power efficiency (cd / A) of the OLED device manufactured as described above are described in Table 13 below until the efficiency drops to 50% at 1,000 cd / m 2 .
  • the organic light emitting device manufactured by using the compound of Preparation Example of the present invention as a phosphorescent light emitting layer material compared to the organic light emitting device using the CBP in the comparative example was confirmed excellent characteristics in driving voltage, efficiency and life. Accordingly, it was confirmed that the pyrazole-containing polycyclic derivative represented by Chemical Formula 1 of the present invention is useful as a material of the phosphorescent light emitting layer in fabricating an organic light emitting device.

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Abstract

L'invention concerne un composé polycyclique contenant du pyrazole et un dispositif électroluminescent organique comprenant ce composé.
PCT/KR2013/012050 2013-09-04 2013-12-23 Composé polycyclique contenant du pyrazole et dispositif électroluminescent organique l'utilisant Ceased WO2015034140A1 (fr)

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US10749118B2 (en) * 2014-06-26 2020-08-18 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
WO2018105775A1 (fr) * 2016-12-07 2018-06-14 주식회사 진웅산업 Composé d'indazole et dispositif électroluminescent organique le contenant
CN111909132A (zh) * 2019-05-07 2020-11-10 北京鼎材科技有限公司 一种有机材料及采用该材料的有机电致发光器件
WO2020262888A1 (fr) * 2019-06-24 2020-12-30 엘티소재주식회사 Composé hétérocyclique et diode électroluminescente organique le comprenant
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US20230265109A1 (en) * 2022-01-14 2023-08-24 Annexon, Inc. Inhibitors of complement factors and uses thereof

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KR101551895B1 (ko) 2015-09-10
TW201509940A (zh) 2015-03-16

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