CA3016778A1 - Organic molecules, in particular for use in optoelectronic devices - Google Patents

Abstract

The invention relates to an organic compound, in particular for the application in optoelectronic devices. According to the invention, the organic compound has a structure of Formula I, X is O, S, NR1 or C=C(CN)2;
R1 is at each occurrence independently from each other selected from the group consisting of: -hydrogen, - deuterium, - C1-C5-alkyl, which is optionally substituted with one or more substituents R2;
- C6-C60-aryl, which is optionally substituted with one or more substituents R2; and - C3-C57-heteroaryl, which is optionally substituted with one or more substituents R2.

Description

I
ORGANIC MOLECULES, IN PARTICULAR FOR USE IN OPTOELECTRONIC DEVICES
The invention relates to organic light-emitting molecules and their use in organic light-emitting diodes (OLEDs) and in other optoelectronic devices.
Description The object of the present invention is to provide molecules which are suitable for use in optoelectronic devices.
This object is achieved by the invention which provides a new class of organic molecules.
According to the invention the organic molecules are purely organic molecules, i.e. they do not contain any metal ions in contrast to metal complexes known for use in optoelectronic devices.
According to the present invention, the organic molecules exhibit emission maxima in the blue, sky-blue or green spectral range. The organic molecules exhibit in particular emission maxima between 420 nm and 520 nm, preferably between 440 nm and 495 nm, more preferably between 450 nm and 470 nm. The photoluminescence quantum yields of the organic molecules according to the invention are, in particular, 20 % or more. The use of the molecules according to the invention in an optoelectronic device, for example an organic light-emitting diode (OLED), leads to higher efficiencies or higher color purity, expressed by the full width at half maximum (FWHM) of emission, of the device. Corresponding OLEDs have a higher stability than OLEDs with known emitter materials and comparable color.
The organic light-emitting molecule of the invention comprises or consists of a structure of Formula I,

2 RIII
Riv RII
X
RI
Rvi Rv Rv X
RI
RIv RNA
RIII RI
Riv X Rv RII
Formula I
In that Formula I:
X is at each occurrence independently from each other selected from the group consisting of: 0, S, NR 1 or C=C(CN)2.
R1 is at each occurrence independently from each other selected from the group consisting of:
hydrogen, deuterium, C1-05-alkyl, which is optionally substituted with one or more substituents R2;
C6-C60-aryl, which is optionally substituted with one or more substituents R2; and C3-057-heteroaryl, which is optionally substituted with one or more substituents R2.
RI, RI', RIII, Rv and Rvl is at each occurrence independently from each other selected from the group consisting of:
hydrogen, deuterium, C1-040-alkyl, which is optionally substituted with one or more substituents R2;
C1-C40-alkoxyl, which is optionally substituted with one or more substituents R2;
C2-C40-alkenyl, which is optionally substituted with one or more substituents R2;
C2-C40ralkynyl, which is optionally substituted with one or more substituents R2;

3 C6-C60-aryl, which is optionally substituted with one or more substituents R2;
C3-057-heteroaryl, which is optionally substituted with one or more substituents R2;
CN, CF3, N(R2)2, OR2, and Si(R2)3.
R2 is at each occurrence independently from another selected from the group consisting of:
hydrogen, deuterium, OPh, CF3, CN, F, C1-05-alkyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
Cl-05-alkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C1-05-thioalkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
02-05-alkenyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C2-05-alkynyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C6-C16-aryl, which is optionally substituted with one or more C1-05-alkyl substituents;
C3-C17-heteroaryl, which is optionally substituted with one or more C1-05-alkyl substituents;
N(C6-C15-ary1)2, N(C3-017-heteroary1)2; and N(C3-017-heteroary1)(C6-C15-aryl).
Optionally, at least one substituent selected from the group consisting of R1, RI, RH, Fe, Riv IR"
and Ry1 forms a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents selected from the group consisting of R1, RI, RII, RIv Ry and RvI.

4 In a further embodiment of the invention, X is 0 at each occurrence.
In a further embodiment of the invention, wherein RI, R", RI", RI", Rv and RvI
is at each occurrence independently from another selected from the group consisting of:
hydrogen, deuterium, halogen, Me, IPr, tBu, ON, CF3, Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, tBu, ON, CF3, and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, tBu, ON, CF3, and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, tBu, ON, CF3, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, tBu, ON, CF3, and Ph, triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, tBu, ON, CF3, and Ph, and N(Ph)2.
In a further embodiment of the invention, R", RIv and Rv is at each occurrence independently from another selected from the group consisting of:
hydrogen, deuterium, halogen, Me, 'Pr, tBu, ON, CF3, Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, tBu, CN, CF3, and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, tBu, ON, CF3, and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, tBu, ON, CF3, and Ph, and triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, tBu, CN, CF3, and Ph;
and RI, RI" and RvI is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, Me, 'Pr, tBu, Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, tBu, and Ph,

5 carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, tBu, CN, CF3, and Ph, and N(Ph)2.
In a further embodiment of the invention, RH, RI" and Rv is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, Me, IPr, 'Bu, CN, CF3, and Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, ON, CF3, and Ph;
and RI, Rill and IV is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, Me, 'Pr, tBu, Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, tBu, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Bu, and Ph, and N(Ph)2.
In a further embodiment of the invention, the organic molecules consist of a structure of one of Formulas ll to IX:
* 0 Formula II Formula III

6 INS
N
OS OS
N N
1.1 B 0 ISI B 0 N N N N
0 N J"CN . N N

1.1 lei Formula IV Formula V
s s 00 N
N

N N
N N
S
S
Formula VI Formula VII

7 INS

= N
(101 N
Formula VIII Formula IX
In one embodiment, the molecule of the invention has a three-fold rotational symmetry with the central B atom of the molecule being the rotational axis.
As used throughout the present application, the terms "aryl" and "aromatic"
may be understood in the broadest sense as any mono-, bi- or polycyclic aromatic moieties.
Accordingly, an aryl group contains 6 to 60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromatic ring atoms, of which at least one is a heteroatom. Notwithstanding, throughout the application the number of aromatic ring atoms may be given as subscripted number in the definition of certain substituents.
In particular, the heteroaromatic ring includes one to three heteroatoms.
Again, the terms "heteroaryl" and "heteroaromatic" may be understood in the broadest sense as any mono-, bi- or polycyclic hetero-aromatic moieties that include at least one heteroatom. The heteroatoms may at each occurrence be the same or different and be individually selected from the group consisting of N, 0 and S. Accordingly, the term "arylene" refers to a divalent substituent that bears two binding sites to other molecular structures and thereby serving as a linker structure. In case, a group in the exemplary embodiments is defined differently from the definitions given here, for example, the number of aromatic ring atoms or number of heteroatoms differs from the given definition, the definition in the exemplary embodiments is to be applied.
According to the invention, a condensed (annulated) aromatic or heteroaromatic polycycle is built of two or more single aromatic or heteroaromatic cycles, which formed the polycycle via a condensation reaction.

8 In particular, as used throughout the present application, the term "aryl group or heteroaryl group"
comprises groups which can be bound via any position of the aromatic or heteroaromatic group, derived from benzene, naphthaline, anthracene, phenanthrene, pyrene, dihydropyrene, 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, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, napthooxazole, anthroxazol, phenanthroxazol, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1,3,5-triazine, quinoxaline, pyrazine, phenazine, naphthyridine, carboline, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3,4-tetrazine, purine, pteridine, indolizine and benzothiadiazole or combinations of the abovementioned groups.
As used throughout the present application, the term "cyclic group" may be understood in the broadest sense as any mono-, bi- or polycyclic moieties.
As used throughout the present application, the term "biphenyl" as a substituent may be understood in the broadest sense as ortho-biphenyl, meta-biphenyl, or para-biphenyl, wherein ortho, meta and para is defined in regard to the binding site to another chemical moiety.
As used throughout the present application, the term "alkyl group" may be understood in the broadest sense as any linear, branched, or cyclic alkyl substituent. In particular, the term alkyl comprises the substituents methyl (Me), ethyl (Et), n-propyl ("Pr), i-propyl ('Pr), cyclopropyl, n-butyl ("Bu), i-butyl (Bu), s-butyl (sBu), t-butyl ('Bu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]-octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluorethyl, 1,1-dimethyl-n-hex-1-yl, 1 ,1-dimethyl-n-hept-1-yl, 1 ,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n-dec-1-yl, 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexadec-1-yl, 1 ,1-d imethyl-n-octadec-1 -yl, 1 ,1-diethyl-n-hex-1-yl, 1 ,1-diethyl-n-hept-1-yl, 1 ,1-diethyl-n-oct-1-yl, 1,1-

9 diethyl-n-dec-1-yl, 1,1-diethyl-n-dodec-1-yl, 1,1-diethyl-n-tetradec-1-yl, 1,1-diethyln-n-hexadec-1-yl, 1,1-diethyl-n-octadec-1-yl, 1-(n-propyI)-cyclohex-1-yl, 1-(n-butyl)-cyclohex-1-yl, 1-(n-hexyl)-cyclohex-1-yl, 1-(n-octy1)-cyclohex-1-y1 and 1-(n-decy1)-cyclohex-1-yl.
As used throughout the present application, the term "alkenyl" comprises linear, branched, and cyclic alkenyl substituents. The term alkenyl group exemplarily comprises the substituents ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.
As used throughout the present application, the term "alkynyl" comprises linear, branched, and cyclic alkynyl substituents. The term alkynyl group exemplarily comprises ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
As used throughout the present application, the term "alkoxy" comprises linear, branched, and cyclic alkoxy substituents. The term alkoxy group exemplarily comprises methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.
As used throughout the present application, the term "thioalkoxy" comprises linear, branched, and cyclic thioalkoxy substituents, in which the 0 of the exemplarily alkoxy groups is replaced by S.
As used throughout the present application, the terms "halogen" and "halo" may be understood in the broadest sense as being preferably fluorine, chlorine, bromine or iodine.
Whenever hydrogen (H) is mentioned herein, it could also be replaced by deuterium at each occurrence.
It is understood that when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g. naphtyl, dibenzofuryl) or as if it were the whole molecule (e.g. naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered to be equivalent.
In one embodiment, the organic molecules according to the invention have an excited state lifetime of not more than 150 ps, of not more than 100 ps, in particular of not more than 50 ps,

10 more preferably of not more than 10 ps or not more than 7 ps in a film of poly(methyl methacrylate) (PMMA) with 10 % by weight of organic molecule at room temperature.
In a further embodiment of the invention, the organic molecules according to the invention have an emission peak in the visible or nearest ultraviolet range, i.e., in the range of a wavelength of from 380 to 800 nm, with a full width at half maximum of less than 0.40 eV, preferably less than 0.35 eV, more preferably less than 0.33 eV, even more preferably less than 0.30 eV or even less than 0.28 eV in a film of poly(methyl methacrylate) (PMMA) with 10 % by weight of organic molecule at room temperature.
Orbital and excited state energies can be determined either by means of experimental methods or by calculations employing quantum-chemical methods, in particular density functional theory calculations. The energy of the highest occupied molecular orbital EFI m is determined by methods known to the person skilled in the art from cyclic voltammetry measurements with an accuracy of 0.1 eV. The energy of the lowest unoccupied molecular orbital Ewm is calculated as EHomo Egap, wherein EgaP is determined as follows: For host compounds, the onset of the emission spectrum of a film with 10 A) by weight of host in poly(methyl methacrylate) (PMMA) is used as EgaP, unless stated otherwise. For emitter molecules, Egag is determined as the energy at which the excitation and emission spectra of a film with 10 % by weight of emitter in PMMA cross.
The energy of the first excited triplet state Ti is determined from the onset of the emission spectrum at low temperature, typically at 77 K. For host compounds, where the first excited singlet state and the lowest triplet state are energetically separated by > 0.4 eV, the phosphorescence is usually visible in a steady-state spectrum in 2-Me-THF. The triplet energy can thus be determined as the onset of the phosphorescence spectrum. For TADF emitter molecules, the energy of the first excited triplet state Ti is determined from the onset of the delayed emission spectrum at 77 K, if not otherwise stated, measured in a film of PMMA with 10% by weight of emitter. Both for host and emitter compounds, the energy of the first excited singlet state Si is determined from the onset of the emission spectrum, if not otherwise stated, measured in a film of PMMA with % by weight of host or emitter compound.
The onset of an emission spectrum is determined by computing the intersection of the tangent to the emission spectrum with the x-axis. The tangent to the emission spectrum is set at the high-

11 energy side of the emission band and at the point at half maximum of the maximum intensity of the emission spectrum.
A further aspect of the invention relates to a process for preparing the organic molecule of the invention (with an optional subsequent reaction), wherein tert-butyllithium (tBuLi) and boron tribromide (BBr3) is used as a reactant:
0 Rvi 0 Cu Br Br K2CO3 Fiv N I" Rv + NH2 ___________ v.
Rv iel Xylene Rvl Rvi Br Br El E2 ZI
.
, 4, 0 Rvi 0 Rvi Pd(0A02 Ftv N Rv CI PtBu3 Rv N
Ry1 40 Rv H2N 0 NH2 NaOtBu lei SI
0 + ______________________________________________________ = CI
Br Br RNA Xylene, Rvi HN 0 NH
reflux Rv Rvi Z1 E3 Rv =
0 Rvi H Rvi RV N RV Rv N Rv Rvi 01 CI Si KOH __________ ),.. RVI 401 CI
HN 0 NH i-PrOH, Xylene HN NH

Rvi el RV RV

12 Rill RIv RII
RVI X
H RI
Rv N RV Me0 X Cu/Cul Rvi OMe K2CO3 R''N
Rv I RIv >
RvI CI $1 + Rvi 0 40 Ph20,190 C
OMe RI RI
HN 0 NH = CI
II RI
X
Rvi RII RH N N Fe/
0 Rvi , RV Rill OMe RI
Rill Z3 E4 Riv x Rv RH

RI" RIII
RIV RH RN R"
X X

OMe RvI LiOH OH Rvi Rv N Rv ___________________ )1.- Rõ v N Rv THF/Me0H/H20 RNA 40 ill OH
RNA 0 40 OMe reflux CI
RI CI X RI
X
RII N N Riv R" N N
RN
IS) Rvi lel Rvi RI" OMe RI RI" RI" RI
RI"
Rv Riv x OH
RV
RN x R" RII

RIII RIII
RN/ R" RN R"
X RI XIIX
RI
OH R" Rvi R''N Rv POCI3 RV N RV
__________________________________________________ ii.
R" 110 (10 OH X
MeCN CI
RI CI X H20 R" R1 Rvi N N
Riv RIII el R" N N Riv reflux - rt Rvi RVI
RI"
R" RI RI"
RN X III
OH RV RIv X Rv R"
RI R

13 Rill RN R" RR/ RH
X X
RI RI
Rvi NA
Rv N RV 1. tBuLi, -30 C to 0 C Rv NR RV
2. BBr3, -30 C to RT to 120 C
X 3. N,N-DIPEA 0 C to 120 C X
RI CI _________________________ x RI B
RvIN RNA
R" N Riv tert-butylbenzene RII N N RR/
Rvi RNA
Rill RI Rol RI" RI RIII
Fe/ X Rv R11 RI" X IV R"

A further aspect of the invention relates to the use of an organic molecule of the invention as a luminescent emitter or as an absorber, and/or as a host material and/or as an electron transport material, and/or as a hole injection material, and/or as a hole blocking material in an optoelectronic device.
A preferred embodiment relates to the use of an organic molecule according to the invention as a luminescent emitter in an optoelectronic device.
The optoelectronic device may be understood in the broadest sense as any device based on organic materials that is suitable for emitting light in the visible or nearest ultraviolet (UV) range, i.e., in the range of a wavelength of from 380 to 800 nm. More preferably, optoelectronic device may be able to emit light in the visible range, i.e., of from 380 nm to 800 nm.
In the context of such use, the optoelectronic device is more particularly selected from the group consisting of:
= organic light-emitting diodes (OLEDs), = light-emitting electrochemical cells, = OLED sensors, especially in gas and vapor sensors that are not hermetically shielded to the surroundings, = organic diodes, = organic solar cells, = organic transistors, = organic field-effect transistors, = organic lasers and

14 = down-conversion elements.
In a preferred embodiment in the context of such use, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light-emitting transistor.
In the case of the use, the fraction of the organic molecule according to the invention in the emission layer in an optoelectronic device, more particularly in an OLED, is 1 % to 99 % by weight, more particularly 3 % to 80 % by weight. In an alternative embodiment, the proportion of the organic molecule in the emission layer is 100 % by weight.
A further aspect of the invention relates to a composition comprising or consisting of:
(a) at least one organic molecule according to the invention, in particular in the form of an emitter and/or a host, and (b) one or more emitter and/or host materials, which differ from the organic molecule according to the invention and (c) optionally, one or more dyes and/or one or more solvents.
In one embodiment, the light-emitting layer of an optoelectronic device, in particular of an OLED, comprises not only the organic molecules according to the invention, but also a host material whose triplet (Ti) and singlet (Si) energy levels are energetically higher than the triplet (Ti) and singlet (Si) energy levels of the organic molecule.
In one embodiment, the light-emitting layer comprises (or essentially consists of) a composition comprising or consisting of:
(a) at least one organic molecule according to the invention, in particular in the form of an emitter and/or a host, and (b) one or more emitter and/or host materials, which differ from the organic molecule according to the invention and (c) optionally, one or more dyes and/or one or more solvents.
In a particular embodiment, the light-emitting layer EML comprises (or essentially consists of) a composition comprising or consisting of:

15 (i) 1-50 % by weight, preferably 5-40 % by weight, in particular 10-30 % by weight, of one or more organic molecules according to the invention;
(ii) 5-99 % by weight, preferably 30-94.9 % by weight, in particular 40-89%
by weight, of at least one host compound H; and (iii) optionally 0-94 % by weight, preferably 0.1-65 % by weight, in particular 1-50 % by weight, of at least one further host compound D with a structure differing from the structure of the molecules according to the invention; and (iv) optionally 0-94 % by weight, preferably 0-65 % by weight, in particular 0-50 % by weight, of a solvent; and (v) optionally 0-30 % by weight, in particular 0-20 % by weight, preferably 0-5 % by weight, of at least one further emitter molecule F with a structure differing from the structure of the molecules according to the invention.
Preferably, energy can be transferred from the host compound H to the one or more organic molecules according to the invention, in particular transferred from the first excited triplet state TI (H) of the host compound H to the first excited triplet state TI (E) of the one or more organic molecules according to the invention E and/or from the first excited singlet state Si (H) of the host compound H to the first excited singlet state S1(E) of the one or more organic molecules according to the invention E.
In a further embodiment, the light-emitting layer EML comprises (or essentially consists of) a composition comprising or consisting of:
(i) 1-50 % by weight, preferably 5-40 % by weight, in particular 10-30 % by weight, of one organic molecule according to the invention;
(ii) 5-99 % by weight, preferably 30-94.9 `)/0 by weight, in particular 40-89% by weight, of one host compound H; and (iii) optionally 0-94% by weight, preferably 0.1-65% by weight, in particular 1-50% by weight, of at least one further host compound D with a structure differing from the structure of the molecules according to the invention; and (iv) optionally 0-94 % by weight, preferably 0-65 % by weight, in particular 0-50 % by weight, of a solvent; and (v) optionally 0-30 % by weight, in particular 0-20 % by weight, preferably 0-5 % by weight, of at least one further emitter molecule F with a structure differing from the structure of the molecules according to the invention.

16 In one embodiment, the host compound H has a highest occupied molecular orbital HOMO(H) having an energy EN m (H) in the range of from -5 to -6.5 eV and the at least one further host compound D has a highest occupied molecular orbital HOMO(D) having an energy Ell m (D), wherein EHOMO(H) > EHOMO(D).
In a further embodiment, the host compound H has a lowest unoccupied molecular orbital LUMO(H) having an energy El-um (H) and the at least one further host compound D has a lowest unoccupied molecular orbital LUMO(D) having an energy ELum (D), wherein ELumo(H) > ELumo(D).
In one embodiment, the host compound H has a highest occupied molecular orbital HOMO(H) having an energy E1-1 "^ (H) and a lowest unoccupied molecular orbital LUMO(H) having an energy El-um (H), and the at least one further host compound D has a highest occupied molecular orbital HOMO(D) having an energy EH m (D) and a lowest unoccupied molecular orbital LUMO(D) having an energy ELum(D), the organic molecule according to the invention E has a highest occupied molecular orbital HOMO(E) having an energy EI-1 m (E) and a lowest unoccupied molecular orbital LUMO(E) having an energy ELum (E), wherein EHomo(d) > EHom (D) and the difference between the energy level of the highest occupied molecular orbital HOMO(E) of the organic molecule according to the invention E
(E1-1 m (E)) and the energy level of the highest occupied molecular orbital HOMO(H) of the host compound H
(EHm (H)) is between -0.5 eV and 0.5 eV, more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV or even between -0.1 eV and 0.1 eV;
and ELumo(H) > ELumoi kD) and the difference between the energy level of the lowest unoccupied molecular orbital LUMO(E) of the organic molecule according to the invention E
(ELum (E)) and the lowest unoccupied molecular orbital LUMO(D) of the at least one further host compound D
(Eww(D)) is between -0.5 eV and 0.5 eV, more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV or even between -0.1 eV and 0.1 eV.
In one embodiment of the invention, the host compound D and/or the host compound H is a thermally-activated delayed fluorescence (TADF)-material. TADF materials exhibit a LEST value, which corresponds to the energy difference between the first excited singlet state (Si) and the

17 first excited triplet state (T1), of less than 2500 cm-1. Preferably the TADF
material exhibits a LEST value of less than 3000 cm-1, more preferably less than 1500 cm-1, even more preferably less than 1000 cm-1 or even less than 500 cm-1.
In one embodiment, the host compound D is a TADF material and the host compound H exhibits a AEsT value of more than 2500 cm-1. In a particular embodiment, the host compound D is a TADF
material and the host compound H is selected from group consisting of CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)pheny1]-9H-carbazole, 9[3-(dibenzofuran-2-yl)pheny1]-9H-carbazole, 943-(dibenzothiophen-2-yflpheny1]-9H-carbazole, 943,5-bis(2-dibenzofuranyflpheny1]-9H-carbazole and 9[3,5-bis(2-dibenzothiophenyl)pheny1]-9H-carbazole.
In one embodiment, the host compound H is a TADF material and the host compound D exhibits a LEST value of more than 2500 cm-1. In a particular embodiment, the host compound H is a TADF
material and the host compound D is selected from group consisting of T2T
(2,4,6-tris(bipheny1-3-y1)-1,3,5-triazine), T3T (2,4,6-tris(tripheny1-3-y1)-1,3,5-triazine) and/or TST (2,4,6-tris(9,9'-spirobifluorene-2-y1)-1,3,5-triazine).
In a further aspect, the invention relates to an optoelectronic device comprising an organic molecule or a composition of the type described here, more particularly in the form of a device selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED sensor, more particularly gas and vapour sensors not hermetically externally shielded, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser and down-conversion element.
In a preferred embodiment, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light-emitting transistor.
In one embodiment of the optoelectronic device of the invention, the organic molecule according to the invention E is used as an emission material in a light-emitting layer EML.
In one embodiment of the optoelectronic device of the invention, the light-emitting layer EML
consists of the composition according to the invention described here.

18 When the optoelectronic device is an OLED, it may, for example, have the following layer structure:
1. substrate 2. anode layer A
3. hole injection layer, HIL
4. hole transport layer, HTL
5. electron blocking layer, EBL
6. emitting layer, EML
7. hole blocking layer, HBL
8. electron transport layer, ETL
9. electron injection layer, EIL
10. cathode layer, wherein the OLED comprises each layer selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL only optionally, different layers may be merged and the OLED may comprise more than one layer of each layer type defined above.
Furthermore, the optoelectronic device may, in one embodiment, comprise one or more protective layers protecting the device from damaging exposure to harmful species in the environment including, for example, moisture, vapor and/or gases.
In one embodiment of the invention, the optoelectronic device is an OLED, with the following inverted layer structure:
1. substrate 2. cathode layer 3. electron injection layer, EIL
4. electron transport layer, ETL
5. hole blocking layer, HBL
6. emitting layer, B
7. electron blocking layer, EBL
8. hole transport layer, HTL
9. hole injection layer, HIL
10. anode layer A

19 wherein the OLED comprises each layer selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL only optionally, different layers may be merged and the OLED may comprise more than one layer of each layer types defined above.
In one embodiment of the invention, the optoelectronic device is an OLED, which may have a stacked architecture. In this architecture, contrary to the typical arrangement in which the OLEDs are placed side by side, the individual units are stacked on top of each other. Blended light may be generated with OLEDs exhibiting a stacked architecture, in particular white light may be generated by stacking blue, green and red OLEDs. Furthermore, the OLED
exhibiting a stacked architecture may comprise a charge generation layer (CGL), which is typically located between two OLED subunits and typically consists of a n-doped and p-doped layer with the n-doped layer of one CGL being typically located closer to the anode layer.
In one embodiment of the invention, the optoelectronic device is an OLED, which comprises two or more emission layers between anode and cathode. In particular, this so-called tandem OLED
comprises three emission layers, wherein one emission layer emits red light, one emission layer emits green light and one emission layer emits blue light, and optionally may comprise further layers such as charge generation layers, blocking or transporting layers between the individual emission layers. In a further embodiment, the emission layers are adjacently stacked. In a further embodiment, the tandem OLED comprises a charge generation layer between each two emission layers. In addition, adjacent emission layers or emission layers separated by a charge generation layer may be merged.
The substrate may be formed by any material or composition of materials. Most frequently, glass slides are used as substrates. Alternatively, thin metal layers (e.g., copper, gold, silver or aluminum films) or plastic films or slides may be used. This may allow for a higher degree of flexibility. The anode layer A is mostly composed of materials allowing to obtain an (essentially) transparent film. As at least one of both electrodes should be (essentially) transparent in order to allow light emission from the OLED, either the anode layer A or the cathode layer C is transparent.
Preferably, the anode layer A comprises a large content or even consists of transparent conductive oxides (TC0s). Such anode layer A may, for example, comprise indium tin oxide, aluminum zinc oxide, fluorine doped tin oxide, indium zinc oxide, Pb0, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrol and/or doped polythiophene.

20 The anode layer A (essentially) may consist of indium tin oxide (ITO) (e.g., (In03)0.9(Sn02)01). The roughness of the anode layer A caused by the transparent conductive oxides (TC0s) may be compensated by using a hole injection layer (HIL). Further, the HIL may facilitate the injection of quasi charge carriers (i.e., holes) in that the transport of the quasi charge carriers from the TCO
to the hole transport layer (HTL) is facilitated. The hole injection layer (H1L) may comprise poly-3,4-ethylendioxy thiophene (PEDOT), polystyrene sulfonate (PSS), Mo02, V205, CuPC or Cul, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) may also prevent the diffusion of metals from the anode layer A into the hole transport layer (HTL). The HIL may exemplarily comprise PEDOT:PSS (poly-3,4-ethylendioxy thiophene: polystyrene sulfonate), PE DOT (poly-3,4-ethylendioxy thiophene), mMTDATA (4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine), Spiro-TAD (2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene), DNTPD (N1 ,N1-(bipheny1-4,4'-diy1)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1 ,4-diamine), NPB (N,N'-nis-(1-naphthalenyI)-N,N'-bis-phenyl-(1,1'-bipheny1)-4,4'-diamine), NPNPB
(N,N1-diphenyl-NN-di-[4-(N,N-diphenyl-amino)phenyl]benzidine), Me0-TPD (N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine), HAT-CN (1 ,4,5,8,9,1 1 -hexaazatriphenylen-hexacarbonitrile) and/or Spiro-NPD (N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diarnine).
Adjacent to the anode layer A or hole injection layer (HIL), a hole transport layer (HTL) is typically located. Herein, any hole transport compound may be used. For example, electron-rich heteroaromatic compounds such as triarylamines and/or carbazoles may be used as hole transport compound. The HTL may decrease the energy barrier between the anode layer A and the light-emitting layer EML. The hole transport layer (HTL) may also be an electron blocking layer (EBL). Preferably, hole transport compounds bear comparably high energy levels of their triplet states T1. For example, the hole transport layer (HTL) may comprise a star-shaped heterocycle such as tris(4-carbazoy1-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenyl-amine)), [alpha]-NPD (poly(4-butylphenyl-diphenyl-amine)), TAPC (4,4'-cyclohexyliden-bis[N,N-bis(4-methylphenyl)benzenamine]), 2-TNATA
(4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine), Spiro-TAD, DNTPD, NPB, NPNPB, Me0-TPD, HAT-CN
and/or TrisPcz (9,9'-dipheny1-6-(9-pheny1-9H-carbazol-3-y1)-9H,9'H-3,3'-bicarbazole). In addition, the HTL may comprise a p-doped layer, which may be composed of an inorganic or organic dopant in an organic hole-transporting matrix. Transition metal oxides such as vanadium oxide, molybdenum oxide or tungsten oxide may exemplarily be used as inorganic dopant.

21 Tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper-pentafluorobenzoate (Cu(l)pFBz) or transition metal complexes may exemplarily be used as organic dopant.
The EBL may exemplarily comprise mCP (1,3-bis(carbazol-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazol-9-yl)biphenyl), tris-Pcz, CzSi (9-(4-tert-Butylpheny1)-3,6-bis(triphenylsily1)-9H-carbazole), and/or DCB (N,N'-dicarbazolyI-1,4-dimethylbenzene).
Adjacent to the hole transport layer (HTL), the light-emitting layer EML is typically located. The light-emitting layer EML comprises at least one light emitting molecule.
Particularly, the EML
comprises at least one light emitting molecule according to the invention E.
In one embodiment, the light-emitting layer comprises only the organic molecules according to the invention. Typically, the EML additionally comprises one or more host materials H. Exemplarily, the host material H is selected from CBP (4,4'-Bis-(N-carbazolyI)-biphenyl), mCP, mCBP Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl] ether oxide), 943-(dibenzofuran-2-yl)pheny1]-9H-carbazole, 943-(dibenzofuran-2-yl)phenyI]-9H-carbazole, 9[3-(dibenzothiophen-2-yl)pheny1]-9H-carbazole, 9-[3,5-bis(2-dibenzofu ranyl)phenyI]-9 H-carbazole, 943,5-bis(2-dibenzothiophenyl)pheny1]-9H-carbazole, T2T (2,4,6-tris(bipheny1-3-y1)-1,3,5-triazine), T3T (2,4,6-tris(tripheny1-3-y1)-1,3,5-triazine) and/or TST (2,4,64ris(9,91-spirobifluorene-2-y1)-1,3,5-triazine).
The host material H
typically should be selected to exhibit first triplet (T1) and first singlet (Si) energy levels, which are energetically higher than the first triplet (Ti) and first singlet (Si) energy levels of the organic molecule.
In one embodiment of the invention, the EML comprises a so-called mixed-host system with at least one hole-dominant host and one electron-dominant host. In a particular embodiment, the EML comprises exactly one light emitting organic molecule according to the invention and a mixed-host system comprising T2T as electron-dominant host and a host selected from CBP, mCP, mCBP, 9[3-(dibenzofuran-2-yl)pheny11-9H-carbazole, 943-(dibenzofuran-2-yl)pheny1]-9H-carbazole, 9[3-(dibenzothiophen-2-yl)pheny1]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyI]-9H-carbazole and 943,5-bis(2-dibenzothiophenyl)pheny1]-9H-carbazole as hole-dominant host. In a further embodiment the EML comprises 50-80 % by weight, preferably 60-75 % by weight of a host selected from CBP, mCP, mCBP, 943-(dibenzofuran-2-yl)phenylj-9H-carbazole, 9[3-(dibenzofuran-2-yl)pheny1]-9H-carbazole, 913-(dibenzothiophen-2-yl)phenylF
9 H-carbazole, 9[3,5-bis(2-dibenzofuranyl)pheny1]-9H-carbazole and 9-[3,5-bis(2-

22 dibenzothiophenyl)phenyI]-9H-carbazole; 10-45 % by weight, preferably 15-30 %
by weight of T2T and 5-40 % by weight, preferably 10-30 % by weight of light emitting molecule according to the invention.
Adjacent to the light-emitting layer EML, an electron transport layer (ETL) may be located. Herein, any electron transporter may be used. Exemplarily, electron-poor compounds such as, e.g., benzimidazoles, pyridines, triazoles, oxadiazoles (e.g., 1,3,4-oxadiazole), phosphinoxides and sulfone, may be used. An electron transporter may also be a star-shaped heterocycle such as 1,3,5-tri(1-pheny1-1H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL may comprise NBphen (2,9-bis(naphthalen-2-y1)-4,7-dipheny1-1,10-phenanth roline), Alq3 (Aluminum-tris(8-hydroxyquinoline)), TSPO1 (dipheny1-4-triphenylsilylphenyl-phosphinoxide), BPyTP2 (2,7-di(2,2'-bipyridin-5-yl)triphenyle), Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB (1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene) and/or BTB (4,4'-bis42-(4,6-dipheny1-1,3,5-triaziny1)]-1,1'-biphenyl).
Optionally, the ETL may be doped with materials such as Liq. The electron transport layer (ETL) may also block holes or a holeblocking layer (HBL) is introduced.
The HBL may, for example, comprise BCP (2,9-dimethy1-4,7-dipheny1-1,10-phenanthroline =
Bathocuproine), BAlq (bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthalen-2-yI)-4,7-dipheny1-1,10-phenanthroline), Alq3 (Aluminum-tris(8-hydroxyquinoline)), TSPO1 (dipheny1-4-triphenylsilylphenyl-phosphinoxide), T2T
(2,4,6-tris(bipheny1-3-y1)-1,3,5-triazine), T3T (2,4,6-tris(tripheny1-3-y1)-1,3,5-triazine), TST (2,4,6-tris(9,9'-spirobifluorene-2-yI)-1,3,5-triazine), and/or TCBTTCP (1,3,5-tris(N-carbazolyl)benzol/
1,3,5-tris(carbazol)-9-y1) benzene).
Adjacent to the electron transport layer (ETL), a cathode layer C may be located. The cathode layer C may, for example, comprise or may consist of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy. For practical reasons, the cathode layer may also consist of (essentially) intransparent metals such as Mg, Ca or Al.
Alternatively or additionally, the cathode layer C may also comprise graphite and or carbon nanotubes (CNTs).
Alternatively, the cathode layer C may also consist of nanoscalic silver wires.
An OLED may further, optionally, comprise a protection layer between the electron transport layer (ETL) and the cathode layer C (which may be designated as electron injection layer (EIL)). This

23 layer may comprise lithium fluoride, cesium fluoride, silver, Liq (8-hydroxyquinolinolatolithium), Li2O, BaF2, MgO and/or NaF.
Optionally, the electron transport layer (ETL) and/or a hole blocking layer (HBL) may also comprise one or more host compounds H.
In order to modify the emission spectrum and/or the absorption spectrum of the light-emitting layer EML further, the light-emitting layer EML may further comprise one or more further emitter molecules F. Such an emitter molecule F may be any emitter molecule known in the art. Preferably such an emitter molecule F is a molecule with a structure differing from the structure of the molecules according to the invention E. The emitter molecule F may optionally be a TADF emitter.
Alternatively, the emitter molecule F may optionally be a fluorescent and/or phosphorescent emitter molecule which is able to shift the emission spectrum and/or the absorption spectrum of the light-emitting layer EML. For example, the triplet and/or singlet excitons may be transferred from the organic emitter molecule according to the invention to the emitter molecule F before relaxing to the ground state SO by emitting light typically red-shifted in comparison to the light emitted by an organic molecule. Optionally, the emitter molecule F may also provoke two-photon effects (i.e., the absorption of two photons of half the energy of the absorption maximum).
Optionally, an optoelectronic device (e.g., an OLED) may, for example, be an essentially white optoelectronic device. Exemplarily such white optoelectronic device may comprise at least one (deep) blue emitter molecule and one or more emitter molecules emitting green and/or red light.
Then, there may also optionally be energy transmittance between two or more molecules as described above.
As used herein, if not defined more specifically in the particular context, the designation of the colors of emitted and/or absorbed light is as follows:
violet: wavelength range of >380-420 nm;
deep blue: wavelength range of >420-480 nm;
sky blue: wavelength range of >480-500 nm;
green: wavelength range of >500-560 nm;
yellow: wavelength range of >560-580 nm;
orange: wavelength range of >580-620 nm;

24 red: wavelength range of >620-800 nm.
With respect to emitter molecules, such colors refer to the emission maximum.
Therefore, exemplarily, a deep blue emitter has an emission maximum in the range of from >420 to 480 nm, a sky blue emitter has an emission maximum in the range of from >480 to 500 nm, a green emitter has an emission maximum in a range of from >500 to 560 nm, a red emitter has an emission maximum in a range of from >620 to 800 nm.
A deep blue emitter may preferably have an emission maximum of below 480 nm, more preferably below 470 nm, even more preferably below 465 nm or even below 460 nm. It will typically be above 420 nm, preferably above 430 nm, more preferably above 440 nm or even above 450 nm.
Accordingly, a further aspect of the present invention relates to an OLED, which exhibits an external quantum efficiency at 1000 cd/m2 of more than 8 %, more preferably of more than 10 %, more preferably of more than 13 %, even more preferably of more than 15 % or even more than 20 % and/or exhibits an emission maximum between 420 nm and 500 nm, preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, even more preferably between 450 nm and 470 nm and/or exhibits a LT80 value at 500 cd/m2 of more than 100 h, preferably more than 200 h, more preferably more than 400 h, even more preferably more than 750 h or even more than 1000 h. Accordingly, a further aspect of the present invention relates to an OLED, whose emission exhibits a ClEy color coordinate of less than 0.45, preferably less than 0.30, more preferably less than 0.20 or even more preferably less than 0.15 or even less than 0.10.
A further aspect of the present invention relates to an OLED, which emits light at a distinct color point. According to the present invention, the OLED emits light with a narrow emission band (small full width at half maximum (FWHM)). In one aspect, the OLED according to the invention emits light with a FWHM of the main emission peak of less than 0.40 eV, preferably less than 0.35 eV, more preferably less than 0.33 eV, even more preferably less than 0.30 eV or even less than 0.28 eV.
A further aspect of the present invention relates to an OLED, which emits light with ClEx and ClEy color coordinates close to the ClEx (= 0.131) and ClEy (= 0.046) color coordinates of the primary color blue (ClEx = 0.131 and ClEy = 0.046) as defined by ITU-R Recommendation BT.2020 (Rec.

25 2020) and thus is suited for the use in Ultra High Definition (UHD) displays, e.g. UHD-TVs.
Accordingly, a further aspect of the present invention relates to an OLED, whose emission exhibits a ClEx color coordinate of between 0.02 and 0.30, preferably between 0.03 and 0.25, more preferably between 0.05 and 0.20 or even more preferably between 0.08 and 0.18 or even between 0.10 and 0.15 and/ or a ClEy color coordinate of between 0.00 and 0.45, preferably between 0.01 and 0.30, more preferably between 0.02 and 0.20 or even more preferably between 0.03 and 0.15 or even between 0.04 and 0.10.
In a further aspect, the invention relates to a method for producing an optoelectronic component.
In this case an organic molecule of the invention is used.
The optoelectronic device, in particular the OLED according to the present invention, can be manufactured by any means of vapor deposition and/ or liquid processing.
Accordingly, at least one layer is prepared by means of a sublimation process, prepared by means of an organic vapor phase deposition process, prepared by means of a carrier gas sublimation process, solution processed or printed.
The general methods used to manufacture the optoelectronic device, in particular the OLED
according to the present invention, are known in the art. The different layers are individually and successively deposited on a suitable substrate by means of subsequent deposition processes.
The individual layers may be deposited using the same or differing deposition methods.
Vapor deposition processes, for example, comprise thermal (co)evaporation, chemical vapor deposition and physical vapor deposition. For active matrix OLED display, an AMOLED backplane is used as substrate. The individual layer may be processed from solutions or dispersions employing adequate solvents. Solution deposition process exemplarily comprise spin coating, dip coating and jet printing. Liquid processing may optionally be carried out in an inert atmosphere (e.g., in a nitrogen atmosphere) and the solvent may optionally be completely or partially removed by means known in the state of the art.

i

26 Examples General synthesis scheme I
=
0 Rvi 0 Cu Br i& Br K2CO3 R''N
Fel + NH2 ___________ lb-RV IW 1101 Xylene R"
IW IW
. 180 C
RA Br Br El E2 Z1 . =
0 Rvi 0 Rvi Pd(0A02 RV i N i Ftv CI PtBu3 RV
Rvl i N
CI i, WI RV
H2N is NH2 NaOtBu IW IW + ___________________________________________________ -Rvl Br Br Rvl Xylene, 1WP
HN lei NH
reflux Rv Rvi Z1 E3 Rv 0 RA H Rvi R"N Rv R''N Rv RvI 10 CI la KOH
0 Rvi lei C 0 I
HN 0 NH i-PrOH, Xylene HN 0 NH

R" R"
RV RV

,

27 RI
RA/

RVI X
H RI
Rv N Rv Me0 X Cu/Cut Rvi R
OMe K2CO3 RFiNA v 0 40 N __ R''Iv a-vI Cl $ + IR
Ph20, 190 C
OMe RI Rill R1 X
Rvi R" RII N . N Riv Rv, Ry Rill OMe RI RI"
Z3 E4 Riv x Rv R"

R"1 R"I
RIv R11 RIv R"
X X
R RI RI
OMe OH vi RR'11LiOH , Rv N RV w R" N ___ R"Rvi 0 up OMe THF/Me0H/H20 R"10 0 OH
RI CI X reflux RI CI X

RIv RII N N RIv VI R" 101 R v 1 RIII OMe RI RIII Rill RI
RI"
Riv X RV R" Riv x OH RV
R"

R"1 RI"
RN R" XLjL
RIv R"
RI X
"RI
, OH Rvl N R-R' N v RV
Rv POCI3 R
VI
Rvl 10 CI 40 OH
X
RI X MeCN

RI" RII RI RvIN
CI
N RIv RII N N RIRID RI" RIv reflux - rt Rvt Rvl RI
RI"
Riv x OH Rv R" R1v x Rv R"

28 RL,R" Riv RII
X X
RI RI
Rvi Rv RV 1. tBuLi, -30 C to 0 C Rv Rvi Rv 2. BBr3, -30 C to RT to 120 C
RI CI X 3. N,N-DIPEA 0 C to 120 C X
Rvi R" I RvN
Rvi tert-butylbenzene Rvi RI" RI RI" RI" RI Rut Riv Rv R" Riv Rv R"

El (1.0 equivalent), E2 (1.0 equivalent), copper (1.5 equivalents) and potassium carbonate (2.5 equivalents) were dissolved in xylene under argon atmosphere. The mixture was heated to 180 C
for 48h. After cooling to room temperature, the mixture was filtered through a short silica gel column and the filtrate concentrated under vacuum. The residue was washed with acetic acid/Me0H and dried to afford Z1.
Z1 (1.0 equivalent), E3 (2.0 equivalents), palladium acetate (0.05 equivalents), tri-tert-butylphosphine (0.10 equivalents) and sodium tertbutoxide (2.5 equivalents) were dissolved in xylene under argon atmosphere. The solution was refluxed for 24h. The solvent was removed under high vacuum, THF added to the residue and the mixture filtered through celite. The filtrate was dried, evaporated and the residue purified by column chromatography to afford Z2.
Z2 (1 equivalent) was dissolved in xylene. Potassium hydroxide (1.5 equivalents) in isopropanol was added and the mixture heated to 70 C for 2 hours. The volatiles were evaporated under high vacuum and the residue washed with ethanol to afford Z3 as a solid.
A mixture of Z3 (1.0 equivalent), E4 (3.0 equivalents), potassium carbonate (7.5 equivalents), copper powder (0.6 equivalents) and copper (I) iodide (1.2 equivalents) in diphenylether was heated to 190 C under argon for 72h. The reaction mixture was diluted with dichloromethane and filtered through celite. The filtrate was concentrated under reduced pressure to remove the DCM
and the residue Z4 purified by column chromatography.
Z4 (1.0 equivalent) was dissolved in a mixture of THF/Me0H/H20 (1/1/1).
Lithium hydroxide hydrate was added to the solution and the mixture heated to 70 C for 16 hours.
After cooling to room temperature, water was added and the pH adjusted to pH = 3 with a 10%
aqueous citric

29 acid solution. The solution was extracted with ethyl acetate, dried, concentrated under vacuum and the residue Z5 purified by column chromatography.
Z5 (1.0 equivalent) was dissolved in CH3CN and heated to reflux. Phosphorus(V) oxychloride (16.6 equivalents) was added over 1 h. The solution was refluxed for further 4 h and then cooled to 10-15 C. H20 was added, and the mixture was heated to reflux for 5 h. The suspension was cooled to 10 C and filtered. The solid Z6 was washed with H20 and CH3CN and then dried under vacuum.
Z6 (1.00 equivalents) was dissolved in tert-butylbenzene and the solution was cooled to -30 C.
tert-butyllithium (tBuLi) (2.00 equivalents) was added dropwise and the reaction mixture was allowed to warm up to 0 C. After stirring for 30 minutes at 0 C, the reaction mixture was cooled again to -30 C.
A solution of boron tribromide (BBr3, 1.1 equivalents) was added dropwise, the bath was removed and the reaction mixture was allowed to warm to room temperature (rt).
Subsequently, the reaction mixture was heated at reflux at 120 C for 5h. The solution was cooled to 0 C, N,N-diisopropylethylamine (4.00 equivalents) was added and the solution heated again to 120 C for 3 hours. Volatiles were removed under reduced pressure, the residue dissolved in toluene and filtered through a silica gel column. The filtrate was dried and evaporated under vacuum to obtain P1.

30 Cyclic voltammetty Cyclic voltammograms are measured from solutions having concentration of 10-3 mol/L of the organic molecules in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g. 0.1 mol/L of tetrabutylammonium hexafluorophosphate). The measurements are conducted at room temperature under nitrogen atmosphere with a three-electrode assembly (Working and counter electrodes: Pt wire, reference electrode: Pt wire) and calibrated using FeCp2/FeCp2+ as internal standard. The HOMO data was corrected using ferrocene as internal standard against SCE.
Density functional theory calculation Molecular structures are optimized employing the BP86 functional and the resolution of identity approach (RI). Excitation energies are calculated using the (BP86) optimized structures employing Time-Dependent DFT (TD-DFT) methods. Orbital and excited state energies are calculated with the B3LYP functional. Def2-SVP basis sets (and a m4-grid for numerical integration are used. The Turbomole program package is used for all calculations.
Photophysical measurements Sample pretreatment: Spin-coating Apparatus: Spin150, SPS euro.
The sample concentration is 10 mg/ml, dissolved in a suitable solvent.
Program: 1) 3 s at 400 U/min; 20 s at 1000 U/min at 1000 Upm/s. 3) 10 s at 4000 U/min at 1000 Upm/s. After coating, the films are tried at 70 C for 1 min.
Photoluminescence spectroscopy and TCSPC (Time-correlated single-photon counting) Steady-state emission spectroscopy is measured by a Horiba Scientific, Modell FluoroMax-4 equipped with a 150 W Xenon-Arc lamp, excitation- and emissions monochromators and a Hamamatsu R928 photomultiplier and a time-correlated single-photon counting option. Emissions and excitation spectra are corrected using standard correction fits.
Excited state lifetimes are determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.
Excitation sources:
NanoLED 370 (wavelength: 371 nm, puls duration: 1,1 ns) NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)

31 SpectraLED 310 (wavelength: 314 nm) SpectraLED 355 (wavelength: 355 nm).
Data analysis (exponential fit) is done using the software suite DataStation and DAS6 analysis software. The fit is specified using the chi-squared-test.
Photoluminescence quantum yield measurements For photoluminescence quantum yield (PLQY) measurements an Absolute PL Quantum Yield Measurement C9920-03G system (Hamamatsu Photonics) is used. Quantum yields and CIE
coordinates are determined using the software U6039-05 version 3.6Ø
Emission maxima are given in nm, quantum yields (1) in % and CIE coordinates as x,y values.
PLQY is determined using the following protocol:
1) Quality assurance: Anthracene in ethanol (known concentration) is used as reference 2) Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength 3) Measurement Quantum yields are measured, for sample, of solutions or films under nitrogen atmosphere. The yield is calculated using the equation:
nphoton, ernited f Ac[Intes maTtPteled (A) Int as abms opri be e d (A) d A
PL =hoton, absorbed = _______________________________________ A [hare f erence ( 1) r,tre ference ( ])-1 c L emitted v" "'absorbed VV.]
dA
wherein nooton denotes the photon count and Int. the intensity.
Production and characterization of organic electroluminescence devices OLED devices comprising organic molecules according to the invention can be produced via vacuum-deposition methods. If a layer contains more than one compound, the weight-percentage of one or more compounds is given in %. The total weight-percentage values amount to 100 %, thus if a value is not given, the fraction of this compound equals to the difference between the given values and 100 %.
The not fully optimized OLEDs are characterized using standard methods and measuring electroluminescence spectra, the external quantum efficiency (in %) in dependency on the intensity, calculated using the light detected by the photodiode, and the current. The OLED device lifetime is extracted from the change of the luminance during operation at constant current density.
The LT50 value corresponds to the time, where the measured luminance decreased to 50 % of the initial luminance, analogously LT80 corresponds to the time point, at which the measured

32 luminance decreased to 80 % of the initial luminance, LT 95 to the time point, at which the measured luminance decreased to 95 % of the initial luminance etc.
Accelerated lifetime measurements are performed (e.g. applying increased current densities).
Exemplarily LT80 values at 500 cd/m2 are determined using the following equation:
Lo )1.6 Cd2 LT80 (500 LT80(4) ______ cd2 \500 __________________________________________ m wherein Lo denotes the initial luminance at the applied current density.
The values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given.
HPLC-MS:
HPLC-MS spectroscopy is performed on a HPLC by Agilent (1100 series) with MS-detector (Thermo LTQ XL). A reverse phase column 4,6mm x 150mm, particle size 5,0 pm from Waters (without pre-column) is used in the HPLC. The HPLC-MS measurements are performed at room temperature (rt) with the solvents acetonitrile, water and THF in the following concentrations:
solvent A: H20 (90%) MeCN (10%) solvent B: H20 (10%) MeCN (90%) solvent C: THF (100%) From a solution with a concentration of 0.5mg/m1 an injection volume of 15 pL
is taken for the measurements. The following gradient is used:
Flow rate [ml/min] time [min] A[%] B[%] D[%]

3 16.01 40 50 10 Ionisation of the probe is performed by APCI (atmospheric pressure chemical ionization).

33 Example 1 Os Example 1 was synthesized according to the general procedure for synthesis, wherein 1,3-Dibromobenzene (El), benzamide (E2), 2-chloro-m-phenylenediamine (E3) and methyl 2-iodobenzoate (E4) were used as reactants.

34 Additional Examples of organic molecules of the invention o N
N
Si B 0 B 0 N N
N N

= 40 N ccrD
05 Os lel 0 o B B
N N N N

N N N N
ilki 0 1.1 o S. s N
N
oBxI
S B S
N N
N N
S
S

INS
N

* N
B S la B N S
N N N N
I N N . N N
S S
0 .
.

Claims (13)

Claims

1. Organic molecule, consisting of a structure of Formula l, wherein X is at each occurrence independently from each other selected from the group consisting of: O, S, NR1, and C=C(CN)2;
R1 is at each occurrence independently from each other selected from the group consisting of:
hydrogen, deuterium, C1-C5-alkyl, which is optionally substituted with one or more substituents R2;
C6-C60-aryl, which is optionally substituted with one or more substituents R2; and C3-C57-heteroaryl, which is optionally substituted with one or more substituents R2;
R I, R II, R III, R IV, R V and R Vl is at each occurrence independently from each other selected from the group consisting of:
hydrogen, deuterium, C1-C40-alkyl, which is optionally substituted with one or more substituents R2;
C1-C40-alkoxyl, which is optionally substituted with one or more substituents R2;
C2-C40-alkenyl, which is optionally substituted with one or more substituents R2;
C2-C40-alkynyl, which is optionally substituted with one or more substituents R2;
C6-C60-aryl, which is optionally substituted with one or more substituents R2;
C3-C57-heteroaryl, which is optionally substituted with one or more substituents R2;
CN;
CF3;
N(R2)2;
OR2; and Si(R2)3;
R2 is at each occurrence independently from another selected from the group consisting of:
hydrogen, deuterium, OPh, CF3, CN, F, C1-C5-alkyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C1-C5-alkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C1-C5-thioalkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkenyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkynyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C6-C15-aryl, which is optionally substituted with one or more C1-C5-alkyl substituents;

C3-C17-heteroaryl, which is optionally substituted with one or more C1-C5-alkyl substituents;
N(C6-C18-aryl)2;
N(C3-C17-heteroaryl)2; and N(C3-C17-heteroaryl)(C6-C18-aryl);
wherein at least one substituent selected from the group consisting of R1, RI, RII, RIII, RIv Rv and Rvl optionally forms a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents selected from the group consisting of R1, RI, RII, RIII, Rlv Rv and RvI.

2. Organic molecule according to claim 1, wherein X is O at each occurrence.

3. Organic molecule according to claim 1 or 2, wherein RI, RII, RIII, RIv, Rv and RvI is at each occurrence independently from another selected from the group consisting of:
hydrogen, deuterium, halogen, Me, iPr tBu, CN, CF3, Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, CN, CF3, and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, CN, CF3, and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, CN, CF3, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, CN, CF3, and Ph, triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, CN, CF3, and Ph, and N(Ph)2.

4. Organic molecule according to claim 3, wherein RH, Rlv and Rv is at each occurrence independently from another selected from the group consisting of:
hydrogen, deuterium, halogen, Me, tBu, Su, CN, CF3, Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, CN, CF3, and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, CN, CF3, and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, CN, CF3, and Ph, and triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, CN, CF3, and Ph;
and RI, RIll and RvI is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, Me, iPr, tBu, Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, iPr, tBu, CN, CF3, and Ph, and N(Ph)2.

5. Organic molecule according to claim 4, wherein - RH, Rlv and Rv is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, Me, iPr, tBu, CN, CF3, and Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF3, and Ph;
and - R I, R III and R VI is at each occurrence independently from another selected from the group consisting of:
hydrogen, deuterium, Me, i Pr, t Bu, Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, t Bu, and Ph, and N(Ph)2.

6. Organic molecule according to claim 5, wherein each R I, R II, R III, R IV, R V and R VI is hydrogen.

7. Organic molecule according to claim 1 consisting of a structure of one of Formulas II to IX:

8. Use of an organic molecule according to one or more of claims 1 to 7 as a luminescent emitter in an optoelectronic device.

9. Use according to claim 8, wherein the optoelectronic device is selected from the group consisting of:
.cndot. organic light-emitting diodes (OLEDS), .cndot. light-emitting electrochemical cells, .cndot. OLED-sensors, .cndot. organic diodes, .cndot. organic solar cells, .cndot. organic transistors, .cndot. organic field-effect transistors, .cndot. organic lasers, and .cndot. down-conversion elements.

10. Composition, comprising or consisting of:
(a) at least one organic molecule according to one or more of claims 1 to 7, in particular in the form of an emitter and/or a host, and (b) one or more emitter and/or host materials, which differ from the organic molecule of one or more of claims 1 to 7, and (c) optionally, one or more dyes and/or one or more solvents.

11. Optoelectronic device, comprising an organic molecule according to one or more of claims 1 to 7 or a composition according to claim 10, in particular in form of a device selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED-sensor, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser and down-conversion element.

12. Optoelectronic device according to claim 11, comprising or consisting of:
- a substrate, - an anode, and - a cathode, wherein the anode or the cathode are disposed on the substrate, and - at least one light-emitting layer, which is arranged between anode and cathode and which comprises the organic molecule according to claims 1 to 7 or a composition according to claim 10.

13. Process for producing an optoelectronic device, wherein an organic molecule according to any one of claims 1 to 7 or a composition according to claim 10 is used, in particular comprising the processing of the organic compound by a vacuum evaporation method or from a solution.