WO2017111439A1 - Organic compound and organic electroluminescent device comprising same - Google Patents

Organic compound and organic electroluminescent device comprising same Download PDF

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WO2017111439A1
WO2017111439A1 PCT/KR2016/014958 KR2016014958W WO2017111439A1 WO 2017111439 A1 WO2017111439 A1 WO 2017111439A1 KR 2016014958 W KR2016014958 W KR 2016014958W WO 2017111439 A1 WO2017111439 A1 WO 2017111439A1
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group
aryl
alkyl
boron
formula
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Korean (ko)
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이용환
김영배
김회문
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주식회사 두산
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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 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 hole blocking layer
  • BCP hole blocking layer
  • electron transporting layer material anthracene derivatives have been reported as the light emitting layer material.
  • 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.
  • 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):
  • At least one of X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 are each independently represented by the following Chemical Formula 2 or 3 Condensed with a ring to form a condensed ring;
  • the dotted line means the part where condensation takes place
  • Y 1 to Y 3 are each independently selected from the group consisting of O, S, N (R 4 ) and C (R 5 ) (R 6 );
  • Z 1 and Z 2 are each independently N or C (R 7 );
  • L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • R 1 to R 7 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 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they
  • Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60 aryl amine group
  • 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 C2-C40 straight or branched chain unsaturated hydrocarbon 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 at least one carbon-carbon triple bond, 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; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl 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 to 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 of 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 represented by Formula 1 according to the present invention is excellent in thermal stability, hole transporting, hole injection performance, electron transporting and electron injection performance, and excellent phosphorescence characteristics of the light emitting layer, so that the organic material layer material of the organic electroluminescent device, preferably May be used as the light emitting layer material.
  • the present invention provides a compound represented by Formula 1:
  • At least one of X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 are each independently represented by the following Chemical Formula 2 or 3 Condensed with a ring to form a condensed ring;
  • X 1 to X 8 which do not form a condensed ring with the ring represented by Formula 2 or 3 are each independently N or C (R 3 );
  • the dotted line means the part where condensation takes place
  • Y 1 to Y 3 are each independently selected from the group consisting of O, S, N (R 4 ) and C (R 5 ) (R 6 );
  • Z 1 and Z 2 are each independently N or C (R 7 );
  • L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • R 1 to R 7 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ of 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 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine
  • Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl 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 of the alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ aryloxy of C 60 group, C 1 ⁇ C 40 alkyloxy group of, C 6
  • the novel compound according to the present invention is a structure in which a 5-membered ring is condensed at the terminal of the fluorene moiety to form a basic skeleton, and various substituents are connected to the basic skeleton, specifically represented by the following Chemical Formula 1 do:
  • X 1 to X 8 which do not form a condensed ring with the ring represented by Formula 2 or 3 are each independently N or C (R 3 );
  • the dotted line means the part where condensation takes place
  • Y 1 to Y 3 are each independently selected from the group consisting of O, S, N (R 4 ) and C (R 5 ) (R 6 );
  • Z 1 and Z 2 are each independently N or C (R 7 );
  • L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • R 1 to R 7 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- aryloxy group of C 60, C 3 ⁇ C 40 alkylsilyl group, C group 6 ⁇ C 60 aryl silyl, C 1 ⁇ arylboronic of C 40 group of an alkyl boron, C 6 ⁇ C 60 group, C 6 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine or adjacent groups bond
  • Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl 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 of the alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ aryloxy of C 60 time, C 1 ⁇ C 40 alkyloxy group of, C 6
  • the compound represented by Chemical Formula 1 is larger in molecular weight than the conventional organic electroluminescent device material [eg, 4,4-dicarbazolybiphenyl (CBP)], and has a wide energy band gap. While having, it is possible to increase the binding force between the hole and the electron. Therefore, when the compound of Formula 1 is used in an organic electroluminescent device, the driving voltage, efficiency (luminescence efficiency, power efficiency), lifetime, and luminance of the device may be improved.
  • the conventional organic electroluminescent device material eg, 4,4-dicarbazolybiphenyl (CBP)
  • At least one of the Y 1 to Y 3 may include a hetero atom.
  • the ring represented by Formula 2 may be a ring represented by any one of the following formulas 4 to 6:
  • the dotted line means the part where condensation takes place
  • R 5 and R 6 are as defined in formula (I).
  • At least one of the Y 1 , Z 1 and Z 2 may include a hetero atom.
  • the ring represented by Formula 3 may be a ring represented by any one of the following Formula 7 to 12:
  • the dotted line means the part where condensation takes place
  • R 4 and R 7 are the same as defined in Chemical Formula 1. However, in Chemical Formula 9, two R 7 are the same as or different from each other.
  • L 1 to L 4 are each independently composed of a single bond, phenylene group, biphenylene group, pyridinyl group, pyrimidinyl group, naphthalenyl group, fluorenyl group and carbazolyl group Can be selected from the group.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms Can be selected.
  • R 1 and R 2 may be independently selected from the group consisting of a methyl group, an ethyl group, a propyl group and substituents represented by the following formulas (13) to (17):
  • T 1 to T 8 are each independently N or C (R 8 );
  • any one of T 1 to T 4 bonded to L 2 or L 4 is C (R 8 ), wherein R 8 is absent;
  • R 8 to R 11 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 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they
  • the substituent represented by Formula 13 or 14 may be selected from the group consisting of the following Formula F-1 to F-13:
  • t is an integer from 0 to 5;
  • l is an integer from 0 to 4.
  • v is an integer from 0 to 3;
  • u is an integer from 0 to 2;
  • R 12 is 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, nuclear atom C 5 to C 60 aryloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 ⁇ C 60 It is selected from the group consisting of mono or diaryl phosphinyl group and C 6 ⁇ C 60 arylsilyl group, or may be combined with adjacent groups to form a condensed ring, when
  • R 8 is as defined in Formulas 13 and 14 above.
  • each of R 9 to R 11 is independently hydrogen, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms It may be selected from the group, more preferably may be selected from the group consisting of phenyl group, biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group, quinolinyl group and quinazolinyl group.
  • L 1 to L 4 is a single bond, R 1 and R 2 may be bonded to form a condensed ring.
  • the compound represented by Formula 1 may be a compound represented by Formula 18:
  • K 1 is selected from the group consisting of a single bond, C (R 13 ) (R 14 ), N (R 15 ), O and S;
  • R 13 to R 15 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 ⁇ for C 60 aryl phosphazene group, and groups bonded to adjacent or 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 which they
  • 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 13 to R 15 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
  • X 1 to X 8 , and X 9 to X 16 which do not form a condensed ring with a ring represented by the following Chemical Formula 2 or 3 are each independently N or C (R 3 );
  • the dotted line means the part where condensation takes place
  • R 3 Y 1 to Y 3 , Z 1 and Z 2 are as defined in Chemical Formulas 1 to 3 above.
  • At least one of the X 9 And X 10 , X 10 And X 11 , X 11 And X 12 , X 13 And X 14 , X 14 And X 15 , And X 15 And X 16 are each independently condensed with a ring represented by Formula 2 or 3 to form a condensed ring;
  • X 9 to X 16 which do not form a condensed ring with the ring represented by Formula 2 or 3 are each independently N or C (R 3 );
  • R 3 is as defined in Formula 1 above.
  • At least one of the R 3 to R 7 may be each independently a substituent represented by the following formula (19):
  • L 5 and L 6 are selected from the group consisting of a single bond, a C 6 -C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
  • R 16 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 Condensation in combination with a group selected from or adjacent to (eg, L 5 or other R 3 to R 7 ) a group consisting of a silyl group, a C 6 -C 60 mono or diarylphosphinyl group and a
  • L 5 and L 6 are each a single bond, each independently, a phenylene group, biphenylene group, a pyridinyl group, a pyrimidinyl group, a naphthyl Frontale group, a fluorenyl group, a carbazolyl group, It may be selected from the group consisting of a quinolinyl group and a quinazolinyl group.
  • R 16 may be a substituent selected from the group consisting of Formulas 20 to 25:
  • M 1 to M 8 are each independently N or C (R 19 );
  • Any one of M 1 to M 4 bonded to L 6 in Formula 21 is C (R 19 ), wherein R 19 is absent;
  • K 2 and K 3 are each independently selected from the group consisting of a single bond, C (R 20 ) (R 21 ), N (R 22 ), O, S and SO 2 , but both K 2 and K 3 are a single bond Not;
  • Y 4 is selected from the group consisting of O, S, C (R 20 ) (R 21 ) and N (R 22 );
  • Z 3 to Z 6 are each independently N or C (R 19 );
  • n are each independently an integer from 0 to 4.
  • R 17 and R 18 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 to C 60 mono or diaryl phosphinyl group, and a C 6 to C 60 arylamine group may be combined with or adjacent to a group to form a condensed ring,
  • R 19 to R 22 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 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they
  • 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 17 to R 22 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
  • the compound represented by Formula 1 of the present invention can increase the binding force between the hole and the electron while having the bipolar (bipolar) characteristics of the entire molecule due to the various aromatic ring substituents connected to the basic skeleton. Therefore, when the compound is applied to the organic electroluminescent device, since it can exhibit excellent characteristics as a host material of the light emitting layer as compared to the conventional CBP, the phosphorescence properties of the device is improved, the hole injection ability and / or transport capacity, the luminous efficiency The driving voltage, lifespan characteristics and the like can be improved.
  • the energy level can be adjusted according to the substituents to have a wide bandgap (sky blue ⁇ red), and thus can be applied not only to the light emitting layer, but also to the electron transport auxiliary layer, electron transport layer, hole transport layer, hole injection layer, etc. Can be.
  • the glass transition temperature can be improved, thereby having a higher thermal stability than the conventional CBP.
  • the thermal stability of the compound may not only be improved, but also effective in suppressing crystallization of the organic layer including the compound of Formula 1. Therefore, the device including the compound of formula 1 according to the present invention can greatly improve the durability and life characteristics.
  • the electron transport auxiliary layer since the electron transport auxiliary layer has a high triplet energy, it may exhibit excellent efficiency due to the triplet-triplet fusion effect.
  • the exciton generated in the light emitting layer can be prevented from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer.
  • the number of excitons contributing to light emission in the light emitting layer may be improved, and thus the luminous efficiency of the device may be improved, and the durability and stability of the device may be improved, and thus the life of the device may be efficiently increased.
  • Most of the materials developed show physical characteristics that can be driven at low voltages, thereby improving their lifetime.
  • the compound of Formula 1 according to the present invention when adopted as a hole injection / transport layer material, an electron injection / transport layer material, a blue, green and / or red phosphorescent host material of an organic electroluminescent device, efficiency and lifespan compared to conventional CBP In terms of excellent effects can be achieved. Therefore, the compound according to the present invention can greatly contribute to improving the performance and lifespan of the organic EL device, and in particular, the device life improvement has a great effect in maximizing the performance in the full color organic light emitting panel.
  • R 16 may be a substituent selected from the group consisting of Formulas 26 to 29:
  • R 23 to R 25 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ of 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 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine
  • 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 23 to R 25 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
  • the R 23 to R 25 are each independently hydrogen, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and a nuclear atoms of 5 to 60 heteroaryl group consisting of It may be selected from the group, more preferably, consisting of hydrogen, methyl, ethyl, propyl, butyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, naphthalenyl, quinolinyl and quinazolinyl Can be selected from the group.
  • the substituent selected from the group consisting of Formula 20 to 25 may be a substituent selected from the group consisting of B-1 to B-22:
  • t is an integer from 0 to 5;
  • l and s are each independently an integer from 0 to 4.
  • v is an integer from 0 to 3;
  • u is an integer from 0 to 2;
  • R 26 and R 27 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 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ⁇ C 60, C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group, or
  • 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 and aryl of the above R 26 and R 27 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
  • R 19 to R 22 are each as defined in Chemical Formulas 20 to 25.
  • two substituents adjacent to each other of the R 3 to R 7 are bonded to each other to form a C 4 ⁇ C 18 condensed aromatic ring or 4 to 14 condensed heteroaromatic ring of nuclear atoms Can be formed.
  • Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
  • the compound represented by Chemical Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) et al. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
  • 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 organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer.
  • the light emitting layer of the organic electroluminescent device may include a host material, and may include a compound represented by Chemical Formula 1 as the host material.
  • the compound represented by Chemical Formula 1 when included as a light emitting layer material of the organic electroluminescent device, preferably a green phosphorescent host, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency and power efficiency), lifespan, brightness and driving voltage can be improved.
  • the structure of the organic EL device according to the present invention described above is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • an electron transport auxiliary layer may be further stacked between the emission layer and the electron transport layer, and an electron injection layer may be further stacked on the electron transport layer.
  • at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron transport auxiliary layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer is represented by the formula (1) It may include a compound represented.
  • the structure of the organic EL device according to the present invention may be a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device of the present invention may be formed using other materials and methods known in the art, except that at least one of the organic material layers (eg, the light emitting layer) is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming an organic material layer and an electrode.
  • 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.
  • examples of the anode material 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
  • Conductive polymers such as polythiophene, poly (3-methylthiophene
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • A-1 (3.44 g, 10.0 mmol) under nitrogen stream, (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (3.53 g, 10.0 mmol), K 2 CO 3 (4.27 g, 30.0 mmol), Pd (PPh 3 ) 4 (0.58 g, 5 mol%) and X-Phos (0.8 g, 5.00 mmol) were added to 120 ml / 40 ml of THF / H 2 O and stirred at 90 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound J-1 (3.08 g, yield 50%) using column chromatography.
  • A-2 (3.45 g, 10.0 mmol) was used instead of A-1 and (4,6 instead of (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid Except for using -diphenyl-1,3,5-triazin-2-yl) boronic acid (2.77 g, 10.0 mmol) was subjected to the same process as in Synthesis Example 1 to J-5 (2.55) g, yield 47%).
  • A-2 (3.45 g, 10.0 mmol) was used instead of A-1 and (4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid was used instead of (4- ( Except for using 4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (3.53 g, 10.0 mmol) was carried out in the same manner as in Synthesis Example 1 J-6 (2.41 g, yield 39%) was obtained.
  • A-6 (5.45 g, 10.0 mmol) was used instead of A-1 and 9,9 'was substituted for (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid.
  • -J-16 (4.04 g, 49% yield) of the target compound by the same procedure as in Synthesis Example 1, except that spirobibi [fluorene] -4-ylboronic acid (3.60 g, 10.0 mmol) was used.
  • A-6 (5.45 g, 10.0 mmol) was used instead of A-1 and (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) dibenzo [b instead of boronic acid , d] furan-4-ylboronic acid (2.12 g, 10.0 mmol) was used in the same manner as in Synthesis Example 1, except that J-17 (3.24 g, yield 48%) was obtained.
  • A-6 (5.45 g, 10.0 mmol) was used instead of A-1 and (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) dibenzo [b instead of boronic acid , d] thiophen-4-ylboronic acid (2.28 g, 10.0 mmol) was used in the same manner as in Synthesis Example 1, except that J-18 (3.25 g, yield 47%) was obtained. .
  • the compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • M-MTDATA 60 nm) / TCTA (80 nm) / 90% of the host compound + 10% Ir (ppy) 3 (300nm) / BCP (10 nm) / Alq 3 (30) nm) / LiF (1 nm) / Al (200 nm) were laminated to fabricate an organic EL device.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound J-1 as the light emitting host material when the emission layer was formed.
  • Example 1-10 For each organic EL device produced in Example 1-10 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.
  • 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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Abstract

The present invention relates to a novel compound and an organic electroluminescent device comprising same, the compound, according to the present invention, being used on an organic layer, preferably a light-emitting layer, of an organic electroluminescent device, thereby enabling the improvement of the light-emitting efficiency, driving voltage and lifespan of the organic electroluminescent device.

Description

유기 화합물 및 이를 포함하는 유기 전계 발광 소자Organic compound and organic electroluminescent device comprising the same
본 발명은 유기 전계 발광 소자용 재료로서 사용될 수 있는 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.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.
1950년대 베르나소스(Bernanose)의 유기 박막 발광 관측을 시점으로 하여, 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent, EL) 소자에 대한 연구가 이어져 오다가, 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 전계 발광 소자가 제시되었다. 이후, 고효율, 고수명의 유기 전계 발광 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다.Investigating organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965, based on observation of Bernanose's organic thin-film emission, followed by Tang in 1987. ), An organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer is proposed. Since then, in order to make a high efficiency, high-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때, 유기물층으로 사용되는 물질은 그 기능에 따라, 발광물질, 정공주입 물질, 정공수송 물질, 전자수송 물질, 전자주입 물질 등으로 분류될 수 있다.In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, 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.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과, 보다 나은 천연색을 구현하기 위한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도펀트 계를 사용할 수 있다.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. In addition, 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.
도펀트 물질은 유기 물질을 사용하는 형광 도펀트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도펀트로 나눌 수 있다. 이때, 인광 재료의 개발은 이론적으로 형광에 비해 4배까지 발광 효율을 향상시킬 수 있기 때문에, 인광 도펀트 뿐만 아니라 인광 호스트 재료들에 대한 연구도 많이 진행되고 있다.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. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층 재료로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광층 재료로는 안트라센 유도체들이 보고되고 있다. 특히, 발광층 재료 중 효율 향상 측면에서 장점을 가지고 있는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색(blue), 녹색(green), 적색(red)의 인광 도판트 재료로 사용되고 있으며, 4,4-디카바졸리비페닐(4,4-dicarbazolybiphenyl, CBP)은 인광 호스트 재료로 사용되고 있다.Hole injection layer, hole transport layer to date. NPB, BCP, Alq 3 and the like are widely known as the hole blocking layer and the electron transporting layer material, and anthracene derivatives have been reported as the light emitting layer material. Particularly, 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.
Figure PCTKR2016014958-appb-I000001
Figure PCTKR2016014958-appb-I000001
그러나 종래의 유기물층 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮아 열적 안정성이 매우 좋지 않기 때문에, 유기 전계 발광 소자의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 성능이 뛰어난 유기물층 재료의 개발이 요구되고 있다.However, 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, development of the organic material layer material which is excellent in performance is calculated | required.
본 발명은 상기한 문제점을 해결하기 위해, 유기 전계 발광 소자의 효율, 수명 및 안정성 등을 향상시킬 수 있는 신규 화합물 및 상기 화합물을 이용한 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.In order to solve the above problems, 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.
상기한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by the following formula (1):
[화학식 1][Formula 1]
Figure PCTKR2016014958-appb-I000002
Figure PCTKR2016014958-appb-I000002
상기 화학식 1에서, In Chemical Formula 1,
X1과 X2, X2와 X3, X3와 X4, X5와 X6, X6과 X7, 및 X7과 X8 중 적어도 하나는 각각 독립적으로 하기 화학식 2 또는 3으로 표시되는 고리와 축합되어 축합고리를 형성하고;At least one of X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 are each independently represented by the following Chemical Formula 2 or 3 Condensed with a ring to form a condensed ring;
하기 화학식 2 또는 3으로 표시되는 고리와 축합고리를 형성하지 않는 X1 내지 X8은 각각 독립적으로 N 또는 C(R3)이며;X 1 to X 8 which do not form a condensed ring with the ring represented by Formula 2 or 3 are each independently N or C (R 3 );
[화학식 2][Formula 2]
Figure PCTKR2016014958-appb-I000003
Figure PCTKR2016014958-appb-I000003
[화학식 3][Formula 3]
Figure PCTKR2016014958-appb-I000004
Figure PCTKR2016014958-appb-I000004
상기 화학식 1 내지 3에서,In Chemical Formulas 1 to 3,
점선은 축합이 이루어지는 부분을 의미하고;The dotted line means the part where condensation takes place;
Y1 내지 Y3는 각각 독립적으로 O, S, N(R4) 및 C(R5)(R6)로 이루어진 군에서 선택되며; Y 1 to Y 3 are each independently selected from the group consisting of O, S, N (R 4 ) and C (R 5 ) (R 6 );
Z1 및 Z2는 각각 독립적으로 N 또는 C(R7)이며;Z 1 and Z 2 are each independently N or C (R 7 );
L1 내지 L4는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
R1 내지 R7은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R3 내지 R7 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 1 to R 7 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 ~ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ~ C 60 of the blood group and a C 6 ~ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they are attached may form a fused ring, wherein When each of R 3 to R 7 is plural, they are the same as or different from each other;
상기 L1 내지 L4의 아릴렌기 및 헤테로아릴렌기와, R1 내지 R7의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 to L 4 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group of R 1 to R 7 , Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 60 aryl amine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group and C When substituted or unsubstituted with one or more substituents selected from the group consisting of 6 to C 60 arylsilyl groups, and substituted with a plurality of substituents, they may be the same or different from each other.
본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자를 제공한다.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. .
본 발명에서의 "알킬"은 탄소수 1 내지 40개의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지 않는다."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.
본 발명에서의 "알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지 않는다."Alkenyl" in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon 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.
본 발명에서의 "알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지 않는다."Alkynyl" in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon triple bond, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
본 발명에서의 "아릴"은 단독 고리 또는 2 이상의 고리가 조합된, 탄소수 6 내지 60개의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 축합되어 있고, 고리 형성 원자로서 탄소만을 포함(예를 들어, 탄소수는 8 내지 60개일 수 있음)하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 치환기도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴, 플루오레닐 등이 있는데, 이에 한정되지 않는다."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. In addition, 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), and 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.
본 발명에서의 "헤테로아릴"은 핵원자수 5 내지 60개의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, P, S 및 Se 중에서 선택된 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합되어 있고, 고리 형성 원자로서 탄소 외에 N, O, P, S 및 Se 중에서 선택된 헤테로 원자를 포함하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 그룹도 포함하는 것으로 해석된다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리; 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리; 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지 않는다."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). Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서의 "아릴옥시"는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 60개의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein 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.
본 발명에서의 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석한다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지 않는다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and is linear, branched or cyclic structure. Interpret as including. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
본 발명에서의 "아릴아민"은 탄소수 6 내지 60개의 아릴로 치환된 아민을 의미한다."Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서의 "시클로알킬"은 탄소수 3 내지 40개의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지 않는다.By "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.
본 발명에서의 "헤테로시클로알킬"은 핵원자수 3 내지 40개의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등이 있는데, 이에 한정되지 않는다."Heterocycloalkyl" in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of 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. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서의 "알킬실릴"은 탄소수 1 내지 40개의 알킬로 치환된 실릴이고, "아릴실릴"은 탄소수 5 내지 60개의 아릴로 치환된 실릴을 의미한다.In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms.
본 발명에서의 "축합 고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다."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.
본 발명에 따른 화학식 1로 표시되는 화합물은 열적 안정성, 정공 수송, 정공 주입 성능, 전자 수송 및 전자 주입 성능이 우수하고, 발광층으로 인광 특성이 우수하기 때문에, 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 발광층 재료로 이용될 수 있다. The compound represented by Formula 1 according to the present invention is excellent in thermal stability, hole transporting, hole injection performance, electron transporting and electron injection performance, and excellent phosphorescence characteristics of the light emitting layer, so that the organic material layer material of the organic electroluminescent device, preferably May be used as the light emitting layer material.
특히 본 발명의 화학식 1로 표시되는 신규 화합물을 발광층 재료로 사용할 경우, 종래 물질에 비해 우수한 발광성능, 낮은 구동전압, 높은 효율 및 장수명을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 크게 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.In particular, when using the novel compound represented by the formula (1) of the present invention as a light emitting layer material, it is possible to manufacture an organic electroluminescent device having excellent luminous performance, low driving voltage, high efficiency and long life compared to the conventional material, furthermore, performance and lifespan This greatly improved full color display panel can also be manufactured.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:The present invention provides a compound represented by Formula 1:
[화학식 1][Formula 1]
Figure PCTKR2016014958-appb-I000005
Figure PCTKR2016014958-appb-I000005
상기 화학식 1에서, In Chemical Formula 1,
X1과 X2, X2와 X3, X3와 X4, X5와 X6, X6과 X7, 및 X7과 X8 중 적어도 하나는 각각 독립적으로 하기 화학식 2 또는 3으로 표시되는 고리와 축합되어 축합고리를 형성하고;At least one of X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 are each independently represented by the following Chemical Formula 2 or 3 Condensed with a ring to form a condensed ring;
하기 화학식 2 또는 3으로 표시되는 고리와 축합고리를 형성하지 않는 X1 내지 X8은 각각 독립적으로 N 또는 C(R3)이며;X 1 to X 8 which do not form a condensed ring with the ring represented by Formula 2 or 3 are each independently N or C (R 3 );
[화학식 2][Formula 2]
Figure PCTKR2016014958-appb-I000006
Figure PCTKR2016014958-appb-I000006
[화학식 3][Formula 3]
Figure PCTKR2016014958-appb-I000007
Figure PCTKR2016014958-appb-I000007
상기 화학식 1 내지 3에서,In Chemical Formulas 1 to 3,
점선은 축합이 이루어지는 부분을 의미하고;The dotted line means the part where condensation takes place;
Y1 내지 Y3는 각각 독립적으로 O, S, N(R4) 및 C(R5)(R6)로 이루어진 군에서 선택되며; Y 1 to Y 3 are each independently selected from the group consisting of O, S, N (R 4 ) and C (R 5 ) (R 6 );
Z1 및 Z2는 각각 독립적으로 N 또는 C(R7)이며;Z 1 and Z 2 are each independently N or C (R 7 );
L1 내지 L4는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
R1 내지 R7은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R3 내지 R7 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 1 to R 7 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ of 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 ~ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ~ C 60 of the blood group and a C 6 ~ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they are attached may form a fused ring, wherein When each of R 3 to R 7 is plural, they are the same as or different from each other;
상기 L1 내지 L4의 아릴렌기 및 헤테로아릴렌기와, R1 내지 R7의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 to L 4 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group of R 1 to R 7 , Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl 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 of the alkynyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ aryloxy of C 60 group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 60 aryl amine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group and C When substituted or unsubstituted with one or more substituents selected from the group consisting of 6 to C 60 arylsilyl groups, and substituted with a plurality of substituents, they may be the same or different from each other.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1. 신규 유기 화합물1. New Organic Compounds
본 발명에 따른 신규 화합물은 플루오렌 모이어티의 말단에 5원환이 축합(fused)되어 기본 골격을 이루며, 이러한 기본 골격에 다양한 치환기가 연결된 구조로서, 구체적으로는 하기 화학식 1로 표시되는 것을 특징으로 한다:The novel compound according to the present invention is a structure in which a 5-membered ring is condensed at the terminal of the fluorene moiety to form a basic skeleton, and various substituents are connected to the basic skeleton, specifically represented by the following Chemical Formula 1 do:
[화학식 1][Formula 1]
Figure PCTKR2016014958-appb-I000008
Figure PCTKR2016014958-appb-I000008
상기 화학식 1에서, In Chemical Formula 1,
X1과 X2, X2와 X3, X3와 X4, X5와 X6, X6과 X7, 및 X7과 X8 중 적어도 하나, 바람직하게는 X1과 X2, X2와 X3, 및 X3와 X4 중 적어도 하나, 보다 바람직하게는 X3와 X4는 하기 화학식 2 또는 3으로 표시되는 고리와 축합되어 축합고리를 형성하고, 상기 X1과 X2, X2와 X3, X3와 X4, X5와 X6, X6과 X7, 및 X7과 X8 중 2개 이상이 하기 화학식 2 또는 3으로 표시되는 고리와 축합되어 축합고리를 형성하는 경우, 이들은 각각 독립적으로 하기 화학식 2 또는 3으로 표시되는 고리와 축합되어 축합고리를 형성하며;At least one of X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 , preferably X 1 and X 2, X 2 and X 3 , and at least one of X 3 and X 4 , more preferably X 3 and X 4 are condensed with a ring represented by the following formula (2) or (3) to form a condensed ring, wherein X 1 and X 2 , Two or more of X 2 and X 3 , X 3 and X 4 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 are condensed with a ring represented by the following Formula 2 or 3 to form a condensed ring. When forming, they are each independently condensed with a ring represented by the following formula (2) or (3) to form a condensed ring;
하기 화학식 2 또는 3으로 표시되는 고리와 축합고리를 형성하지 않는 X1 내지 X8은 각각 독립적으로 N 또는 C(R3)이며;X 1 to X 8 which do not form a condensed ring with the ring represented by Formula 2 or 3 are each independently N or C (R 3 );
[화학식 2][Formula 2]
Figure PCTKR2016014958-appb-I000009
Figure PCTKR2016014958-appb-I000009
[화학식 3][Formula 3]
Figure PCTKR2016014958-appb-I000010
Figure PCTKR2016014958-appb-I000010
상기 화학식 1 내지 3에서,In Chemical Formulas 1 to 3,
점선은 축합이 이루어지는 부분을 의미하고;The dotted line means the part where condensation takes place;
Y1 내지 Y3는 각각 독립적으로 O, S, N(R4) 및 C(R5)(R6)로 이루어진 군에서 선택되며; Y 1 to Y 3 are each independently selected from the group consisting of O, S, N (R 4 ) and C (R 5 ) (R 6 );
Z1 및 Z2는 각각 독립적으로 N 또는 C(R7)이며;Z 1 and Z 2 are each independently N or C (R 7 );
L1 내지 L4는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
R1 내지 R7은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R3 내지 R7 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 1 to R 7 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- aryloxy group of C 60, C 3 ~ C 40 alkylsilyl group, C group 6 ~ C 60 aryl silyl, C 1 ~ arylboronic of C 40 group of an alkyl boron, C 6 ~ C 60 group, C 6 ~ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ~ C 60 of the blood group and a C 6 ~ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they are attached may form a fused ring, wherein When each of R 3 to R 7 is plural, they are the same as or different from each other;
상기 L1 내지 L4의 아릴렌기 및 헤테로아릴렌기와, R1 내지 R7의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 to L 4 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group of R 1 to R 7 , Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl 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 of the alkynyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ aryloxy of C 60 time, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 60 aryl amine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group and C When substituted or unsubstituted with one or more substituents selected from the group consisting of 6 to C 60 arylsilyl groups, and substituted with a plurality of substituents, they may be the same or different from each other.
본 발명에서 상기 화학식 1로 표시되는 화합물은 종래 유기 전계 발광 소자용 재료 [예: 4,4-디카바졸리비페닐(4,4-dicarbazolybiphenyl, CBP)]보다 분자량이 클 뿐만 아니라, 넓은 에너지 밴드갭을 가지면서, 정공과 전자의 결합력을 높일 수 있다. 따라서, 상기 화학식 1의 화합물을 유기 전계 발광 소자에 이용할 경우, 소자의 구동 전압, 효율(발광효율, 전력효율), 수명 및 휘도 측면이 향상될 수 있다.In the present invention, the compound represented by Chemical Formula 1 is larger in molecular weight than the conventional organic electroluminescent device material [eg, 4,4-dicarbazolybiphenyl (CBP)], and has a wide energy band gap. While having, it is possible to increase the binding force between the hole and the electron. Therefore, when the compound of Formula 1 is used in an organic electroluminescent device, the driving voltage, efficiency (luminescence efficiency, power efficiency), lifetime, and luminance of the device may be improved.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Y1 내지 Y3 중 적어도 하나는 헤테로 원자를 포함할 수 있다. 구체적으로, 본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 2로 표시되는 고리는 하기 화학식 4 내지 6 중 어느 하나로 표시되는 고리일 수 있다:According to one preferred embodiment of the present invention, at least one of the Y 1 to Y 3 may include a hetero atom. Specifically, according to one preferred embodiment of the present invention, the ring represented by Formula 2 may be a ring represented by any one of the following formulas 4 to 6:
[화학식 4][Formula 4]
Figure PCTKR2016014958-appb-I000011
Figure PCTKR2016014958-appb-I000011
[화학식 5][Formula 5]
Figure PCTKR2016014958-appb-I000012
Figure PCTKR2016014958-appb-I000012
[화학식 6][Formula 6]
Figure PCTKR2016014958-appb-I000013
Figure PCTKR2016014958-appb-I000013
상기 화학식 4 내지 6에서, In Chemical Formulas 4 to 6,
점선은 축합이 이루어지는 부분을 의미하고;The dotted line means the part where condensation takes place;
R5 및 R6은 상기 화학식 1에서 정의된 바와 같다. R 5 and R 6 are as defined in formula (I).
본 발명의 바람직한 한 구현 예에 따르면, 상기 Y1, Z1 및 Z2 중 적어도 하나는 헤테로 원자를 포함할 수 있다. 구체적으로, 본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 3으로 표시되는 고리는 하기 화학식 7 내지 12 중 어느 하나로 표시되는 고리일 수 있다:According to one preferred embodiment of the present invention, at least one of the Y 1 , Z 1 and Z 2 may include a hetero atom. Specifically, according to one preferred embodiment of the present invention, the ring represented by Formula 3 may be a ring represented by any one of the following Formula 7 to 12:
[화학식 7][Formula 7]
Figure PCTKR2016014958-appb-I000014
Figure PCTKR2016014958-appb-I000014
[화학식 8][Formula 8]
Figure PCTKR2016014958-appb-I000015
Figure PCTKR2016014958-appb-I000015
[화학식 9][Formula 9]
Figure PCTKR2016014958-appb-I000016
Figure PCTKR2016014958-appb-I000016
[화학식 10][Formula 10]
Figure PCTKR2016014958-appb-I000017
Figure PCTKR2016014958-appb-I000017
[화학식 11][Formula 11]
Figure PCTKR2016014958-appb-I000018
Figure PCTKR2016014958-appb-I000018
[화학식 12][Formula 12]
Figure PCTKR2016014958-appb-I000019
Figure PCTKR2016014958-appb-I000019
상기 화학식 7 내지 12에서, In Chemical Formulas 7 to 12,
점선은 축합이 이루어지는 부분을 의미하고;The dotted line means the part where condensation takes place;
R4 및 R7은 상기 화학식 1에서 정의된 바와 같다. 단, 상기 화학식 9에서, 2개의 R7은 서로 동일하거나 상이하다.R 4 and R 7 are the same as defined in Chemical Formula 1. However, in Chemical Formula 9, two R 7 are the same as or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 L1 내지 L4는 각각 독립적으로 단일결합, 페닐렌기, 비페닐렌기, 피리디닐기, 피리미디닐기, 나프탈레닐기, 플루오레닐기 및 카바졸릴기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, L 1 to L 4 are each independently composed of a single bond, phenylene group, biphenylene group, pyridinyl group, pyrimidinyl group, naphthalenyl group, fluorenyl group and carbazolyl group Can be selected from the group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R1 및 R2는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 1 and R 2 are each independently selected from the group consisting of C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms Can be selected.
본 발명의 보다 바람직한 한 구현 예에 따르면, 상기 R1 및 R2는 각각 독립적으로 메틸기, 에틸기, 프로필기 및 하기 화학식 13 내지 17로 표시되는 치환기로 이루어진 군에서 선택될 수 있다:According to a more preferred embodiment of the present invention, R 1 and R 2 may be independently selected from the group consisting of a methyl group, an ethyl group, a propyl group and substituents represented by the following formulas (13) to (17):
[화학식 13][Formula 13]
Figure PCTKR2016014958-appb-I000020
Figure PCTKR2016014958-appb-I000020
[화학식 14][Formula 14]
Figure PCTKR2016014958-appb-I000021
Figure PCTKR2016014958-appb-I000021
[화학식 15][Formula 15]
Figure PCTKR2016014958-appb-I000022
Figure PCTKR2016014958-appb-I000022
[화학식 16][Formula 16]
Figure PCTKR2016014958-appb-I000023
Figure PCTKR2016014958-appb-I000023
[화학식 17][Formula 17]
Figure PCTKR2016014958-appb-I000024
Figure PCTKR2016014958-appb-I000024
상기 화학식 13 내지 17에서, In Chemical Formulas 13 to 17,
*는 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
T1 내지 T8은 각각 독립적으로 N 또는 C(R8)이며;T 1 to T 8 are each independently N or C (R 8 );
상기 화학식 14에서 L2 또는 L4에 결합되는 T1 내지 T4 중 어느 하나는 C(R8)이고, 이때 상기 R8은 부재이며;In Formula 14, any one of T 1 to T 4 bonded to L 2 or L 4 is C (R 8 ), wherein R 8 is absent;
R8 내지 R11은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R8이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 8 to R 11 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 ~ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ~ C 60 of the blood group and a C 6 ~ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they are attached may form a fused ring, wherein When there are a plurality of R 8 , they are the same or different from each other;
상기 R8 내지 R11의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The 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 8 to R 11 boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C 1 ~ alkenyl group of the C 40 alkyl group, C 2 ~ C 40 of, 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 atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ selected from the group consisting of C 60 aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 13 또는 14로 표시되는 치환기는 하기 화학식 F-1 내지 F-13으로 이루어진 군에서 선택될 수 있다:According to a preferred embodiment of the present invention, the substituent represented by Formula 13 or 14 may be selected from the group consisting of the following Formula F-1 to F-13:
Figure PCTKR2016014958-appb-I000025
Figure PCTKR2016014958-appb-I000025
상기 화학식 F-1 내지 F-13에서, In Chemical Formulas F-1 to F-13,
*는 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
t는 0 내지 5의 정수이며;t is an integer from 0 to 5;
l은 0 내지 4의 정수이며;l is an integer from 0 to 4;
v는 0 내지 3의 정수이며;v is an integer from 0 to 3;
u는 0 내지 2의 정수이며;u is an integer from 0 to 2;
R12는 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R12가 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 12 is 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, nuclear atom C 5 to C 60 aryloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 ~ C 60 It is selected from the group consisting of mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group, or may be combined with adjacent groups to form a condensed ring, when there are a plurality of R 12 Same or different from each other;
상기 R12의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있으며;The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group of R 12 , 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, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 At least one member selected from the group consisting of an aryl boron group, a C 6 to C 60 arylphosphanyl group, a C 6 to C 60 mono or diaryl phosphinyl group, and a C 6 to C 60 arylsilyl group When unsubstituted or substituted with a substituent, and substituted with a plurality of substituents, they may be the same as or different from each other;
R8은 상기 화학식 13 및 14에서 정의된 바와 같다.R 8 is as defined in Formulas 13 and 14 above.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R9 내지 R11은 각각 독립적으로 수소, C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택될 수 있고, 보다 바람직하게는 페닐기, 비페닐기, 나프탈레닐기, 피리디닐기, 피리미디닐기, 퀴놀리닐기 및 퀴나졸리닐기로 이루어진 군에서 선택될 수 있다. According to a preferred embodiment of the present invention, each of R 9 to R 11 is independently hydrogen, C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms It may be selected from the group, more preferably may be selected from the group consisting of phenyl group, biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group, quinolinyl group and quinazolinyl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 L1 내지 L4는 단일결합이며, R1 및 R2는 결합하여 축합 고리를 형성할 수 있다. 구체적으로는 상기 화학식 1로 표시되는 화합물은 하기 화학식 18로 표시되는 화합물일 수 있다:According to one preferred embodiment of the present invention, L 1 to L 4 is a single bond, R 1 and R 2 may be bonded to form a condensed ring. Specifically, the compound represented by Formula 1 may be a compound represented by Formula 18:
[화학식 18][Formula 18]
Figure PCTKR2016014958-appb-I000026
Figure PCTKR2016014958-appb-I000026
상기 화학식 18에서,In Chemical Formula 18,
K1은 단일결합, C(R13)(R14), N(R15), O 및 S로 이루어진 군에서 선택되며;K 1 is selected from the group consisting of a single bond, C (R 13 ) (R 14 ), N (R 15 ), O and S;
R13 내지 R15는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고;R 13 to R 15 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 ~ for C 60 aryl phosphazene group, and groups bonded to adjacent or 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 which they are attached may form a condensed ring;
상기 R13 내지 R15의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있으며;The 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 13 to R 15 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 atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ selected from the group consisting of C 60 aryl silyl When unsubstituted or substituted with one or more substituents substituted with a plurality of substituents, they may be the same or different from each other;
X1과 X2, X2와 X3, X3와 X4, X5와 X6, X6과 X7, 및 X7과 X8 중 적어도 하나, 바람직하게는 X1과 X2, X2와 X3, 및 X3와 X4 중 적어도 하나는 하기 화학식 2 또는 3으로 표시되는 고리와 축합되어 축합고리를 형성하며, 상기 X1과 X2, X2와 X3, X3와 X4, X5와 X6, X6과 X7, 및 X7과 X8 중 2개 이상이 하기 화학식 2 또는 3으로 표시되는 고리와 축합되어 축합고리를 형성하는 경우, 이들은 각각 독립적으로 하기 화학식 2 또는 3으로 표시되는 고리와 축합되어 축합고리를 형성하며;At least one of X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 , preferably X 1 and X 2, X At least one of 2 and X 3 , and X 3 and X 4 is condensed with a ring represented by the following Formula 2 or 3 to form a condensed ring, wherein X 1 and X 2 , X 2 and X 3 , X 3 and X When two or more of 4 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 are condensed with a ring represented by the following Chemical Formula 2 or 3 to form a condensed ring, they are each independently represented by the following Chemical Formula Condensed with a ring represented by 2 or 3 to form a condensed ring;
하기 화학식 2 또는 3으로 표시되는 고리와 축합고리를 형성하지 않는 X1 내지 X8, 및 X9 내지 X16은 각각 독립적으로 N 또는 C(R3)이며;X 1 to X 8 , and X 9 to X 16 which do not form a condensed ring with a ring represented by the following Chemical Formula 2 or 3 are each independently N or C (R 3 );
[화학식 2][Formula 2]
Figure PCTKR2016014958-appb-I000027
Figure PCTKR2016014958-appb-I000027
[화학식 3][Formula 3]
Figure PCTKR2016014958-appb-I000028
Figure PCTKR2016014958-appb-I000028
상기 화학식 2, 3 및 18에서,In Chemical Formulas 2, 3, and 18,
점선은 축합이 이루어지는 부분을 의미하고;The dotted line means the part where condensation takes place;
R3, Y1 내지 Y3, Z1 및 Z2는 상기 화학식 1 내지 3에서 정의된 바와 같다. R 3, Y 1 to Y 3 , Z 1 and Z 2 are as defined in Chemical Formulas 1 to 3 above.
본 발명의 바람직한 한 구현 예에 따르면, 상기 X9와 X10, X10과 X11, X11과 X12, X13과 X14, X14와 X15, 및 X15와 X16 중 적어도 하나는 각각 독립적으로 상기 화학식 2 또는 3으로 표시되는 고리와 축합되어 축합고리를 형성하고;According to a preferred embodiment of the present invention, at least one of the X 9 And X 10 , X 10 And X 11 , X 11 And X 12 , X 13 And X 14 , X 14 And X 15 , And X 15 And X 16 Are each independently condensed with a ring represented by Formula 2 or 3 to form a condensed ring;
상기 화학식 2 또는 3으로 표시되는 고리와 축합고리를 형성하지 않는 X9 내지 X16은 각각 독립적으로 N 또는 C(R3)이며;X 9 to X 16 which do not form a condensed ring with the ring represented by Formula 2 or 3 are each independently N or C (R 3 );
R3는 상기 화학식 1에서 정의된 바와 같다. R 3 is as defined in Formula 1 above.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R3 내지 R7 중 적어도 하나는 각각 독립적으로 하기 화학식 19로 표시되는 치환기일 수 있다:According to one preferred embodiment of the present invention, at least one of the R 3 to R 7 may be each independently a substituent represented by the following formula (19):
[화학식 19][Formula 19]
Figure PCTKR2016014958-appb-I000029
Figure PCTKR2016014958-appb-I000029
상기 화학식 19에서, In Chemical Formula 19,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
L5 및 L6은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 5 and L 6 are selected from the group consisting of a single bond, a C 6 -C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
R16은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기(예컨대, L5 또는 다른 R3 내지 R7)와 결합하여 축합 고리를 형성할 수 있으며;R 16 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 Condensation in combination with a group selected from or adjacent to (eg, L 5 or other R 3 to R 7 ) a group consisting of a silyl group, a C 6 -C 60 mono or diarylphosphinyl group and a C 6 -C 60 arylamine group May form a ring;
상기 L5 및 L6의 아릴렌기 및 헤테로아릴렌기와, R16의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 5 and L 6 , alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine of R 16 Group, alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group and aryl silyl 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 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom of 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 When substituted by one or more substituents selected from the group consisting of a reel, or silyl which is Beach ring, substituted with a plurality of substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 L5 및 L6은 각각 독립적으로 단일결합, 페닐렌기, 비페닐렌기, 피리디닐기, 피리미디닐기, 나프탈레닐기, 플루오레닐기, 카바졸릴기, 퀴놀리닐기 및 퀴나졸리닐기로 이루어진 군에서 선택될 수 있다.According to one embodiment, it preferred according to the present invention, wherein L 5 and L 6 are each a single bond, each independently, a phenylene group, biphenylene group, a pyridinyl group, a pyrimidinyl group, a naphthyl Frontale group, a fluorenyl group, a carbazolyl group, It may be selected from the group consisting of a quinolinyl group and a quinazolinyl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R16은 하기 화학식 20 내지 25로 이루어진 군에서 선택되는 치환기일 수 있다:According to one preferred embodiment of the present invention, R 16 may be a substituent selected from the group consisting of Formulas 20 to 25:
[화학식 20][Formula 20]
Figure PCTKR2016014958-appb-I000030
Figure PCTKR2016014958-appb-I000030
[화학식 21][Formula 21]
Figure PCTKR2016014958-appb-I000031
Figure PCTKR2016014958-appb-I000031
[화학식 22][Formula 22]
Figure PCTKR2016014958-appb-I000032
Figure PCTKR2016014958-appb-I000032
[화학식 23][Formula 23]
Figure PCTKR2016014958-appb-I000033
Figure PCTKR2016014958-appb-I000033
[화학식 24][Formula 24]
Figure PCTKR2016014958-appb-I000034
Figure PCTKR2016014958-appb-I000034
[화학식 25][Formula 25]
Figure PCTKR2016014958-appb-I000035
Figure PCTKR2016014958-appb-I000035
상기 화학식 20 내지 25에서,In Formula 20 to 25,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
M1 내지 M8은 각각 독립적으로 N 또는 C(R19)이며;M 1 to M 8 are each independently N or C (R 19 );
상기 화학식 21에서 L6에 결합되는 M1 내지 M4 중 어느 하나는 C(R19)이고, 이때 상기 R19는 부재이며;Any one of M 1 to M 4 bonded to L 6 in Formula 21 is C (R 19 ), wherein R 19 is absent;
K2 및 K3는 각각 독립적으로 단일결합, C(R20)(R21), N(R22), O, S 및 SO2로 이루어진 군에서 선택되나, K2 및 K3 모두가 단일결합은 아니며;K 2 and K 3 are each independently selected from the group consisting of a single bond, C (R 20 ) (R 21 ), N (R 22 ), O, S and SO 2 , but both K 2 and K 3 are a single bond Not;
Y4는 O, S, C(R20)(R21) 및 N(R22)로 이루어진 군에서 선택되며; Y 4 is selected from the group consisting of O, S, C (R 20 ) (R 21 ) and N (R 22 );
Z3 내지 Z6은 각각 독립적으로 N 또는 C(R19)이며;Z 3 to Z 6 are each independently N or C (R 19 );
m 및 n은 각각 독립적으로 0 내지 4의 정수이며;m and n are each independently an integer from 0 to 4;
R17 및 R18은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R17 및 R18 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 17 and R 18 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 to C 60 mono or diaryl phosphinyl group, and a C 6 to C 60 arylamine group may be combined with or adjacent to a group to form a condensed ring, and R 17 and R 18, respectively In this case, these are the same or different, and plural individual;
R19 내지 R22는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R19 내지 R22 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 19 to R 22 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 ~ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ~ C 60 of the blood group and a C 6 ~ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they are attached may form a fused ring, wherein When each of R 19 to R 22 plural is the same or different from each other;
상기 R17 내지 R22의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The 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 17 to R 22 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 atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they may be the same or different from each other.
또한, 본 발명의 화학식 1로 표시되는 화합물은 상기 기본 골격에 연결되는 다양한 방향족 환 치환기로 인해 분자 전체가 양극성(bipolar)의 특성을 가지면서, 정공과 전자의 결합력을 높일 수 있다. 따라서, 유기 전계 발광 소자에 상기 화합물을 적용할 경우, 종래 CBP에 비해 발광층의 호스트 재료로서의 우수한 특성을 나타낼 수 있기 때문에, 소자의 인광 특성이 개선됨과 동시에 정공 주입 능력 및/또는 수송 능력, 발광 효율, 구동 전압, 수명 특성 등이 개선될 수 있다. 그리고 상기 치환기들에 따라 에너지 레벨이 조절될 수 있어 넓은 밴드갭(sky blue ~ red)을 갖게 되고, 따라서 발광층뿐만 아니라, 전자 수송 보조층, 전자 수송층, 정공 수송층, 정공 주입층 등으로도 응용될 수 있다. In addition, the compound represented by Formula 1 of the present invention can increase the binding force between the hole and the electron while having the bipolar (bipolar) characteristics of the entire molecule due to the various aromatic ring substituents connected to the basic skeleton. Therefore, when the compound is applied to the organic electroluminescent device, since it can exhibit excellent characteristics as a host material of the light emitting layer as compared to the conventional CBP, the phosphorescence properties of the device is improved, the hole injection ability and / or transport capacity, the luminous efficiency The driving voltage, lifespan characteristics and the like can be improved. And the energy level can be adjusted according to the substituents to have a wide bandgap (sky blue ~ red), and thus can be applied not only to the light emitting layer, but also to the electron transport auxiliary layer, electron transport layer, hole transport layer, hole injection layer, etc. Can be.
또한, 화합물의 분자량이 유의적으로 증대됨으로써, 유리전이온도가 향상될 수 있고, 이로 인해 종래 CBP 보다 높은 열적 안정성을 가질 수 있다. 또한, 화합물의 열적 안정성이 향상될 수 있을 뿐만 아니라, 상기 화학식 1의 화합물을 포함하는 유기층의 결정화 억제에도 효과가 있다. 따라서, 본 발명에 따른 화학식 1의 화합물을 포함하는 소자는 내구성 및 수명 특성을 크게 향상시킬 수 있다. In addition, by significantly increasing the molecular weight of the compound, the glass transition temperature can be improved, thereby having a higher thermal stability than the conventional CBP. In addition, the thermal stability of the compound may not only be improved, but also effective in suppressing crystallization of the organic layer including the compound of Formula 1. Therefore, the device including the compound of formula 1 according to the present invention can greatly improve the durability and life characteristics.
또한, 전자 수송 보조층의 역할로는 높은 삼중항 에너지를 갖고 있기 때문에 TTF(triplet-triplet fusion) 효과로 인한 우수한 효율 상승을 나타낼 수 있다. 또한, 발광층에서 생성된 엑시톤이 발광층에 인접하는 전자 수송층 또는 정공 수송층으로 확산되는 것을 방지할 수 있다. 발광층 내에서 발광에 기여하는 엑시톤의 수가 증가되어 소자의 발광 효율이 개선될 수 있고, 소자의 내구성 및 안정성이 향상되어 소자의 수명이 효율적으로 증가될 수 있다. 개발된 재료들이 대부분 저전압 구동이 가능하여 이로 인한 수명이 개선되는 물리적 특징들을 나타낸다.In addition, since the electron transport auxiliary layer has a high triplet energy, it may exhibit excellent efficiency due to the triplet-triplet fusion effect. In addition, the exciton generated in the light emitting layer can be prevented from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. The number of excitons contributing to light emission in the light emitting layer may be improved, and thus the luminous efficiency of the device may be improved, and the durability and stability of the device may be improved, and thus the life of the device may be efficiently increased. Most of the materials developed show physical characteristics that can be driven at low voltages, thereby improving their lifetime.
아울러, 본 발명에 따른 화학식 1의 화합물을 유기 전계 발광 소자의 정공 주입/수송층 재료, 전자 주입/수송층재료, 청색, 녹색 및/또는 적색의 인광 호스트 재료로 채택할 경우, 종래 CBP 대비 효율 및 수명 면에서 월등히 우수한 효과를 발휘할 수 있다. 따라서, 본 발명에 따른 화합물은 유기 전계 발광 소자의 성능 개선 및 수명 향상에 크게 기여할 수 있으며, 특히 이러한 소자 수명 향상은 풀 칼라 유기 발광 패널에서의 성능 극대화에도 큰 효과가 있다.In addition, when the compound of Formula 1 according to the present invention is adopted as a hole injection / transport layer material, an electron injection / transport layer material, a blue, green and / or red phosphorescent host material of an organic electroluminescent device, efficiency and lifespan compared to conventional CBP In terms of excellent effects can be achieved. Therefore, the compound according to the present invention can greatly contribute to improving the performance and lifespan of the organic EL device, and in particular, the device life improvement has a great effect in maximizing the performance in the full color organic light emitting panel.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R16은 하기 화학식 26 내지 29로 이루어진 군에서 선택되는 치환기일 수 있다:According to one preferred embodiment of the present invention, R 16 may be a substituent selected from the group consisting of Formulas 26 to 29:
[화학식 26][Formula 26]
Figure PCTKR2016014958-appb-I000036
Figure PCTKR2016014958-appb-I000036
[화학식 27][Formula 27]
Figure PCTKR2016014958-appb-I000037
Figure PCTKR2016014958-appb-I000037
[화학식 28][Formula 28]
Figure PCTKR2016014958-appb-I000038
Figure PCTKR2016014958-appb-I000038
[화학식 29][Formula 29]
Figure PCTKR2016014958-appb-I000039
Figure PCTKR2016014958-appb-I000039
상기 화학식 26 내지 29에서,In Chemical Formulas 26 to 29,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
R23 내지 R25는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;R 23 to R 25 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ of 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 ~ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ~ C 60 of the blood group and a C 6 ~ C 60 selected from the group consisting of an aryl amine, or a, combination group adjacent to form a condensed ring;
상기 R23 내지 R25의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The 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 23 to R 25 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 atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R23 내지 R25는 각각 독립적으로 수소, C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택될 수 있고, 보다 바람직하게는, 수소, 메틸기, 에틸기, 프로필기, 부틸기, 페닐기, 비페닐기, 피리디닐기, 피리미디닐길, 나프탈레닐기, 퀴놀리닐기 및 퀴나졸리닐기로 이루어진 군에서 선택될 수 있다.According to one embodiment, the preferred of the invention, the R 23 to R 25 are each independently hydrogen, C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group and a nuclear atoms of 5 to 60 heteroaryl group consisting of It may be selected from the group, more preferably, consisting of hydrogen, methyl, ethyl, propyl, butyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, naphthalenyl, quinolinyl and quinazolinyl Can be selected from the group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 20 내지 25로 이루어진 군에서 선택되는 치환기는 하기 B-1 내지 B-22로 이루어진 군에서 선택되는 치환기일 수 있다:According to a preferred embodiment of the present invention, the substituent selected from the group consisting of Formula 20 to 25 may be a substituent selected from the group consisting of B-1 to B-22:
Figure PCTKR2016014958-appb-I000040
Figure PCTKR2016014958-appb-I000040
상기 화학식 B-1 내지 B-22에서,In Chemical Formulas B-1 to B-22,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
t는 0 내지 5의 정수이며;t is an integer from 0 to 5;
l 및 s는 각각 독립적으로 0 내지 4의 정수이며;l and s are each independently an integer from 0 to 4;
v는 0 내지 3의 정수이며;v is an integer from 0 to 3;
u는 0 내지 2의 정수이며;u is an integer from 0 to 2;
R26 및 R27은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R26 및 R27 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 26 and R 27 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 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ~ C 60, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring, and When there are a plurality of R 26 and R 27 s , they are the same as or different from each other;
상기 R26 및 R27의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있으며, The 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 and aryl of the above R 26 and R 27 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 atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group selected from the group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they may be the same or different from each other,
R19 내지 R22 각각은 상기 화학식 20 내지 25에서 정의된 바와 같다.R 19 to R 22 are each as defined in Chemical Formulas 20 to 25.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R3 내지 R7 중 인접하여 존재하는 2개의 치환기는 서로 결합하여 C4~C18의 축합 방향족 고리 또는 핵원자수 4 내지 14개의 축합 헤테로방향족 고리를 형성할 수 있다. According to one preferred embodiment of the present invention, two substituents adjacent to each other of the R 3 to R 7 are bonded to each other to form a C 4 ~ C 18 condensed aromatic ring or 4 to 14 condensed heteroaromatic ring of nuclear atoms Can be formed.
본 발명의 화학식 1로 표시되는 화합물은 하기 화합물로 나타낼 수 있으나 이에 한정되는 것은 아니다: Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
Figure PCTKR2016014958-appb-I000041
Figure PCTKR2016014958-appb-I000041
Figure PCTKR2016014958-appb-I000042
Figure PCTKR2016014958-appb-I000042
Figure PCTKR2016014958-appb-I000043
Figure PCTKR2016014958-appb-I000043
Figure PCTKR2016014958-appb-I000044
Figure PCTKR2016014958-appb-I000044
Figure PCTKR2016014958-appb-I000045
Figure PCTKR2016014958-appb-I000045
Figure PCTKR2016014958-appb-I000046
Figure PCTKR2016014958-appb-I000046
Figure PCTKR2016014958-appb-I000047
Figure PCTKR2016014958-appb-I000047
본 발명에서 상기 화학식 1로 표시되는 화합물은 일반적인 합성방법에 따라 합성될 수 있다(Chem. Rev., 60:313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) 등 참조). 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다.In the present invention, the compound represented by Chemical Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) et al. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
2. 유기 2. Organic 전계Electric field 발광 소자  Light emitting element
한편, 본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(유기 EL 소자)에 관한 것이다.On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.
구체적으로, 본 발명은 양극(anode), 음극(cathode), 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독 또는 2 이상 혼합되어 사용될 수 있다.Specifically, 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). In this case, the compound may be used alone or mixed two or more.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광층, 발광 보조층, 수명 개선층, 전자 수송층, 전자수송 보조층 및 전자 주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 바람직하게는 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 발광층일 수 있다.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. Preferably, the organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer.
본 발명의 일례에 따르면, 유기 전계 발광 소자의 발광층은 호스트 재료를 포함할 수 있는데, 이때 호스트 재료로서 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 이와 같이, 상기 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 발광층 재료, 바람직하게는 녹색의 인광 호스트로 포함할 경우, 발광층에서 정공과 전자의 결합력이 높아지기 때문에, 유기 전계 발광 소자의 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등이 향상될 수 있다.According to the exemplary embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, and may include a compound represented by Chemical Formula 1 as the host material. As such, when the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a green phosphorescent host, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency and power efficiency), lifespan, brightness and driving voltage can be improved.
전술한 본 발명에 따른 유기 전계 발광 소자의 구조는 특별히 한정되지 않으며, 예컨대 기판, 양극, 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 발광층과 전자 수송층 사이에는 전자 수송 보조층이 추가로 적층될 수 있고, 상기 전자수송층 위에는 전자 주입층이 추가로 적층될 수 있다. 본 발명에서 상기 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 수송 보조층 및 전자 주입층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 발광층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. The structure of the organic EL device according to the present invention described above is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, an electron transport auxiliary layer may be further stacked between the emission layer and the electron transport layer, and an electron injection layer may be further stacked on the electron transport layer. In the present invention, at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron transport auxiliary layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer is represented by the formula (1) It may include a compound represented.
또, 본 발명의 유기 전계 발광 소자의 구조는 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층될 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.In addition, the structure of the organic EL device according to the present invention may be a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
본 발명의 유기 전계 발광 소자는 상기 유기물층 중 적어도 하나 이상(예컨대, 발광층)이 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 다른 유기물층 및 전극을 형성하여 제조될 수 있다.The organic electroluminescent device of the present invention may be formed using other materials and methods known in the art, except that at least one of the organic material layers (eg, the light emitting layer) is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming an organic material layer and an electrode.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명에서 사용 가능한 기판으로는 특별히 한정되지 않으며, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 사용될 수 있다.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.
또, 양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등이 있으나, 이에 한정되지는 않는다.In addition, examples of the anode material 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.
또, 음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이에 한정되지는 않는다.The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.
[[ 준비예Preparation 1] A-1의 합성 1] Synthesis of A-1
<단계 1> 5-<Step 1> 5- 브로모Bromo -1-(4--1- (4- 클로로페닐Chlorophenyl )-1H-) -1H- 인다졸의Indazole 합성 synthesis
Figure PCTKR2016014958-appb-I000048
Figure PCTKR2016014958-appb-I000048
질소 기류 하에서 5-브로모-1H-인다졸 (1.32 g, 6.7 mmol), 1-클로로-4-요오드벤젠 (1.90 g, 8.0 mmol), Pd(OAc)2 (0.08 g, 0.34 mmol), P(t-Bu)3 (0.16 ml, 0.67 mmol), NaO(t-Bu) (1.29 g, 13.4 mmol) 및 톨루엔 (70 ml)를 혼합하고 110℃ 에서 2시간 동안 교반하였다. 반응이 종결된 후 톨루엔을 농축하고, 고체염을 여과한 뒤, 재결정으로 정제하여 목적 화합물인 5-브로모-1-(4-클로로페닐)-1H-인다졸 (1.32 g, 수율 64%)을 얻었다.5-bromo-1H-indazole (1.32 g, 6.7 mmol), 1-chloro-4-iodobenzene (1.90 g, 8.0 mmol), Pd (OAc) 2 (0.08 g, 0.34 mmol), P under nitrogen stream ( t -Bu) 3 (0.16 ml, 0.67 mmol), NaO ( t -Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 2 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to give 5-bromo-1- (4-chlorophenyl) -1H-indazole (1.32 g, 64% yield) as a target compound. Got.
1H-NMR: δ 7.35 (m, 2H), 7.53 (m, 3H), 8.01 (s, 1H), 8.20 (d, 1H), 8.37 (s, 1H) 1 H-NMR: δ 7.35 (m, 2H), 7.53 (m, 3H), 8.01 (s, 1H), 8.20 (d, 1H), 8.37 (s, 1H)
<단계 2> 1-(4-<Step 2> 1- (4- 클로로페닐Chlorophenyl )-5-(4,4,5,5-) -5- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)-1H-인다졸의 합성Synthesis of 2-yl) -1H-indazole
Figure PCTKR2016014958-appb-I000049
Figure PCTKR2016014958-appb-I000049
질소 기류 하에서 5-브로모-1-(4-클로로페닐)-1H-인다졸 (39.37 g, 0.128 mol), 4,4,4',4',5,5,5',5'-옥타메틸-2,2'-비(1,3,2-디옥사보로란) (48.58 g, 0.191 mol), Pd(dppf)Cl2 (5.2 g, 5 mol), KOAc (37.55 g, 0.383 mol) 및 1,4-디옥산 (500 ml)를 혼합한 다음, 130℃에서 12시간 동안 교반하였다.5-bromo-1- (4-chlorophenyl) -1H-indazole (39.37 g, 0.128 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octa under nitrogen stream Methyl-2,2'-ratio (1,3,2-dioxaborolane) (48.58 g, 0.191 mol), Pd (dppf) Cl 2 (5.2 g, 5 mol), KOAc (37.55 g, 0.383 mol ) And 1,4-dioxane (500 ml) were mixed and then stirred at 130 ° C. for 12 hours.
반응이 종결된 후 에틸아세테이트로 추출한 다음, MgSO4로 수분을 제거하고, 컬럼크로마토그래피 (Hexane:EA = 10:1 (v/v))로 정제하여 1-(4-클로로페닐)-5-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-1H-인다졸 (25.42 g, 수율: 56%)을 얻었다.Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO 4 and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to give 1- (4-chlorophenyl) -5 (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole (25.42 g, yield: 56%) was obtained.
1H-NMR: δ 1.20 (s, 12H), 7.35 (m, 2H), 7.57 (m, 3H), 8.13 (s, 1H), 8.35 (m, 2H) 1 H-NMR: δ 1.20 (s, 12H), 7.35 (m, 2H), 7.57 (m, 3H), 8.13 (s, 1H), 8.35 (m, 2H)
<단계 3> 2-(2-(1-(4-<Step 3> 2- (2- (1- (4- 클로로페닐Chlorophenyl )-1H-) -1H- 인다졸Indazole -5-일)페닐)프로판-2-올의 합성Synthesis of -5-yl) phenyl) propan-2-ol
Figure PCTKR2016014958-appb-I000050
Figure PCTKR2016014958-appb-I000050
1-(4-클로로페닐)-5-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-1H-인다졸 (3.54 g, 10 mmol), 2-(2-브로모페닐)프로판-2-올 (2.36 g, 11 mmol), K2CO3 (2.07 g, 15 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol) 및 톨루엔(60 mL)과 정제수(15ml)을 혼합하고 110℃에서 12시간 동안 교반하였다. 상온으로 식힌 후 H2O를 첨가하고 염수를 이용하여 추출하였다. Na2SO4로 수분을 제거한 후 유기층을 농축한 후 컬럼크로마토그래피를 실시하여 2-(2-(1-(4-클로로페닐)-1H-인다졸-5-일)페닐)프로판-2-올 (1.99 g, 55%)를 얻었다. 1- (4-chlorophenyl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole (3.54 g, 10 mmol ), 2- (2-bromophenyl) propan-2-ol (2.36 g, 11 mmol), K 2 CO 3 (2.07 g, 15 mmol), Pd (PPh 3 ) 4 (0.58 g, 0.5 mmol) and Toluene (60 mL) and purified water (15 ml) were mixed and stirred at 110 ° C. for 12 hours. After cooling to room temperature, H 2 O was added and extracted with brine. After removal of water with Na 2 SO 4 , the organic layer was concentrated, and then subjected to column chromatography to 2- (2- (1- (4-chlorophenyl) -1H-indazol-5-yl) phenyl) propan-2- Obtained (1.99 g, 55%).
1H-NMR: δ 1.35 (s, 6H), 5.50 (s, 1H), 7.40 (m, 7H), 7.77 (m, 2H), 8.19 (s, 1H), 8.37 (s, 1H), 8.50 (d, 1H) 1 H-NMR: δ 1.35 ( s, 6H), 5.50 (s, 1H), 7.40 (m, 7H), 7.77 (m, 2H), 8.19 (s, 1H), 8.37 (s, 1H), 8.50 ( d, 1H)
<단계 4> A-1의 합성Step 4 Synthesis of A-1
Figure PCTKR2016014958-appb-I000051
Figure PCTKR2016014958-appb-I000051
0℃로 온도를 냉각하고 톨루엔 1L에 2-(2-(1-(4-클로로페닐)-1H-인다졸-5-일)페닐)프로판-2-올 108.8 g (0.3 mol)을 넣어준 후 메탄술폰산 19.5 mL (0.03 mol)를 한 방울씩 첨가하였다. 상온으로 온도를 올린 후 정제수 300 mL를 첨가하여 반응을 종결하였다. 혼합액을 CH2Cl2 로 추출한 후, 분리한 유기층을 포화탄산칼슘 20 mL로 중화하고 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물인 A-1 (31.03 g, 수율 30%)을 얻었다.Cool to 0 ° C. and add 108.8 g (0.3 mol) of 2- (2- (1- (4-chlorophenyl) -1H-indazol-5-yl) phenyl) propan-2-ol to 1 L of toluene. Then 19.5 mL (0.03 mol) of methanesulfonic acid was added dropwise. After the temperature was raised to room temperature, 300 mL of purified water was added to terminate the reaction. The mixture was extracted with CH 2 Cl 2 , and the separated organic layer was neutralized with 20 mL of saturated calcium carbonate and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure and purified by silica gel column chromatography to obtain A-1 (31.03 g, yield 30%) as a target compound.
1H-NMR : δ 1.69 (s, 6H), 7.36 (m, 3H), 7.55 (m, 3H), 7.74 (m, 2H), 8.24 (d, 1H), 8.40 (m, 2H) 1 H-NMR: δ 1.69 (s, 6H), 7.36 (m, 3H), 7.55 (m, 3H), 7.74 (m, 2H), 8.24 (d, 1H), 8.40 (m, 2H)
[[ 준비예Preparation 2] A-2의 합성 2] Synthesis of A-2
<단계 1> 2-(2-(1-(4-<Step 1> 2- (2- (1- (4- 클로로페닐Chlorophenyl )-1H-) -1H- 벤조[d][1,2,3]트리아졸Benzo [d] [1,2,3] triazole -6-일)페닐)프로판-2-올의 합성Synthesis of -6-yl) phenyl) propan-2-ol
Figure PCTKR2016014958-appb-I000052
Figure PCTKR2016014958-appb-I000052
준비예 1의 <단계 3>에서 사용된 1-(4-클로로페닐)-5-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-1H-인다졸 대신 1-(4-클로로페닐)-6-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-1H-벤조[d][1,2,3]트리아졸 (3.55 g, 10 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>과 동일한 과정을 수행하여 2-(2-(1-(4-클로로페닐)-1H-벤조[d][1,2,3]트리아졸-6-일)페닐)프로판-2-올 를 얻었다.1- (4-chlorophenyl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) used in <Step 3> of Preparation Example 1 1- (4-chlorophenyl) -6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-benzo instead of -1H-indazole [ d] [1,2,3] triazole (3.55 g, 10 mmol) was subjected to the same procedure as in <Step 3> of Preparation Example 1 except that 2- (2- (1- (4) -Chlorophenyl) -1H-benzo [d] [1,2,3] triazol-6-yl) phenyl) propan-2-ol was obtained.
1H-NMR: δ 1.35 (s, 6H), 5.50 (s, 1H), 7.40 (m, 7H), 7.79 (m, 2H), 8.15 (d, 1H), 8.32 (s, 1H) 1 H-NMR: δ 1.35 (s, 6H), 5.50 (s, 1H), 7.40 (m, 7H), 7.79 (m, 2H), 8.15 (d, 1H), 8.32 (s, 1H)
<단계 2> A-2의 합성<Step 2> Synthesis of A-2
Figure PCTKR2016014958-appb-I000053
Figure PCTKR2016014958-appb-I000053
준비예 1의 <단계 4>에서 사용된 2-(2-(1-(4-클로로페닐)-1H-인다졸-5-일)페닐)프로판-2-올 대신 상기 준비예 2의 <단계 1>에서 얻은 2-(2-(1-(4-클로로페닐)-1H-벤조[d][1,2,3]트리아졸-6-일)페닐)프로판-2-올 (109.15 g, 0.3 mol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>와 동일한 과정을 수행하여 A-2를 얻었다.<Step of Preparation Example 2 instead of 2- (2- (1- (4-chlorophenyl) -1H-indazol-5-yl) phenyl) propan-2-ol used in <Step 4> of Preparation Example 1 2- (2- (1- (4-chlorophenyl) -1H-benzo [d] [1,2,3] triazol-6-yl) phenyl) propan-2-ol (109.15 g, obtained in 1); A-2 was obtained by performing the same process as <Step 4> of Preparation Example 1, except that 0.3 mol) was used.
1H-NMR: δ 1.69 (s, 6H), 7.37 (m, 3H), 7.56 (m, 3H), 7.74 (d, 1H), 8.24 (d, 1H), 8.33 (m, 2H) 1 H-NMR: δ 1.69 (s, 6H), 7.37 (m, 3H), 7.56 (m, 3H), 7.74 (d, 1H), 8.24 (d, 1H), 8.33 (m, 2H)
[[ 준비예Preparation 3] A-3의 합성 3] Synthesis of A-3
<단계 1> 2-(4-<Step 1> 2- (4- 클로로Chloro -2-(1-페닐-1H--2- (1-phenyl-1H- 피라졸로[3,4-b]피리딘Pyrazolo [3,4-b] pyridine -5-일)페닐)프로판-2-올의 합성Synthesis of -5-yl) phenyl) propan-2-ol
Figure PCTKR2016014958-appb-I000054
Figure PCTKR2016014958-appb-I000054
준비예 1의 <단계 3>에서 사용된 1-(4-클로로페닐)-5-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-1H-인다졸 대신 1-페닐-5-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-1H-피라졸로[3,4-b]피리딘 (3.21 g, 10 mmol)를 사용하고 2-(2-브로모페닐)프로판-2-올 대신 2-(2-브로모-4-클로로페닐)프로판-2-올 (2.74 g, 11 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>과 동일한 과정을 수행하여 2-(2-(1-(4-클로로페닐)-1H-벤조[d][1,2,3]트리아졸-6-일)페닐)프로판-2-올을 얻었다.1- (4-chlorophenyl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) used in <Step 3> of Preparation Example 1 1-phenyl-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-pyrazolo [3,4- instead of -1H-indazole b] 2- (2-bromo-4-chlorophenyl) propan-2-ol (2.74 g, using pyridine (3.21 g, 10 mmol) instead of 2- (2-bromophenyl) propan-2-ol Except for using 11 mmol) in the same manner as in <Step 3> of Preparation Example 1 2- (2- (1- (4-chlorophenyl) -1H-benzo [d] [1,2 , 3] triazol-6-yl) phenyl) propan-2-ol.
1H-NMR: δ 1.35 (s, 6H), 5.50 (s, 1H), 7.55 (m, 5H), 8.00 (s, 1H), 8.09 (s, 1H), 8.22 (m, 3H), 9.24 (s, 1H) 1 H-NMR: δ 1.35 (s, 6H), 5.50 (s, 1H), 7.55 (m, 5H), 8.00 (s, 1H), 8.09 (s, 1H), 8.22 (m, 3H), 9.24 ( s, 1 H)
<단계 2> A-3의 합성<Step 2> Synthesis of A-3
Figure PCTKR2016014958-appb-I000055
Figure PCTKR2016014958-appb-I000055
준비예 1의 <단계 4>에서 사용된 2-(2-(1-(4-클로로페닐)-1H-인다졸-5-일)페닐)프로판-2-올 대신 상기 준비예 3의 <단계 1>에서 얻은 2-(2-(1-(4-클로로페닐)-1H-벤조[d][1,2,3]트리아졸-6-일)페닐)프로판-2-올 (109.15 g, 0.3 mol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>와 동일한 과정을 수행하여 A-3를 얻었다.<Step of Preparation Example 3 instead of 2- (2- (1- (4-chlorophenyl) -1H-indazol-5-yl) phenyl) propan-2-ol used in <Step 4> of Preparation Example 1 2- (2- (1- (4-chlorophenyl) -1H-benzo [d] [1,2,3] triazol-6-yl) phenyl) propan-2-ol (109.15 g, obtained in 1); A-3 was obtained by the same procedure as <Step 4> of Preparation Example 1, except that 0.3 mol) was used.
1H-NMR: δ 1.69 (s, 6H), 7.31 (d, 1H), 7.50 (m, 4H), 7.96 (s, 1H), 8.20 (m, 3H), 9.24 (s, 1H) 1 H-NMR: δ 1.69 (s, 6H), 7.31 (d, 1H), 7.50 (m, 4H), 7.96 (s, 1H), 8.20 (m, 3H), 9.24 (s, 1H)
[[ 준비예Preparation 4] A-4의 합성 4] Synthesis of A-4
<단계 1> (2-(2-<Step 1> (2- (2- (4-클로로페닐)벤조[d]옥사졸(4-chlorophenyl) benzo [d] oxazole -5-일)페닐)-5-yl) phenyl) 디페닐메탄올의Diphenylmethanol 합성 synthesis
Figure PCTKR2016014958-appb-I000056
Figure PCTKR2016014958-appb-I000056
준비예 1의 <단계 3>에서 사용된 1-(4-클로로페닐)-5-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-1H-인다졸 대신 2-(4-클로로페닐)-5-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)벤조[d]옥사졸 (3.55 g, 10 mmol)를 사용하고 2-(2-브로모페닐)프로판-2-올 대신 (2-브로모페닐)디페닐메탄올 (3.73 g, 11 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>과 동일한 과정을 수행하여 (2-(2-(4-클로로페닐)벤조[d]옥사졸-5-일)페닐)디페닐메탄올을 얻었다.1- (4-chlorophenyl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) used in <Step 3> of Preparation Example 1 2- (4-chlorophenyl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxa instead of -1H-indazole Except using sol (3.55 g, 10 mmol) and (2-bromophenyl) diphenylmethanol (3.73 g, 11 mmol) instead of 2- (2-bromophenyl) propan-2-ol The same procedure as in <Step 3> of Preparation Example 1 was performed to obtain (2- (2- (4-chlorophenyl) benzo [d] oxazol-5-yl) phenyl) diphenylmethanol.
1H-NMR: δ 6.72 (s, 1H), 7.28 (m, 10H), 7.50 (m, 5H), 7.75 (m, 5H), 8.09 (s, 1H) 1 H-NMR: δ 6.72 (s, 1H), 7.28 (m, 10H), 7.50 (m, 5H), 7.75 (m, 5H), 8.09 (s, 1H)
<단계 2> A-4의 합성<Step 2> Synthesis of A-4
Figure PCTKR2016014958-appb-I000057
Figure PCTKR2016014958-appb-I000057
준비예 1의 <단계 4>에서 사용된 2-(2-(1-(4-클로로페닐)-1H-인다졸-5-일)페닐)프로판-2-올 대신 상기 준비예 4의 <단계 1>에서 얻은 (2-(2-(4-클로로페닐)벤조[d]옥사졸-5-일)페닐)디페닐메탄올 (149.69 g, 0.3 mol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>와 동일한 과정을 수행하여 A-4를 얻었다.<Step of Preparation Example 4 instead of 2- (2- (1- (4-chlorophenyl) -1H-indazol-5-yl) phenyl) propan-2-ol used in <Step 4> of Preparation Example 1 Preparation Example 1, except that (2- (2- (4-chlorophenyl) benzo [d] oxazol-5-yl) phenyl) diphenylmethanol (149.69 g, 0.3 mol) obtained in 1> was used. A-4 was obtained by performing the same procedure as in <Step 4>.
1H-NMR: δ 7.20 (m, 11H), 7.38 (m, 2H), 7.55 (m, 3H), 7.71 (m, 2H), 7.90 (m, 2H) 1 H-NMR: δ 7.20 (m, 11H), 7.38 (m, 2H), 7.55 (m, 3H), 7.71 (m, 2H), 7.90 (m, 2H)
[[ 준비예Preparation 5] A-5의 합성 5] Synthesis of A-5
<단계 1> 9-(2-(2-<Step 1> 9- (2- (2- (4-클로로페닐)벤조[d]티아졸(4-chlorophenyl) benzo [d] thiazole -4-일)페닐)-9H--4-yl) phenyl) -9H- 플루오렌Fluorene -9-올의 합성Synthesis of -9-ol
Figure PCTKR2016014958-appb-I000058
Figure PCTKR2016014958-appb-I000058
준비예 1의 <단계 3>에서 사용된 1-(4-클로로페닐)-5-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-1H-인다졸 대신 2-(4-클로로페닐)-4-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)벤조[d]티아졸 (3.72 g, 10 mmol)를 사용하고 2-(2-브로모페닐)프로판-2-올 대신 9-(2-브로모페닐)-9H-플루오렌-9-올 (3.71 g, 11 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>과 동일한 과정을 수행하여 9-(2-(2-(4-클로로페닐)벤조[d]티아졸-4-일)페닐)-9H-플루오렌-9-올 를 얻었다.1- (4-chlorophenyl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) used in <Step 3> of Preparation Example 1 2- (4-chlorophenyl) -4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] thia instead of -1H-indazole 9- (2-bromophenyl) -9H-fluorene-9-ol (3.71 g, 11 mmol) using sol (3.72 g, 10 mmol) and replacing 2- (2-bromophenyl) propan-2-ol 9- (2- (2- (4-chlorophenyl) benzo [d] thiazol-4-yl) phenyl) by following the same procedure as in <Step 3> of Preparation Example 1, except that -9H-fluorene-9-ol was obtained.
1H-NMR: δ 6.72 (s, 1H), 7.38 (m, 11H), 7.75 (m, 2H), 7.90 (m, 3H), 8.02 (m, 2H), 8.12 (d, 1H) 1 H-NMR: δ 6.72 (s, 1H), 7.38 (m, 11H), 7.75 (m, 2H), 7.90 (m, 3H), 8.02 (m, 2H), 8.12 (d, 1H)
<단계 2> A-5의 합성<Step 2> Synthesis of A-5
Figure PCTKR2016014958-appb-I000059
Figure PCTKR2016014958-appb-I000059
준비예 1의 <단계 4>에서 사용된 2-(2-(1-(4-클로로페닐)-1H-인다졸-5-일)페닐)프로판-2-올 대신 상기 준비예 5의 <단계 1>에서 얻은 9-(2-(2-(4-클로로페닐)벤조[d]티아졸-4-일)페닐)-9H-플루오렌-9-올 (150.61 g, 0.3 mol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>와 동일한 과정을 수행하여 A-5를 얻었다.<Step of Preparation Example 5 instead of 2- (2- (1- (4-chlorophenyl) -1H-indazol-5-yl) phenyl) propan-2-ol used in <Step 4> of Preparation Example 1 Using 9- (2- (2- (4-chlorophenyl) benzo [d] thiazol-4-yl) phenyl) -9H-fluorene-9-ol (150.61 g, 0.3 mol) obtained in 1> A-5 was obtained by the same procedure as in <Step 4> of Preparation Example 1, except that.
1H-NMR: δ 7.40 (m, 11H), 7.74 (d, 1H), 7.89 (m, 2H), 8.02 (m, 3H), 8.24 (d, 1H) 1 H-NMR: δ 7.40 (m, 11H), 7.74 (d, 1H), 7.89 (m, 2H), 8.02 (m, 3H), 8.24 (d, 1H)
[[ 준비예Preparation 6] A-6의 합성 6] Synthesis of A-6
<단계 1> (3-(2-(4-<Step 1> (3- (2- (4- 클로로페닐Chlorophenyl )-1-페닐-1H-인돌-5-일)피리딘-4-일)) -1-phenyl-1H-indol-5-yl) pyridin-4-yl) 디페닐메탄올의Diphenylmethanol 합성 synthesis
Figure PCTKR2016014958-appb-I000060
Figure PCTKR2016014958-appb-I000060
준비예 1의 <단계 3>에서 사용된 1-(4-클로로페닐)-5-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-1H-인다졸 대신 2-(4-클로로페닐)-1-페닐-5-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-1H-인돌 (4.30 g, 10 mmol)를 사용하고 2-(2-브로모페닐)프로판-2-올 대신 (3-브로모피리딘-4-일)디페닐메탄올 (3.74 g, 11 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>과 동일한 과정을 수행하여 (3-(2-(4-클로로페닐)-1-페닐-1H-인돌-5-일)피리딘-4-일)디페닐메탄올을 얻었다.1- (4-chlorophenyl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) used in <Step 3> of Preparation Example 1 2- (4-chlorophenyl) -1-phenyl-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) instead of -1H-indazole Use 1H-indole (4.30 g, 10 mmol) and (3-bromopyridin-4-yl) diphenylmethanol (3.74 g, 11 mmol) instead of 2- (2-bromophenyl) propan-2-ol Except for using the same process as in <Step 3> of Preparation Example 1 to (3- (2- (4-chlorophenyl) -1-phenyl-1H-indol-5-yl) pyridin-4- To obtain diphenylmethanol.
1H-NMR: δ 6.71 (s, 1H), 6.80 (s, 1H), 7.16 (d, 1H), 7.25 (m, 10H), 7.60 (m, 7H), 7.98 (m, 2H), 8.13 (d, 1H), 8.20 (d, 1H), 8.30 (m, 2H), 9.24 (s, 1H) 1 H-NMR: δ 6.71 (s, 1H), 6.80 (s, 1H), 7.16 (d, 1H), 7.25 (m, 10H), 7.60 (m, 7H), 7.98 (m, 2H), 8.13 ( d, 1H), 8.20 (d, 1H), 8.30 (m, 2H), 9.24 (s, 1H)
<단계 2> A-6의 합성<Step 2> Synthesis of A-6
Figure PCTKR2016014958-appb-I000061
Figure PCTKR2016014958-appb-I000061
준비예 1의 <단계 4>에서 사용된 2-(2-(1-(4-클로로페닐)-1H-인다졸-5-일)페닐)프로판-2-올 대신 상기 준비예 6의 <단계 1>에서 얻은 (3-(2-(4-클로로페닐)-1-페닐-1H-인돌-5-일)피리딘-4-일)디페닐메탄올 (168.93 g, 0.3 mol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>와 동일한 과정을 수행하여 A-6를 얻었다.<Step of Preparation Example 6 instead of 2- (2- (1- (4-chlorophenyl) -1H-indazol-5-yl) phenyl) propan-2-ol used in <Step 4> of Preparation Example 1 Except using (3- (2- (4-chlorophenyl) -1-phenyl-1H-indol-5-yl) pyridin-4-yl) diphenylmethanol (168.93 g, 0.3 mol) obtained in 1>. Then, the same procedure as in <Step 4> of Preparation Example 1 was performed to obtain A-6.
1H-NMR: δ 6.80 (s, 1H), 7.20 (m, 11H), 7.56 (m, 7H), 8.00 (m, 3H), 8.20 (d, 1H), 8.29 (d, 1H), 9.24 (s, 1H) 1 H-NMR: δ 6.80 (s, 1H), 7.20 (m, 11H), 7.56 (m, 7H), 8.00 (m, 3H), 8.20 (d, 1H), 8.29 (d, 1H), 9.24 ( s, 1 H)
[[ 준비예Preparation 7] A-7의 합성 7] Synthesis of A-7
<단계 1> (4-<Step 1> (4- 클로로페닐Chlorophenyl )(2-(1-페닐-2-(피리딘-2-일)-1H-) (2- (1-phenyl-2- (pyridin-2-yl) -1H- 벤조[d]이미다졸Benzo [d] imidazole -5-일)페닐)(피리딘-3-일)메탄올의 합성Synthesis of -5-yl) phenyl) (pyridin-3-yl) methanol
Figure PCTKR2016014958-appb-I000062
Figure PCTKR2016014958-appb-I000062
준비예 1의 <단계 3>에서 사용된 1-(4-클로로페닐)-5-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-1H-인다졸 대신 1-페닐-2-(피리딘-2-일)-5-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-1H-벤조[d]이미다졸 (3.97 g, 10 mmol)를 사용하고 2-(2-브로모페닐)프로판-2-올 대신 (2-브로모페닐)(4-클로로페닐)(피리딘-3-일)메탄올 (4.12 g, 11 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>과 동일한 과정을 수행하여 (4-클로로페닐)(2-(1-페닐-2-(피리딘-2-일)-1H-벤조[d]이미다졸-5-일)페닐)(피리딘-3-일)메탄올을 얻었다.1- (4-chlorophenyl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) used in <Step 3> of Preparation Example 1 1-phenyl-2- (pyridin-2-yl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) instead of -1H-indazole (2-Bromophenyl) (4-chlorophenyl) (pyridine- instead of 2- (2-bromophenyl) propan-2-ol using 1H-benzo [d] imidazole (3.97 g, 10 mmol) Except for using 3-yl) methanol (4.12 g, 11 mmol), the same procedure as in <Step 3> of Preparation Example 1 was carried out to give (4-chlorophenyl) (2- (1-phenyl-2- (Pyridin-2-yl) -1H-benzo [d] imidazol-5-yl) phenyl) (pyridin-3-yl) methanol.
1H-NMR: δ 6.71 (s, 1H), 7.22 (m, 2H), 7.41 (m, 11H), 7.62 (t, 1H), 7.85 (m, 3H), 8.04 (s, 1H), 8.20 (m, 2H), 8.33 (d, 1H), 8.41 (d, 1H), 8.55 (m, 2H) 1 H-NMR: δ 6.71 (s, 1H), 7.22 (m, 2H), 7.41 (m, 11H), 7.62 (t, 1H), 7.85 (m, 3H), 8.04 (s, 1H), 8.20 ( m, 2H), 8.33 (d, 1H), 8.41 (d, 1H), 8.55 (m, 2H)
<단계 2> A-7의 합성<Step 2> Synthesis of A-7
Figure PCTKR2016014958-appb-I000063
Figure PCTKR2016014958-appb-I000063
준비예 1의 <단계 4>에서 사용된 2-(2-(1-(4-클로로페닐)-1H-인다졸-5-일)페닐)프로판-2-올 대신 상기 준비예 7의 <단계 1>에서 얻은 (4-클로로페닐)(2-(1-페닐-2-(피리딘-2-일)-1H-벤조[d]이미다졸-5-일)페닐)(피리딘-3-일)메탄올 (169.52 g, 0.3 mol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>와 동일한 과정을 수행하여 A-7를 얻었다.<Step of Preparation Example 7 instead of 2- (2- (1- (4-chlorophenyl) -1H-indazol-5-yl) phenyl) propan-2-ol used in <Step 4> of Preparation Example 1 (4-chlorophenyl) (2- (1-phenyl-2- (pyridin-2-yl) -1H-benzo [d] imidazol-5-yl) phenyl) (pyridin-3-yl) obtained in 1> A-7 was obtained by the same procedure as <Step 4> of Preparation Example 1, except that methanol (169.52 g, 0.3 mol) was used.
1H-NMR: δ 7.12 (m, 2H), 7.24 (t, 1H), 7.50 (m, 12H), 7.85 (t, 1H), 8.24 (m, 6H), 8.59 (d, 1H) 1 H-NMR: δ 7.12 (m, 2H), 7.24 (t, 1H), 7.50 (m, 12H), 7.85 (t, 1H), 8.24 (m, 6H), 8.59 (d, 1H)
[[ 합성예Synthesis Example 1] J-1의 합성 1] Synthesis of J-1
Figure PCTKR2016014958-appb-I000064
Figure PCTKR2016014958-appb-I000064
질소 기류 하에서 A-1 (3.44 g, 10.0 mmol), (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 (3.53 g, 10.0 mmol), K2CO3 (4.27 g, 30.0 mmol), Pd(PPh3)4 (0.58 g, 5 mol%), X-Phos (0.8 g, 5.00 mmol)를 120 ml / 40 ml의 THF/H2O에 넣고 90℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 J-1 (3.08 g, 수율 50%)를 획득하였다.A-1 (3.44 g, 10.0 mmol) under nitrogen stream, (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (3.53 g, 10.0 mmol), K 2 CO 3 (4.27 g, 30.0 mmol), Pd (PPh 3 ) 4 (0.58 g, 5 mol%) and X-Phos (0.8 g, 5.00 mmol) were added to 120 ml / 40 ml of THF / H 2 O and stirred at 90 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound J-1 (3.08 g, yield 50%) using column chromatography.
[Mass]: 617[Mass]: 617
[[ 합성예Synthesis Example 2] J-2의 합성 2] Synthesis of J-2
Figure PCTKR2016014958-appb-I000065
Figure PCTKR2016014958-appb-I000065
(3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (3-(4-([1,1'-bi페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)페닐)보로닉산 (4.29 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-2 (4.57 g, 수율 66%)를 얻었다.(3- (4-([1,1'-biphenyl] -4-yl) instead of (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid Except for using -6-phenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (4.29 g, 10.0 mmol), the same procedure as in Synthesis Example 1 was conducted to obtain the target compound J- 2 (4.57 g, yield 66%) was obtained.
[Mass]: 693[Mass]: 693
[[ 합성예Synthesis Example 3] J-3의 합성 3] Synthesis of J-3
Figure PCTKR2016014958-appb-I000066
Figure PCTKR2016014958-appb-I000066
(3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (3'-(4,6-디페닐-1,3,5-트리아진-2-일)-[1,1'-비페닐]-3-일)보로닉산 (4.29 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-3 (4.57 g, 수율 66%)를 얻었다.(3 '-(4,6-diphenyl-1,3,5-triazine-) instead of (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid Except for using 2-yl)-[1,1'-biphenyl] -3-yl) boronic acid (4.29 g, 10.0 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the target compound J-3 (4.57 g, yield 66%) was obtained.
[Mass]: 693[Mass]: 693
[[ 합성예Synthesis Example 4] J-4의 합성 4] Synthesis of J-4
Figure PCTKR2016014958-appb-I000067
Figure PCTKR2016014958-appb-I000067
A-1 대신 A-2 (3.45 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (3-(6-([1,1'-비페닐]-4-일)-2-페닐피리미딘-4-일)페닐)보로닉산 (4.28 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-4 (4.23 g, 수율 61%)를 얻었다.Use A-2 (3.45 g, 10.0 mmol) instead of A-1 and (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid instead of (3- ( Synthesis Example 1, except that 6-([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) phenyl) boronic acid (4.28 g, 10.0 mmol) was used The same procedure was followed to obtain the title compound J-4 (4.23 g, yield 61%).
[Mass]: 693[Mass]: 693
[[ 합성예Synthesis Example 5] J-5의 합성 5] Synthesis of J-5
Figure PCTKR2016014958-appb-I000068
Figure PCTKR2016014958-appb-I000068
A-1 대신 A-2 (3.45 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (4,6-디페닐-1,3,5-트리아진-2-일)보로닉산 (2.77 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-5 (2.55 g, 수율 47%)를 얻었다.A-2 (3.45 g, 10.0 mmol) was used instead of A-1 and (4,6 instead of (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid Except for using -diphenyl-1,3,5-triazin-2-yl) boronic acid (2.77 g, 10.0 mmol) was subjected to the same process as in Synthesis Example 1 to J-5 (2.55) g, yield 47%).
[Mass]: 542[Mass]: 542
[[ 합성예Synthesis Example 6] J-6의 합성 6] Synthesis of J-6
Figure PCTKR2016014958-appb-I000069
Figure PCTKR2016014958-appb-I000069
A-1 대신 A-2 (3.45 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (4-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 (3.53 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-6 (2.41 g, 수율 39%)를 얻었다.A-2 (3.45 g, 10.0 mmol) was used instead of A-1 and (4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid was used instead of (4- ( Except for using 4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (3.53 g, 10.0 mmol) was carried out in the same manner as in Synthesis Example 1 J-6 (2.41 g, yield 39%) was obtained.
[Mass]: 618[Mass]: 618
[[ 합성예Synthesis Example 7] J-7의 합성 7] Synthesis of J-7
Figure PCTKR2016014958-appb-I000070
Figure PCTKR2016014958-appb-I000070
A-1 대신 A-3 (3.45 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (4-(2,6-디페닐피리미딘-4-일)페닐)보로닉산 (3.52 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-7 (3.58 g, 수율 58%)를 얻었다.Use A-3 (3.45 g, 10.0 mmol) instead of A-1 and (4- (4- (6-diphenyl-1,3,5-triazin-2-yl) phenyl) instead of boronic acid Except for using 2,6-diphenylpyrimidin-4-yl) phenyl) boronic acid (3.52 g, 10.0 mmol) was subjected to the same procedure as in Synthesis Example 1 to obtain the target compound J-7 (3.58 g, Yield 58%).
[Mass]: 617[Mass]: 617
[[ 합성예Synthesis Example 8] J-8의 합성 8] Synthesis of J-8
Figure PCTKR2016014958-appb-I000071
Figure PCTKR2016014958-appb-I000071
A-1 대신 A-3 (3.45 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (4-(2-([1,1'-비페닐]-4-일)-6-(4-플루오로페닐)피리미딘-4-일)페닐)보로닉산 (4.46 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-8 (2.34 g, 수율 33%)를 얻었다.Use A-3 (3.45 g, 10.0 mmol) instead of A-1 and (4- (4- (6-diphenyl-1,3,5-triazin-2-yl) phenyl) instead of boronic acid Except for using 2-([1,1'-biphenyl] -4-yl) -6- (4-fluorophenyl) pyrimidin-4-yl) phenyl) boronic acid (4.46 g, 10.0 mmol) Then, the same procedure as in Synthesis Example 1 was performed to obtain J-8 (2.34 g, yield 33%) as a target compound.
[Mass]: 711[Mass]: 711
[[ 합성예Synthesis Example 9] J-9의 합성 9] Synthesis of J-9
Figure PCTKR2016014958-appb-I000072
Figure PCTKR2016014958-appb-I000072
A-1 대신 A-3 (3.45 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (4-(트리페닐렌-2-일)페닐)보로닉산 (3.48 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-9 (2.70 g, 수율 44%)를 얻었다.Use A-3 (3.45 g, 10.0 mmol) instead of A-1 and (4- (4- (6-diphenyl-1,3,5-triazin-2-yl) phenyl) instead of boronic acid Except for using triphenylen-2-yl) phenyl) boronic acid (3.48 g, 10.0 mmol) was subjected to the same process as in Synthesis Example 1 to obtain the target compound J-9 (2.70 g, yield 44%). Got it.
[Mass]: 613[Mass]: 613
[[ 합성예Synthesis Example 10] J-10의 합성 10] Synthesis of J-10
Figure PCTKR2016014958-appb-I000073
Figure PCTKR2016014958-appb-I000073
A-1 대신 A-4 (4.69 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (4,6-디([1,1'-비페닐]-4-일)-1,3,5-트리아진-2-일)보로닉산 (4.29 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-10 (3.68 g, 수율 45%)를 얻었다.Use A-4 (4.69 g, 10.0 mmol) instead of A-1 and (4,6 instead of (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid Synthesis Example 1, except that -di ([1,1'-biphenyl] -4-yl) -1,3,5-triazin-2-yl) boronic acid (4.29 g, 10.0 mmol) was used The same procedure as in the following to obtain the target compound J-10 (3.68 g, yield 45%).
[Mass]: 818[Mass]: 818
[[ 합성예Synthesis Example 11] J-11의 합성 11] Synthesis of J-11
Figure PCTKR2016014958-appb-I000074
Figure PCTKR2016014958-appb-I000074
A-1 대신 A-4 (4.69 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (9-페닐-9H-카바졸-3-일)보로닉산 (2.87 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-11 (3.11 g, 수율 46%)를 얻었다.Use A-4 (4.69 g, 10.0 mmol) instead of A-1 and (9-phenyl instead of (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid Except for using -9H-carbazol-3-yl) boronic acid (2.87 g, 10.0 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the target compound J-11 (3.11 g, yield 46%). Got it.
[Mass]: 676[Mass]: 676
[[ 합성예Synthesis Example 12] J-12의 합성 12] Synthesis of J-12
Figure PCTKR2016014958-appb-I000075
Figure PCTKR2016014958-appb-I000075
A-1 대신 A-4 (4.69 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (4-(디페닐아미노)페닐)보로닉산 (2.89 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-12 (3.19 g, 수율 47%)를 얻었다.Use A-4 (4.69 g, 10.0 mmol) instead of A-1 and (4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid instead of (4- ( Except for using diphenylamino) phenyl) boronic acid (2.89 g, 10.0 mmol) was carried out the same procedure as in Synthesis Example 1 to obtain the title compound J-12 (3.19 g, yield 47%).
[Mass]: 678[Mass]: 678
[[ 합성예Synthesis Example 13] J-13의 합성 13] Synthesis of J-13
Figure PCTKR2016014958-appb-I000076
Figure PCTKR2016014958-appb-I000076
A-1 대신 A-5 (4.84 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (4-(4-(나프탈렌-1-일)페닐)퀴나졸린-2-일)보로닉산 (3.76 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-13 (3.74 g, 수율 48%)를 얻었다.Use A-5 (4.84 g, 10.0 mmol) instead of A-1 and (4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) instead of boronic acid Except for using 4- (naphthalen-1-yl) phenyl) quinazolin-2-yl) boronic acid (3.76 g, 10.0 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the target compound J-13 ( 3.74 g, yield 48%) was obtained.
[Mass]: 779[Mass]: 779
[[ 합성예Synthesis Example 14] J-14의 합성 14] Synthesis of J-14
Figure PCTKR2016014958-appb-I000077
Figure PCTKR2016014958-appb-I000077
A-1 대신 A-5 (4.84 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (4-페닐퀴나졸린-2-일)보로닉산 (2.50 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-14 (3.20 g, 수율 49%)를 얻었다.Use A-5 (4.84 g, 10.0 mmol) instead of A-1 and (4- (phenyl) instead of (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid Except for using quinazolin-2-yl) boronic acid (2.50 g, 10.0 mmol) was carried out the same procedure as in Synthesis Example 1 to obtain the target compound J-14 (3.20 g, 49% yield).
[Mass]: 653[Mass]: 653
[[ 합성예Synthesis Example 15] J-15의 합성 15] Synthesis of J-15
Figure PCTKR2016014958-appb-I000078
Figure PCTKR2016014958-appb-I000078
A-1 대신 A-5 (4.84 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (9,9-디메틸-9H-플루오렌-2-일)보로닉산 (2.38 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-15 (3.20 g, 수율 50%)를 얻었다.Use A-5 (4.84 g, 10.0 mmol) instead of A-1 and (9,9 instead of (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid Except for using -dimethyl-9H-fluoren-2-yl) boronic acid (2.38 g, 10.0 mmol) was subjected to the same procedure as in Synthesis Example 1 to obtain the target compound J-15 (3.20 g, yield 50% )
[Mass]: 641[Mass]: 641
[[ 합성예Synthesis Example 16] J-16의 합성 16] Synthesis of J-16
Figure PCTKR2016014958-appb-I000079
Figure PCTKR2016014958-appb-I000079
A-1 대신 A-6 (5.45 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 9,9'-스피로비[플루오렌]-4-일보로닉산 (3.60 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-16 (4.04 g, 수율 49%)를 얻었다.A-6 (5.45 g, 10.0 mmol) was used instead of A-1 and 9,9 'was substituted for (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid. -J-16 (4.04 g, 49% yield) of the target compound by the same procedure as in Synthesis Example 1, except that spirobibi [fluorene] -4-ylboronic acid (3.60 g, 10.0 mmol) was used. Got.
[Mass]: 825[Mass]: 825
[[ 합성예Synthesis Example 17] J-17의 합성 17] Synthesis of J-17
Figure PCTKR2016014958-appb-I000080
Figure PCTKR2016014958-appb-I000080
A-1 대신 A-6 (5.45 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 디벤조[b,d]퓨란-4-일보로닉산 (2.12 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-17 (3.24 g, 수율 48%)를 얻었다.A-6 (5.45 g, 10.0 mmol) was used instead of A-1 and (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) dibenzo [b instead of boronic acid , d] furan-4-ylboronic acid (2.12 g, 10.0 mmol) was used in the same manner as in Synthesis Example 1, except that J-17 (3.24 g, yield 48%) was obtained.
[Mass]: 676[Mass]: 676
[[ 합성예Synthesis Example 18] J-18의 합성 18] Synthesis of J-18
Figure PCTKR2016014958-appb-I000081
Figure PCTKR2016014958-appb-I000081
A-1 대신 A-6 (5.45 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 디벤조[b,d]티오펜-4-일보로닉산 (2.28 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-18 (3.25 g, 수율 47%)를 얻었다.A-6 (5.45 g, 10.0 mmol) was used instead of A-1 and (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) dibenzo [b instead of boronic acid , d] thiophen-4-ylboronic acid (2.28 g, 10.0 mmol) was used in the same manner as in Synthesis Example 1, except that J-18 (3.25 g, yield 47%) was obtained. .
[Mass]: 692[Mass]: 692
[[ 합성예Synthesis Example 19] J-19의 합성 19] Synthesis of J-19
Figure PCTKR2016014958-appb-I000082
Figure PCTKR2016014958-appb-I000082
A-1 대신 A-7 (5.47 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (4-(트리페닐실릴)페닐)보로닉산 (3.80 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-19 (3.89 g, 수율 46%)를 얻었다.Instead of A-1, use A-7 (5.47 g, 10.0 mmol) and replace (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (4- ( Except for using triphenylsilyl) phenyl) boronic acid (3.80 g, 10.0 mmol) was subjected to the same procedure as in Synthesis Example 1 to obtain the target compound J-19 (3.89 g, yield 46%).
[Mass]: 847[Mass]: 847
[[ 합성예Synthesis Example 20] J-20의 합성 20] Synthesis of J-20
Figure PCTKR2016014958-appb-I000083
Figure PCTKR2016014958-appb-I000083
A-1 대신 A-7 (5.47 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (3,5-디시아노페닐)보로닉산 (1.71 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-20 (2.87 g, 수율 45%)를 얻었다.Use A-7 (5.47 g, 10.0 mmol) instead of A-1 and (3,5 instead of (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid Except for using dicyanophenyl) boronic acid (1.71 g, 10.0 mmol) was carried out the same procedure as in Synthesis Example 1 to obtain the target compound J-20 (2.87 g, yield 45%).
[Mass]: 638[Mass]: 638
[[ 합성예Synthesis Example 21] J-21의 합성 21] Synthesis of J-21
Figure PCTKR2016014958-appb-I000084
Figure PCTKR2016014958-appb-I000084
A-1 대신 A-7 (5.47 g, 10.0 mmol) 를 사용하고 (3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보로닉산 대신 (4-(디페닐포스포릴)페닐)보로닉산 (3.22 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 J-21 (3.47 g, 수율 44%)를 얻었다.Instead of A-1, use A-7 (5.47 g, 10.0 mmol) and replace (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (4- ( Except for using diphenylphosphoryl) phenyl) boronic acid (3.22 g, 10.0 mmol) was subjected to the same procedure as in Synthesis Example 1 to obtain the target compound J-21 (3.47 g, 44% yield).
[Mass]: 788[Mass]: 788
[[ 실시예Example 1 ~ 10] 유기  1 to 10] organic 전계Electric field 발광 소자의 제작 Fabrication of light emitting device
상기 합성예에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제작하였다.The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate is cleaned for 5 minutes by UV and vacuum evaporator The substrate was transferred to.
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 90% 하기 표 1의 호스트 화합물 + 10 % Ir(ppy)3 (300nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다. M-MTDATA (60 nm) / TCTA (80 nm) / 90% of the host compound + 10% Ir (ppy) 3 (300nm) / BCP (10 nm) / Alq 3 (30) nm) / LiF (1 nm) / Al (200 nm) were laminated to fabricate an organic EL device.
m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP and BCP are as follows.
Figure PCTKR2016014958-appb-I000085
Figure PCTKR2016014958-appb-I000085
Figure PCTKR2016014958-appb-I000086
Figure PCTKR2016014958-appb-I000086
[[ 비교예Comparative example 1] 유기  1] organic 전계Electric field 발광 소자의 제작 Fabrication of light emitting device
발광층 형성시 발광 호스트 물질로서 화합물 J-1 대신 CBP를 사용하는 것을 제외하고는 실시예 1과 동일한 과정으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound J-1 as the light emitting host material when the emission layer was formed.
[[ 평가예Evaluation example ]]
실시예 1-10 및 비교예 1에서 제작한 각각의 유기 EL 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.For each organic EL device produced in Example 1-10 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.
샘플Sample 호스트Host 구동 전압(V)Drive voltage (V) 발광 피크(nm)Emission Peak (nm) 전류효율(cd/A)Current efficiency (cd / A)
실시예 1Example 1 J-1J-1 6.726.72 517517 41.341.3
실시예 2Example 2 J-2J-2 6.736.73 515515 39.739.7
실시예 3Example 3 J-3J-3 6.736.73 518518 38.938.9
실시예 4Example 4 J-4J-4 6.736.73 518518 41.341.3
실시예 5Example 5 J-5J-5 6.486.48 518518 41.341.3
실시예 6Example 6 J-6J-6 6.866.86 517517 43.143.1
실시예 7Example 7 J-7J-7 6.776.77 515515 43.543.5
실시예 8Example 8 J-8J-8 6.666.66 518518 41.441.4
실시예 9Example 9 J-9J-9 6.656.65 518518 42.242.2
실시예 10Example 10 J-10J-10 6.656.65 517517 4242
비교예 1Comparative Example 1 CBPCBP 6.936.93 516516 38.238.2
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물(J-1 ~ J-10)을 녹색 유기 전계 발광 소자의 발광층으로 사용하였을 경우(실시예 1 ~ 10) 종래 CBP를 사용한 녹색 유기 전계 발광 소자(비교예 1)와 비교해 볼 때 효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 1 above, when the compounds (J-1 to J-10) according to the present invention were used as the light emitting layer of the green organic electroluminescent device (Examples 1 to 10), the green organic electroluminescent device using the conventional CBP Compared with (Comparative Example 1), it can be seen that excellent performance is achieved in terms of efficiency and driving voltage.
본 발명은 유기 전계 발광 소자용 재료로서 사용될 수 있는 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.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.

Claims (18)

  1. 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2016014958-appb-I000087
    Figure PCTKR2016014958-appb-I000087
    상기 화학식 1에서, In Chemical Formula 1,
    X1과 X2, X2와 X3, X3와 X4, X5와 X6, X6과 X7, 및 X7과 X8 중 적어도 하나는 각각 독립적으로 하기 화학식 2 또는 3으로 표시되는 고리와 축합되어 축합고리를 형성하고;At least one of X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 are each independently represented by the following Chemical Formula 2 or 3 Condensed with a ring to form a condensed ring;
    하기 화학식 2 또는 3으로 표시되는 고리와 축합고리를 형성하지 않는 X1 내지 X8은 각각 독립적으로 N 또는 C(R3)이며;X 1 to X 8 which do not form a condensed ring with the ring represented by Formula 2 or 3 are each independently N or C (R 3 );
    [화학식 2][Formula 2]
    Figure PCTKR2016014958-appb-I000088
    Figure PCTKR2016014958-appb-I000088
    [화학식 3][Formula 3]
    Figure PCTKR2016014958-appb-I000089
    Figure PCTKR2016014958-appb-I000089
    상기 화학식 1 내지 3에서,In Chemical Formulas 1 to 3,
    점선은 축합이 이루어지는 부분을 의미하고;The dotted line means the part where condensation takes place;
    Y1 내지 Y3는 각각 독립적으로 O, S, N(R4) 및 C(R5)(R6)로 이루어진 군에서 선택되며; Y 1 to Y 3 are each independently selected from the group consisting of O, S, N (R 4 ) and C (R 5 ) (R 6 );
    Z1 및 Z2는 각각 독립적으로 N 또는 C(R7)이며;Z 1 and Z 2 are each independently N or C (R 7 );
    L1 내지 L4는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
    R1 내지 R7은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R3 내지 R7 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 1 to R 7 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ of 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 ~ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ~ C 60 of the blood group and a C 6 ~ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they are attached may form a fused ring, wherein When each of R 3 to R 7 is plural, they are the same as or different from each other;
    상기 L1 내지 L4의 아릴렌기 및 헤테로아릴렌기와, R1 내지 R7의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 to L 4 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group of R 1 to R 7 , Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl 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 of the alkynyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ aryloxy of C 60 time, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 60 aryl amine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group and C When substituted or unsubstituted with one or more substituents selected from the group consisting of 6 to C 60 arylsilyl groups, and substituted with a plurality of substituents, they may be the same or different from each other.
  2. 제1항에 있어서,The method of claim 1,
    상기 화학식 2로 표시되는 고리는 하기 화학식 4 내지 6 중 어느 하나로 표시되는 고리인 화합물:The ring represented by Formula 2 is a compound represented by any one of the following formulas 4 to 6:
    [화학식 4][Formula 4]
    Figure PCTKR2016014958-appb-I000090
    Figure PCTKR2016014958-appb-I000090
    [화학식 5][Formula 5]
    Figure PCTKR2016014958-appb-I000091
    Figure PCTKR2016014958-appb-I000091
    [화학식 6][Formula 6]
    Figure PCTKR2016014958-appb-I000092
    Figure PCTKR2016014958-appb-I000092
    상기 화학식 4 내지 6에서, In Chemical Formulas 4 to 6,
    점선은 축합이 이루어지는 부분을 의미하고;The dotted line means the part where condensation takes place;
    R5 및 R6은 제1항에서 정의된 바와 같다. R 5 and R 6 are as defined in claim 1.
  3. 제1항에 있어서,The method of claim 1,
    상기 화학식 3으로 표시되는 고리는 하기 화학식 7 내지 12 중 어느 하나로 표시되는 고리인 화합물:The ring represented by Formula 3 is a compound represented by any one of the following formulas 7 to 12:
    [화학식 7][Formula 7]
    Figure PCTKR2016014958-appb-I000093
    Figure PCTKR2016014958-appb-I000093
    [화학식 8][Formula 8]
    Figure PCTKR2016014958-appb-I000094
    Figure PCTKR2016014958-appb-I000094
    [화학식 9][Formula 9]
    Figure PCTKR2016014958-appb-I000095
    Figure PCTKR2016014958-appb-I000095
    [화학식 10][Formula 10]
    Figure PCTKR2016014958-appb-I000096
    Figure PCTKR2016014958-appb-I000096
    [화학식 11][Formula 11]
    Figure PCTKR2016014958-appb-I000097
    Figure PCTKR2016014958-appb-I000097
    [화학식 12][Formula 12]
    Figure PCTKR2016014958-appb-I000098
    Figure PCTKR2016014958-appb-I000098
    상기 화학식 7 내지 12에서, In Chemical Formulas 7 to 12,
    점선은 축합이 이루어지는 부분을 의미하고;The dotted line means the part where condensation takes place;
    R4 및 R7은 제1항에서 정의된 바와 같으나, 상기 화학식 9에서, 2개의 R7은 서로 동일하거나 상이하다. R 4 and R 7 are gateuna as defined in claim 1, wherein in the formula (9), two R 7 are the same or different from each other.
  4. 제1항에 있어서,The method of claim 1,
    상기 L1 내지 L4는 각각 독립적으로 단일결합, 페닐렌기, 비페닐렌기, 피리디닐기, 피리미디닐기, 나프탈레닐기, 플루오레닐기 및 카바졸릴기로 이루어진 군에서 선택되는 화합물.L 1 to L 4 are each independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a pyridinyl group, a pyrimidinyl group, a naphthalenyl group, a fluorenyl group, and a carbazolyl group.
  5. 제1항에 있어서,The method of claim 1,
    상기 R1 및 R2는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되는 화합물.R 1 and R 2 are each independently selected from the group consisting of C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms.
  6. 제1항에 있어서,The method of claim 1,
    상기 R1 및 R2는 각각 독립적으로 메틸기, 에틸기, 프로필기 및 하기 화학식 13 내지 17로 표시되는 치환기로 이루어진 군에서 선택되는 화합물:Wherein R 1 and R 2 are each independently selected from the group consisting of a methyl group, an ethyl group, a propyl group and a substituent represented by the following Formulas 13 to 17:
    [화학식 13][Formula 13]
    Figure PCTKR2016014958-appb-I000099
    Figure PCTKR2016014958-appb-I000099
    [화학식 14][Formula 14]
    Figure PCTKR2016014958-appb-I000100
    Figure PCTKR2016014958-appb-I000100
    [화학식 15][Formula 15]
    Figure PCTKR2016014958-appb-I000101
    Figure PCTKR2016014958-appb-I000101
    [화학식 16][Formula 16]
    Figure PCTKR2016014958-appb-I000102
    Figure PCTKR2016014958-appb-I000102
    [화학식 17][Formula 17]
    Figure PCTKR2016014958-appb-I000103
    Figure PCTKR2016014958-appb-I000103
    상기 화학식 13 내지 17에서, In Chemical Formulas 13 to 17,
    *는 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
    T1 내지 T8은 각각 독립적으로 N 또는 C(R8)이며;T 1 to T 8 are each independently N or C (R 8 );
    상기 화학식 14에서 L2 또는 L4에 결합되는 T1 내지 T4 중 어느 하나는 C(R8)이고, 이때 상기 R8은 부재이며;In Formula 14, any one of T 1 to T 4 bonded to L 2 or L 4 is C (R 8 ), wherein R 8 is absent;
    R8 내지 R11은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R8이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 8 to R 11 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 ~ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ~ C 60 of the blood group and a C 6 ~ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they are attached may form a fused ring, wherein When there are a plurality of R 8 , they are the same or different from each other;
    상기 R8 내지 R11의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The 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 8 to R 11 boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C 1 ~ alkenyl group of the C 40 alkyl group, C 2 ~ C 40 of, 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 atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ selected from the group consisting of C 60 aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.
  7. 제1항에 있어서,The method of claim 1,
    상기 R1 및 R2 중 적어도 하나는 하기 화학식 F-1 내지 F-13으로 이루어진 군에서 선택되는 치환기인 화합물:At least one of R 1 and R 2 is a substituent selected from the group consisting of Formulas F-1 to F-13:
    Figure PCTKR2016014958-appb-I000104
    Figure PCTKR2016014958-appb-I000104
    상기 화학식 F-1 내지 F-13에서, In Chemical Formulas F-1 to F-13,
    *는 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
    t는 0 내지 5의 정수이며;t is an integer from 0 to 5;
    l은 0 내지 4의 정수이며;l is an integer from 0 to 4;
    v는 0 내지 3의 정수이며;v is an integer from 0 to 3;
    u는 0 내지 2의 정수이며;u is an integer from 0 to 2;
    R8은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;R 8 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 condensed ring may be formed by combining with or adjacent to a group selected from the group consisting of a silyl group, a C 6 -C 60 mono or diarylphosphinyl group and a C 6 -C 60 arylamine group;
    R12는 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R12가 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 12 is 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, nuclear atom C 5 to C 60 aryloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group selected from the group or may be combined with adjacent groups to form a condensed ring, when there are a plurality of R 12 They are the same or different from each other;
    상기 R8 및 R12의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The 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 and aryl of R 8 and R 12 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 atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group selected from the group When substituted or unsubstituted with one or more substituents and substituted with a plurality of substituents, they may be the same or different from each other.
  8. 제6항에 있어서,The method of claim 6,
    상기 R9 내지 R11은 각각 독립적으로 수소, C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되는 화합물.R 9 to R 11 are each independently hydrogen, C 1 ~ C 40 Alkyl group, C 6 ~ C 60 An aryl group and a nuclear atom of 5 to 60 heteroaryl group selected from the group consisting of.
  9. 제1항에 있어서,The method of claim 1,
    상기 화합물은 하기 화학식 18로 표시되는 화합물:The compound is a compound represented by the following formula (18):
    [화학식 18][Formula 18]
    Figure PCTKR2016014958-appb-I000105
    Figure PCTKR2016014958-appb-I000105
    상기 화학식 18에서,In Chemical Formula 18,
    K1은 단일결합, C(R13)(R14), N(R15), O 및 S로 이루어진 군에서 선택되며;K 1 is selected from the group consisting of a single bond, C (R 13 ) (R 14 ), N (R 15 ), O and S;
    R13 내지 R15는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고;R 13 to R 15 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 ~ for C 60 aryl phosphazene group, and groups bonded to adjacent or 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 which they are attached may form a condensed ring;
    상기 R13 내지 R15의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있으며;The 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 13 to R 15 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 atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ selected from the group consisting of C 60 aryl silyl When unsubstituted or substituted with one or more substituents substituted with a plurality of substituents, they may be the same or different from each other;
    X1과 X2, X2와 X3, X3와 X4, X5와 X6, X6과 X7, 및 X7과 X8 중 적어도 하나는 각각 독립적으로 하기 화학식 2 또는 3으로 표시되는 고리와 축합되어 축합고리를 형성하며;At least one of X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 are each independently represented by the following Chemical Formula 2 or 3 Condensed with the ring to form a condensed ring;
    하기 화학식 2 또는 3으로 표시되는 고리와 축합고리를 형성하지 않는 X1 내지 X8, 및 X9 내지 X16은 각각 독립적으로 N 또는 C(R3)이며;X 1 to X 8 , and X 9 to X 16 which do not form a condensed ring with a ring represented by the following Chemical Formula 2 or 3 are each independently N or C (R 3 );
    [화학식 2][Formula 2]
    Figure PCTKR2016014958-appb-I000106
    Figure PCTKR2016014958-appb-I000106
    [화학식 3][Formula 3]
    Figure PCTKR2016014958-appb-I000107
    Figure PCTKR2016014958-appb-I000107
    상기 화학식 2, 3 및 18에서,In Chemical Formulas 2, 3, and 18,
    점선은 축합이 이루어지는 부분을 의미하고;The dotted line means the part where condensation takes place;
    Y1 내지 Y3는 각각 독립적으로 O, S, N(R4) 및 C(R5)(R6)로 이루어진 군에서 선택되며; Y 1 to Y 3 are each independently selected from the group consisting of O, S, N (R 4 ) and C (R 5 ) (R 6 );
    Z1 및 Z2는 각각 독립적으로 N 또는 C(R7)이며;Z 1 and Z 2 are each independently N or C (R 7 );
    R3 내지 R7은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R3 내지 R7 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 3 to R 7 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 ~ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ~ C 60 of the blood group and a C 6 ~ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they are attached may form a fused ring, wherein When each of R 3 to R 7 is plural, they are the same as or different from each other;
    상기 R3 내지 R7의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The 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 3 to R 7 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 atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ selected from the group consisting of C 60 aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.
  10. 제1항에 있어서,The method of claim 1,
    상기 R3 내지 R7 중 적어도 하나는 각각 독립적으로 하기 화학식 19로 표시되는 치환기인 화합물:At least one of the R 3 to R 7 are each independently a substituent represented by the formula (19):
    [화학식 19][Formula 19]
    Figure PCTKR2016014958-appb-I000108
    Figure PCTKR2016014958-appb-I000108
    상기 화학식 19에서, In Chemical Formula 19,
    *은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
    L5 및 L6은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 5 and L 6 are selected from the group consisting of a single bond, a C 6 -C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
    R16은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;R 16 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 condensed ring may be formed by combining with or adjacent to a group selected from the group consisting of a silyl group, a C 6 -C 60 mono or diarylphosphinyl group and a C 6 -C 60 arylamine group;
    상기 L5 및 L6의 아릴렌기 및 헤테로아릴렌기와, R16의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 5 and L 6 , alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine of R 16 Group, alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group and aryl silyl 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 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom of 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 When substituted by one or more substituents selected from the group consisting of a reel, or silyl which is Beach ring, substituted with a plurality of substituents, they may be the same or different from each other.
  11. 제10항에 있어서,The method of claim 10,
    상기 L5 및 L6은 각각 독립적으로 단일결합, 페닐렌기, 비페닐렌기, 피리디닐기, 피리미디닐기, 나프탈레닐기, 플루오레닐기, 카바졸릴기, 퀴놀리닐기 및 퀴나졸리닐기로 이루어진 군에서 선택되는 화합물.L 5 and L 6 are each independently a group consisting of a single bond, phenylene group, biphenylene group, pyridinyl group, pyrimidinyl group, naphthalenyl group, fluorenyl group, carbazolyl group, quinolinyl group and quinazolinyl group Compound selected from.
  12. 제10항에 있어서,The method of claim 10,
    상기 R16은 하기 화학식 20 내지 25로 이루어진 군에서 선택되는 치환기인 화합물:Wherein R 16 is a substituent selected from the group consisting of Formulas 20 to 25:
    [화학식 20][Formula 20]
    Figure PCTKR2016014958-appb-I000109
    Figure PCTKR2016014958-appb-I000109
    [화학식 21][Formula 21]
    Figure PCTKR2016014958-appb-I000110
    Figure PCTKR2016014958-appb-I000110
    [화학식 22][Formula 22]
    Figure PCTKR2016014958-appb-I000111
    Figure PCTKR2016014958-appb-I000111
    [화학식 23][Formula 23]
    Figure PCTKR2016014958-appb-I000112
    Figure PCTKR2016014958-appb-I000112
    [화학식 24][Formula 24]
    Figure PCTKR2016014958-appb-I000113
    Figure PCTKR2016014958-appb-I000113
    [화학식 25][Formula 25]
    Figure PCTKR2016014958-appb-I000114
    Figure PCTKR2016014958-appb-I000114
    상기 화학식 20 내지 25에서,In Formula 20 to 25,
    *은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
    M1 내지 M8은 각각 독립적으로 N 또는 C(R19)이며;M 1 to M 8 are each independently N or C (R 19 );
    상기 화학식 21에서 L6에 결합되는 M1 내지 M4 중 어느 하나는 C(R19)이고, 이때 상기 R19는 부재이며;Any one of M 1 to M 4 bonded to L 6 in Formula 21 is C (R 19 ), wherein R 19 is absent;
    K2 및 K3는 각각 독립적으로 단일결합, C(R20)(R21), N(R22), O, S 및 SO2로 이루어진 군에서 선택되나, K2 및 K3 모두가 단일결합은 아니며;K 2 and K 3 are each independently selected from the group consisting of a single bond, C (R 20 ) (R 21 ), N (R 22 ), O, S and SO 2 , but both K 2 and K 3 are a single bond Not;
    Y4는 O, S, C(R20)(R21) 및 N(R22)로 이루어진 군에서 선택되며; Y 4 is selected from the group consisting of O, S, C (R 20 ) (R 21 ) and N (R 22 );
    Z3 내지 Z6은 각각 독립적으로 N 또는 C(R19)이며;Z 3 to Z 6 are each independently N or C (R 19 );
    m 및 n은 각각 독립적으로 0 내지 4의 정수이며;m and n are each independently an integer from 0 to 4;
    R17 및 R18은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R17 및 R18 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 17 and R 18 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 to C 60 mono or diaryl phosphinyl group, and a C 6 to C 60 arylamine group may be combined with or adjacent to a group to form a condensed ring, and R 17 and R 18, respectively In this case, these are the same or different, and plural individual;
    R19 내지 R22는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R19 내지 R22 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 19 to R 22 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 ~ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ~ C 60 of the blood group and a C 6 ~ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they are attached may form a fused ring, wherein When each of R 19 to R 22 plural is the same or different from each other;
    상기 R17 내지 R22의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The 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 17 to R 22 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 atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they may be the same or different from each other.
  13. 제10항에 있어서,The method of claim 10,
    상기 R16은 하기 화학식 26 내지 29로 이루어진 군에서 선택되는 치환기인 화합물:R 16 is a compound selected from the group consisting of the following Formulas 26 to 29:
    [화학식 26][Formula 26]
    Figure PCTKR2016014958-appb-I000115
    Figure PCTKR2016014958-appb-I000115
    [화학식 27][Formula 27]
    Figure PCTKR2016014958-appb-I000116
    Figure PCTKR2016014958-appb-I000116
    [화학식 28][Formula 28]
    Figure PCTKR2016014958-appb-I000117
    Figure PCTKR2016014958-appb-I000117
    [화학식 29][Formula 29]
    Figure PCTKR2016014958-appb-I000118
    Figure PCTKR2016014958-appb-I000118
    상기 화학식 26 내지 29에서,In Chemical Formulas 26 to 29,
    *은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
    R23 내지 R25는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고;R 23 to R 25 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 ~ for C 60 aryl phosphazene group, and groups bonded to adjacent or 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 which they are attached may form a condensed ring;
    상기 R23 내지 R25의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The 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 23 to R 25 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 atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they may be the same or different from each other.
  14. 제13항에 있어서,The method of claim 13,
    상기 R23 내지 R25는 각각 독립적으로 수소, C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되는 화합물.R 23 to R 25 are each independently hydrogen, a C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group and a nuclear atom of 5 to 60 heteroaryl group selected from the group consisting of.
  15. 제10항에 있어서,The method of claim 10,
    상기 R16은 하기 B-1 내지 B-22로 이루어진 군에서 선택되는 치환기인 화합물:R 16 is a substituent selected from the group consisting of B-1 to B-22:
    Figure PCTKR2016014958-appb-I000119
    Figure PCTKR2016014958-appb-I000119
    상기 화학식 B-1 내지 B-22에서,In Chemical Formulas B-1 to B-22,
    *은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
    t는 0 내지 5의 정수이며;t is an integer from 0 to 5;
    l 및 s는 각각 독립적으로 0 내지 4의 정수이며;l and s are each independently an integer from 0 to 4;
    v는 0 내지 3의 정수이며;v is an integer from 0 to 3;
    u는 0 내지 2의 정수이며;u is an integer from 0 to 2;
    R19 내지 R22는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고;R 19 to R 22 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 ~ for C 60 aryl phosphazene group, and groups bonded to adjacent or 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 which they are attached may form a condensed ring;
    R26 및 R27은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R26 및 R27 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 26 and R 27 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 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ~ C 60, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring, and When there are a plurality of R 26 and R 27 s , they are the same as or different from each other;
    상기 R19 내지 R22, R26 및 R27의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.R 19 to R 22 , Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group of R 26 and R 27 , 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, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ aryloxy C 60, C 1 ~ alkyloxy group of C 40 of, C 6 ~ C 60 arylamine group, C 3 -C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ for C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, one selected from the group consisting of a C 6 ~ C 60 aryl silyl mono- or diaryl phosphine blood group and C 6 ~ C 60 of the If the ring is substituted or unsubstituted, substituted by a plurality of substituent on the substituents, they may be the same or different from each other.
  16. 제1항에 있어서,The method of claim 1,
    상기 화합물은 아래의 화합물로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물:The compound is selected from the group consisting of the following compounds:
    Figure PCTKR2016014958-appb-I000120
    Figure PCTKR2016014958-appb-I000120
    Figure PCTKR2016014958-appb-I000121
    Figure PCTKR2016014958-appb-I000121
    Figure PCTKR2016014958-appb-I000122
    Figure PCTKR2016014958-appb-I000122
    Figure PCTKR2016014958-appb-I000123
    Figure PCTKR2016014958-appb-I000123
    Figure PCTKR2016014958-appb-I000124
    Figure PCTKR2016014958-appb-I000124
    Figure PCTKR2016014958-appb-I000125
    Figure PCTKR2016014958-appb-I000125
    Figure PCTKR2016014958-appb-I000126
    Figure PCTKR2016014958-appb-I000126
  17. (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode,
    상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항의 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.At least one of the one or more organic material layer is an organic electroluminescent device, characterized in that it comprises a compound represented by the formula (1) of claim 1.
  18. 제17항에 있어서,The method of claim 17,
    상기 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 전자 수송층, 전자 수송 보조층, 전자 주입층, 수명 개선층, 발광층 및 발광 보조층으로 이루어진 군에서 선택되는 유기 전계 발광 소자.The organic material layer including the compound is selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a life improvement layer, a light emitting layer and a light emitting auxiliary layer.
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