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WO2016116521A1 - Molécules organiques à utiliser en particulier dans des composants optoélectroniques - Google Patents

Molécules organiques à utiliser en particulier dans des composants optoélectroniques Download PDF

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WO2016116521A1
WO2016116521A1 PCT/EP2016/051162 EP2016051162W WO2016116521A1 WO 2016116521 A1 WO2016116521 A1 WO 2016116521A1 EP 2016051162 W EP2016051162 W EP 2016051162W WO 2016116521 A1 WO2016116521 A1 WO 2016116521A1
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David Ambrosek
Michael Danz
Harald FLÜGGE
Jana Friedrichs
Tobias Grab
Andreas Jacob
Stefan Seifermann
Daniel Volz
Liaptsis GEORGIOS
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Cynora GmbH
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Definitions

  • the invention relates to purely organic molecules and their use in organic light-emitting diodes (OLEDs) and in other optoelectronic components.
  • OLED organic light-emitting diodes
  • OLEDs are usually realized in layer structures, which consist predominantly of organic materials.
  • layer structures consist predominantly of organic materials.
  • FIG. 1 The heart of such components is the emitter layer, in which usually emitting molecules are embedded in a matrix.
  • the energy contained in the excitons can be emitted by the corresponding emitters in the form of light, in this case speaking of electroluminescence.
  • An overview of the function of OLEDs can be found, for example, in H. Yersin, Top. Curr. Chem., 2004, 241, 1 and H. Yersin, "Highly Efficient OLEDs with Phosphorescent Materials”; Wiley-VCH, Weinheim, Germany, 2008.
  • a new generation of OLEDs is based on the utilization of delayed fluorescence (TADF: thermally activated delayed fluorescence or singlet harvesting).
  • TADF thermally activated delayed fluorescence or singlet harvesting
  • Cu (I) complexes can be used which, due to a small energy gap between the lowest triplet state ⁇ and the overlying singlet state Si (AE (Si-Ti)), can thermally recombine triplet exitones into a singlet state.
  • AE overlying singlet state Si
  • transition metal complexes purely organic molecules (without metal ion) can exploit this effect.
  • the invention relates to purely organic molecules that can be used in optoelectronic components.
  • Such organic molecules have a structure of the formula 1 or have a structure of the formula 1:
  • pi system dicyclic substituted or unsubstituted aromatic pi system which has no heteroatoms;
  • AF Organic chemical entity (remainder).
  • the organic molecule of formula 1 has two different chemical entities AF1 and AF2; AF1: a first chemical entity comprising a conjugated system, in particular at least six conjugated ⁇ -electrons (eg in the form of at least one aromatic system); AF2: a second chemical entity comprising a conjugated system, in particular at least six conjugated ⁇ -electrons (eg in the form of at least one aromatic system); AF2 always has a lower (mathematical) HOMO value compared to AF1 (and correspondingly a lower LUMO number than AF1).
  • AF1 a first chemical entity comprising a conjugated system, in particular at least six conjugated ⁇ -electrons (eg in the form of at least one aromatic system)
  • AF2 a second chemical entity comprising a conjugated system, in particular at least six conjugated ⁇ -electrons (eg in the form of at least one aromatic system)
  • AF2 always has
  • the energy values HOMO (AF1), HOMO (AF2), LUMO (AF1), LUMO (AF2) are calculated using the density functional theory (DFT), whereby the attachment positions of the chemical units and the separators are saturated with a hydrogen atom according to their chemical valences.
  • DFT density functional theory
  • the limits given refer to orbital energies in eV calculated with the BP86 functional (Becke, A.D. Phys Rev. A1988, 38, 3098-3100, Perdew, J.P. Phys. Rev. B1986, 33, 8822-8827).
  • the organic molecules have a structure of the formula Ia or consist of a structure of the formula Ia:
  • one chemical unit AF1 is bound to exactly one carbon atom which is not part of both rings A and B, while a residue R * is bound to all other carbon atoms.
  • a chemical unit AF2 is bound to exactly one carbon atom which is not a constituent of both rings A and B, while a residue R * is bound to all other carbon atoms.
  • rings A and B each have one C atom of the nuclei which are not part of two ring systems and each has one chemical unit AF1 and AF2 bound to it and one residue R * attached to all other C atoms.
  • R 3 is independently selected for each occurrence from the group consisting of H, deuterium, phenyl, naphthyl, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 carbon atoms, in which also one or more H Atoms may be replaced by F or CF 3 ; two or more substituents R 3 may also together form a mono- or polycyclic aliphatic ring system;
  • R 8 is independently selected in each occurrence from the group consisting of H, deuterium, phenyl, naphthyl, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 carbon atoms, in which also one or more H atoms can be replaced by F or CF 3 ; two or more substituents R 8 may also together form a mono- or polycyclic aliphatic ring system;
  • the organic molecules have a structure of the formula 2a to 2b or have a structure of the formula 2a to 2b, wherein the definitions given in formula 1 and 2 apply and the organic molecule has at least two different AF
  • Formula 2a Formula 2b wherein AF1, AF2 and R * are defined as in Formula 1 a.
  • An aryl group in the sense of this invention contains 6 to 60 aromatic ring atoms;
  • a heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which represents a heteroatom.
  • the heteroatoms are in particular N, O, and S. If different definitions are given elsewhere in the description of the present invention, for example with regard to the number of aromatic ring atoms or the heteroatoms contained therein, these deviating definitions apply.
  • an aryl group or heteroaryl group is a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine or thiophene, or a heteroaromatic polycycle, for example naphthalene, Phenanthrene, quinoline or carbazole understood.
  • a condensed (fused) aromatic or heteroaromatic polycycle consists in the context of the present application of two or more fused simple aromatic or heteroaromatic cycles.
  • An aryl or heteroaryl group which may be substituted in each case by the abovementioned radicals and which may be linked via any position on the aromatic or heteroaromatic compounds is understood in particular to mean groups which are derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, Dihydropyrenes, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; Pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, isoquinoline
  • An aromatic ring system in the sense of this invention contains 6 to 60 carbon atoms in the ring system.
  • a heteroaromatic ring system in the context of this invention contains 5 to 60 aromatic ring atoms, at least one of which represents a heteroatom.
  • the heteroatoms are in particular selected from N, O and / or S.
  • an aromatic or heteroaromatic ring system within the meaning of this invention is meant a system which does not necessarily contain only aryl or heteroaryl groups, but in which also several aryl or heteroaryl groups by a non-aromatic moiety (especially less than 10% of the various atoms), such as. For example, a sp3 -hybridized.
  • C, Si, or N atom an sp 2 -hybridized.
  • C-, N- or O-atom or a sp-hybridized C-atom may be connected.
  • systems such as 9, T-diaryl fluorene, triarylamine, diaryl ethers, stilbene, etc. are to be understood as aromatic ring systems in the context of this invention, and also systems in which two or more aryl groups, for example by a linear or cyclic alkyl, alkenyl or alkynyl groups or by a silyl group.
  • systems in which two or more aryl or heteroyrayl groups are linked together via single bonds as aromatic or heteroaromatic ring systems for the purposes of this invention, such as systems such as biphenyl, terphenyl or diphenyltriazine.
  • aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted in each case with radicals as defined above and which may be linked via any positions on the aromatic or heteroaromatic, are understood in particular groups which are derived from benzene, naphthalene , Anthracene, benzanthracene, phenanthrene, benzphenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, terphenyls, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydro-pyrene, cis- or trans- indenofluorene, truxene, isotruxene, spirotruxene, spiroiso
  • the chemical units AF1 and AF2 are connected to one another via a separator such that the electronic communication between them is interrupted, which is characterized by the localization of the frontier orbitals HOMO and LUMO on separate parts of the molecule.
  • the separator may have any structure as long as an interruption of the electronic communication is ensured.
  • the electronic communication between the two chemical entities AF1 and AF2 via conjugated bonds with an optional separator is disrupted when the frontier orbitals HOMO and LUMO are located on separate parts of the molecule, allowing for a charge-transfer transition.
  • the localization of the frontier orbit HOMO or LUMO is visualized using density functional theory (DFT) with the BP86 functional (Becke, AD Phys Rev. A1988, 38, 3098-3100, Perdew, JP Phys Rev. B1986, 33, 8822-8827): From the One-electron -Well function, the single-electron density is calculated by squaring and integrated over the space occupied by the examined moiety.
  • DFT density functional theory
  • This space can be determined from the atomic coordinates and van der Waals radii of the atoms.
  • the resulting number corresponds to the proportion of orbital on the moiety.
  • a majority separation of the frontier orbitals corresponds to an overlap parameter O in the range of 0.1-20% to allow a charge-transfer transition.
  • ) b results from the integral over the entire space over the respective smaller value of the squared wave function:
  • the organic molecules are selected from formulas 2-1 and 2-2:
  • separator S The part of the organic molecule according to formula 1, formula 2a to formula 2b or formula 2-1 to formula 2-2, which represents non-chemical units AF, is also referred to as separator S.
  • separator S If the AF is omitted in formulas 1 and 2-1 to 2-2, then the molecular fragments remain, which are referred to here as separator S.
  • the separator is a molecular fragment having one of the following structures, where # denotes the location at which the AF binds to the separator, with exactly one AF1 and exactly one AF2 present in the molecule:
  • the unit AF1 has a structure of sub-formula 1 or has a structure of sub-formula 1
  • VG3 bridging group is independently selected from the group consisting of each occurrence
  • Z is independently CR ** or N at each occurrence
  • At least 1 of the units VG3, Z is a group other than C-H containing at least one nitrogen or one oxygen or one sulfur atom;
  • R ** is independently at each occurrence either a radical R *, or a chemical bond to a separator S, wherein exactly one R ** is a chemical bond to a separator S and wherein the connection to the separator only via an R * *, that is bound to a pure C-aromatic or C-ring takes place, wherein a pure C-aromatic or a pure C-ring consists exclusively of carbon atoms, that has no heteroatoms.
  • R * is defined as in formula 1 a.
  • the unit AF1 has a structure of the sub-formulas 1 .1 to 1 .7 or has a structure of the sub-formulas 1 .1 to 1 .7
  • R ** is independently at each occurrence either a residue R *, or a chemical bond to a separator S, where exactly one R ** is a chemical bond to a separator S.
  • R * is defined as in Formula 1.
  • the unit AF1 has a structure of the sub-formulas 1 .1 1 to 1 .12 or has a structure of the sub-formulas 1.1 1 to 1 .12
  • W is' ⁇ - ⁇ or an element-element single bond, where two units W are not simultaneously an element-element single bond, NR *, where two units W are not simultaneously NR *;
  • R ** is independently at each occurrence either a residue R *, or a chemical bond to a separator S, where exactly one R ** is a chemical bond to a separator S.
  • R * is defined as in formula 1 a.
  • the unit AF1 has a structure of sub-formula 1.14 or has a structure of sub-formula 1.14
  • Alk is selected from the group consisting of methyl, ethyl, propyl, / 'so-propyl, butyl, tert-butyl, pentyl, hexyl, 2-ethylhexyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl;
  • R ** is independently at each occurrence either a residue R *, or a chemical bond to a separator S, where exactly one R ** is a chemical bond to a separator S.
  • R * is defined as in formula 1 a.
  • the unit AF1 has a structure of the sub-formulas 1 .15 to 1 .22 or has a structure of the sub-formulas 1 .15 to 1.22
  • M is independently selected from the group consisting of H, deuterium, alk, phenyl, pyridyl and CN, with a maximum of 4 units M are simultaneously CN, or denotes a chemical bond to a separator S, where exactly one M is a chemical bond denotes a separator s;
  • the unit AF1 has a structure of the sub-formulas 1.23 or has a structure of the sub-formulas 1.23
  • D is N, CR *
  • T is CR **
  • R ** is independently at each occurrence either a residue R *, or a chemical bond to a separator S, where exactly one R ** is a chemical bond to a separator S.
  • R * is defined as in formula 1 a.
  • the unit AF1 has a structure of the sub-formulas 1 .25 to 1 .35 or has a structure of the sub-formulas 1.25 to 1.35
  • V is at each occurrence CR ** or N, where at least one unit V is equal to N; and wherein a maximum of two units V are N at a time; and wherein two adjacent units V are not equal to N at a time.
  • R ** is independently at each occurrence either a radical R *, or a chemical bond to a separator S, wherein exactly one R ** is a chemical bond to a separator S and wherein the connection to the separator only via an R * * that is bound to a pure C-aromatic or C-ring takes place.
  • R * is defined as in formula 1 a.
  • unit AF2 has a structure of sub-formula 2 or has a structure of sub-formula 2
  • n 0, 1;
  • o 0, 1;
  • p 0, 1;
  • VG1 bridging group, is selected from the group consisting of
  • VG2 bridging group at each occurrence is independently selected from the group consisting of CR ** 2 , NR **, O, S and a CC single bond, where two units VG2 are not simultaneously equal to one CC single bond;
  • E is selected from the group consisting of NR **, , O and S;
  • R *** is R ** or is selected from the following units, wherein a maximum of two of the radicals R *** are simultaneously one of the following units:
  • R ** is independently a residue R * at each occurrence and / or marks a point of attachment to a separator S, where exactly one R ** is a point of attachment to a separator S.
  • R * is defined as in formula 1 a.
  • the unit AF2 has a structure of the sub-formula 3 or has a structure of the sub-formula 3
  • Sub-formula 3 wherein in sub-formula 3: p is 0 or 1; X is CR ** 2 , NR **, oxygen, sulfur, a direct bond, with a maximum of two placeholders X being simultaneously a direct bond, which are not part of the same ring; and, moreover, the definitions given for sub-formula 2 apply.
  • At least one AF2 of the organic molecule has a structure of the formula 4A1-4A7 or has a structure of the formula 4A1 -4A7;
  • X is C (R **) 2 , NR **, oxygen, sulfur; and, moreover, the definitions given for sub-formula 2 apply.
  • the organic molecule has a structure of formula 5 or has a structure of formula 5;
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units: and R * is defined as in Formula 1 a.
  • the organic molecule has a structure of the formula 6 or has a structure of the formula 6.
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • R * is defined as in Formula 1 a.
  • the organic molecule has a structure of formula 7 or has a structure of formula 7;
  • X is selected from the group consisting of CR * 2 , NR *, oxygen, sulfur, a direct bond, wherein a maximum of two wildcards X are simultaneously a direct bond, which are not part of the same ring;
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • R * is defined as in sub-formula 1 a.
  • the organic molecule has a structure of the formula 8 or has a structure of the formula 8;
  • X is CR * 2 , NR *, oxygen, sulfur, a direct bond, with a maximum of two wildcards X being simultaneously a direct bond, which are not part of the same ring;
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • the organic molecule has a structure of formula 9 or has a structure of formula 9;
  • X is selected from the group consisting of CR * 2 , NR *, oxygen, sulfur, a direct bond, wherein a maximum of two wildcards X are simultaneously a direct bond, which are not part of the same ring;
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • the chemical moieties AF are selected from the chemical moieties listed in Table 1.
  • Chemical Units AF A given chemical entity may represent one chemical entity AF1 in one organic molecule and one chemical entity AF2 in another molecule. Provided that two different AFs always occur in one molecule, additional AFs may be identical to the former. Possible connecting points of the chemical unit AF to a separator S are denoted by lowercase letters.
  • Table 2 Examples of organic molecules according to the invention ((AF1) 0 -S- (AF2) P ).
  • the naming of the molecules on the left contains the first chemical group AF1 from Table 1, which is bound via a separator S (molecular unit without AFs) to a second chemical group AF2 (from Table 1), which is mentioned on the right, where o and p are the number the respective chemical units AF indicates.
  • Table 1 shows possible attachment positions of the chemical entity AF for linking to a separator S of the molecule according to the invention with lowercase letters a to z.
  • Each aromatic CH and NH bond is optionally substituted with a solubilising and / or a polymerisable R.
  • the separator S functionally distinguishes the organic molecules from prior art molecules, as the type of separation of AFs (or donors and acceptors) shown here is not yet known.
  • Known organic emitters usually consist of directly linked chemical units. Separation of the conjugated aromatic systems has not taken place so far, especially in connection with the localization of HOMO and LUMO on separate parts of the molecule. Separators serve to interrupt the electronic communication between the chemical units AF1 and AF2 by linking the units such that the frontier orbitals HOMO and LUMO lie on mostly separate parts of the molecule, which need not necessarily be the case without the separator.
  • separators do not significantly alter the position of the HOMO or LUMO of the AFs shown in Table 1. Not significant in the context of this invention is a change of not more than +/- 0.4 eV. The calculation of such energies is known and works according to the manner described above by DFT calculation.
  • spectroscopic selection rules symmetric molecules
  • UV / VIS spectroscopy UV / VIS spectroscopy
  • quantum chemical calculation of the oscillator strength it can be predicted whether a quantum mechanical transition is allowed.
  • the goal is a decay time of ⁇ 50 ps. With a long decay time of the (organic) emitter, saturation effects quickly occur at high current intensities, which adversely affects the component lifetime and prevents the achievement of high brightness levels.
  • a measure of the decay time is the quantum mechanical overlap integral, which is approximately represented by the overlap parameter O defined above.
  • the smaller the overlap integral the more separated the frontier orbitals HOMO and LUMO, and the more likely the charge-transfer transition.
  • the probability of TADF emission decreases due to decreasing oscillator strengths.
  • the overlap integral must be controlled in a targeted manner.
  • the desired overlap is achieved by the suitable choice of a separator S according to the invention.
  • a measure of the decay time is the AE (Si-T-i) distance. This is influenced by the overlap of HOMO and LUMO.
  • the size of the quantum mechanical overlap integral which can be calculated by the above-mentioned DFT method, can be controlled in a targeted manner by selecting the separator. If it comes to the complete separation of HOMO and LUMO this has a value of 0.
  • the probability of an efficient emission of the organic molecule decreases drastically. At a value of 1 there is no longer delayed fluorescence (TADF) but spontaneous emission.
  • TADF delayed fluorescence
  • the HOMO energy is lower than the HOMO energy of the donor chemical unit AF and
  • the LUMO energy is higher than the LUMO energy of the acceptor chemical entity AF.
  • organic molecules according to the invention are shown in Table 3, which result from the combination of the above-defined pairs of chemical entities AF1 and AF2, the separator S and the definition of the linkage. Further organic molecules can be obtained by combining said molecular units, wherein at least two different chemical units AF are contained in the molecule.
  • the organic molecule comprises a separator S having a molecular fragment of one of the structures given in formula 3, wherein # denotes the site at which the AF is bound to the separator.
  • 53 - S-291 (2.13 1.73 1.42)
  • 53 - S-292 (1.46 1.39 1.76)
  • 53 - S-293 (0.96 1.20 1.95)
  • 53 - S-293 (0.96 1.20 1.95)
  • 64 - S - 133 (1.54 1.43 1.53)
  • 64 - S - 144 (0.88 1.34 1.62)
  • 64 - S - 145 (0.86 1.99 0.97)
  • 64 - S - 150 (2.36 1.30 1.66)
  • 64 - S-249 (0.83 1.67 1.29)
  • 64 - S- 255 (1.68 1.50 1.46)
  • 64 - S-260 (0.80 1.95 1.01)
  • 64 - S-265 (1.25 1.42 1.54)
  • 64 - S-279 (0.83 0.83 2.13)
  • 64 - S-290 (0.89 1.03 1.93)
  • 64 - S-291 (2.02 1.44 1.52)
  • 64 - S-292 (1.36 1.10 1.86)

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

Abstract

L'invention concerne des molécules organiques, à utiliser en particulier dans des composants optoélectroniques, tels que des OLED. Selon l'invention, la molécule organique présente une structure de formule (1a) dans laquelle AF représente une unité chimique organique. La molécule organique comporte une première unité chimique AF1 sur le cycle A , et une seconde unité chimique AF2 sur le cycle B, AF1 et AF2 n'étant pas identiques. L'unité AF1 comprend une structure de sous-formule (1) ou présente une structure de sous-formule (1), dans laquelle q représente 0 ou 1; r représente 0 ou 1; et s représente 0 ou 1.
PCT/EP2016/051162 2015-01-20 2016-01-20 Molécules organiques à utiliser en particulier dans des composants optoélectroniques Ceased WO2016116521A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190093009A1 (en) * 2017-09-26 2019-03-28 Luminescence Technology Corporation Delayed fluorescence compound and organic electroluminescent device using the same

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2610937A1 (fr) * 2011-12-26 2013-07-03 Samsung Display Co., Ltd. Dispositif électroluminescent organique présentant une meilleure durée de vie
KR20140006708A (ko) * 2012-07-05 2014-01-16 (주)씨에스엘쏠라 신규한 유기발광화합물 및 이를 포함하는 유기전기발광소자
US20140361268A1 (en) * 2013-06-07 2014-12-11 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
WO2014204464A1 (fr) * 2013-06-20 2014-12-24 Universal Display Corporation Dispositifs électroluminescents organiques phosphorescents ayant un hôte transportant des trous dans la région émissive
US20150171337A1 (en) * 2013-12-12 2015-06-18 Samsung Display Co., Ltd. Amine-based compounds and organic light-emitting devices comprising the same
WO2015178740A2 (fr) * 2014-05-22 2015-11-26 주식회사 엘지화학 Composé hétérocyclique et dispositif électroluminescent organique contenant ce composé
KR101584626B1 (ko) * 2014-07-03 2016-01-12 주식회사 엘엠에스 신규한 화합물 및 이를 포함하는 발광소자

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2610937A1 (fr) * 2011-12-26 2013-07-03 Samsung Display Co., Ltd. Dispositif électroluminescent organique présentant une meilleure durée de vie
KR20140006708A (ko) * 2012-07-05 2014-01-16 (주)씨에스엘쏠라 신규한 유기발광화합물 및 이를 포함하는 유기전기발광소자
US20140361268A1 (en) * 2013-06-07 2014-12-11 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
WO2014204464A1 (fr) * 2013-06-20 2014-12-24 Universal Display Corporation Dispositifs électroluminescents organiques phosphorescents ayant un hôte transportant des trous dans la région émissive
US20150171337A1 (en) * 2013-12-12 2015-06-18 Samsung Display Co., Ltd. Amine-based compounds and organic light-emitting devices comprising the same
WO2015178740A2 (fr) * 2014-05-22 2015-11-26 주식회사 엘지화학 Composé hétérocyclique et dispositif électroluminescent organique contenant ce composé
KR101584626B1 (ko) * 2014-07-03 2016-01-12 주식회사 엘엠에스 신규한 화합물 및 이를 포함하는 발광소자

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
BECKE, A. D., PHYS. REV. A, vol. 38, 1988, pages 3098 - 3100
CUI, SYNTHESIS, 2007, pages 393 - 399
H. YERSIN, TOP. CURR. CHEM., vol. 241, 2004, pages 1
H. YERSIN: "Highly Efficient OLEDs with Phosphorescent Materials", 2008, WILEY-VCH
M. A. BALDO; D. F. O'BRIEN; M. E. THOMPSON; S. R. FORREST, PHYS. REV. B, vol. 60, 1999, pages 14422
PERDEW, J. P., PHYS. REV. B, vol. 33, 1986, pages 8822 - 8827
Q. SHENG; J. F. HARTWIG, ORG. LETT.,, vol. 10, 2008, pages 4109 - 4112
TANG ET AL., APPL. PHYS. LETT., vol. 51, 1987, pages 913

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190093009A1 (en) * 2017-09-26 2019-03-28 Luminescence Technology Corporation Delayed fluorescence compound and organic electroluminescent device using the same
US10472564B2 (en) * 2017-09-26 2019-11-12 Feng-wen Yen Delayed fluorescence compound and organic electroluminescent device using the same

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