WO2021190380A1 - Composé organique, composant électronique et dispositif électronique - Google Patents

Composé organique, composant électronique et dispositif électronique Download PDF

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WO2021190380A1
WO2021190380A1 PCT/CN2021/081373 CN2021081373W WO2021190380A1 WO 2021190380 A1 WO2021190380 A1 WO 2021190380A1 CN 2021081373 W CN2021081373 W CN 2021081373W WO 2021190380 A1 WO2021190380 A1 WO 2021190380A1
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carbon atoms
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groups
ring
substituted
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郑奕奕
马天天
刘新颖
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陕西莱特光电材料股份有限公司
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    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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Definitions

  • This application relates to the technical field of organic materials, in particular to an organic compound, an electronic component and an electronic device.
  • OLED Organic electroluminescent materials
  • Organic light-emitting devices generally include an anode, a cathode, and an organic material layer in between.
  • the organic material layer is usually formed in a multi-layer structure composed of different materials to improve the brightness, efficiency and life of the organic electroluminescent device.
  • the organic material layer may be a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and Electron injection layer and other components.
  • holes and electrons are injected into the organic material layer from the anode and the cathode respectively, and excitons are formed when the injected holes and electrons meet, and when these excitons return Glows in the ground state.
  • the purpose of this application is to provide an organic compound, electronic component and electronic device to improve the performance of the organic electroluminescent device.
  • an organic compound is provided, and the organic compound includes the structures shown in Chemical Formula 1 and Chemical Formula 2:
  • * represents the connection point where the chemical formula 2 and the chemical formula 1 are fused
  • the ring A 1 , the ring A 2 and the ring B are the same or different from each other, and are each independently selected from a benzene ring or a fused aromatic ring having 10-14 ring carbon atoms, and at least the ring A 1 and the ring A 2 One is a fused aromatic ring with 10-14 ring carbon atoms, and the structure shown in Chemical Formula 2 is combined with any one of Ring A 1 and Ring A 2 of Chemical Formula 1 through two * to form a fused ring;
  • L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
  • R 1 , R 2 , and R 3 are the same or different from each other, and are each independently selected from deuterium, cyano, halogen group, substituted or unsubstituted alkyl group with 1-20 carbon atoms, substituted or unsubstituted carbon An aryl group having 6 to 30 atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms;
  • R 4 is selected from substituted or unsubstituted alkyl groups with 1-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heterocyclic groups with 3-30 carbon atoms Aryl, substituted or unsubstituted cycloalkyl with 3-20 carbon atoms;
  • n 1 -n 3 to n-t represents, R 1 -R 3 to R & lt t represents, t is a variable indicating an arbitrary integer of 1-3, n-t t represents the number of substituents R < when t is 1, 2, When 3, n t is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10; when n t is greater than 1, any two R t are the same or different;
  • R 1 , R 2 , R 3 , R 4 and L are each independently selected from: deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3-20 carbon atoms, and 6 carbon atoms -20 aryl, 3-12 trialkylsilyl, 8-12 arylsilyl, 1-10 alkyl, 1 carbon -10 haloalkyl, carbon 2-6 alkenyl, carbon 2-6 alkynyl, carbon 3-10 cycloalkyl, carbon 2-10 heterocycle Alkyl groups, cycloalkenyl groups with 5-10 carbon atoms, heterocycloalkenyl groups with 4-10 carbon atoms, alkoxy groups with 1-10 carbon atoms, and alkylamines with 1-10 carbon atoms Group, alkylthio group with 1-10 carbon atoms, aryloxy group with 6-18 carbon atoms, arylthio group with 6-18 carbon atoms, phosphoroxy group with 6-18 carbon atoms, An alkylthio group
  • R 4 and L when there are two substituents on the same atom, optionally, the two substituents are connected to each other to form a 5-13 membered saturated or unsaturated ring together with the atoms to which they are commonly connected.
  • an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer provided between the anode and the cathode; the functional layer includes the above-mentioned organic compound.
  • an electronic device including the above-mentioned electronic component.
  • FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • FIG. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
  • FIG. 3 is a schematic structural diagram of an electronic device according to another embodiment of the present application.
  • Anode 100 hole injection layer 310; first hole transport layer 321; second hole transport layer 322; organic electroluminescent layer 330; hole blocking layer 340; electron transport layer 350; electron injection layer 360; cathode 200 ;Electronic device 400; Electronic device 500.
  • the organic compound of this embodiment includes the structures shown in Chemical Formula 1 and Chemical Formula 2:
  • * represents the connection point where the chemical formula 2 and the chemical formula 1 are fused
  • the ring A 1 , the ring A 2 and the ring B are the same or different from each other, and are each independently selected from a benzene ring or a fused aromatic ring having 10-14 ring carbon atoms, and at least the ring A 1 and the ring A 2 One is a fused aromatic ring with 10-14 ring carbon atoms, and the structure shown in Chemical Formula 2 is combined with any one of Ring A 1 and Ring A 2 of Chemical Formula 1 through two * to form a fused ring;
  • L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
  • R 1 , R 2 , and R 3 are the same or different from each other, and are each independently selected from deuterium, cyano, halogen group, substituted or unsubstituted alkyl group with 1-20 carbon atoms, substituted or unsubstituted carbon An aryl group having 6 to 30 atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms;
  • R 4 is selected from substituted or unsubstituted alkyl groups with 1-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heterocyclic groups with 3-30 carbon atoms Aryl, substituted or unsubstituted cycloalkyl with 3-20 carbon atoms;
  • n 1 -n 3 to n-t represents, R 1 -R 3 to R & lt t represents, t is a variable indicating an arbitrary integer of 1-3, n-t t represents the number of substituents R < when t is 1, 2, When 3, n t is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10; when n t is greater than 1, any two R t are the same or different;
  • R 1 , R 2 , R 3 , R 4 and L are each independently selected from: deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3-20 carbon atoms, and 6 carbon atoms -20 aryl, 3-12 trialkylsilyl, 8-12 arylsilyl, 1-10 alkyl, 1 carbon -10 haloalkyl, carbon 2-6 alkenyl, carbon 2-6 alkynyl, carbon 3-10 cycloalkyl, carbon 2-10 heterocycle Alkyl groups, cycloalkenyl groups with 5-10 carbon atoms, heterocycloalkenyl groups with 4-10 carbon atoms, alkoxy groups with 1-10 carbon atoms, and alkylamines with 1-10 carbon atoms Group, alkylthio group with 1-10 carbon atoms, aryloxy group with 6-18 carbon atoms, arylthio group with 6-18 carbon atoms, phosphoroxy group with 6-18 carbon atoms, An alkylthio group
  • R 4 and L when there are two substituents on the same atom, optionally, the two substituents are connected to each other to form a 5-13 membered saturated or unsaturated ring together with the atoms to which they are commonly connected.
  • the organic compound includes the structures shown in Chemical Formula 1 and Chemical Formula 2
  • the organic compound of the present application has a structure formed by condensing Chemical Formula 1 and Chemical Formula 2.
  • the rings A 1 , A 2 , and B may be a benzene ring or a naphthalene ring.
  • two substituents are connected to each other to form a 5-13 membered saturated or unsaturated ring together with the atoms to which they are connected
  • two substituents can be connected to each other to connect to them.
  • the atoms together form a 5-13-membered saturated or unsaturated ring, or they may not form a 5-13-membered saturated or unsaturated ring together with the atoms they are connected to together.
  • each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine", and its meaning is:
  • formula Q-1 represents q substituents R" on the benzene ring , Each R" can be the same or different, and the options of each R" do not affect each other;
  • formula Q-2 means that there are q substituents R" on each benzene ring of biphenyl, and R on two benzene rings The number q of "substituents can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.
  • substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for ease of description, the substituents are collectively referred to as Rc).
  • the "substituted or unsubstituted aryl group” refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • the above-mentioned substituents, namely Rc can be, for example, deuterium, halogen groups, cyano groups, heteroaryl groups with 3-20 carbon atoms, aryl groups with 6-20 carbon atoms, and those with 3-12 carbon atoms.
  • Trialkylsilyl group triarylsilyl group with 18-30 carbon atoms, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, alkene with 2-6 carbon atoms Group, alkynyl with 2-6 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, cycloalkenyl with 5-10 carbon atoms, Heterocyclenyl groups with 4-10 carbon atoms, alkoxy groups with 1-10 carbon atoms, alkylthio groups with 1-10 carbon atoms, aryloxy groups with 6-18 carbon atoms, carbon An arylthio group with 6-18 atoms, a phosphoroxy group with 6-18 carbon atoms, an alkylsulfonyl group with 6-18 carbon atoms, a trialkylphosphino group with 3-18 carbon atoms, A trialkylboron group having 3-18 carbon atoms.
  • the organic compound of the present application may have any structure in the following chemical formulas:
  • a 1 cannot be a benzene ring.
  • the core structure of this application is a planar structure formed by fused indole on adamantane spirofluorene fused with aromatic ring; this structure introduces indolyl modification, and fused aromatic ring on adamantane spirofluorene ,
  • enhancing the rigidity of the compound increasing the hole mobility, and having a high first triplet energy level, so it is suitable for the host material of the light-emitting layer in organic electroluminescent materials; it is applied to single-component bipolar It can enhance the efficiency and life of organic electroluminescent device when it is one of the host materials of the two-component mixed type.
  • adamantane is combined with the condensed planar structure in a spiral manner, it can effectively reduce the intermolecular stacking. Improve the film-forming properties of the compound and further increase the life of the device.
  • the number of carbon atoms of L, R 1 , R 2 , R 3 , and R 4 refers to the total number of carbon atoms.
  • L is selected from substituted arylene groups having 10 carbon atoms, all carbon atoms of the arylene group and the substituents thereon are 10.
  • hetero means that a functional group includes at least one heteroatom such as B, N, O, S, Si, Se, or P, and the remaining atoms are carbon and hydrogen.
  • the unsubstituted alkyl group may be a "saturated alkyl group" without any double or triple bonds.
  • alkyl may include linear or branched alkyl.
  • Alkyl groups can have 1 to 20 carbon atoms.
  • a numerical range such as “1 to 20” refers to each integer in the given range; for example, "1 to 20 carbon atoms” means that it can contain 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.
  • the alkyl group may also be a medium-sized alkyl group having 1 to 10 carbon atoms.
  • the alkyl group may also be a lower alkyl group having 1 to 5 carbon atoms.
  • alkyl groups having 1-20 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl Base, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, n-dodecyl, n-tetradecyl , N-hexadecyl and so on.
  • alkenyl refers to a hydrocarbon group containing one or more double bonds in a straight or branched hydrocarbon chain. Alkenyl groups can be unsubstituted or substituted. Alkenyl groups can have 1 to 20 carbon atoms, and whenever appearing herein, a numerical range such as “1 to 20" refers to each integer in the given range; for example, "1 to 20 carbon atoms” means that Contains 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms , 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms or 20 carbon atoms ⁇ alkenyl.
  • the alkenyl group may be vinyl, butadiene,
  • cycloalkyl refers to a saturated hydrocarbon containing an alicyclic structure, including monocyclic and condensed ring structures.
  • Cycloalkyl groups can have 3-20 carbon atoms, and a numerical range such as “3 to 20" refers to each integer in the given range; for example, "3 to 20 carbon atoms” means that it can contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, A cycloalkyl group of 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms, or 20 carbon atoms.
  • the cycloalkyl group may be a small ring, an ordinary ring, or a large ring having 3 to 20 carbon atoms. Cycloalkyl groups can also be classified as monocyclic-only one ring, bicyclic-two rings-or polycyclic-three or more rings. Cycloalkyl groups can also be divided into two rings sharing one carbon atom-a spiro ring, two rings sharing two carbon atoms-a fused ring, and two rings sharing two or more carbon atoms-a bridged ring. In addition, cycloalkyl groups may be substituted or unsubstituted.
  • an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • the aryl group can be a monocyclic aryl group or a polycyclic aryl group.
  • the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups conjugated by a carbon-carbon bond, through A monocyclic aryl group and a fused ring aryl group conjugated by carbon-carbon bonds, and two or more fused ring aryl groups conjugated by a carbon-carbon bond. That is, two or more aromatic groups conjugated through carbon-carbon bonds can also be regarded as aryl groups in the present application.
  • the aryl group does not contain heteroatoms such as B, N, O, S, P, and Si.
  • biphenyl, terphenyl, etc. are aryl groups.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] Phenanthryl, pyrenyl, benzofluoranthene, Base and so on.
  • the substituted aryl group may be one or more hydrogen atoms in the aryl group, such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group.
  • a substituted aryl group with 18 carbon atoms refers to an aryl group and a substituted group. The number of carbon atoms of the group is 18.
  • aryl group as the substituent include, but are not limited to: phenyl, naphthyl, anthracenyl, phenanthryl, dimethylfluorenyl, biphenyl and the like.
  • a heteroaryl group refers to a monovalent aromatic ring containing at least one heteroatom in the ring or a derivative thereof.
  • the heteroatom may be at least one of B, O, N, P, Si, and S.
  • the heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
  • the heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic
  • the ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, Acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazine Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thienyl, benzofur
  • thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type
  • N-arylcarbazolyl and N-heteroarylcarbazolyl are multiple groups conjugated through carbon-carbon bonds.
  • Heteroaryl group of ring system type is heteroaryl group of ring system type.
  • the substituted heteroaryl group may be one or more hydrogen atoms in the heteroaryl group, such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkane Group, cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • the number of carbon atoms of the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.
  • heteroaryl groups as substituents include but are not limited to: pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolinyl, quinazolinyl , Quinoxalinyl, etc.
  • aryl can be applied to arylene
  • heteroaryl can be applied to heteroarylene
  • alkyl can be applied to alkylene
  • cycloalkyl can be Applied to cycloalkylene
  • a ring system formed by n atoms is an n-membered ring.
  • phenyl is a 6-membered aryl group.
  • 6-10 membered aromatic ring refers to benzene ring, indene ring, naphthalene ring and so on.
  • the non-positioned link in this application refers to the single bond extending from the ring system It means that one end of the link can be connected to any position in the ring system that the bond penetrates, and the other end is connected to the rest of the compound molecule.
  • the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two non-positional linkages that penetrate the bicyclic ring, and the meaning represented by the formula (f) -1) Any possible connection mode shown in formula (f-10).
  • the phenanthryl group represented by the formula (X') is connected to other positions of the molecule through a non-localized bond extending from the middle of the benzene ring on one side, which means The meaning of includes any possible connection mode as shown in formula (X'-1) ⁇ formula (X'-4).
  • the non-positional substituent in this application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be attached to any possible position in the ring system.
  • the substituent R group represented by the formula (Y) is connected to the quinoline ring through a non-localized linkage, and its meaning includes the following formula (Y-1) to Any possible connection mode shown in formula (Y-7).
  • the halogen group can be, for example, fluorine, chlorine, bromine, or iodine.
  • the haloalkyl group may be, for example, trifluoromethyl, trichloromethyl, tribromomethyl, and the like.
  • trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
  • triarylsilyl examples include, but are not limited to, triphenylsilyl and the like.
  • the ring A 1 , the ring A 2 and the ring B are the same or different from each other, and are each independently selected from a benzene ring, a naphthalene ring, an anthracene ring or a phenanthrene ring, and the ring A 1 and the ring A 2 are At most one is a benzene ring.
  • ring B may be a benzene ring or a naphthalene ring.
  • R 1 , R 2 , R 3 , R 4 and L are the same or different from each other, and are each independently selected from the group consisting of deuterium, fluorine, cyano, and heterocycles with 3-20 carbon atoms.
  • chemical formula 1 is selected from any structure of chemical formula 1-1 to chemical formula 1-11:
  • * represents the connection point where the chemical formula 2 and the chemical formula 1 are condensed.
  • the chemical formula 2 is selected from any structure of chemical formulas 2-1, 2-2, 2-3, and 2-4:
  • each R 1 , R 2 , and R 3 are the same or different from each other, and are each independently selected from deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group with 1-10 carbon atoms, or the following The group consisting of groups (i-1) ⁇ (i-16);
  • R 4 is independently selected from the group consisting of substituted or unsubstituted alkyl groups with 1-10 carbon atoms or the following groups (i-1) to (i-16):
  • M 1 is selected from a single bond or
  • G 1 ⁇ G 5 and G '1 ⁇ G' 5 are each independently selected from N or C (F 1), and in G 1 ⁇ G 5 is selected from at least one N; when two or more of G 1 ⁇ G 5 when selected from C (F 1), the same as or different from any two F 1; when G '1 ⁇ G' in two or more selected from 4 C (F 1), any two identical or different F 1 ;
  • G 6 to G 13 are each independently selected from N or C(F 2 ), and at least one of G 6 to G 13 is selected from N; when two or more of G 6 to G 13 are selected from C(F 2 ) , Any two F 2 are the same or different;
  • G 14 to G 23 are each independently selected from N or C(F 3 ), and at least one of G 14 to G 23 is selected from N; when two or more of G 14 to G 23 are selected from C(F 3 ) , Any two F 3 are the same or different;
  • G 24 to G 33 are each independently selected from N or C(F 4 ), and at least one of G 24 to G 33 is selected from N; when two or more of G 24 to G 33 are selected from C(F 4 ) , Any two F 4 are the same or different;
  • H 1 is each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl with 3-12 carbon atoms, arylsilyl with 8-12 carbon atoms, carbon Alkyl groups with 1-10 atoms, haloalkyl groups with 1-10 carbon atoms, alkenyl groups with 2-6 carbon atoms, alkynyl groups with 2-6 carbon atoms, 3-10 carbon atoms Cycloalkyl groups with 2-10 carbon atoms, cycloalkenyl groups with 5-10 carbon atoms, heterocycloalkenyl groups with 4-10 carbon atoms, and 1-10 carbon atoms
  • H 2 to H 9 and H 21 are independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3-20 carbon atoms, trioxane with 3-12 carbon atoms Silyl group, arylsilyl group with 8-12 carbon atoms, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, and alkenyl group with 2-6 carbon atoms , Alkynyl with 2-6 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, cycloalkenyl with 5-10 carbon atoms, carbon Heterocyclenyl groups with 4-10 atoms, alkoxy groups with 1-10 carbon atoms, alkylamino groups with 1-10 carbon atoms, alkylthio groups with 1-10 carbon atoms, carbon atoms Aryloxy groups with 6-18 carbon atoms, arylthio groups with 6-18
  • H 10 to H 20 and F 1 to F 4 are independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, aryl groups with 6-20 carbon atoms, and those with 3-20 carbon atoms Heteroaryl groups, trialkylsilyl groups with 3-12 carbon atoms, arylsilyl groups with 8-12 carbon atoms, alkyl groups with 1-10 carbon atoms, 1-10 carbon atoms
  • h 1 ⁇ h 21 are represented by h k
  • H 1 ⁇ H 21 are represented by H k
  • k is a variable, representing any integer from 1 to 21
  • h k is the number of substituents H k ; wherein, when k is selected from 5 Or when 17, h k is selected from 1, 2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, h k is selected from 1, 2, 3 or 4; when k is selected When 1, 3, 4, 6, 9 or 14, h k is selected from 1, 2, 3, 4 or 5; when k is 13, h k is selected from 1, 2, 3, 4, 5 or 6; When k is selected from 10 or 19, h k is selected from 1, 2, 3, 4, 5, 6 or 7; when k is selected from 20, h k is selected from 1, 2, 3, 4, 5, 6, 7 or 8; when k is 11, h k is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; when h k is greater than 1, any two H k are the same or different;
  • K 1 is selected from O, S, Se, N(H 22 ), C(H 23 H 24 ), Si(H 25 H 26 ); wherein, H 22 to H 26 are each independently selected from: the number of carbon atoms is 6. -20 aryl, carbon 3-20 heteroaryl, carbon 1-10 alkyl, carbon 2-6 alkenyl, carbon 2-6 alkynyl , Cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, cycloalkenyl with 5-10 carbon atoms, heterocycloalkenyl with 4-10 carbon atoms , Or H 23 and H 24 are connected to each other to form a 5-13 membered saturated or unsaturated ring with the atoms they are connected to together, or H 25 and H 26 are connected to each other to form a 5 to 13 membered ring together with their commonly connected atoms
  • the saturated or unsaturated ring for example, in the chemical formula i-10 In, when M 1 is a single bond, H 19
  • Atoms forming a 5-13 membered saturated or unsaturated ring means H 23 and H 24 can be connected to each other to form a ring, or they can exist independently of each other; when H 23 and H 24 form a ring, the carbon of the ring
  • the number of atoms can be a 5-membered ring, for example It can also be a 6-membered ring, for example It can also be a 13-membered ring, for example
  • the number of carbon atoms forming the ring of H 23 and H 24 can also be other values, which will not be listed here, and this application does not specifically limit the number of carbon atoms of the ring;
  • K 2 is selected from a single bond, O, S, Se, N(H 27 ), C(H 28 H 29 ), Si(H 30 H 31 ); wherein, H 27 to H 31 are each independently selected from: carbon atoms Aryl groups with 6-20, heteroaryl groups with 3-20 carbon atoms, alkyl groups with 1-10 carbon atoms, alkenyl groups with 2-6 carbon atoms, 2-6 carbon atoms The alkynyl group, the cycloalkyl group with 3-10 carbon atoms, the heterocycloalkyl group with 2-10 carbon atoms, the cycloalkenyl group with 5-10 carbon atoms, the heterocyclic alkyl group with 4-10 carbon atoms Cycloalkenyl, or H 28 and H 29 are connected to each other to form a 5-13 membered saturated or unsaturated ring with the atoms they are connected to together , or H 30 and H 31 are connected to each other to form 5 For the -13-membered saturated or unsaturated ring,
  • each R 1 , R 2 , and R 3 are the same or different from each other, and are each independently selected from deuterium, cyano, fluorine, substituted or unsubstituted alkyl with 1-10 carbon atoms, substituted or unsubstituted Substituted aryl groups with 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-25 carbon atoms;
  • R 4 is selected from substituted or unsubstituted alkyl groups with 1-10 carbon atoms, substituted or unsubstituted aryl groups with 6-20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3-25 carbon atoms Aryl.
  • R 4 is selected from an alkyl group having 1 to 5 carbon atoms or substituted or unsubstituted W, and the unsubstituted W is selected from the group consisting of the following groups:
  • the substituent of W is selected from deuterium, fluorine, chlorine, cyano, silyl, alkyl with 1-5 carbon atoms, haloalkyl with 1-4 carbon atoms, carbon An aryl group having 6 to 12 atoms, an alkenyl group having 2 to 4 carbon atoms, and a heteroaryl group having 3 to 12 carbon atoms; when there are multiple substituents of W, the multiple substituents are the same or different.
  • R 4 is selected from alkyl groups having 1 to 5 carbon atoms or substituted or unsubstituted groups as follows:
  • the substituent is selected from deuterium, fluorine, chlorine, cyano, silyl, C1-5 alkyl, C1-4 haloalkyl, C6
  • the group consisting of -12 aryl group, carbon number 2-4 alkenyl group, and carbon number 3-12 heteroaryl group; when there are multiple substituents, the multiple substituents are the same or different.
  • R 4 is selected from:
  • the R 4 is selected from the group consisting of an alkyl group having 1 to 5 carbon atoms or the following groups:
  • R 4 is selected from substituted or unsubstituted alkyl groups with 1-5 carbon atoms, substituted or unsubstituted aryl groups with 6-18 carbon atoms, or substituted or unsubstituted carbon atoms with 12 -21 heteroaryl.
  • R 4 is selected from substituted or unsubstituted alkyl groups with 1-5 carbon atoms, substituted or unsubstituted aryl groups with 6-15 carbon atoms, or substituted or unsubstituted carbon atoms with 12 -23 heteroaryl.
  • the substituents on R 4 are the same or different, and are each independently selected from deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, pyridyl, and optionally Phenyl substituted by cyano or methyl, biphenyl, methyl, ethyl, isopropyl, tert-butyl, naphthyl, carbazolyl, dimethylfluorenyl, dibenzofuranyl, diphenyl And thienyl.
  • each of R 1 , R 2 , and R 3 are the same or different from each other, and are each independently selected from deuterium, cyano, fluorine, substituted or unsubstituted alkyl with 1-5 carbon atoms, substituted or unsubstituted The substituted aryl group having 6 to 18 carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms.
  • each R 1 , R 2 , and R 3 are the same or different from each other, and are each independently selected from deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl, dibenzofuranyl , Dibenzothienyl, phenyl, biphenyl, naphthyl, carbazolyl and N-phenylcarbazolyl.
  • L is selected from a single bond or a group consisting of a group represented by chemical formula j-1 to a group represented by chemical formula j-14:
  • M 2 is selected from a single bond or
  • Q 1 ⁇ Q 5 and Q '1 ⁇ Q' 5 are each independently selected from N or C (F 5), and in Q 1 ⁇ Q 5 is selected from at least one N; when two or more of Q 1 ⁇ Q 5 when C is selected from (F 5), any two F 5 identical or different, when Q '1 ⁇ Q' 4 is two or more selected from a C (F 5), any two identical or different F 5 ;
  • Q 6 to Q 13 are each independently selected from N or C(F 6 ), and at least one of Q 6 to Q 13 is selected from N; when two or more of Q 6 to Q 13 are selected from C(F 6 ) , Any two F 6 are the same or different;
  • Q 14 to Q 23 are each independently selected from N or C(F 7 ), and at least one of Q 14 to Q 23 is selected from N; when two or more of Q 14 to Q 23 are selected from C(F 7 ) , Any two F 7s are the same or different;
  • Q 24 to Q 33 are each independently selected from N or C(F 8 ), and at least one of Q 24 to Q 33 is selected from N; when two or more of Q 24 to Q 33 are selected from C(F 8 ) , Any two F 8s are the same or different;
  • E 1 to E 14 and F 5 to F 9 are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl groups with 3-20 carbon atoms, and those with 6-20 carbon atoms
  • Haloalkyl alkenyl having 2-6 carbon atoms, alkynyl having 2-6 carbon atoms, cycloalkyl having 3-10 carbon atoms, heterocycloalkyl having 2-10 carbon atoms, Cycloalkenyl with 5-10 carbon atoms, heterocycloalkenyl with 4-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylamino with 1-10 carbon atoms, carbon Alkylthio groups with 1-10 atoms, aryloxy groups with 6-18 carbon atoms,
  • E r E 1 ⁇ E 14 to E represented by r
  • r is a variable, represents any integer of 1 to 14, E r E r represents the number of substituents; and when r is selected from 1,2 , 3, 4, 5, 6, 9, 13, or 14, e r is selected from 1, 2, 3 or 4; when r is selected from 7 or 11, e r is selected from 1, 2, 3, 4, 5 Or 6; when r is 12, e r is selected from 1, 2, 3, 4, 5, 6 or 7; when r is selected from 8 or 10, e r is selected from 1, 2, 3, 4, 5, 6, 7, or 8; when e r is greater than 1, any two E r are the same or different;
  • K 3 is selected from O, S, Se, N (E 15 ), C (E 16 E 17 ), Si (E 18 E 19 ); wherein, E 15 , E 16 , E 17 , E 18 , and E 19 are each independent Is selected from: aryl groups with 6-20 carbon atoms, heteroaryl groups with 3-20 carbon atoms, alkyl groups with 1-10 carbon atoms, alkenyl groups with 2-6 carbon atoms, carbon Alkynyl with 2-6 atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, cycloalkenyl with 5-10 carbon atoms, number of carbon atoms Is a 4-10 heterocycloalkenyl group, or E 16 and E 17 are connected to each other to form a 5-13 membered saturated or unsaturated ring with the atoms they are connected to together; or E 18 and E 19 are connected to each other to share with them The connected atoms together form a 5-13-
  • This application does not specifically limit the number of carbon atoms forming a ring of E 16 and E 17 , and the number of carbon atoms forming a ring of E 18 and E 19.
  • E 16 and E The number of carbon atoms forming a ring of 17 and forming a ring of E 18 and E 19 is the same as that of forming a ring of H 23 and H 24 , which will not be repeated here;
  • K 4 is selected from single bond, O, S, Se, N (E 20 ), C (E 21 E 22 ), Si (E 23 E 24 ); wherein, E 20 to E 24 are each independently selected from: carbon atoms Aryl groups with 6-20 carbon atoms, heteroaryl groups with 3-20 carbon atoms, alkyl groups with 1-10 carbon atoms, alkenyl groups with 2-6 carbon atoms, and 2-6 carbon atoms The alkynyl group, the cycloalkyl group with 3-10 carbon atoms, the heterocycloalkyl group with 2-10 carbon atoms, the cycloalkenyl group with 5-10 carbon atoms, the heterocyclic alkyl group with 4-10 carbon atoms Cycloalkenyl, or E 21 and E 22 are connected to each other to form a 5-13 membered saturated or unsaturated ring with the atoms they are connected to together , or E 23 and E 24 are connected to each other to form 5 -13-membered saturated or unsaturated ring
  • the L is selected from a single bond, a substituted or unsubstituted arylene group with 6-20 carbon atoms, and a substituted or unsubstituted heteroarylene group with 3-20 carbon atoms.
  • the L is selected from a single bond or from the group consisting of the following groups:
  • the L is selected from a single bond or from the group consisting of the following groups:
  • the L is selected from a single bond or from the group consisting of the following groups:
  • L is selected from a single bond, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.
  • L is selected from a single bond, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroaryl group having 8 to 15 carbon atoms.
  • the substituents in L are each independently selected from: deuterium, fluorine, chlorine, bromine, cyano, pyridyl, phenyl, naphthyl, trimethylsilyl, methyl, ethyl, isopropyl , Tert-butyl.
  • L is selected from a single bond, or substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted dibenzofuranyl, Substituted or unsubstituted dibenzothienylene, substituted or unsubstituted 9,9-dimethylfluorenylene, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolylidene , Substituted or unsubstituted biphenylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted benzo[f]quinazolinylene, substituted or Unsubstituted benzo[h]quinazolinyl, substituted or unsubstituted fluoren
  • the organic compound is selected from the group consisting of the following compounds:
  • the application also provides an electronic component for realizing electro-optical conversion.
  • the electronic component includes an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer includes the organic compound of the present application.
  • the electronic component is an organic electroluminescent device.
  • the organic electroluminescent device includes an anode 100 and a cathode 200 disposed oppositely, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes the organic compound provided in the present application.
  • the functional layer 300 includes an organic electroluminescent layer 330, and the organic electroluminescent layer 330 includes an organic compound provided in the present application.
  • the organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 321, an electron blocking layer 322, and an organic electroluminescence as an energy conversion layer which are sequentially stacked.
  • the organic compound provided in the present application can be applied to the organic electroluminescent layer 330 of an organic electroluminescent device, and can effectively improve the lifetime of the organic electroluminescent device.
  • the anode 100 includes the following anode material, which is preferably a material with a large work function (work function) that facilitates injection of holes into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ] (PEDT), polypyrrole and polyaniline, but not limited thereto. It is preferable to include a transparent electrode containing indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the first hole transport layer 321 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds.
  • the hole transport layer 321 is composed of the compound HT-01 or HT-03.
  • the second hole transport layer 322 includes one or more electron blocking materials, and the electron blocking materials may be selected from carbazole polymers or other types of compounds, which are not specifically limited in this application.
  • the second hole transport layer 322 is composed of compounds HT-02, HT-04 or HT-05.
  • the organic electroluminescent layer 330 is composed of a host material and a guest material, and the compound of the present application may be used as the host material.
  • the holes injected into the organic light emitting layer 330 and the electrons injected into the organic electroluminescent layer 330 can recombine in the organic electroluminescent layer 330 to form excitons.
  • the excitons transfer energy to the host material, and the host material transfers energy to the guest material.
  • the guest material can emit light.
  • the guest material of the organic electroluminescent layer 330 may be a compound with a condensed aryl ring or a derivative thereof, a compound with a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials, which are not described in this application. Special restrictions.
  • the guest material of the organic electroluminescent layer 330 may be Ir(piq) 2 (acac) or Ir(ppy) 3 .
  • the cathode 200 includes the following cathode material, which is a material with a small work function that facilitates injection of electrons into the functional layer.
  • cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multilayer materials such as LiF/Al, Liq/ Al, LiO 2 /Al, LiF/Ca, LiF/Al, and BaF 2 /Ca, but not limited thereto. It is preferable to include a metal electrode containing silver and magnesium as a cathode.
  • a hole injection layer 310 may be further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321.
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application.
  • the hole injection layer 310 may be composed of F4-TCNQ.
  • an electron injection layer 360 may be further provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350.
  • the electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic substances.
  • the electron injection layer 360 may include ytterbium (Yb).
  • a hole blocking layer 340 may also be provided between the organic electroluminescent layer 330 and the electron transport layer 350.
  • the embodiments of the present application also provide an electronic device, which includes any one of the electronic components described in the above-mentioned electronic component embodiments. Since the electronic device has any one of the electronic components described in the above-mentioned electronic component embodiments, it has the same beneficial effects, which will not be repeated here in this application.
  • the present application provides an electronic device 400, which includes any one of the organic electroluminescent devices described in the foregoing organic electroluminescent device embodiments.
  • the electronic device 400 may be a display device, a lighting device, an optical communication device or other types of electronic devices, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, etc. Since the electronic device 400 has any one of the organic electroluminescent devices described in the foregoing organic electroluminescent device embodiments, it has the same beneficial effects, which will not be repeated here in this application.
  • the present application provides an electronic device 500, which includes any one of the photoelectric conversion devices described in the foregoing photoelectric conversion device embodiments.
  • the electronic device 500 may be a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera, or other types of electronic devices. Since the electronic device 500 has any one of the photoelectric conversion devices described in the foregoing photoelectric conversion device embodiments, it has the same beneficial effects, which will not be repeated here in this application.
  • the organic compound of the present application can be prepared by the method described in the present application.
  • the meaning of the substituent symbols in this application is the same as the meaning of the substituent symbols in Chemical Formula 1.
  • the chemical reactions described in this application can be used to appropriately prepare many other compounds in this application, and other methods for preparing organic compounds in this application are all considered to be within the scope of this application. within.
  • those skilled in the art can synthesize other organic compounds in this application by referring to or appropriately modifying the preparation methods provided in this application. Reagents, modification of reaction conditions, etc.
  • the anode is prepared by the following process: the thickness of ITO is
  • the ITO substrate is cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (thickness), and the photolithography process is used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns, and can use ultraviolet ozone and O 2 :N 2 plasma is used for surface treatment to increase the work function of the anode, and organic solvents can be used to clean the surface of the ITO substrate to remove impurities and grease on the surface of the ITO substrate.
  • the ITO substrate can also be cut into other sizes according to actual needs, and the size of the ITO substrate in this application is not specifically limited here.
  • F4-TCNQ was vacuum evaporated on the experimental substrate (anode) to form a thickness of Hole injection layer (HIL), and HT-01 is vapor-deposited on the hole injection layer to form a thickness of The first hole transport layer.
  • HIL Hole injection layer
  • the compound 1: GHn1: Ir(ppy) 3 was co-evaporated at a ratio of 50%: 45%: 5% to form a thickness of The green light-emitting layer (EML).
  • ET-01 and LiQ were mixed at a weight ratio of 1:1 and evaporated to form Thick electron transport layer (ETL), LiQ is vapor-deposited on the electron transport layer to form a thickness of The electron injection layer (EIL) is then mixed with magnesium (Mg) and silver (Ag) at a deposition rate of 1:9, and then vacuum deposited on the electron injection layer to form a thickness of The cathode.
  • ETL Thick electron transport layer
  • EIL Thick electron transport layer
  • Mg magnesium
  • Ag silver
  • the vapor deposition thickness on the above cathode is CP-1 to form an organic cover layer (CPL) to complete the manufacture of organic light-emitting devices.
  • Example 13 Except that the mixed components shown in Table 13 below replaced the mixed components in Example 1 when forming the light-emitting layer, the organic electroluminescent device was fabricated in the same manner as in Example 1.
  • Example 13 Except that the mixed components shown in Table 13 below replaced the mixed components in Example 1 when forming the light-emitting layer, the organic electroluminescent device was fabricated in the same manner as in Example 1.
  • Example 1-8 the compound of the present application was used as the host material for the green light-emitting layer. Compared with Comparative Example 1-3, under the premise of similar driving voltage and luminous efficiency, the method of Example 1-8 Compared with Comparative Examples 1-3, the lifetime of the device is increased by at least 44.7%.
  • the novel compound of the present application when used to prepare a green organic electroluminescent device, it can effectively extend the life of the organic electroluminescent device and improve the luminous efficiency to a certain extent.
  • Example 9 Red organic electroluminescent device
  • the anode is prepared by the following process: the thickness of ITO is
  • the ITO substrate is cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (thickness), and the photolithography process is used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns, and can use ultraviolet ozone and O 2 :N 2 plasma is used for surface treatment to increase the work function of the anode, and organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil on the surface of the ITO substrate.
  • the ITO substrate can also be cut into other sizes according to actual needs, and the size of the ITO substrate in this application is not specifically limited here.
  • F4-TCNQ was vacuum evaporated on the experimental substrate (anode) to form a thickness of Hole injection layer (HIL), and HT-03 is vapor-deposited on the hole injection layer to form a thickness of The first hole transport layer.
  • HIL Hole injection layer
  • the compound 44: Ir(piq) 2 (acac) was co-evaporated at a ratio of 95%: 5% to form a thickness of The red light-emitting layer (EML).
  • ET-02 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form Thick electron transport layer (ETL), LiQ is vapor-deposited on the electron transport layer to form a thickness of The electron injection layer (EIL) is then mixed with magnesium (Mg) and silver (Ag) at a deposition rate of 1:9, and then vacuum deposited on the electron injection layer to form a thickness of The cathode.
  • ETL Thick electron transport layer
  • EIL Thick electron transport layer
  • Mg magnesium
  • Ag silver
  • the vapor deposition thickness on the above cathode is CP-1 to form an organic cover layer (CPL) to complete the manufacture of organic light-emitting devices.
  • An organic electroluminescence device was produced in the same manner as in Example 9, except that the compound shown in Table 15 below was used instead of Compound 44 when forming the light-emitting layer.
  • the compounds of the present application are used as the host material of the red light-emitting layer.
  • the driving voltage of the device is reduced by at least 17.4%, the luminous efficiency is increased by at least 17.5%, and the lifetime is also improved.
  • the device driving voltage is equivalent, the luminous efficiency is increased by at least 17.2%, and the life of the device is increased by at least 85.9%.
  • the novel compound of the present application when used to prepare a red organic electroluminescent device, it can effectively improve the efficiency of the organic electroluminescent device, and at the same time, it has a great improvement effect on the lifetime.
  • Example 15 Red organic electroluminescent device
  • the anode is prepared by the following process: the thickness of ITO is
  • the ITO substrate is cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (thickness), and the photolithography process is used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns, and can use ultraviolet ozone and O 2 :N 2 plasma is used for surface treatment to increase the work function of the anode, and organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil on the surface of the ITO substrate.
  • the ITO substrate can also be cut into other sizes according to actual needs, and the size of the ITO substrate in this application is not specifically limited here.
  • F4-TCNQ was vacuum evaporated on the experimental substrate (anode) to form a thickness of Hole injection layer (HIL), and HT-03 is vapor-deposited on the hole injection layer to form a thickness of The first hole transport layer.
  • HIL Hole injection layer
  • the compound 76: RHn1: Ir(piq) 2 (acac) was co-evaporated at a ratio of 50%: 45%: 5% to form a thickness of The red light-emitting layer (EML).
  • ET-03 and LiQ were mixed in a weight ratio of 2:1 and evaporated to form Thick electron transport layer (ETL), LiQ is vapor-deposited on the electron transport layer to form a thickness of The electron injection layer (EIL) is then mixed with magnesium (Mg) and silver (Ag) at a deposition rate of 1:9, and then vacuum deposited on the electron injection layer to form a thickness of The cathode.
  • ETL Thick electron transport layer
  • EIL Thick electron transport layer
  • Mg magnesium
  • Ag silver
  • the vapor deposition thickness on the above cathode is CP-1 to form an organic cover layer (CPL), thereby completing the manufacture of organic light-emitting devices.
  • the organic electroluminescent device was fabricated in the same manner as in Example 15 except that the mixed components shown in Table 17 below were substituted for the mixed components in Example 15 when forming the light-emitting layer.
  • the organic electroluminescent device was fabricated in the same manner as in Example 15 except that the mixed components shown in Table 17 below were substituted for the mixed components in Example 15 when forming the light-emitting layer.
  • Examples 15-22 use the compound of the present application as the mixed host material for the red light-emitting layer. Compared with Comparative Examples 6 and 7, under the premise of similar driving voltage and luminous efficiency, the device life is increased by at least 17 %.
  • the novel compound of the present application when used to prepare a mixed-host red organic electroluminescent device, it can effectively increase the life of the organic electroluminescent device.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne le domaine technique des matériaux organiques, et concerne un composé organique comprenant des structures représentées par les formules chimiques 1 et 2, un composant électronique comprenant le composé, et un dispositif électronique. Le composé organique permet d'améliorer le rendement d'un dispositif organique électroluminescent, et d'en prolonger la durée de vie. Dans les structures, * indique un point de liaison au niveau duquel il y a une fusion entre la formule chimique 2 et la formule chimique 1; un anneau A1, un anneau A2, et un anneau B sont identiques ou différents les uns des autres et sont individuellement indépendamment choisis parmi un anneau benzène ou un anneau aromatique fusionné possédant 10 à 14 atomes de carbone de formation d'anneau, et au moins un anneau entre l'anneau A1 et l'anneau A2 est un anneau aromatique fusionné possédant de 10 à 14 atomes de carbone de formation d'anneau; dans la structure représentée par la formule chimique 2, un anneau fusionné est formé par combinaison de deux * soit avec l'anneau A1 soit avec l'anneau A2 de la formule chimique 1.
PCT/CN2021/081373 2020-03-27 2021-03-17 Composé organique, composant électronique et dispositif électronique WO2021190380A1 (fr)

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