CN117105989A - Compound as phosphorescent emitter in organic electroluminescent device and application thereof - Google Patents
Compound as phosphorescent emitter in organic electroluminescent device and application thereof Download PDFInfo
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- CN117105989A CN117105989A CN202311075810.9A CN202311075810A CN117105989A CN 117105989 A CN117105989 A CN 117105989A CN 202311075810 A CN202311075810 A CN 202311075810A CN 117105989 A CN117105989 A CN 117105989A
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- 125000004414 alkyl thio group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007647 flexography Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
- 229940125670 thienopyridine Drugs 0.000 description 1
- 239000002175 thienopyridine Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- INQOMBQAUSQDDS-FIBGUPNXSA-N trideuterio(iodo)methane Chemical compound [2H]C([2H])([2H])I INQOMBQAUSQDDS-FIBGUPNXSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0086—Platinum compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to the technical field of emitter compounds, in particular to a compound serving as a phosphorescence emitter in an organic electroluminescent device and application thereof. The compounds of the present invention comprise: at least one aromatic or heteroaromatic ring having at least one substituent of formula (I). The compound is introduced into five-membered ring ligand containing boron atom, and can be used as phosphorescence emitter in organic electroluminescent device to narrow emission spectrum, reduce sublimation temperature and improve luminous efficiency of device. At the same time, the five-membered ring ligand containing boron atoms is introduced into iridium or platinum complex to improve sublimation stability of the iridium complex and platinum complex, and improve the complexesPhosphorescent quantum yield of the compound.
Description
Technical Field
The invention relates to the technical field of emitter compounds, in particular to a compound serving as a phosphorescence emitter in an organic electroluminescent device and application thereof.
Background
Organic electroluminescence (OLED for short) and related studies were first discovered by pope et al in 1963 as early as the electroluminescence phenomenon of single crystal anthracene, an organic compound. In 1987, kodak corporation in U.S. made an amorphous film device by evaporating small organic molecules, and the driving voltage was reduced to within 20V. The device has the advantages of ultra-thin, full-cured, self-luminous, high brightness, wide viewing angle, high response speed, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristics, soft display realization and the like, and can be widely applied to flat panel displays and surface light sources, so that the device is widely researched, developed and used.
Organic electroluminescence is largely classified into fluorescence and phosphorescence, but according to spin quantum statistics theory, the probability of singlet excitons and triplet excitons is 1:3, i.e., the theoretical limit of fluorescence from singlet exciton radiative transitions is 25% and the theoretical limit of fluorescence from triplet exciton radiative transitions is 75%. How to use the energy of 75% of triplet excitons becomes urgent. The fact that the phosphorescence electroluminescence phenomenon breaks through the limit of 25% efficiency of the quantum efficiency of the organic electroluminescence material in 1997 is found by Forrest and the like, and the wide attention of people on the metal complex phosphorescence material is brought.
It is believed that the ligand directly contributes to the photosensitive properties of the phosphorescent material, and that the ligand may be referred to as "photosensitive". When the ligand does not contribute to the photosensitive properties of the luminescent material, the ligand may be referred to as "ancillary", but the ancillary ligand may alter the properties of the photosensitive ligand.
Therefore, it is desirable to provide a ligand capable of improving the quantum efficiency of a phosphorescent material while reducing the sublimation temperature, adjusting the arrangement of the phosphorescent material thin film, and improving the lifetime of the device.
Disclosure of Invention
A first object of the present invention is to provide a compound as a phosphorescent emitter in an organic electroluminescent device.
A second object of the present invention is to provide an organic light emitting device comprising the compound.
In order to achieve the first object, the present invention adopts the following technical scheme:
a compound as a phosphorescent emitter in an organic electroluminescent device, the compound comprising: at least one aromatic or heteroaromatic ring having at least one substituent of formula (I):
in formula (I):
ring a represents a 5 membered carbocycle, a 5 membered heterocycle, a 6 membered carbocycle, a 6 membered heterocycle, or no ring a;
R 1 、R 2 identical or different, each independently selected from hydrogen, deuterium, nitrile groups, substituted or unsubstituted C 1 ～C 40 Straight chain alkyl, substituted or unsubstituted C 1 ～C 40 Straight chain heteroalkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic alkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic heteroalkyl, substituted or unsubstituted C 6 ～C 60 Arylalkyl, substituted or unsubstituted C 3 ～C 40 Silyl, substituted or unsubstituted C 2 ～C 40 Alkenyl, substituted or unsubstituted C 4 ～C 40 Cycloalkenyl, substituted or unsubstituted C 2 ～C 40 Heteroalkenyl, substituted or unsubstituted C 2 ～C 40 Alkynyl group,Substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl groups;
R 3 represents one or more to saturated substituents, each independently selected from hydrogen, deuterium, halogen, nitrile, acyl, carboxyl, ether, ester, isonitrile, thio, seleno, sulfinyl, sulfonyl, phosphino, substituted or unsubstituted C 1 ～C 40 Straight chain alkyl, substituted or unsubstituted C 1 ～C 40 Straight chain heteroalkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic alkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic heteroalkyl, substituted or unsubstituted C 1 ～C 40 Straight chain alkoxy, substituted or unsubstituted C 3 ～C 40 Branched or cyclic alkoxy, substituted or unsubstituted C 6 ～C 60 Arylalkyl, substituted or unsubstituted C 6 ～C 60 Aryloxy, substituted or unsubstituted C 6 ～C 60 Arylamine group, substituted or unsubstituted C 3 ～C 40 Silyl, substituted or unsubstituted C 2 ～C 40 Alkenyl, substituted or unsubstituted C 4 ～C 40 Cycloalkenyl, substituted or unsubstituted C 2 ～C 40 Heteroalkenyl, substituted or unsubstituted C 2 ～C 40 Alkynyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl groups;
the dashed line represents the bond of formula (I) to the aromatic ring;
represents a single bond or a double bond.
A 5 membered carbocycle in the sense of the present invention means a cyclic alkane or cycloalkene ring containing 5 carbon atoms, a 5 membered heterocycle means a total number of carbon atoms and heteroatoms constituting the ring of 5, said heteroatoms preferably being selected from N, O, B or S, where the five membered carbocycle, five membered heterocycle may be an aliphatic or heteroaromatic ring, for example: cyclopentane, cyclopentene, cyclopentadiene, furan, tetrahydrofuran, thiophene, tetrahydrothiophene, pyrrole, pyrrolidine, imidazole, triazole, pyrazole, oxazole, oxadiazole, and the like. By 6-membered carbocyclic ring is meant a cycloalkane, cycloalkene or aromatic ring containing 6 carbon atoms, by 6-membered heterocyclic ring is meant an aliphatic or heteroaromatic ring having 6 total carbon atoms and heteroatoms constituting the ring, by 6-membered carbocyclic ring, by 6-membered heterocyclic ring herein, as non-limiting examples cyclohexane, cyclohexene, cyclohexadiene, pyran, tetrahydropyran, piperidine, pyridine, benzene, thiopyran, tetrahydrothiopyran, dioxane, dithiane, piperazine, pyrimidine, triazine, etc., or by fused 6-membered carbocyclic or 6-membered heterocyclic ring, for example naphthalene, tetrahydronaphthalene, quinoline, isoquinoline, tetrahydroquinoline, chromane, quinazoline, quinoxaline, etc.
Aryl or aromatic ring in the sense of the present invention contains 6 to 60 carbon atoms, heteroaryl or heteroaromatic ring in the sense of the present invention contains 2 to 60 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O, B or S. Aryl, aromatic ring, heteroaryl or heteroaromatic ring is understood here to mean a simple aromatic ring, i.e. benzene, biphenyl, terphenyl, naphthalene, phenanthrene, etc., or simple heteroaromatic rings, e.g. pyridine, pyrimidine, thiophene, pyrazole, oxazole, triazole, etc., or condensed aryl or heteroaryl groups, e.g. anthracene, fluoranthene,Quinoline, isoquinoline, benzofuran, benzothiophene, indazole, quinazoline, quinoxaline, thienopyridine, benzothiophenopyridine, and the like.
Alkyl having 1 to 40 carbon atoms in the sense of the present invention is preferably understood to mean the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. Impurity(s) Alkyl is preferably an alkyl having from 1 to 40 carbon atoms, meaning wherein the hydrogen atom or-CH is alone 2 Groups which may be substituted by oxygen, sulfur, halogen atoms are considered to mean alkoxy, alkylthio, fluoroalkoxy, fluoroalkylthio, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2-trifluoroethoxy, 2-trifluoroethylthio, ethyleneoxy, ethylenethio, propyleneoxy, propylenethio, butylenethio, butyleneoxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexene thio, acetylenyloxy, acetylenylthio, propynyloxy, butynylthio, pentynyloxy, pentynylthio, hexyloxy, hexylynylthio.
Alkenyl or alkynyl in the sense of the present invention is preferably taken to mean the following radicals: cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, or octynyl.
Alkoxy in the sense of the present invention is preferably an alkoxy group having 1 to 40 carbon atoms, which is understood to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexoxy, pentafluoroethoxy and 2, 2-trifluoroethoxy.
In general, cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more-CH 2 The groups may be replaced by the groups described above; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms or nitrile groups。
Aralkyl or arylalkyl in the sense of the present invention is used interchangeably and refers to alkyl substituted with aryl. In addition, aralkyl groups may be optionally substituted.
"halogen", "halogen atom", "halo" in the sense of the present invention are used interchangeably and refer to fluorine, chlorine, bromine or iodine.
"acyl" in the sense of the present invention refers to a substituted carbonyl group (COR).
"ester" in the sense of the present invention means a substituted oxycarbonyl group (-OCOR or CO) 2 R)。
"Ether" in the sense of the present invention means an-OR group.
"thio" or "thioether" as described herein is used interchangeably and refers to an-SR group.
"sulfinyl" in the sense of the present invention means a-SOR group.
"sulfonyl" in the sense of the present invention means-SO 2 An R group.
"phosphino" in the sense of the present invention means-PR 3 A group, wherein each R may be the same or different.
"silane group" in the sense of the present invention means-SiR 3 A group, wherein each R may be the same or different.
"selenoalkyl" in the sense of the present invention means a-SeR group.
Each R mentioned above is preferably selected from the group consisting of C 1 -C 40 Alkyl, C of (2) 3 -C 40 Cycloalkyl, C 6 -C 60 Aryl, C 2 -C 60 Is selected from the group consisting of heteroaryl groups.
In many cases, the substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxyl, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, and phosphine groups.
As used herein, "combination" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can contemplate from the applicable list. For example, alkyl and deuterium can combine to form a partially or fully deuterated alkyl group; halogen and alkyl groups may combine to form haloalkyl substituents such as trifluoromethyl and the like; and halogen, alkyl and aryl may combine to form a haloaralkyl.
In one example, the term substitution includes a combination of two to four of the listed groups.
In another example, the term substitution includes a combination of two to three groups. In yet another example, the term substitution includes a combination of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms other than hydrogen or deuterium, or combinations comprising up to forty atoms other than hydrogen or deuterium, or combinations comprising up to thirty atoms other than hydrogen or deuterium. In many cases, a preferred combination of substituents will include up to twenty atoms that are not hydrogen or deuterium.
Further preferably, the substituent represented by the formula (I) mainly includes structures represented by RA1 to RA100 as follows:
wherein part or all of the hydrogen atoms in each group may be replaced with deuterium atoms.
Preferably, the compound as phosphorescent emitter in the organic electroluminescent device is a metal coordination complex having a metal-carbon bond, and has the formula M (L A ) x (L B ) y (L C ) z The method comprises the steps of carrying out a first treatment on the surface of the Wherein L is A As first ligand, L B As a second ligand, L C Is a third ligand, and L A 、L B 、L C May be the same or different;
the metal M is selected from the group consisting of: ir, rh, re, ru, os, pt, pd and Au;
Wherein x is 1, 2 or 3;
wherein y is 0, 1 or 2;
wherein z is 0, 1 or 2;
and x+y+z is the oxidation valence state of the metal M;
the oxidation valence state of the metal M, for example: the oxidation valence of Pt is 2, the oxidation valence of Ir is 3, the oxidation valence of Rh is 3, and the oxidation valence of Pd is 2.
Wherein L is A 、L B And L C Each independently selected from the group consisting of:
or a metal coordination complex, and has the following structure:
each Ar of the above 1 Independently selected from the group consisting of:
wherein L is B And L C It is also possible that each independently is:
wherein each R 4 、R 5 、R 6 、R 7 Or R is 8 Can represent mono-, di-, tri-, tetra-or unsubstituted;
wherein each R is 4 、R 5 、R 6 、R 7 、R 8 Or R is 9 Each independently selected from hydrogen, deuterium, halogen, nitrile, acyl, carboxyl, ether, ester, isonitrile, thio, seleno, sulfinyl, sulfonyl, phosphino, substituted or unsubstituted C 1 ～C 40 Straight chain alkyl, substituted or unsubstituted C 1 ～C 40 Straight chain heteroalkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic alkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic heteroalkyl, substituted or unsubstituted C 1 ～C 40 Straight chain alkoxy, substituted or unsubstituted C 3 ～C 40 Branched or cyclic alkoxy, substituted or unsubstituted C 6 ～C 60 Arylalkyl, substituted or unsubstituted C 6 ～C 60 Aryloxy, substituted or unsubstituted C 6 ～C 60 Arylamine group, substituted or unsubstituted C 3 ～C 40 Silyl, substituted or unsubstituted C 2 ～C 40 Alkenyl, substituted or unsubstituted C 4 ～C 40 Cycloalkenyl, substituted or unsubstituted C 2 ～C 40 Heteroalkenyl, substituted or unsubstituted C 2 ～C 40 Alkynyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl groups, and wherein any two or more adjacent substituents may optionally be linked together to form a ring, or to form a multidentate ligand;
wherein X is selected from the group consisting of-O-, -S-, and-S (=o) -, -S (O) 2 ) -Se-, -C (R ' R "), -Si (R ' R"), -C (=o) -, or-N (R ') -;
wherein each T is independently selected from the group consisting of-B (R '), -N (R '), - -P (R '), -O-, -S-, -Se-, -S (=o) -, -S (O) 2 ) -C (R ' R "), -Si (R ' R") -or-Ge (R ' R "); and R ', R' are each independently selected from substituted or unsubstituted C 1 ～C 40 Straight chain alkyl, substituted or unsubstituted C 1 ～C 40 Straight chain heteroalkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic alkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic heteroalkyl, substituted or unsubstituted C 6 ～C 60 Arylalkyl, substituted or unsubstituted C 3 ～C 40 Silyl, substituted or unsubstituted C 2 ～C 40 Alkenyl, substituted or unsubstituted C 4 ～C 40 Cycloalkenyl, substituted or unsubstituted C 2 ～C 40 Heteroalkenyl, substituted or unsubstituted C 2 ～C 40 Alkynyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl groups; r ', R' may optionally be joined or fused to form a ring;
wherein at least one R present in said compound 4 、R 5 、R 6 、R 7 Or R is 8 Comprising at least one substituent of formula (I).
In a preferred example, the metal M is Ir or Pt.
In a preferred embodiment, each R present in the compound 4 、R 5 、R 6 、R 7 Or R is 8 Independently selected from the group consisting of RA 1-RA 100 described above or RB 1-RB 65, and R present in the compound 4 、R 5 、R 6 、R 7 Or R is 8 At least one selected from the group consisting of RA 1-RA 100; wherein RB1 to RB65 are as follows:
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wherein part or all of the hydrogen atoms in each group may be replaced with deuterium atoms.
In a preferred example, ligand L A 、L B 、L C At least one of the structures or combinations of the following L1 to L232:
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wherein part or all of the hydrogen atoms in each structure may be replaced with deuterium atoms. Preferably, the L B Any one structure or combination of the following LB1 to LB432 can be selected:
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Preferably, the L C May also be selected from any one of the following structures or combinations of LC 1-LC 60:
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wherein part or all of the hydrogen atoms in each structure may be replaced with deuterium atoms.
Preferably, x is 1, y is 2, and z is 0.
Preferably, x is 2, y is 1, and z is 0.
Preferably, x is 2, y is 0, and z is 1.
Preferably, x is 3, y is 0, and z is 0.
Preferably, the compound as a phosphorescent emitter in an organic electroluminescent device is a metal coordination complex having a metal-carbon bond, having the structure shown below:
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wherein part or all of the hydrogen atoms in each structure may be replaced with deuterium atoms.
In order to achieve the second object, the present invention provides the following technical solutions:
an organic light-emitting device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the above-described compound as a phosphorescent emitter.
In a preferred example, the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.
In a preferred example, wherein the organic layer further comprises a host material.
In a preferred example, wherein the host material is selected from structures of the following formulas X-1 to X-11,
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wherein R is a A group selected from the group consisting of Y-1 to Y-13, the Y-1 to Y-13 being as follows:
y-1 to Y-13:
each Z 1 、Z 2 Independently selected from hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl, carboxylate, sulfonate, phosphate, C 1 -C 60 Chain alkyl of C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Is C 3 -C 60 Cycloalkenyl radical, C 6 -C 60 Aryl, C of (2) 6 -C 60 Condensed ring aryl, C 6 -C 60 Aryloxy group, C 6 -C 60 Aryl sulfide group or C 2 -C 60 Is a heterocyclic aryl group of (2);
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
represents the attachment of a substituent to the host structure;
said T and R 4 With the definitions given above.
In a preferred example, the organic light emitting device may be a consumer product, an organic light emitting device, and/or a lighting panel.
The beneficial effects of the invention are as follows:
the compounds provided herein are metal complexes containing novel ligands of the boron-nitrogen five membered heterocyclic group formula (I). The introduction of the ligand containing the group of formula (I) can narrow the emission spectrum, reduce the sublimation temperature and improve the luminous efficiency of the device. The introduction of these ligands containing formula (I) into iridium or platinum complexes can improve the sublimation stability of the iridium complexes and platinum complexes, and increase the phosphorescence quantum yield of these complexes.
Drawings
Fig. 1 shows a schematic diagram of an organic electroluminescent device 100 according to the present invention.
Fig. 1 marks: 110-substrate, 115-anode, 120-hole injection layer, 125-hole transport layer, 130-electron blocking layer, 135-light emitting layer, 140-hole blocking layer, 145-electron transport layer, 150-electron injection layer, 155-protective layer, 160-cathode, 162-first conductive layer, 164-second conductive layer, 170-barrier layer.
Fig. 2 shows a schematic diagram of an inverted organic electroluminescent device 200 provided by the present invention.
Fig. 2 marks: 210-substrate, 215-cathode, 220-light emitting layer, 225-hole transport layer, 230-anode.
Detailed Description
In order to more clearly illustrate the present invention, the present invention will be further described with reference to preferred embodiments and the accompanying drawings. Like parts in the drawings are denoted by the same reference numerals. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and that this invention is not limited to the details given herein.
In general, an organic light emitting device includes at least one organic layer disposed between and electrically connected to an anode and a cathode. Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, a light emitting layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a barrier layer 170. Cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. The device 100 may be fabricated by sequentially depositing the layers described.
Fig. 2 shows a schematic diagram of an inverted organic light emitting device 200. The device includes a substrate 210, a cathode 215, a light emitting layer 220, a hole transport layer 225, and an anode 230. The device 200 may be prepared by sequentially depositing the layers described. Because the most common OLED device has a cathode disposed on an anode, and device 200 has a cathode 215 disposed under anode 230, device 200 may be referred to as an "inverted" organic light emitting device. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of how some layers may be omitted from the structure of device 100.
The simple layered structure illustrated in fig. 1 and 2 is provided as a non-limiting example, and it should be understood that embodiments of the present invention may be used in conjunction with a wide variety of other structures. The particular materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be implemented by combining the various layers described in different ways based on design, performance, and cost factors, or several layers may be omitted entirely. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe the various layers as comprising a single material, it will be understood that combinations of materials may be used, such as mixtures of host and dopant, or more generally, mixtures. Also, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into light emitting layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an organic layer disposed between a cathode and an anode. This organic layer may comprise a single layer or may further comprise multiple layers of different organic materials as described in fig. 1 and 2.
Structures and materials not specifically described, such as PLEDs comprising polymeric materials, may also be used. As another example, an OLED with a single organic layer or multiple stacks may be used. The OLED structure may deviate from the simple layered structure illustrated in fig. 1 and 2. For example, the substrate may include an angled reflective surface to improve optical coupling.
Any of the layers of the various embodiments may be deposited by any suitable method unless otherwise specified. For organic layers, preferred methods include thermal evaporation, organic vapor deposition methods, or application of one or more layers by means of carrier gas sublimation, wherein at 10 -5 The material is applied at a pressure between mbar and 1 bar. A particular example of such a process is organic vapor sprayingPrinting methods in which the material is applied directly through a nozzle and is thus structured. Other suitable deposition methods include producing one or more layers, for example, by spin coating, or by means of any desired printing method, such as screen printing, flexography, lithography, photoinitiated thermal imaging, thermal transfer, inkjet printing, or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, a hybrid method is possible, in which one or more layers are applied, for example from a solution, and one or more further layers are applied by vapor deposition.
Devices fabricated according to embodiments of the present invention may further optionally include a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damage due to exposure to harmful substances in the environment, including moisture, vapors and/or gases, etc. The barrier layer may be deposited on the substrate, electrode, under the substrate, electrode, or beside the substrate, electrode, or on any other portion of the device, including the edges. The barrier layer may comprise a single layer or multiple layers. The barrier layer may be formed by a variety of known chemical vapor deposition techniques and may comprise a composition having a single phase as well as a composition having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic or organic compounds or both. Preferably, the barrier layer comprises a mixture of polymeric and non-polymeric materials. To be considered a mixture, the aforementioned polymeric and non-polymeric materials that make up the barrier layer should be deposited under the same conditions and/or at the same time. The weight ratio of polymeric material to non-polymeric material may be in the range of 95/5 to 5/95. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric silicon and inorganic silicon.
In any of the above mentioned compounds used in each layer of the above mentioned OLED device, the hydrogen atoms may be partially or fully deuterated. Thus, any of the specifically listed substituents, such as (but not limited to) methyl, phenyl, pyridyl, and the like, can be in their non-deuterated, partially deuterated, and fully deuterated forms. Similarly, substituent classes (e.g., without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc.) can also be in their non-deuterated, partially deuterated, and fully deuterated forms.
The materials and structures described herein may be applied in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may use the materials and structures. Further, such materials and structures may be used for organic devices such as organic transistors.
These methods are generally known to those of ordinary skill in the art and they can be applied to organic electroluminescent devices comprising the compounds according to the present invention without inventive effort.
According to one embodiment, novel ligands for metal complexes are disclosed. The inventors have found that the introduction of these ligands containing trans double bonds unexpectedly narrows the emission spectrum, lowers the sublimation temperature, and increases the luminous efficiency of the device.
In order to more clearly illustrate the present invention, the following description of the technical solution of the present invention is provided in connection with some specific embodiments:
in the embodiment of the invention, the performance detection conditions of the prepared electroluminescent device are as follows:
luminance and chromaticity coordinates: photoresearch PR-715 was tested using a spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: NEWPORT 1931-C test was used.
Synthetic examples
The invention also provides a preparation method of the ligand LA, LB or LC containing the group of the formula (I), which comprises the following scheme;
wherein R is an aromatic or heteroaromatic ring, and the other symbols used are as defined above.
The specific preparation method comprises the following steps taking the compound L40 as an example;
the first step: preparation of Compound Int0
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Under the protection of nitrogen, 20.0mmol of sub-1 is dispersed in 120mL of dry toluene, 40.0mmol of o-phenylenediamine, 22.0mmol of p-toluenesulfonic acid and 4.0mmol of anhydrous magnesium sulfate are added, the mixture is heated to reflux and stirred for reaction for 24 hours, the mixture is cooled to room temperature, filtered, the filtrate is concentrated to dryness under reduced pressure, and the compound Int0 is obtained by separating and purifying with a silica gel column, and is a yellow solid with the yield of 75%.
And a second step of: preparation of Compound L40
Under the protection of nitrogen, 20.0mmol of intermediate Int0 is dissolved in 80mL of dry THF, the temperature is reduced to 0 ℃, 45.0mmol of 60% sodium hydride oil dispersion solid is added in batches, the mixture is stirred for reaction for 1 hour, 44.0mmol of methyl iodide-d 3 is added, the mixture is stirred for reaction for 15 hours at room temperature, 20mL of saturated brine is added dropwise, the mixture is extracted with ethyl acetate, the organic phase is washed with saturated brine, washed with water, dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and the compound L40, yellow solid with the yield of 92% is obtained by separation and purification through a silica gel column (MALDI-TOF): m/z=306.20 [ m+h ]] + 。
Compounds L1 to L39 and L41 to L232 were prepared by similar synthetic methods as described above.
Example 1
Metal complexes M (L) A ) x (L B ) y (L C ) Z Is synthesized by the following steps:
(A) When x is 1, y is 2, z is 0, and M is Ir, the metal complex: ir (L) A )(L B ) 2 Wherein L is A Selected from any one of L1 to L232, L B Any one selected from LB1 to LB432, comprising the following steps;
the first step: preparation of the triflate salt of the bis-LB iridium complex:
10.0mmol of compound LB and 4.5mmol of IrCl 3 ·3H 2 O is dispersed in 60mL of ethylene glycol diethyl ether and 20mL of water, under the protection of nitrogen, the mixture is heated and refluxed for 24 hours, cooled to room temperature, filtered, and the filter cake is washed with water and ethanol and dried in vacuum to obtain yellow solid, the obtained yellow solid is dissolved in 100mL of dichloromethane and 10mL of methanol, 5.0mmol of silver triflate is added, the mixture is stirred for 24 hours, the mixture is filtered, and the filtrate is concentrated to dryness under reduced pressure to obtain the triflate of the compound double LB iridium complex.
And a second step of: ir (L) metal complex A )(L B ) 2 Is prepared from
4.8mmol of compound LA and 2.3mmol of triflate of the compound double LB iridium complex prepared in the first step are dispersed in 50mL of ethylene glycol diethyl ether and 50mL of DMF, and the mixture is heated to 100 ℃ under the protection of nitrogen, stirred and reacted for 7 days, cooled to room temperature, concentrated to dryness under reduced pressure, separated and purified by a silica gel column, and eluted by methylene dichloride-normal hexane to obtain a metal complex Ir (L) A )(L B ) 2 The L1 to L232 and LB1 to LB432 are as defined above.
Reference is made to the above metal complexes: ir (L) A )(L B ) 2 Is prepared by the general preparation method of Ir (L36) (LB 105) only as a metal complex 2 Is illustrated in more detail by the preparation examples:
the first step: preparation of Compound Int-1
10.0g of compound LB105 and 9.5g of IrCl 3 ·3H 2 O is dispersed in 150mL of ethylene glycol diethyl ether and 50mL of water, under the protection of nitrogen, the mixture is heated and refluxed for 24 hours, cooled to room temperature, filtered, and filter cakes are washed with water and ethanol and dried in vacuum to obtain 14.8g of yellow solid, the obtained yellow solid is dissolved in 250mL of dichloromethane and 25mL of methanol, 6.5g of silver triflate is added, the mixture is stirred and reacted for 24 hours, the mixture is filtered, and the filtrate is concentrated under reduced pressure to obtain a compound Int-1, and the yield is: 83%.
And a second step of: ir (L36) metal complex (LB 105) 2 Is prepared from
4.8mmol of compound L36 and 2.3mmol of intermediate Int-1 are dispersed in 50mL of ethylene glycol diethyl ether and 50mL of DMF, and the mixture is heated to 100 ℃ under the protection of nitrogen, stirred and reacted for 7 days, cooled to room temperature, concentrated to dryness under reduced pressure, separated and purified by a silica gel column, and eluted by methylene dichloride-normal hexane to obtain a metal complex Ir (L36) (LB 105) 2 Yellow solid, yield: 44%, HRMS (MALDI-TOF): m/z=991.41 [ m + ]。
Example 2
(B) When x is 2, y is 1, z is 0, and M is Ir, the metal complex: ir (L) A ) 2 (L B ) Wherein L is A Selected from any one of L1 to L232, L B Any one selected from LB1 to LB432, comprising the following steps;
the first step: preparation of triflate salt of bis-LA iridium complex:
referring to the synthesis of the first step of example 1, the intermediate compound bis LA iridium complex triflate was prepared by substituting LA for only LB in the first step of example 1.
And a second step of: metal complex:Ir(L A ) 2 (L B ) Is prepared from
Referring to the synthesis method of the second step of example 1, only LA in the second step of example 1 was replaced with LB, and the triflate of the compound bis-LB iridium complex was replaced with that of the compound bis-LA iridium complex, to prepare the metal complex Ir (L A ) 2 (L B )。
The L1 to L232 and LB1 to LB432 are as defined above.
Reference is made to the above metal complexes: ir (L) A ) 2 (L B ) Is prepared by the general preparation method of the metal complex Ir (L66) 2 The preparation of (LB 78) is described in more detail;
ir metal complex (L66) 2 Preparation of (LB 78):
the first step: preparation of Compound Int-2
10.0mmol of compound L66 and 4.5mmol of IrCl 3 ·3H 2 O is dispersed in 60mL of ethylene glycol diethyl ether and 20mL of water, under the protection of nitrogen, the mixture is heated and refluxed for 24 hours, cooled to room temperature, filtered, and the filter cake is washed with water and ethanol and dried in vacuum to obtain yellow solid, the obtained yellow solid is dissolved in 50mL of dichloromethane and 5mL of methanol, 20.0mmol of silver triflate is added, the mixture is stirred for 24 hours, the mixture is filtered, and the filtrate is concentrated under reduced pressure to obtain a compound Int-2, the yellow solid is obtained, and the yield is: 78%.
And a second step of: ir metal complex (L66) 2 Preparation of (LB 78)
5.0mmol of compound LB78 and 2.5mmol of intermediate Int-2 are dispersed in 15mL of ethylene glycol diethyl ether and 15mL of DMF, and the mixture is heated to 100 ℃ under the protection of nitrogen, stirred and reacted for 7 days, cooled to room temperature, the reaction solution is poured into 250mL of ice water, extracted by methylene dichloride, an organic phase is collected, dried, filtered, and the filtrate is concentrated to dryness under reduced pressure, separated and purified by a silica gel column, and the methylene dichloride-n-hexane is eluted to obtain a metal complex Ir (L66) 2 (LB 78), dark yellow solid, yield: 48%, HRMS (MALDI-TOF): m/z=1096.66 [ m + ]。
Example 3
(C) When x is 3, y is 0, z is 0, and M is Ir, the metal complex: ir (L) A ) 3 Wherein L is A Selected from any one of L1 to L232;
the first step: preparation of bis-LA iridium chloride bridge complex
5.0mmol of Compound LA and 2.5mmol of IrCl 3 ·3H 2 Dispersing O in 60mL of ethylene glycol diethyl ether and 20mL of water, heating and refluxing for reaction for 24 hours under the protection of nitrogen, cooling to room temperature, filtering, washing a filter cake with water and ethanol, and vacuum drying to obtain the double LA iridium-chloride bridge complex.
And a second step of: ir (L) metal complex A ) 3 Is prepared from
5.0mmol of the bis-LA iridium-chloride bridge complex prepared in the first step, 10.0mmol of silver triflate and 12.0mmol of LA are dispersed in 20mL of ethylene glycol diethyl ether, and under the protection of nitrogen, the mixture is heated, refluxed and stirred for reaction for 24 hours, cooled to room temperature, filtered, and the filter cake is dissolved by methylene dichloride, and separated and purified by a silica gel column to obtain a metal complex Ir (L) A ) 3 The definitions of L1 to L232 are the same as those described above.
Reference is made to the aboveMetal complex: ir (LA) 3 Is prepared by the general preparation method of (1) only using a metal complex Ir (L28) 3 Is illustrated in more detail by way of example;
ir metal complex (L28) 3 Is prepared from the following steps:
the first step: preparation of Compound Int-3
9.5mmol of compound L28 and 4.5mmol of IrCl 3 ·3H 2 Dispersing O in 60mL of ethylene glycol diethyl ether and 20mL of water, heating and refluxing under the protection of nitrogen for reaction for 24 hours, cooling to room temperature, filtering, washing a filter cake with water and ethanol, and vacuum drying to obtain a compound Int-3 as a yellow solid, wherein the yield is: 68%.
And a second step of: ir metal complex (L28) 3 Is prepared from
5.0 Dispersing Int-3 prepared in the first step, 10.0 mmol of silver triflate and 12.0 mmol of L28 in 20mL glycol diethyl ether, heating, refluxing and stirring for reaction for 24 hours under the protection of nitrogen, cooling to room temperature, filtering, dissolving a filter cake with dichloromethane, and separating and purifying by a silica gel column to obtain a metal complex Ir (L28) 3 Brown solid, yield: 37%, HRMS (MALDI-TOF): m/z=1057.69 [ m ] + ]。
Example 4
(D) When x is 2, y is 0, z is 1, and M is Ir, the metal complex: ir (L) A ) 2 (L C ) Wherein L is A Selected from any one of L1 to L232, L C Any one selected from LC 1-LC 60, comprising the following steps;
the first step: preparation of bis-LA iridium chloro-bridge complex:
with reference to the synthesis method of the first step of example 3, a bis-LA iridium chloro-bridge complex was prepared.
And a second step of: ir (L) metal complex A ) 2 (L C ) Is prepared from
5.0 Dispersing the double LA iridium chloride bridge complex prepared in the first step, 12.5 mmol LC and 50.0 mmol alkali in 40 mL acetonitrile and 40 mL chloroform, heating, refluxing and stirring under nitrogen protection for 16 hours, cooling to room temperature, pouring the reaction solution into 120 mL ice water, separating out an organic phase, extracting the aqueous phase with dichloromethane, collecting the organic phase, drying, filtering, concentrating the filtrate under reduced pressure, separating and purifying by a silica gel column to obtain a metal complex Ir (L) A ) 2 (L C ) The definitions of L1 to L232 are the same as those described above.
Reference is made to the above metal complexes: ir (L) A ) 2 (L C ) Is prepared by the general preparation method of (1) only using a metal complex Ir (L118) 2 The preparation of (LC 4) is described in more detail;
ir metal complex (L118) 2 Preparation of (LC 4):
the first step: preparation of Compound Int-4
9.5 mmol of compound L118 and 4.5 mmol of IrCl 3 ·3H 2 Dispersing O in 60 mL glycol diethyl ether and 20 mL water, heating and refluxing for reaction for 24 hours under the protection of nitrogen, cooling to room temperature, filtering, washing a filter cake with water and ethanol, and vacuum drying to obtain a compound Int-4 as a red solid, wherein the yield is: 76%.
And a second step of: ir metal complex (L118) 2 (LC 4) preparation
5.0 Dispersing Int-4 prepared in the first step, 12.5 mmol LC4 and 50.0 mmol anhydrous sodium carbonate in 40 mL acetonitrile and 40 mL chloroform, heating, refluxing and stirring under nitrogen protection for 16 hours, cooling to room temperature, pouring the reaction solution into 120 mL ice water, separating out an organic phase, extracting the aqueous phase with dichloromethane, collecting the organic phase, drying, filtering, concentrating the filtrate under reduced pressure, separating and purifying by a silica gel column to obtain a metal complex Ir (L118) 2 (LC 4), red solid, yield: 55%, HRMS (MALDI-TOF): m/z=1116.58 [ m + ]。
Example 5
(E) When M is Pt, the metal complex: pt (L) A ) x (L B ) y (L C ) Z The preparation method is similar to the synthesis method, wherein x can be 1, y is 1, and z is 0; or x is 1, y is 0, z is 1; wherein L is A Selected from any one of L1 to L232, L B Selected from any one of LB1 to LB432, L C Any one selected from LC1 to LC 60;
(F) When M is Pt, the compound used as the phosphorescent emitter can be selected from PT1 to PT72, and the preparation method thereof takes PT60 as an example;
under nitrogen protection, 15.0 mmol of PL60 was dissolved in 150 mL of acetic acid and 16.5 mmol of K was added 2 PtCl 4 And 1.5 mmol of tetrabutylammonium bromide, stirring and heating to reflux reaction for 15 hours, cooling to room temperature, concentrating and drying under reduced pressure, adding dichloromethane for extraction, filtering, concentrating and drying the filtrate under reduced pressure, and separating and purifying by a silica gel column to obtain a compound PT60, yellow solid and yield: 59%. HRMS (MALDI-TOF): m/z=983.31 [ m ] + ]。
Referring to the similar synthetic methods described above, compounds PT 1-PT 59 and PT 61-PT 72 were prepared.
Example 6
Preparation of organic electroluminescent device
1) Ultrasonic treating the glass substrate coated with the ITO conductive layer in a cleaning agent for 30 minutes, flushing in deionized water, ultrasonic treating in an acetone/ethanol mixed solvent for 30 minutes, baking in a clean environment until the glass substrate is completely dried, irradiating for 10 minutes by an ultraviolet cleaning machine, and bombarding the surface by a low-energy cation beam;
2) Placing the above ITO glass substrate in vacuum chamber, and vacuumizing to less than 1×10 -5 Pa, continuing to vapor-deposit the compound DNTPD as the hole injection layer and TAPC as the hole transport layer on the anode layer film, wherein the vapor-deposited film thicknesses are respectively
Wherein, the structural formulas of DNTPD and TAPC are as follows:
3) Continuously evaporating a layer of the compound and a host material on the hole transport layer to form an organic light-emitting layer of the device, wherein the compound is 3% of the mass of the host material, and the evaporation film thickness is
4) And continuing to vapor deposit a layer of compounds LiQ and ET205 on the light-emitting layer as an electron transport layer of the device, wherein the mass ratio of the LiQ to the ET205 is 1:1, and the vapor deposition film thickness is
The structural formulas of LiQ and ET205 are as follows:
5) Continuously evaporating a LiF layer on the organic light-emitting layer to form an electron injection layer of the device, wherein the evaporating film thickness is
6) Continuously evaporating metal aluminum on the electron transport layer to form a cathode layer of the device, wherein the film thickness of the evaporated metal aluminum isThe device provided by the invention is obtained.
Example 7
Preparation of electroluminescent devices RD 1-RD 4
According to the same procedure as in example 6, the compounds of the present invention used in step 3) were replaced with RD-1 to RD-8, and the host material with RH451, to obtain electroluminescent devices RD1 to RD8 provided by the present invention.
Wherein the structures of RD-1 to RD-8 and RH451 are:
comparative example 1 device RD9 was prepared
Following the same procedure as in example 6, substituting RD-9 for the compound of the invention used in step 3) and RH451 for the host material gave a comparative device RD9.
The organic electroluminescent device prepared by the above process is subjected to the following performance test:
the driving voltage and current efficiency and the lifetime of the devices were measured using a digital source meter and a luminance meter for the electroluminescent devices RD1 to RD9 prepared in the above examples and comparative example 1. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the current density of the organic electroluminescent device reached 10mA/cm 2 The voltage at that time, i.e. the driving voltage, is measured at the same time Is a luminance of (2); the ratio of brightness to current density is the current efficiency; LT95% life test is as follows: at 1000cd/m using a luminance meter 2 The luminance decay of the organic electroluminescent device was measured to be 950cd/m while maintaining a constant current at luminance 2 Time in hours. The data listed in table 1 are relative data compared to the comparative device RD9 (test data in brackets).
Performance test results of tables 1, RD1 to RD9
As is apparent from the above, the organic light emitting device manufactured using the compound manufactured using the ligand containing boron-nitrogen five-membered heterocyclic group of the present invention has low driving voltage, higher light emitting efficiency, and more excellent LT95% lifetime performance of the device, indicating that the compound of the present invention is a light emitting material having excellent performance.
Example 8
Preparation of electroluminescent devices GD1 to GD10
According to the same procedure as in example 6, the compounds of the present invention used in step 3) were replaced with GD-1 to GD-10 and the host material was replaced with H1, to obtain electroluminescent devices GD1 to GD10 according to the present invention.
The structures of GD-1 to GD-10 and H1 are as follows:
comparative example 2 device GD11 was prepared
According to the same procedure as in example 6, the compound of the present invention used in step 3) was replaced with GD-11 and the host material was replaced with H1, to obtain an electroluminescent device GD11 provided by the present invention.
The results of performance tests of the obtained devices GD1 to GD11 are shown in table 2 below, and the data listed in table 2 are relative data compared with the comparative device GD11 (test data in parentheses).
Table 2, results of Performance detection of GD1 to GD11
As is apparent from the above, the organic light emitting device manufactured using the compound manufactured using the ligand containing a boron-nitrogen five-membered heterocyclic group of the present invention has lower driving voltage, high light emitting efficiency, and more excellent life LT 95%.
Example 9
Preparation of electroluminescent devices BD1 to BD3
According to the same procedure as in example 6, the compounds of the present invention used in step 3) were replaced with BD-1 to BD-3, and the host material was replaced with H2, to obtain electroluminescent devices BD1 to BD3 according to the present invention.
The structures of BD-1 to BD-3 and H2 are as follows:
comparative example 3 device BD4 was fabricated
According to the same procedure as in example 6, the compound of the present invention used in step 3) was replaced with BD-4 and the host material was replaced with H2, to obtain an electroluminescent device BD4 provided in the present invention.
The performance test results of the obtained devices BD1 to BD4 are shown in table 3 below, and the data listed in table 3 are relative data compared with the comparative device BD4 (test data in parentheses).
Table 3, BD1 to BD4 performance test results
As is apparent from the above, the organic light emitting device manufactured using the compound manufactured using the ligand containing a boron-nitrogen five-membered heterocyclic group of the present invention has lower driving voltage, high light emitting efficiency, and more excellent life LT90% performance.
It should be understood that the foregoing examples of the present invention are provided merely for clearly illustrating the present invention and are not intended to limit the embodiments of the present invention, and that various other changes and modifications may be made therein by one skilled in the art without departing from the spirit and scope of the present invention as defined by the appended claims.
Claims (10)
1. A compound as a phosphorescent emitter in an organic electroluminescent device, the compound comprising: at least one aromatic or heteroaromatic ring having at least one substituent of formula (I):
in formula (I):
ring a represents a 5 membered carbocycle, a 5 membered heterocycle, a 6 membered carbocycle, a 6 membered heterocycle, or no ring a;
R 1 、R 2 identical or different, each independently selected from hydrogen, deuterium, nitrile groups, substituted or unsubstituted C 1 ～C 40 Straight chain alkyl, substituted or unsubstituted C 1 ～C 40 Straight chain heteroalkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic alkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic heteroalkyl, substituted or unsubstituted C 6 ～C 60 Arylalkyl, substituted or unsubstituted C 3 ～C 40 Silyl, substituted or unsubstituted C 2 ～C 40 Alkenyl, substituted or unsubstituted C 4 ～C 40 Cycloalkenyl, substituted or unsubstituted C 2 ～C 40 Heteroalkenyl, substituted or unsubstituted C 2 ～C 40 Alkynyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl groups;
R 3 represents one or more to saturated substituents, each independently selected from hydrogen, deuterium, halogen, nitrile, acyl, carboxyl, ether, ester, isonitrile, thio, seleno, sulfinyl, sulfonyl, phosphino, substituted or unsubstituted C 1 ～C 40 Straight chain alkyl, substituted or unsubstituted C 1 ～C 40 Straight chain heteroalkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic alkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic heteroalkyl, substituted or unsubstituted C 1 ～C 40 Straight chain alkoxy, substituted or unsubstituted C 3 ～C 40 Branched or cyclic alkoxy, substituted or unsubstituted C 6 ～C 60 Arylalkyl, substituted or unsubstituted C 6 ～C 60 Aryloxy, substituted or unsubstituted C 6 ～C 60 Arylamine group, substituted or unsubstituted C 3 ～C 40 Silyl, substituted or unsubstituted C 2 ～C 40 Alkenyl, substituted or unsubstituted C 4 ～C 40 Cycloalkenyl, substituted or unsubstituted C 2 ～C 40 Heteroalkenyl, substituted or unsubstituted C 2 ～C 40 Alkynyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl groups;
the dashed line represents the bond of formula (I) to the aromatic ring;
represents a single bond or a double bond.
2. The compound as claimed in claim 1, wherein the compound is a metal coordination complex having a metal-carbon bond.
3. The compound as phosphorescent emitter in an organic electroluminescent device according to claim 2, characterized in that the metal is selected from Ir, rh, re, ru, os, pt, pd or Au.
4. The compound as phosphorescent emitter in an organic electroluminescent device according to claim 2, characterized in that the compound has the formula M (L A ) x (L B ) y (L C ) z The method comprises the steps of carrying out a first treatment on the surface of the Wherein L is A As first ligand, L B As a second ligand, L C Is a third ligand, and L A 、L B 、L C May be the same or different;
wherein the metal M is Ir or Pt;
wherein x is 1, 2 or 3;
wherein y is 0, 1 or 2;
wherein z is 0, 1 or 2;
and x+y+z is the oxidation valence state of the metal M;
Wherein L is A 、L B And L C Each independently selected from the group consisting of:
or the compound has the following structure:
wherein each Ar is 1 Independently selected from the group consisting of:
wherein L is B And L C It is also possible that each independently is:
wherein each R 4 、R 5 、R 6 、R 7 Or R is 8 Can represent mono-, di-, tri-, tetra-or unsubstituted;
wherein each R is 4 、R 5 、R 6 、R 7 、R 8 Or R is 9 Each independently selected from hydrogen, deuterium, halogen, nitrile, acyl, carboxyl, ether, ester, isonitrile, thio, seleno, sulfinyl, sulfonyl, phosphino, substituted or unsubstituted C 1 ～C 40 Straight chain alkyl, substituted or unsubstituted C 1 ～C 40 Straight chain heteroalkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic alkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic heteroalkyl, substituted or unsubstituted C 1 ～C 40 Straight chain alkoxy, substituted or unsubstituted C 3 ～C 40 Branched or cyclic alkoxy, substituted or unsubstituted C 6 ～C 60 Arylalkyl, substituted or unsubstituted C 6 ～C 60 Aryloxy, substituted or unsubstituted C 6 ～C 60 Arylamine group, substituted or unsubstituted C 3 ～C 40 Silyl, substituted or unsubstituted C 2 ～C 40 Alkenyl, substituted or unsubstituted C 4 ～C 40 Cycloalkenyl, substituted or unsubstituted C 2 ～C 40 Heteroalkenyl, substituted or unsubstituted C 2 ～C 40 Alkynyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl groups, and wherein any two or more adjacent substituents may optionally be linked together to form a ring, or to form a multidentate ligand;
wherein X is selected from the group consisting of-O-, -S-, and-S (=o) -, -S (O) 2 ) -Se-, -C (R ' R "), -Si (R ' R"), -C (=o) -, or-N (R ') -;
wherein each T is independently selected from the group consisting of-B (R '), -N (R '), - -P (R '), -O-, -S-, -Se-, -S (=o) -, -S (O) 2 ) -C (R ' R "), -Si (R ' R") -or-Ge (R ' R "); and R ', R' are each independently selected from substituted or unsubstituted C 1 ～C 40 Straight chain alkyl, substituted or unsubstituted C 1 ～C 40 Straight chain heteroalkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic alkyl, substituted or unsubstituted C 3 ～C 40 Branched or cyclic heteroalkyl, substituted or unsubstituted C 6 ～C 60 Arylalkyl, substituted or unsubstituted C 3 ～C 40 Silyl, substituted or unsubstituted C 2 ～C 40 Alkenyl, substituted or unsubstituted C 4 ～C 40 Cycloalkenyl, substituted or unsubstituted C 2 ～C 40 Heteroalkenyl, substituted or unsubstituted C 2 ～C 40 Alkynyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl groups; r ', R' may optionally be joined or fused to form a ring;
Wherein said compound is present inAt least one R of (2) 4 、R 5 、R 6 、R 7 Or R is 8 Comprising at least one substituent of formula (I).
5. The compound according to any one of claim 4, wherein the substituent represented by formula (I) is mainly selected from the group consisting of RA1 to RA 100:
wherein part or all of the hydrogen atoms in each group may be replaced with deuterium atoms.
6. The compound as claimed in claim 5 as phosphorescent emitter in organic electroluminescent devices, characterized in that each R present in the compound 4 、R 5 、R 6 、R 7 Or R is 8 Independently selected from the group consisting of RA 1-RA 100 or RB 1-RB 65, and R is present in the compound 4 、R 5 、R 6 、R 7 Or R is 8 At least one selected from the group consisting of RA 1-RA 100; wherein RB1 to RB65 are as follows:
wherein part or all of the hydrogen atoms in each group may be replaced with deuterium atoms.
7. The compound as claimed in claim 4 as a phosphorescent emitter in an organic electroluminescent device, wherein L A 、L B And L C At least one of the structures or combinations of the following L1 to L232:
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wherein part or all of the hydrogen atoms in each structure may be replaced with deuterium atoms.
8. The compound as phosphorescent emitter in an organic electroluminescent device according to claim 4, further comprising the structure:
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wherein part or all of the hydrogen atoms in each structure may be replaced with deuterium atoms.
9. The compound as claimed in claim 4 as a phosphorescent emitter in an organic electroluminescent device, wherein L B Any one structure or combination of the following LB1 to LB432 can be selected:
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the L is C May also be selected from any one of the following structures or combinations of LC 1-LC 60:
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wherein part or all of the hydrogen atoms in each structure may be replaced with deuterium atoms.
10. An organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises the compound as a phosphorescent emitter according to any one of claims 1 to 9.
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