CN111057013A - Organic electroluminescent compound and organic electroluminescent device containing same - Google Patents
Organic electroluminescent compound and organic electroluminescent device containing same Download PDFInfo
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Abstract
The invention relates to an organic electroluminescent compound shown as a formula (III):
wherein R is1To R4Each independently selected from the group consisting of: hydrogen and the groups shown belowThe group consisting of: formula (i), formula (ii), formula (iii), formula (iv), formula (v), formula (vi), formula (vii) and formula (viii), and R1To R4At least two of which are each independently selected from the group consisting of: formula (i), formula (ii), formula (iii), formula (iv), formula (v), formula (vi), formula (vii), and formula (viii):
wherein R is5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16P, q, r, s, t, u, v, A, B and D are as described in the specification.
Description
Technical Field
(related applications description) this application claims the priority of U.S. patent application No. 16/162,833, filed on day 10, month 17, 2018 and U.S. patent application No. 16/236,075, filed on day 12, month 28, 2018, U.S. patent application No. 16/162,833 is a division of U.S. patent application No. 15/703,506, filed on day 9, month 13, 2017, and U.S. patent application No. 16/236,075 is a partial continuation of U.S. patent application No. 15/703,506, filed on day 9, month 13, 2017. The entire disclosure of the aforementioned application is incorporated herein by reference.
The invention relates to an organic electroluminescent compound and an organic electroluminescent device using the same.
Background
Since the flexible device has a promising application prospect, organic light-emitting diode (OLED) devices are very important technologies for scientific research and display industries in recent years, and have become the focus of research and development. An OLED is a light-emitting diode (LED) in which a thin film of organic compound is placed between two conductors and emits light in response to a stimulus such as from an electrical current. OLEDs may be used in display devices such as television screens, computer screens, mobile phones, and tablet computers. OLED devices are self-emitting devices and are widely studied for their brightness, better visibility, and better ability to display clearer images compared to liquid crystal devices.
However, the current development of OLED display technology encounters bottlenecks. One of the major problems is that the luminous efficiency does not meet the practical requirements, so the development of the OLED technology is severely limited. One reason for affecting the luminous efficiency of an OLED device is the efficiency of transporting carriers, including electrons and holes.
Disclosure of Invention
In the present disclosure, an organic electroluminescent compound represented by the formula (III):
wherein R is1To R4Each independently selected from the group consisting of: hydrogen and a group consisting of: formula (i), formula (ii), formula (iii), formula (iv), formula (v), formula (vi), formula (vii) and formula (viii), and R1To R4At least two of which are each independently selected from the group consisting of: formula (i), formula (ii), formula (iii), formula (iv), formula (v), formula (vi), formula (vii), and formula (viii):
wherein R is5、R6、R7、R8、R9And R10Each independently selected from the group consisting of: hydrogen, a aryl group, an heteroaryl group, a C1-C6Alkyl radical, mono C1-C6Alkenyl and a C1-C6An alkynyl group; p, q, r, s, t, u and v are each independently integers between 1 and 4; x is selected from the group consisting of: NR (nitrogen to noise ratio)17、O、S、CR18 2，SiR19 2、PR20And Se; r17、R18、R19And R20Each independently selected from the group consisting of: hydrogen, a aryl group, an heteroaryl group, a C1-C6Alkyl radical, mono C1-C6Alkenyl and a C1-C6 alkynyl; A. b and D are each independently selected from the group consisting of: carbon and nitrogen; and R is11、R12、R13、R14、R15And R16Each independently selected from the group consisting of: hydrogen, a aryl group, an heteroaryl group, a C1-C6Alkyl radical, mono C1-C6Alkenyl and a C1-C6Alkynyl.
Drawings
To assist the reader in achieving the best understanding, it is suggested that, upon reading this disclosure, reference is made to the accompanying drawings and detailed description thereof. Note that in order to comply with industry standards, various features are not drawn to scale. In fact, the dimensions of the various features may be exaggerated or minimized for clarity.
FIG. 1 is an embodiment of an organic electroluminescent device, according to some embodiments of the present disclosure.
Detailed Description
The following disclosure provides many different embodiments, or examples, for implementing different features of the application. Specific examples of components and arrangements are described below to simplify the present disclosure. These are, of course, merely examples and are not intended to limit the present application.
OLED compounds rely on radiative decay of molecular excited states (excitons) generated by recombination of electrons and holes in a bulk transport material. The nature of the excitation results in an interaction between the electron and the hole, which causes the excited state to split into a bright singlet state and a dark triplet state. Conventional phosphorescent OLEDs rely on the mixing of singlet and triplet states due to spin-orbital (SO) interaction. This results in energy harvesting from all higher singlet and triplet states followed by phosphorescence (relative time opposed light from excited triplet states). The short lifetime of the triplet state results in destruction of the triplet exciton by charge and other excitons.
There is therefore a need in the art to provide an OLED that can reach higher excited states without rapid decay. TADF is known to be capable of transferring populations between singlet and triplet energy order in a relative timing (e.g., 110 μ s). The organic electroluminescent compounds proposed in the present disclosure are capable of emitting fluorescence or phosphorescence in a higher energy excited state than conventional organic electroluminescent compounds. The organic electroluminescent compounds of the present disclosure can improve carrier transport ability. In certain embodiments, the organic electroluminescent compounds of the present disclosure can be used in electronic or optoelectronic devices, such as light-emitting elements, light-emitting devices, or lighting devices.
In certain embodiments, the present invention provides an organic electroluminescent compound according to the following formula (I):
wherein R is1、R2、R3And R4Each independently is a substituted or unsubstituted (C6-C30) group, a substituted or unsubstituted 3-to 30-membered heteroaryl group, -NR5R6、-SiR7R8R9、-SR10、-OR11A cyano group, a nitro group or a hydroxyl group;
R5to R11Each independently hydrogen, deuterium, halogen, mono-or unsubstituted (Cl-C30) alkyl, mono-or unsubstituted (C6-C30) aryl, or mono-or unsubstituted 3-to 30-membered heteroaryl; or are linked to one or more adjacent substituents to form a mono-or polycyclic, alicyclic or aromatic ring, one or more carbon atoms of which are substituted with at least one atom selected from: nitrogen, oxygen and sulfur;
a and c are each independently an integer of 1 to 3; wherein a or c is an integer of 1 or more, and R1And each R3The same or different;
b and d are each independently an integer from 1 to 3; wherein b or d is an integer of 1 or more, and R2Or each R4The same or different; and wherein the heteroaryl group contains at least one atom selected from the group consisting of: B. n, O, S, P (═ O), Si, and P.
In certain embodiments, R1To R4And R5To R11The substituents of the substituted groups each independently comprise at least one group selected from: deuterium, halogen, (C1-C30) alkyl, (C1-C30) alkyl substituted with monohalogen, (C6-C30) aryl, 3-to 30-membered heteroaryl substituted with (C6-C30) aryl, 3-to 30-membered heteroaryl substituted with 3-to 30-membered heteroaryl, (C6-C30) aryl, (C3-C30) cycloalkyl, 5-to 7-membered heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, di (C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, di (C6-C30) arylboron, di (C1-C30) alkylboron, (C1-C30) alkyl (C6-C30) arylboron, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro and hydroxyl.
In some embodiments, the terms "alkyl" and "alkoxy" and the like, as any alkyl moiety included in a substituent, include linear structures and branched structures; and the term "cycloalkyl" includes a mono-or polycyclic hydrocarbon, or a substituted or unsubstituted (C7-C30) bicycloalkyl. The term "aryl" refers to an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom; comprising monocyclic or fused rings (fused rings), wherein each ring has from 4 to 7, preferably 5 or 6 ring backbone atoms; the ring may be formed by connecting two or more aryl groups to another ring through one or more single bonds; and include phenyl (phenyl), biphenyl (biphenyl), terphenyl (terphenyl), naphthyl (naphthynyl), anthryl (anthryl), indenyl (indenyl), fluorenyl (fluoronyl), phenanthrenyl (phenanthryl), triphenylenyl (triphenylenyl), pyrenyl (pyrenyl), perylenyl (perylenyl),
Mesityl (chrysenyl), naphthacenyl (naphthacenyl), fluoranthenyl (fluoranthenyl), and the like, wherein the naphthyl group comprises a 1-naphthyl group and a 2-naphthyl group, the anthracenyl group comprises a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group, and the fluorenyl group comprises a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, and a 9-fluorenyl group. The term "heteroaryl" refers to an aryl group having 1 to 4 heteroatoms selected from the group; B. n, O, S, P (═ O), Si and P, and the remaining ring backbone atoms, other than the heteroatoms, are carbon atoms; it may be a monocyclic ring or a condensed ring condensed with at least one benzene ring; it may be partially saturated; the heteroaryl group may be formed by connecting at least one heteroaryl group to another heteroaryl or aryl group through one or more single bonds; it may be a divalent aromatic radical, the hetero atoms of its ring skeleton being, for example, oxidized or quaternized to form an N-oxide or a quaternary salt; and it comprises a single-ring type heteroAryl, a compound containing a furyl (furyl), thiophenyl (thiophenyl), pyrrolyl (pyridyl), imidazolyl (imidiazolyl), pyrazolyl (pyrazolyl), thiazolyl (thiazolyl), thiadiazolyl (thiadiazolyl), isothiazolyl (isothiazolyl), isoxazolyl (isoxazolazolyl), oxazolyl (oxazoyl), oxadiazolyl (oxazoyl), triazinyl (triazoyl), tetrazinyl (tetrazinyl), triazolyl (triazoyl), tetrazolyl (tetrazoyl), furoyl (furazanyl), pyridyl (pyridyloxy), pyrazinyl (pyrazoyl), pyrimidinyl (pyrimidinyl), pyridazinyl (pyrimidinyloxy) and the like, a fused heteroaryl containing benzofuranyl (benzothiophenyl), benzothiophenyl (thiophenyl), benzisoxazolyl (thiazoyl), benzisothiazolyl (benzisothiazolyl), benzoxazolyl (benzoxazolyl), benzoxazolyl (benzoxazolyl), and the like, benzoxazolyl (benzil), and the like, benzoxazolyl), the like, quinolyl (quinolyl), isoquinolyl (isoquinolyl), cinnolinyl (cinnolinyl), quinazolinyl (quinazolinolinyl), quinoxalinyl (quinoxalinyl), carbazolyl (carbazolyl), phenanthridinyl (phenanthridinyl), benzodioxolyl (benzodioxolyl), dibenzofuranyl (dibenzofuranyl), dibenzothiophenyl (dibenzothiophenyl) and the like, and N-oxides thereof (e.g., pyridyl N-oxide, quinolyl N-oxide) and quaternary salts thereof.
In certain embodiments, R1To R4Each independently hydrogen, deuterium, chlorine, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, fluorenyl, fluoranthenyl, triphenylene, pyrenyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoro,
Phenyl, tetracenyl, perylene, pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, benzimidazolyl, indenyl, pyrazinyl, pyrimidinylPyridyl, pyridazinyl, quinolyl, triazinyl, benzofuryl, dibenzofuryl, benzothienyl, dibenzothienyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl or N-carbazolyl.
In certain embodiments, R1To R4And R5To R11May each be independently further substituted with at least one group selected from: deuterium, chlorine, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl,
a phenyl group, a tetracenyl group, a perylene group, a fluorotrimethylsilyl group (butyldimethylsilyl group), a triethylsilyl group (triethylsilyl group), a tripropylsilyl group (tripropylsilyl group), a tri (t-butyl) silyl group (tri (t-butyl) silyl group), a t-butyldimethylsilyl group (t-butyldimethylsilyl group), a dimethylphenylsilyl group (dimethylphenylsilyl), a carbazolyl group and a triphenylsilyl group (triphenylsilyl), and preferably at least one group selected from the group consisting of: deuterium, chlorine, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl and decyl.
Thus, in an embodiment, the organic electroluminescent compounds according to the invention are represented by the following formula (II):
wherein R is1To R12Each independently is hydrogen, deuterium, a halogen, a substituted or unsubstituted (Cl-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted 3-toA 30-membered heteroaryl; or are linked to one or more adjacent substituents to form a mono-or polycyclic, alicyclic or aromatic ring, one or more carbon atoms of which are substituted with at least one atom selected from the group consisting of: nitrogen, oxygen and sulfur; and the heteroaryl group comprises at least one atom selected from the group consisting of: B. n, O, S, P (═ O), Si, and P.
In certain embodiments, R1To R12Wherein the substituents of the substituent group each independently comprise at least one group selected from: deuterium, halogen, (C1-C30) alkyl, monohalogen-substituted (C1-C30) alkyl, (C6-C30) aryl, 3-to 30-membered heteroaryl substituted with (C6-C30) aryl, 3-to 30-membered heteroaryl substituted with 3-to 30-membered heteroaryl, (C6-C30) aryl, (C3-C30) cycloalkyl, 5-to 7-membered heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, di (C72-C30) alkylamino, di (C8472-C30) alkylamino, (30) C30-C30) arylamino, (30) arylamino, Di (C6-C30) arylboron, di (C1-C30) alkylboron, (C1-C30) alkyl (C6-C30) arylboron, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro and hydroxyl.
In some embodiments, the terms "alkyl" and "alkoxy" and the like, as any alkyl moiety included in a substituent, include linear structures and branched structures; and the term "cycloalkyl" includes a mono-or polycyclic hydrocarbon, or a substituted or unsubstituted (C7-C30) bicycloalkyl. The term "aryl" refers to an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom; comprising monocyclic or fused rings (fused rings), wherein each ring has from 4 to 7, preferably 5 or 6 ring backbone atoms; the ring may be formed by connecting two or more aryl groups to another ring through one or more single bonds; and include phenyl (phenyl), biphenyl (biphenyl), terphenyl (terphenyl), naphthyl (naphthynyl), anthryl (anthryl), indenyl (indenyl), fluorenyl (fluoronyl), phenanthrenyl (phenanthryl), triphenylenyl (triphenylenyl), pyrenyl (pyrenyl), perylenyl (perylenyl),
Mesityl (chrysenyl), naphthacenyl (naphthacenyl), fluoranthenyl (fluoranthenyl), and the like, wherein the naphthyl group comprises a 1-naphthyl group and a 2-naphthyl group, the anthracenyl group comprises a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group, and the fluorenyl group comprises a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, and a 9-fluorenyl group. The term "heteroaryl" refers to an aryl group having 1 to 4 heteroatoms selected from the group; B. n, O, S, P (═ O), Si and P, and the remaining ring backbone atoms, other than the heteroatoms, are carbon atoms; it may be a monocyclic ring or a condensed ring condensed with at least one benzene ring; it may be partially saturated; the heteroaryl group may be formed by connecting at least one heteroaryl group to another heteroaryl or aryl group through one or more single bonds; it may be a divalent aromatic radical, the hetero atoms of its ring skeleton being, for example, oxidized or quaternized to form an N-oxide or a quaternary salt; and which comprises a monocyclic heteroaryl group, a fused heteroaryl group comprising a furyl (furyl), a thiophenyl (thiophenyl), a pyrrolyl (pyrrolyl), an imidazolyl (imidazolyl), a pyrazolyl (pyrazolyl), a thiazolyl (thiazolyl), a thiadiazolyl (thiadiazolyl), an isothiazolyl (isothiazolinyl), an isoxazolyl (isooxazolyl), an oxazolyl (oxazoyl), an oxadiazolyl (oxazoyl), a triazinyl (triazonyl), a tetrazinyl (tetrazinyl), a triazolyl (triazoyl), a tetrazolyl (tetrazoyl), a furoyl (furazanyl), a pyridyl (pyridinyl), a pyrazinyl (pyrazoylnyl), a pyrimidinyl (pyrimidinyl), a pyridazinyl (pyridazinyl) and the like, a fused heteroaryl group comprising a benzofuranyl (benzothiophenyl), a benzothiophenyl (thiophenyl), a benzothiophenyl (indolephenyl), a thiophenyl (benzoxazolyl), a benzisothiazolyl (benzisothiazolyl), a thiadiazolyl (thiazoyl), a triazolyl (triazolyl), a (triazonyl) and the like, Indazolyl (indazolyl), benzothiadiazolyl (benzothiazolinyl), quinolyl (quinolyl), isoquinolyl (isoquinolyl), cinnolinyl (cinnolinyl), quinazolinyl (quinazolinyl), quinoxalinyl (quinoxalinyl), carbazolyl (carbazolyl), phenanthridinyl (phenanthridinyl), benzodioxolyl (benzodioxolyl), dibenzofuranyl (dibenzofuranyl), dibenzothiophenyl (dibenzothiophenyl)zothiophenyl), and the like, N-oxides thereof (e.g., pyridyl N-oxide, quinolyl N-oxide) and quaternary salts thereof.
In certain embodiments, R1 through R12 may each be independently further substituted with at least one group selected from: deuterium, chlorine, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl,
a mesityl, tetracenyl, peryleneyl, fluorotrimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl, t-butyldimethylsilyl, dimethylphenylsilyl, carbazolyl and triphenylsilyl (triphenylsilyl), and preferably at least one group selected from the group consisting of: deuterium, chlorine, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl and decyl.
In certain embodiments, the organic electroluminescent compounds of the present invention are represented by the following formula (III):
wherein R is1To R4Each independently selected from the group consisting of: hydrogen and a group consisting of: formula (i), formula (ii), formula (iii), formula (iv), formula (v), formula (vi), formula (vii), and formula (viii), and at least two of R1 through R4 are each independently selected from the group consisting of: formula (i), formula (ii), formula (iii), formula (iv), formula (v), formula (vi), formula (vii), and formula (viii):
wherein R is5、R6、R7、R8、R9And R10Each independently selected from the group consisting of: hydrogen, a aryl group, an heteroaryl group, a C1-C6Alkyl radical, mono C1-C6Alkenyl and a C1-C6An alkynyl group; p, q, r, s, t, u and v are each independently integers between 1 and 4; x is selected from the group consisting of: NR (nitrogen to noise ratio)17、O、S、CR18 2、SiR19 2、PR20And Se; r17、R18、R19And R20Each independently selected from the group consisting of: hydrogen, a aryl group, an heteroaryl group, a C1-C6Alkyl radical, mono C1-C6Alkenyl and a C1-C6An alkynyl group; A. b and D are each independently selected from the group consisting of: carbon and nitrogen; and R is11、R12、R13、R14、R15And R16Each independently selected from the group consisting of: hydrogen, a aryl group, an heteroaryl group, a C1-C6Alkyl radical, mono C1-C6Alkenyl and a C1-C6Alkynyl.
In certain embodiments, the organic electroluminescent compounds of formula (III) have two substituents. In certain embodiments, the organic electroluminescent compounds of formula (III) have three substituents. In certain embodiments, the organic electroluminescent compounds of formula (III) have four substituents.
In certain embodiments, R in formula (III)1To R4Each of at least two of which is independently selected from the group consisting of: structures shown in formula (iii) and formula (iv).
In certain embodiments, R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15And R16Each independently selected from the group consisting of: hydrogen and-C1-C6An alkyl group.
In certain embodiments, a and D are each independently nitrogen, and B is carbon.
In certain embodiments, R in formula (III)1And R3At least one of which is a group of the formula (III) and R in the formula (III)2And R4At least one of them is a group represented by the formula (iv).
In certain embodiments, R in formula (III)1And R3At least one of which is a group of the formula (III) and R in the formula (III)2And R4At least one of which is a group of formula (iv); and R is9And R10Each independently selected from the group consisting of: hydrogen and-C1-C6Alkyl, u and v are each independently an integer of 1, A and D are each independently nitrogen, B is carbon, and R is11And R12Each independently selected from the group consisting of: hydrogen and-C1-C6An alkyl group.
In certain embodiments, the organic electroluminescent compounds of the present invention are represented by the following formula (IV):
in certain embodiments, the present invention provides a method of preparing an organic electroluminescent compound represented by the following formula (IV). In certain embodiments, organic electroluminescent compounds of the following formula (IV) can be synthesized according to scheme 1:
in scheme 1, the organic electroluminescent compounds represented by the following formula (IV) are synthesized using both the first step and the second step.
In the first step, a compound represented by the formula (IV-a) was synthesized by the following method. Under an inert gas atmosphere, 1,3,5,7-tetraiodoadamantane (1,3,5, 7-tetraiododiamantane; 1mmol) and dimethylamine(ditolylamine; 2mmol), copper iodide (0.1mmol),1,10-phenanthroline (C)1,10-phenanthroline; 0.1mmol) and potassium carbonate (2.5mmol) were added to the flask. Further, DMSO (5mL) was added to the flask under an inert gas atmosphere, and the flask was heated to 120 ℃ for 24 hours to obtain a reaction mixture. The reaction mixture was filtered to obtain a solution. The organic solvent of the solution was washed twice with brine. Combining the organic layers with Na2SO4The organic solvent was dried and removed to give a residue. And purifying the residue by silica gel chromatography to obtain the organic electroluminescent compound represented by the formula (IV-a).
In the second step, an organic electroluminescent compound represented by formula (IV) was synthesized by the following method. A compound represented by the formula (IV-a) (0.5mmol) and THF (10mL) were charged under nitrogen into a round-bottomed flask. Using acetone-N2(l)The round bottom flask was cooled to-78 ℃. N-butyllithium (1.1mmol) was further slowly added to the flask using a syringe and stirred at-78 ℃ for 30 minutes. 2-Chloropyrimidine (1.1mmol) was further added to the flask and stirred at-78 deg.C for 30 minutes to form a reaction mixture. The reaction mixture was warmed to room temperature, after which the reaction was quenched with brine and extracted with EA. With Na2SO4The organic layer of the mixture was dried to obtain an extract. The solvent of the extract was evaporated, and the remaining residue was purified by silica gel chromatography to obtain the organic electroluminescent compound represented by formula (IV).
In certain embodiments, the present invention provides organic electroluminescent compounds according to formula (V):
in certain embodiments, the present invention provides a method of preparing an organic electroluminescent compound represented by formula (V). In certain embodiments, the organic electroluminescent compounds of formula (V) may be prepared according to scheme 2:
in scheme 2, the synthesis of the organic electroluminescent compound represented by formula (V) is similar to that of the organic electroluminescent compound represented by formula (IV), except that 1,3-diiodoadamantane (1,3-diiodoadamantane) is used as a starting material and the equivalent ratio of diiodoadamantane to 2-chloropyrimidine is 1.0 to 1.1.
In certain embodiments, the present invention provides an organic electroluminescent compound of formula (VI):
in certain embodiments, the present invention provides a method of preparing an organic electroluminescent compound of formula (VI). In certain embodiments, the organic electroluminescent compounds of formula (VI) can be synthesized according to scheme 3:
in scheme 3, the synthesis of the organic electroluminescent compound represented by formula (VI) is similar to that of the organic electroluminescent compound represented by formula (IV), except that 1,3, 5-triiodoadamantane (1,3, 5-triiododiamantane) is used as a starting material, and the equivalent ratio of triiodoadamantane to 2-chloropyrimidine is 1.0 to 2.2.
In some embodiments of the present disclosure, an organic electroluminescent device comprises: an anode, a cathode, at least one light-emitting layer and an electron transport layer are arranged between the anode and the cathode; the light-emitting layer contains an organic electroluminescent compound represented by the formula (I) as a host material:
wherein R is1、R2、R3And R4Each independently is a substituted or unsubstituted (C6-C30) aryl, a mono-or unsubstituted 3-to 30-membered heteroAryl, -NR5R6、-SiR7R8R9、-SR10、-OR11A cyano group, a nitro group or a hydroxyl group;
R5to R11Each independently hydrogen, deuterium, a halogen, a mono-or unsubstituted (Cl-C30) alkyl, a mono-or unsubstituted (C6-C30) aryl, or a mono-or unsubstituted 3-to 30-membered heteroaryl; or are linked to one or more adjacent substituents to form a mono-or polycyclic, alicyclic or aromatic ring, one or more carbon atoms of which are substituted with at least one atom selected from the group consisting of: nitrogen, oxygen and sulfur;
a and c are each independently an integer of 1 to 3; wherein a or c is an integer of 1 or more, and R1Or each R3The same or different;
b and d are each independently an integer from 1 to 3; wherein b or d is an integer of 1 or more, each R2Or each R4The same or different; and wherein the heteroaryl group contains at least one atom selected from the group consisting of: B. n, O, S, P (═ O), Si, and P.
In some embodiments of the present disclosure, the organic electroluminescent device comprises: an anode, a cathode, at least one light-emitting layer and an electron transport layer are arranged between the anode and the cathode; the light-emitting layer contains an organic electroluminescent compound represented by the formula (II):
wherein R is1To R12Each independently hydrogen, deuterium, a halogen, a mono-or unsubstituted (Cl-C30) alkyl, a mono-or unsubstituted (C6-C30) aryl, or a mono-or unsubstituted 3-to 30-membered heteroaryl; or are linked to one or more adjacent substituents to form a mono-or polycyclic, alicyclic or aromatic ring, one or more carbon atoms of which are substituted with at least one atom selected from the group consisting of: nitrogen, oxygen and sulfur.
In some embodiments of the present disclosure, an organic electroluminescent device comprises: an anode, a cathode, at least one light-emitting layer and an electron transport layer are arranged between the anode and the cathode; the light-emitting layer contains an organic electroluminescent compound represented by the formula (III):
wherein R is1To R4Each independently selected from the group consisting of: hydrogen and a group consisting of: formula (i), formula (ii), formula (iii), formula (iv), formula (v), formula (vi), formula (vii) and formula (viii), and R1To R4At least two of which are each independently selected from the group consisting of: formula (i), formula (ii), formula (iii), formula (iv), formula (v), formula (vi), formula (vii), and formula (viii):
wherein R is5、R6、R7、R8、R9And R10Each independently selected from the group consisting of: hydrogen, a aryl group, an heteroaryl group, a C1-C6Alkyl radical, mono C1-C6Alkenyl and a C1-C6An alkynyl group; p, q, r, s, t, u and v are each independently integers between 1 and 4; x is selected from the group consisting of: NR (nitrogen to noise ratio)17、O、S、CR18 2、SiR19 2、PR20And Se; r17、R18、R19And R20Each independently selected from the group consisting of: hydrogen, a aryl group, an heteroaryl group, a C1-C6Alkyl radical, mono C1-C6Alkenyl and a C1-C6An alkynyl group; A. b and D are each independently selected from the group consisting of: carbon and nitrogen; and R is11、R12、R13、R14、R15And R16Each independently selected from the group consisting of: hydrogen, aryl, heteroaryl, C1-C6Alkyl radical, C1-C6Alkenyl and C1-C6Alkynyl.
In some embodiments of the present disclosure, an organic electroluminescent device comprises: an anode, a cathode, at least one light-emitting layer and an electron transport layer are arranged between the anode and the cathode; the light-emitting layer contains an organic electroluminescent compound represented by the formula (IV), (V) or (VI) as a host material:
in some embodiments of the present disclosure, an organic Electroluminescent (EL) device comprises at least a light-emitting layer and an electron-transporting layer disposed between a cathode and an anode, the light-emitting layer comprising an organic electroluminescent compound represented by the above formula (I), (II), (III), (IV), (V) or (VI) as a host material.
Fig. 1 shows an example of an organic EL device according to some embodiments of the present invention. In the structure of the organic EL device 10, an anode 200, a hole injection layer 300, a hole transport layer 400, a light emitting layer 500, an electron transport layer 600, an electron injection layer 700, and a cathode 800 are sequentially stacked on a substrate 100. In some embodiments, the light-emitting layer 500 contains an organic electroluminescent compound represented by formula (I) above as a host material. In some embodiments, the light-emitting layer 500 contains an organic electroluminescent compound represented by formula (II) above as a host material. In some embodiments, the light-emitting layer 500 contains an organic electroluminescent compound represented by formula (III) above as a host material. In some embodiments, the light-emitting layer 500 contains an organic electroluminescent compound represented by formula (IV) above as a host material. In some embodiments, the light-emitting layer 500 contains an organic electroluminescent compound represented by formula (V) above as a host material. In some embodiments, the light-emitting layer 500 contains an organic electroluminescent compound represented by formula (VI) above as a host material.
In some embodiments, the organic EL device is of a bottom emission type or a bottom emission type, in which light is emitted through a substrate. In some embodiments, the organic EL devices of the present disclosure are formed on a transparent substrate. In some embodiments, the transparent substrate is suitable for supporting a substrate of an organic EL device, and is preferably a planar and smooth substrate having a light transmittance of 50% or more. In some embodiments, the organic EL device is of a top-emission or top-emission type, in which light is emitted from an upper portion of the device and a light-reflecting metal, such as aluminum, is disposed over the substrate.
In some embodiments, in the organic electroluminescent device, a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant may be provided on at least one surface of the pair of electrodes. In some embodiments, the electron transport compound is reduced to an anion, thereby facilitating the injection and transport of electrons from the mixing region into the electroluminescent medium. In some embodiments, the hole transport compound is oxidized to a cation, thereby facilitating the injection and transport of holes from the mixing region into the electroluminescent medium. In certain embodiments, the oxidizing dopant comprises a plurality of lewis and acceptor compounds, wherein the reducing dopant comprises an alkali metal, an alkali metal compound, an alkaline earth metal, a rare earth metal, or mixtures thereof. In some embodiments, a reductive dopant layer can be used as a charge generation layer to produce an electroluminescent device with two or more electroluminescent layers that can emit white light.
In some embodiments, the organic EL device includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode. In some embodiments, the organic layer comprises a light-emitting layer. In some embodiments, the light-emitting layer comprises a combination of an organic electroluminescent device of the present disclosure and a phosphorus dopant. In some embodiments, the composition of the organic electroluminescent device comprises a host material.
In some embodiments, the organic layer of the organic EL device may further comprise at least one compound selected from the group consisting of: the arylamine group is a compound or a styrene arylamine group compound.
In some embodiments, in the organic EL device, the organic layer may further include organic electroluminescent compounds represented by formulas (I), (II), (III), (IV), (V), and (VI), at least one metal selected from the group consisting of: an organometallic of a metal of group I, a metal of group II, a transition metal of period IV, a transition metal of period V, a metal of lanthanide and a d-transition element of the periodic Table, or at least one complex comprising a metal. In some embodiments, the organic layer may further comprise a light-emitting layer and a charge-generating layer.
In some embodiments, an organic EL device can emit white light by employing at least one light emitting layer including a blue electroluminescent compound, a red electroluminescent compound, or a green electroluminescent compound other than the compounds described in the present disclosure. In some embodiments, the organic EL device may further include a yellow light emitting layer or an orange light emitting layer.
In some embodiments, at least one layer (referred to as a "surface layer") selected from the following may be provided on one or more inner surfaces of one or both electrodes of the organic EL device: a chalcogenide layer, a metal halide layer, and a metal oxide layer. In some embodiments, a silicon or aluminum chalcogenide (including oxide) layer may be preferably disposed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer may be preferably disposed on the cathode surface of the electroluminescent medium layer. Such a surface layer provides the organic electroluminescent device with operational stability. In a preferred case, the sulfide includes SiOX(1≤X≤2)、AlOX(X is more than or equal to 1 and less than or equal to 1.5), SiON, SiAlON and the like; the metal halide comprises LiF, MgF2、CaF2Rare earth metal fluorides, etc.; and the organic oxide comprises Cs2O、Li2O, MgO, SrO, BaO, CaO, etc.
In some embodiments, the use of an organic electroluminescent compound of formula (I), (II), (III), (IV), (V), or (VI) as a host material for an organic EL device can provide practical performance and lifetime to the organic EL device.
The foregoing outlines features of some embodiments so that those skilled in the art may better understand the aspects of the present disclosure. Those skilled in the art should appreciate that they may readily use the present disclosure as a basis for designing or modifying other processes and structures for carrying out the same purposes and/or achieving the same advantages of the embodiments introduced herein. Those skilled in the art should also realize that such equivalent constructions do not depart from the spirit and scope of the present disclosure, and that they may make various changes, substitutions and alterations herein without departing from the spirit and scope of the present disclosure.
[ notation ] to show
10 organic EL device
100 substrate
200 anode
300 hole injection layer
400 hole transport layer
500 light emitting layer
600 electron transport layer
700 electron injection layer
800 cathode
Claims (9)
1. An organic electroluminescent compound represented by the formula (III):
wherein R is1To R4Each independently selected from the group consisting of: hydrogen and a group consisting of: formula (i), formula (ii), formula (iii), formula (iv), formula (v), formula (vi), formula (vii) and formula (viii), and R1To R4At least two of which are each independently selected from the group consisting of: formula (i), formula (ii), formula (iii), formula (iv), formula (v), formula (vi), formula (vii), and formula (viii):
wherein R is5、R6、R7、R8、R9And R10Each independently of the otherIs selected from the group consisting of: hydrogen, a aryl group, an heteroaryl group, a C1-C6Alkyl radical, mono C1-C6Alkenyl and a C1-C6An alkynyl group; p, q, r, s, t, u and v are each independently integers between 1 and 4; x is selected from the group consisting of: NR (nitrogen to noise ratio)17、O、S、CR18 2，SiR19 2、PR20And Se; r17、R18、R19And R20Each independently selected from the group consisting of: hydrogen, a aryl group, an heteroaryl group, a C1-C6Alkyl radical, mono C1-C6Alkenyl and a C1-C6An alkynyl group; A. b and D are each independently selected from the group consisting of: carbon and nitrogen; and R is11、R12、R13、R14、R15And R16Each independently selected from the group consisting of: hydrogen, a aryl group, an heteroaryl group, a C1-C6Alkyl radical, mono C1-C6Alkenyl and a C1-C6Alkynyl.
2. The organic electroluminescent compound as claimed in claim 1, wherein R is1To R4Each of at least two of which is independently selected from the group consisting of: groups of formula (iii) and formula (iv).
3. The organic electroluminescent compound as claimed in claim 1, wherein R is5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15And R16Each independently selected from the group consisting of: hydrogen and-C1-C6An alkyl group.
4. The organic electroluminescent compound according to claim 1, wherein a and D are each independently nitrogen, and B is carbon.
5. The method of claim 1An organic electroluminescent compound wherein R1And R3At least one of which is a group of the formula (iii), and R2And R4At least one of them is a group represented by the formula (iv).
6. The organic electroluminescent compound as claimed in claim 1, wherein R is1And R3At least one of which is a group of the formula (iii), and R2And at least one of R is a group represented by the formula (iv); and R is9And R10Each independently selected from the group consisting of: hydrogen and-C1-C6Alkyl, u and v are each independently integers 1, A and D are each independently nitrogen, B is carbon, and R is11And R12Each independently selected from the group consisting of: hydrogen and-C1-C6An alkyl group.
7. The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is represented by the following formula (IV):
8. the organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is represented by the following formula (V):
9. the organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is represented by the following formula (VI):
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| US16/236,075 US10651393B2 (en) | 2017-09-13 | 2018-12-28 | Organic electroluminescent compound and organic electroluminescent device containing the same |
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