DE102016115851B3 - Organic molecules, in particular for use in organic optoelectronic devices - Google Patents

Abstract

The invention relates to an organic molecule, in particular for use in optoelectronic components. According to the invention contains the organic molecule - a first chemical entity comprising or consisting of a structure according to formula I and - a second chemical entity D comprising or consisting of a structure according to formula II, Here, the first chemical entity via a single bond with the second chemical Unit D linked. X is H or the point of attachment of the single bond between the echemical unit of Formula I and the second chemical entity D. Y is H or the point of attachment of the single bond between the chemical entity of Formula I and the second chemical entity D. W is CN or CF3. # is the point of attachment of the single bond between the second chemical entity D and the chemical entity of Formula I. Precisely one residue is selected from the group consisting of X and Y is equal to the point of attachment of a single bond between the first chemical entity of Formula I and the second chemical Unit D.

Description

The invention relates to purely organic molecules and their use in organic light emitting diodes (OLEDs) and in other organic optoelectronic devices.

description

The object of the present invention was to provide molecules which are suitable for use in optoelectronic devices.

This object is achieved with the invention, which provides a new class of organic molecules.

The organic molecules according to the invention are purely organic molecules, ie have no metal ions and are thus different from the metal complex compounds known for use in organic optoelectronic devices.

The organic molecules according to the invention are distinguished by emissions in the blue, sky-blue or green spectral range. The photoluminescence quantum yields of the organic molecules according to the invention are in particular 20% or more. In particular, the molecules according to the invention exhibit thermally activated delayed fluorescence (TADF). 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 of the device. Corresponding OLEDs have a higher stability than OLEDs with known emitter materials and comparable color.

The blue spectral range here means the visible range of less than 470 nm. The sky-blue spectral range is understood to mean the range from 470 nm to 499 nm. The green spectral range is understood to mean the range from 500 nm to 599 nm. The emission maximum lies within the respective range.

• – eine erste chemische Einheit aufweisend eine oder bestehend aus einer Struktur gemäß Formel I
  
  und
• – eine zweite chemische Einheit D aufweisend eine oder bestehend aus einer Struktur gemäß Formel II,
  

The organic molecules contain:

• A first chemical entity comprising one or consisting of a structure according to formula I.
  
  and
• A second chemical entity D comprising one or consisting of a structure according to formula II,
  

Here, the first chemical unit is linked via a single bond with the second chemical entity D.

X is H or point of attachment of the single bond between the first chemical entity and the second chemical entity D.

Y is H or the point of attachment of the single bond between the first chemical entity I and the second chemical entity D.

W is CN or CF ₃ .

# is the point of attachment of the single bond between the second chemical entity D and the first chemical entity.

Z is a direct bond or selected from the group consisting of CR ³ R ⁴ , C = CR ³ R ⁴ , C = O, C = NR ³ , NR ³ , O, SiR ³ R ⁴ , S, S (O) and S (O) ₂ .

R ¹ and R ² are each the same or different H, deuterium, a linear alkyl group having 1 to 5 C atoms, a linear alkenyl or alkynyl group having 2 to 8 C atoms, a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms, wherein one or more H atoms may be replaced by deuterium, or an aromatic or heteroaromatic ring system having 5 to 15 aromatic ring atoms, each of which may be substituted by one or more R ⁶ radicals.

R ^a , R ³ and R ⁴ are each the same or different at each occurrence H, deuterium, N (R ⁵ ) ₂ , OH, Si (R ⁵ ) ₃ , B (OR ⁵ ) ₂ , OSO ₂ R ⁵ , CF ₃ , CN, F, Br, I, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl -, alkoxy or Thioalkoxygruppe having 3 to 40 carbon atoms, each of which may be substituted with one or more radicals R ⁵ , wherein one or more non-adjacent CH ₂ groups by R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R ⁵ , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R ⁵ or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R ⁵ .

R ⁵ is the same or different H, deuterium, N (R ⁶ ) ₂ , OH, Si (R ⁶ ) ₃ , B (OR ⁶ ) ₂ , OSO ₂ R ⁶ , CF ₃ , CN, F, Br at each occurrence. I, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having from 3 to 40 carbon atoms, each of which may be substituted by one or more R ⁶ radicals, one or more non-adjacent CH ₂ groups represented by R ⁶ C = CR ⁶ , C≡C, Si (R ⁶ ) ₂ , Ge (R ⁶ ) ₂ , Sn (R ⁶ ) ₂ , C = O, C = S, C = Se, C = NR ⁶ , P (= O) (R ⁶ ), SO, SO ₂ , NR ⁶ , O , S or CONR ⁶ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R ⁶ , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R ⁶ or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R ⁶ .

R ⁶ is the same or different H, Deuterium, OH, CF ₃ , CN, F, a linear alkyl, alkoxy or thioalkoxy group having 1 to 5 C atoms or a linear alkenyl or alkynyl group having 2 to 5 C at each occurrence Atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 5 C atoms, wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms or an aryloxy or heteroaryloxy group having from 5 to 60 aromatic ring atoms or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having from 10 to 40 aromatic ring atoms.

Each of the radicals R ^a , R ³ , R ⁴ or R ⁵ may also form with one or more further radicals R ^a , R ³ , R ⁴ or R ⁵ a mono- or polycyclic, aliphatic, aromatic and / or benzoanelliertes ring system.

In this case, exactly one radical selected from X and Y is the point of attachment of a single bond between the first chemical entity and the second chemical entity D.

In one embodiment, R ¹ and R ^{2 are the} same or different at each occurrence, being H, methyl or phenyl.

In one embodiment, W is CN.

wobei für # und R^a die für Formel I und II genannten Definitionen gelten.In a further embodiment of the organic molecules, the second chemical group D has a structure of the formula IIa or consists of a structure of the formula IIa:

where # and R ^{a are} the definitions given for formulas I and II.

wobei
R^b bei jedem Auftreten gleich oder verschieden ist N(R⁵)₂, OH, Si(R⁵)₃, B(OR⁵)₂, OSO₂R⁵, CF₃, CN, F, Br, I, eine lineare Alkyl-, Alkoxy- oder Thioalkoxygruppe mit 1 bis 40 C-Atomen oder eine lineare Alkenyl- oder Alkinylgruppe mit 2 bis 40 C-Atomen oder eine verzweigte oder cyclische Alkyl-, Alkenyl-, Alkinyl-, Alkoxy- oder Thioalkoxygruppe mit 3 bis 40 C-Atomen, die jeweils mit einem oder mehreren Resten R⁵ substituiert sein kann, wobei eine oder mehrere nicht benachbarte CH₂-Gruppen durch R⁵C=CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C=O, C=S, C=Se, C=NR⁵, P(=O)(R⁵), SO, SO₂, NR⁵, O, S oder CONR⁵ ersetzt sein können und wobei ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können; oder ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 60 aromatischen Ringatomen, das jeweils durch einen oder mehrere Reste R⁵ substituiert sein kann, oder eine Aryloxy- oder Heteroaryloxygruppe mit 5 bis 60 aromatischen Ringatomen, die durch einen oder mehrere Reste R⁵ substituiert sein kann, oder eine Diarylaminogruppe, Diheteroarylaminogruppe oder Arylheteroarylaminogruppe mit 10 bis 40 aromatischen Ringatomen, welche durch einen oder mehrere Reste R⁵ substituiert sein kann. Ansonsten gelten die oben genannten Definitionen.In a further embodiment of the organic molecules according to the invention, the second chemical entity D has a structure of the formula IIb, of the formula IIb-2, of the formula IIb-3 or of the formula IIb-4 or consists thereof:

in which
R ^{b is the} same or different at each occurrence, N (R ⁵ ) ₂ , OH, Si (R ⁵ ) ₃ , B (OR ⁵ ) ₂ , OSO ₂ R ⁵ , CF ₃ , CN, F, Br, I, is a linear one Alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may each be substituted by one or more radicals R ⁵ , wherein one or more non-adjacent CH ₂ groups by R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R ⁵ , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R ⁵ or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R ⁵ . Otherwise, the above definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment of the organic molecules according to the invention, the second chemical entity D has a structure of the formula IIc, of the formula IIc-2, of the formula IIc-3 or of the formula IIc-4 or consists thereof:

where the definitions above apply.

In a further embodiment of the organic molecules according to the invention, R ^{b is} independently selected from the group consisting of Me, ⁱ Pr, t Bu, CN, CF ₃ , Ph by one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted pyridinyl by one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or ph may be substituted, pyrimidinyl which by one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or ph may be substituted, carbazolyl, which is selected by one or more radicals selected from Me, ⁱ Pr, tBu, CN, CF ₃ or Ph may be substituted, triazinyl which by one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted, and N (Ph). ₂

wobei für #, Z, R^a, R³, R⁴ und R⁵ die oben genannten Definitionen gelten. In einer Ausführungsform ist der Rest R⁵ bei jedem Auftreten gleich oder verschieden ausgewählt aus der Gruppe bestehend aus H, Methyl, Ethyl, Phenyl und Mesityl. In einer Ausführungsform ist R^a bei jedem Auftreten gleich oder verschieden ausgewählt aus der Gruppe bestehend aus H, Methyl (Me), i-Propyl (CH(CH₃)₂) (ⁱPr), t-Butyl (^tBu), Phenyl (Ph), CN, CF₃ und Diphenylamin (NPh₂).Exemplary embodiments of the chemical group D are shown below:

where #, Z, R ^a , R ³ , R ⁴ and R ^{5 are} the abovementioned definitions. In one embodiment, the radical R ⁵ on each occurrence is identically or differently selected from the group consisting of H, methyl, ethyl, phenyl and mesityl. In one embodiment, R ^a in each occurrence is the same or different selected from the group consisting of H, methyl (Me), i-propyl (CH (CH ₃ ) ₂ ) ( ⁱ Pr), t -butyl ( ^t Bu), phenyl (Ph), CN, CF ₃ and diphenylamine (NPh ₂ ).

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of the formula III or consist of:

where the definitions above apply.

wobei
R^c bei jedem Auftreten unabhängig voneinander ausgewählt aus der Gruppe bestehend aus Me, ⁱPr, ^tBu, CN, CF₃, Ph, das jeweils durch einen oder mehrere Reste ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann, Pyridinyl, das jeweils durch einen oder mehrere Reste ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann, Pyrimidinyl, das jeweils durch einen oder mehrere Reste ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann, Carbazolyl, das jeweils durch einen oder mehrere Reste ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann, Triazinyl, das jeweils durch einen oder mehrere Reste ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann, und N(Ph)₂ ist.In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIa or consist of:

in which
R ^c in each occurrence independently selected from the group consisting of Me, ⁱ Pr, ^t Bu, CN, CF ₃ , Ph, each by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph substituted may be pyridinyl by one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted, pyrimidinyl which by one or more groups selected from Me, ⁱ Pr, ^Bu , CN, CF ₃ or Ph may be substituted, carbazolyl, which by one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted, triazinyl which is selected by one or more radicals may be substituted from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph, and N is (Ph) ₂ .

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIb or consist of:

where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIc or consist of:

where the definitions above apply.

wobei die oben genannten Definitionen gelten. In a further embodiment, the organic molecules according to the invention have a structure of the formula IIId or consist thereof:

where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIe or consist of:

where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIf or consist of:

where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIg or consist of:

where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIh or consist thereof:

where the definitions above apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of the formula IV or consist of:

where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVa or consist thereof:

where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVb or consist of:

where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVc or consist of:

where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVd or consist of:

where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVe or consist thereof:

where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVf or consist of:

where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVg or consist of:

where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVh or consist of:

where the definitions above apply.

In one embodiment, R ^c is independently selected in each occurrence from the group consisting of Me, ⁱ Pr, ^t Bu, Ph, each by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or ph may be substituted, and carbazolyl, which may each be substituted by one or more groups selected from Me, ⁱ Pr, Bu ^t, ph or substituted.

For the purposes of this invention, an aryl group contains from 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 / or S. If in the description of certain embodiments of the invention other definitions deviating from the abovementioned definition are given, for example with regard to the number of aromatic ring atoms or the heteroatoms contained therein, these apply.

An aryl group or heteroaryl group is understood as meaning a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine or thiophene, or a heteroaromatic polycycle, for example phenanthrene, quinoline or carbazole. 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, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, Indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazine imidazole, quinoxaline imidazole, oxazole, benzoxazole, napthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzpyrimidine, Quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, 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 said groups.

A cyclic alkyl, alkoxy or thioalkoxy group is understood here to mean a monocyclic, a bicyclic or a polycyclic group.

In the context of the present invention, a C ₁ - to C ₄₀ -alkyl group in which individual H atoms or CH ₂ groups may be substituted by the abovementioned groups, for example the radicals methyl, ethyl, n-propyl, i Propyl, cyclopropyl, n -butyl, i -butyl, s -butyl, t -butyl, 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, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, 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-dimethyl-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-diethyl-n-decyl 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-propyl) -cyclohex-1-yl, 1- (n-butyl) -cyclohex-1-yl, 1- (n- Hexyl) -cyclohex-1-yl, 1- (n-octyl) -cyclohex-1-yl and 1- (n-decyl) -cyclohex-1-yl. An alkenyl group is understood as meaning, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl. By an alkynyl group is meant, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. A C ₁ - to C ₄₀ -alkoxy group is understood as meaning, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.

One embodiment of the invention relates to organic molecules which have a ΔE (S ₁ -T ₁ ) value between the lowest excited singlet (S ₁ ) and the underlying triplet (T ₁ ) state of not higher than 5000 cm ^-1 , in particular not higher than 3000 cm ^-1 , or not higher than 1500 cm ^-1 or 1000 cm ^-1 and / or have an emission lifetime of at most 150 μs, in particular of at most 100 μs, of the highest 50 μs, or of at most 10 μs and / or a main emission band with a Having a half-width of less than 0.55 eV, in particular less than 0.50 eV, less than 0.48 eV, or less than 0.45 eV.

One embodiment of the invention relates to organic molecules having an emission maximum at between 420 and 500 nm, more preferably between 430 and 480 nm, even more preferably between 450 and 470 nm.

In one embodiment, the molecules have a blue material index (BMI), the quotients of the PLQY (in%) and their CIE _y color coordinate of the light emitted by the molecule according to the invention, of greater than 150, in particular greater than 200, larger 250 or from more than 300 on.

In a further aspect, the invention relates to a process for preparing an organic molecule of the invention of the type described herein (with a possible follow-up reaction) wherein a 3,5-bis (trifluoromethyl) -phenylboronic acid substituted in 2,4,6-position R ¹ or a corresponding in 2,4,6-position R ¹ -substituierter 3,5-bis (trifluoromethyl) -phenylboronsäureester is used as starting material.

In the above scheme, in one embodiment, the chemical group CN is replaced by CF ₃ .

In one embodiment, a R ¹ -substituted 3,5-bis (trifluoromethyl) phenylboronic acid or in 2,4,6-position, a corresponding in 2,4,6-position, R ¹ -substituted 3,5-bis (trifluoromethyl) Phenylboronsäureester reacted as starting material with a bromofluorobenzonitrile in a palladium-catalyzed cross-coupling reaction. In this case, 4-bromo-2-fluorobenzonitrile, 4-bromo-3-fluorobenzonitrile, 4-bromo-2-fluorobenzotrifluoride or 4-bromo-3-fluorobenzotrifluoride can be used according to the invention. The product is obtained by deprotonation of the corresponding amine and subsequent nucleophilic substitution of the two fluoro groups. Here, a nitrogen heterocycle is implemented in the sense of a nucleophilic aromatic substitution with a starting material E1. Typical conditions include the use of a base such as tribasic potassium phosphate or sodium hydride in an aprotic polar solvent such as dimetylsulfoxide (DMSO) or N, N-dimethylformamide (DMF).

• • organischen lichtemittierenden Dioden (OLEDs),
• • lichtemittierenden elektrochemischen Zellen,
• • OLED-Sensoren, insbesondere in nicht hermetisch nach außen abgeschirmten Gas- und Dampf-Sensoren,
• • organischen Dioden,
• • organischen Solarzellen,
• • organischen Transistoren,
• • organischen Feldeffekttransistoren,
• • organischen Lasern und
• • Down-Konversions-Elementen.

In a further aspect, the invention relates to the use of the organic molecules as a luminescent emitter or as a host material in an organic optoelectronic device, in particular wherein the organic optoelectronic device is selected from the group consisting of:

• Organic light-emitting diodes (OLEDs),
• Light-emitting electrochemical cells,
• OLED sensors, especially in non-hermetically shielded gas and vapor sensors,
• Organic diodes,
• • organic solar cells,
• Organic transistors,
• Organic field effect transistors,
• • organic lasers and
• • Down conversion elements.

• (a) mindestens einem erfindungsgemäßen organischen Molekül, insbesondere als Emitter und/oder Host, und
• (b) mindestens ein, d. h. ein oder mehrere Emitter- und/oder Hostmaterialien, die von dem erfindungsgemäßen organischen Molekül verschiedenen ist bzw. sind und
• (c) optional eine oder mehreren Farbstoffen und/ oder einem oder mehreren organischen Lösungsmitteln.

In a further aspect, the invention relates to a composition comprising or consisting of:

• (a) at least one organic molecule according to the invention, in particular as emitter and / or host, and
• (b) at least one, ie, one or more emitter and / or host materials other than the organic molecule of the invention, and
• (c) optionally one or more dyes and / or one or more organic solvents.

In one embodiment, the composition of the invention consists of an organic molecule of the invention and one or more host materials. The host material or materials in particular have triplet (T ₁ ) and singlet (S ₁ ) energy levels which are higher in energy than the triplet (T ₁ ) and singlet (S ₁ ) energy levels of the organic molecule of the invention. In one embodiment, in addition to the organic molecule of the invention, the composition comprises an electron-dominant and a hole-dominant host material. The highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) of the hole-dominant host material are in particular higher in energy than that of the electron-dominant host material. The HOMO of the hole-dominant host material is energetically lower than the HOMO of the organic molecule of the invention, while the LUMO of the electron-dominant host material is higher in energy than the LUMO of the organic molecule of the invention. In order to avoid exciplex formation between emitter and host material or host materials, the materials should be chosen so that the energy gaps between the respective orbitals are small. The distance between the LUMO of the electron-dominant host material and the LUMO of the organic molecule according to the invention is in particular less than 0.5 eV, preferably less than 0.3 eV, more preferably less than 0.2 eV. The distance between the HOMO of the hole-dominant host material and the HOMO of the organic molecule according to the invention is in particular less than 0.5 eV, preferably less than 0.3 eV, more preferably less than 0.2 eV.

In a further aspect, the invention relates to an organic optoelectronic device comprising an organic molecule or a composition according to the invention. In particular, the organic optoelectronic device is formed as a device selected from the group consisting of organic light emitting diode (OLED); light-emitting electrochemical cell; OLED sensor, in particular non-hermetically shielded gas and vapor sensors; organic diode; organic solar cell; organic transistor; organic field effect transistor; organic laser and down-conversion element.

• – ein Substrat,
• – eine Anode und
• – eine Kathode, wobei die Anode oder die Kathode auf das Substrat aufgebracht sind, und
• – mindestens eine lichtemittierende Schicht, die zwischen Anode und Kathode angeordnet ist und die ein erfindungsgemäßes organisches Molekül aufweist, stellt einen weitere Ausführungsform der Erfindung dar.

An organic optoelectronic device comprising

• A substrate,
• An anode and
• A cathode, wherein the anode or the cathode are applied to the substrate, and
• - At least one light-emitting layer, which is arranged between the anode and cathode and having an inventive organic molecule, represents a further embodiment of the invention.

• 1. Substrat (Trägermaterial)
• 2. Anode
• 3. Lochinjektionsschicht (hole injection layer, HIL)
• 4. Lochtransportschicht (hole transport layer, HTL)
• 5. Elektronenblockierschicht (electron blocking layer, EBL)
• 6. Emitterschicht (emitting layer, EML)
• 7. Lochblockierschicht (hole blocking layer, HBL)
• 8. Elektronenleitschicht (electron transport layer, ETL)
• 9. Elektroneninjektionsschicht (electron injection layer, EIL)
• 10. Kathode.

In one embodiment, the optoelectronic device is an OLED. A typical OLED has, for example, the following layer structure:

• 1st substrate (carrier material)
• 2. anode
• 3. hole injection layer (HIL)
• 4. hole transport layer (HTL)
• 5. Electron blocking layer (EBL)
• 6. emitter layer (EML)
• 7. hole blocking layer (HBL)
• 8. electron transport layer (ETL)
• 9. Electron Injection Layer (EIL)
• 10. Cathode.

In this case, individual layers are only available in an optional manner. Furthermore, several of these layers can coincide. And there may be multiple layers in the component multiple times.

According to one embodiment, at least one electrode of the organic component is made translucent. Here, "translucent" refers to a layer that is transparent to visible light. In this case, the translucent layer can be clear translucent, that is transparent, or at least partially light-absorbing and / or partially light-scattering, so that the translucent layer can also be translucent, for example, diffuse or milky. In particular, a layer designated here as translucent is formed as transparent as possible, so that in particular the absorption of light is as low as possible.

• 1. Substrat (Trägermaterial)
• 2. Kathode
• 3. Elektroneninjektionsschicht (electron injection layer, EIL)
• 4. Elektronenleitschicht (electron transport layer, ETL)
• 5. Lochblockierschicht (hole blocking layer, HBL)
• 6. Emissionsschicht bzw. Emitterschicht (emitting layer, EML)
• 7. Elektronenblockierschicht (electron blocking layer, EBL)
• 8. Lochtransportschicht (hole transport layer, HTL)
• 9. Lochinjektionsschicht (hole injection layer, HIL)
• 10. Anode

According to a further embodiment, the organic component, in particular an OLED, has an inverted structure. The inverted structure is characterized in that the cathode is located on the substrate and the other layers are applied correspondingly inverted:

• 1st substrate (carrier material)
• 2nd cathode
• 3. electron injection layer (EIL)
• 4. electron transport layer (ETL)
• 5. hole blocking layer (HBL)
• 6. Emission layer or emitter layer (EML)
• 7. Electron blocking layer (EBL)
• 8. hole transport layer (HTL)
• 9. Hole injection layer (HIL)
• 10. anode

In this case, individual layers are only available in an optional manner. Furthermore, several of these layers can coincide. And there may be multiple layers in the component multiple times.

In one embodiment, in the inverted OLED, the anode layer of the typical structure, e.g. an ITO layer (indium tin oxide), connected as a cathode.

According to a further embodiment, the organic component, in particular an OLED, has a stacked construction. In this case, the individual OLEDs are arranged one above the other and not next to each other as usual. By a stacked structure, the generation of mixed light can be made possible. For example, this design can be used in the generation of white light, the entire visible spectrum of which is typically imaged by the combination of the emitted light from blue, green and red emitters. Furthermore, significantly longer lifetimes compared to conventional OLEDs can be achieved with virtually the same efficiency and identical luminance. For the stacked construction, a so-called charge generation layer (CGL) is optionally inserted between two OLEDs. This consists of an n-doped and a p-doped layer, wherein the n-doped layer is typically applied closer to the anode.

In one embodiment - a so-called tandem OLED - occur two or more emission layers between the anode and cathode. In one embodiment, three emission layers are arranged one above the other, wherein an emission layer emits red light, an emission layer emits green light, and an emission layer emits blue light, and optionally further charge generation, blocking or transport layers are applied between the individual emission layers. In a further embodiment, the respective emission layers are applied directly adjacent. In a further embodiment, a charge generation layer is in each case located between the emission layers. Furthermore, emission layers directly adjacent and separated by charge generation layers can be combined in an OLED.

Furthermore, an encapsulation may be arranged above the electrodes and the organic layers. The encapsulation can be embodied, for example, in the form of a glass cover or in the form of a thin-layer encapsulation.

The carrier material of the optoelectronic device may be, for example, glass, quartz, plastic, metal, a silicon wafer or any other suitable solid or flexible, optionally transparent material. The carrier material may comprise, for example, one or more materials in the form of a layer, a film, a plate or a laminate.

As the anode of the optoelectronic device, for example, transparent conductive metal oxides such as ITO (indium tin oxide), zinc oxide, tin oxide, cadmium oxide, titanium oxide, indium oxide or aluminum zinc oxide (AZO), Zn ₂ SnO ₄ , CdSnO ₃ , ZnSnO ₃ , MgIn ₂ O ₄ , GaInO ₃ , Zn ₂ In ₂ O ₅ or In ₄ Sn ₃ O ₁₂ or mixtures of different transparent conductive oxides.

As materials of a HIL, for example, PEDOT: PSS (poly-3,4-ethylenedioxythiophene: polystyrenesulfonic acid), PEDOT (poly-3,4-ethylenedioxythiophene), m-MTDATA (4,4 ', 4''- tris [phenyl (m -tolyl) amino] triphenylamine), spiro-TAD (2,2 ', 7,7'-tetrakis (N, N-diphenylamino) -9,9-spirobifluorene), DNTPD (4,4'-bis [N- [ 4- {N, N-bis (3-methylphenyl) amino} phenyl] -N-phenylamino] biphenyl), NPB (N, N'-bis (1-naphthalenyl) -N, N'-bis-phenyl ( 1,1'-biphenyl) -4,4'-diamine), NPNPB (N, N'-diphenyl-N, N'-di- [4- (N, N-diphenyl-amino) -phenyl] -benzene), MeO -TPD (N, N, N ', N'-tetrakis (4-methoxyphenyl) benzene), HAT-CN (1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile) or spiro-NPD (N, N '-Diphenyl-N, N'-bis (1-naphthyl) -9,9'-spirobifluoren-2,7-diamine). By way of example, the layer thickness can be 10-80 nm. Furthermore, small molecules can be used (eg copper phthalocyanine (CuPc eg 10 nm thick)) or metal oxides such as, for example, MoO ₃ , V ₂ O ₅ .

As materials of an HTL, tertiary amines, carbazole derivatives, polystyrenesulfonic acid-doped polyethylenedioxythiophene, camphorsulfonic acid-doped polyaniline poly-TPD (poly (4-butylphenyl-diphenyl-amine)), [alpha] -NPD (poly (4-butylphenyl-diphenyl-amine) )), TAPC (4,4'-cyclohexylidene bis [N, N-bis (4-methylphenyl) benzenamine]), TCTA (tris (4-carbazoyl-9-ylphenyl) amine), 2-TNATA (4.4 ', 4 "-tris [2-naphthyl (phenyl) amino] triphenylamine), spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN or TrisPcz (9,9'-diphenyl-6- (9 -phenyl-9H-carbazol-3-yl) -9H, 9'H-3,3'-bicarbazole). By way of example, the layer thickness is 10 nm to 100 nm.

The HTL may comprise a p-doped layer comprising an inorganic or organic dopant in an organic hole-conducting matrix. As inorganic dopant, for example, transition metal oxides such as vanadium oxide, molybdenum oxide or tungsten oxide can be used. As organic dopants, for example, tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper pentafluorobenzoate (Cu (I) pFBz) or transition metal complexes can be used. By way of example, the layer thickness is 10 nm to 100 nm.

As materials of an electron-blocking layer it is possible to use, for example, mCP (1,3-bis (carbazol-9-yl) benzene), TCTA, 2-TNATA, mCBP (3,3-di (9H-carbazol-9-yl) biphenyl), tris Pcz (9,9'-diphenyl-6- (9-phenyl-9H-carbazol-3-yl) -9H, 9'H-3,3'-bicarbazole), CzSi (9- (4-tert-butylphenyl) 3,6-bis (triphenylsilyl) -9H-carbazole) or DCB (N, N'-dicarbazolyl-1,4-dimethylbenzene). By way of example, the layer thickness is 10 nm to 50 nm.

The emitter layer EML or emission layer consists of or comprises emitter material or a mixture comprising at least two emitter materials and optionally one or more host materials. Suitable host materials include mCP, TCTA, 2-TNATA, mCBP, CBP (4,4'-bis- (N-carbazolyl) -biphenyl), Sif87 (dibenzo [b, d] thiophen-2-yltriphenylsilane), Sif88 (Dibenzo [b, d] thiophen-2-yl) diphenylsilane) or DPEPO (bis [2 - ((oxo) diphenylphosphino) phenyl] ether). For green or red-emitting emitter material or a mixture comprising at least two emitter materials, the common matrix materials such as CBP are suitable. For emitter material emitting in the blue or a mixture comprising at least two emitter materials, UHG matrix materials (ultra-high energy gap materials) (see, for example, Thompson, BME, et al., Chem., 2004, 16, 4743) or other so-called wide-gap Matrix materials are used. By way of example, the layer thickness is 10 nm to 250 nm.

The hole blocking layer HBL may be, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = bathocuproine), bis (2-methyl-8-hydroxyquinolinato) - (4-phenylphenolato) aluminum (III) (BAlq), Nbphen (2,9-bis (naphthalen-2-yl) -4,7-diphenyl-1,10-phenanthroline), Alq3 (aluminum tris (8-hydroxyquinoline)), TSPO1 (diphenyl-4-) triphenylsilylphenylphosphine oxide) or TCB / TCP (1,3,5-tris (N-carbazolyl) benzene / 1,3,5-tris (carbazol) -9-yl) benzene). By way of example, the layer thickness is 10 nm to 50 nm.

The electron transport layer ETL can be, for example, materials based on AlQ ₃ , TSPO 1, BPyTP 2 (2,7-di (2,2'-bipyridin-5-yl) triphenyl), Sif 87, Sif 88, BmPyPhB (1,3-bis [3, 5-di (pyridin-3-yl) phenyl] benzene) or BTB (4,4'-bis [2- (4,6-diphenyl-1,3,5-triazinyl)] - 1,1'-biphenyl). By way of example, the layer thickness is 10 nm to 200 nm.

As materials of a thin electron injection layer EIL, for example, CsF, LiF, 8-hydroxyquinolinolatolithium (Liq), Li ₂ O, BaF ₂ , MgO or NaF can be used.

The materials of the cathode layer may be metals or alloys, for example Al, Al> AlF, Ag, Pt, Au, Mg, Ag: Mg. Typical layer thicknesses are from 100 nm to 200 nm. In particular, one or more metals are used which are stable in air and / or which are self-passivating, for example by forming a thin protective oxide layer.

As materials for encapsulation, for example, alumina, vanadium oxide, zinc oxide, zirconium oxide, titanium oxide, hafnium oxide, lanthanum oxide, tantalum oxide are suitable.

In one embodiment of the organic optoelectronic device according to the invention, the organic molecule according to the invention is used as the emission material in a light-emitting layer EML, wherein it is used either as a pure layer or in combination with one or more host materials.

One embodiment of the invention relates to organic optoelectronic devices which have an external quantum efficiency (EQE) at 1000 cd / m ² of greater than 5%, in particular greater than 8%, in particular greater than 10%, or greater than 13%, or greater than 16%. and in particular of greater than 20% and / or an emission maximum at a wavelength between 420 nm and 500 nm, in particular between 430 nm and 490 nm, or between 440 nm and 480 nm and in particular between 450 nm and 470 nm and / or an LT80 value at 500 cd / m ² of greater than 30 h, in particular greater than 70 h, or of greater than 100 h, or of greater than 150 h and in particular greater than 200 h.

The mass fraction of the organic molecule according to the invention at the emitter layer EML is in a further embodiment in a light-emitting layer in optical light-emitting devices, in particular in OLEDs, between 1% and 80%. In one embodiment of the organic optoelectronic device according to the invention, the light-emitting layer is applied to a substrate, wherein preferably an anode and a cathode are applied to the substrate and the light-emitting layer is applied between anode and cathode.

In one embodiment, the light-emitting layer may comprise only an organic molecule according to the invention in 100% concentration, wherein the anode and the cathode are applied to the substrate, and the light-emitting layer is applied between the anode and cathode.

In one embodiment of the organic optoelectronic device according to the invention, a hole and electron injecting layer between anode and cathode, and a hole and electron transporting layer between hole and electron injecting layer, and the light emitting layer between holes and electron transporting layer are applied.

The organic optoelectronic device comprises in a further embodiment of the invention: a substrate, an anode, a cathode and at least one hole- and electron-injecting layer, and at least one hole- and electron-transporting layer, and at least one light-emitting layer, the organic according to the invention Molecule and one or more host materials whose triplet (T ₁ ) and singlet (S ₁ ) energy levels are higher in energy than the triplet (T ₁ ) and singlet (S ₁ ) energy levels of the organic molecule, the anode and the cathode is deposited on the substrate, and the hole and electron injecting layer is disposed between the anode and the cathode, and the hole and electron transporting layer is applied between the hole and electron injecting layer, and the light emitting layer is applied between the hole and electron transporting layer ,

In a further aspect, the invention relates to a method for producing an optoelectronic component. In this case, an organic molecule according to the invention is used.

In one embodiment, the manufacturing method comprises processing the organic molecule of the invention by a vacuum evaporation method or from a solution.

• – mit einem Sublimationsverfahren beschichtet wird,
• – mit einem OVPD (Organic Vapor Phase Deposition) Verfahren beschichtet wird,
• – mit einer Trägergassublimation beschichtet wird, und/oder
• – aus Lösung oder mit einem Druckverfahren hergestellt wird.

The invention also provides a method for producing an optoelectronic device according to the invention, in which at least one layer of the optoelectronic device

• Is coated with a sublimation process,
• Is coated with an OVPD (Organic Vapor Phase Deposition) method,
• Is coated with a carrier gas sublimation, and / or
• - made from solution or with a printing process.

In the production of the optoelectronic device according to the invention known methods are used. Generally, the layers are individually applied to a suitable substrate in successive deposition steps. In the vapor deposition process, conventional methods such as thermal evaporation, chemical vapor deposition (CVD), physical vapor deposition (PVD) can be used. For active matrix OLED (AMOLED) displays, the deposition onto an AMOLED backplane takes place as a substrate.

Alternatively, layers of solutions or dispersions may be applied in suitable solvents. Exemplary suitable coating methods are spin-coating, dip-coating and jet-printing methods. According to the invention, the individual layers can be produced both via the same and via different coating methods.

Examples

General Synthetic Scheme I

General Synthesis AAV1:

3,5-bis (trifluoromethyl) -phenylboronic acid, (1.50 equivalents), 4-bromo-2-fluorobenzonitrile (1.00 equivalents), Pd ₂ (dba) ₃ (0.02 equivalents), 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl (SPhos) (0.08 equiv.) And potassium phosphate tribasic (2.50 equiv.) Are stirred under nitrogen in a toluene / water mixture (20: 1 ratio) at 100 ° C for 16 h. Subsequently, the reaction mixture is poured into saturated sodium chloride solution and extracted twice with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over MgSO4 and the solvent is removed. The product is filtered through a little silica gel and then recrystallized. The product is obtained as a solid.

According to the invention, instead of a boronic acid, it is also possible to use a corresponding boronic acid ester. General Synthesis AAV2:

The synthesis of Z2 is analogous to AAV1, wherein 3,5-bis (trifluoromethyl) phenylboronic acid is reacted with 4-bromo-3-fluorobenzonitrile. General Synthesis AAV3:

Z1 or Z2 (1.00 equivalents each), the corresponding donor molecule D-H (2.00 equivalents) and tribasic potassium phosphate (4.00 equivalents) are suspended under nitrogen in DMSO and stirred at 110 ° C (16 h). Then the reaction mixture is poured into saturated sodium chloride solution and extracted three times with dichloromethane. The combined organic phases are washed twice with saturated sodium chloride solution, dried over magnesium sulfate and the solvent is then removed. The crude product was finally purified by recrystallization from toluene or by flash chromatography. The product is obtained as a solid.

Specifically, DH corresponds to a 3,6-substituted carbazole (e.g., 3,6-dimethylcarbazole, 3,6-diphenylcarbazole, 3,6-di-tert-butylcarbazole), a 2,7-substituted carbazole (e.g. 2,7-dimethylcarbazole, 2,7-diphenylcarbazole, 2,7-di-tert-butylcarbazole), a 1,8-substituted carbazole (e.g., 1,8-dimethylcarbazole, 1,8-diphenylcarbazole, 1, 8-di-tert-butylcarbazole), a 1-substituted carbazole (e.g., 1-methylcarbazole, 1-phenylcarbazole, 1-tert-butylcarbazole), a 2-substituted carbazole (e.g., 2-methylcarbazole, 2- Phenylcarbazole, 2-tert-butylcarbazole) or a 3-substituted carbazole (e.g., 3-methylcarbazole, 3-phenylcarbazole, 3-tert-butylcarbazole).

Photophysical measurements

Pretreatment of optical glasses

All jars (cuvettes and substrates of quartz glass, diameter: 1 cm) were cleaned after each use: Rinse three times with dichloromethane, acetone, ethanol, demineralized water, place in 5% Hellmanex solution for 24 h, rinse thoroughly with demineralized water. For drying, the optical glasses were purged with nitrogen.

Sample preparation, film: spin-coating

• Device: Spin150, SPS euro.

The sample concentration corresponded to 10 mg / ml, stated in toluene or chlorobenzene. Program: 1) 3 s at 400 rpm; 2) 20 s at 1000 rpm at 1000 rpm / s. 3) 10 s at 4000 rpm at 1000 rpm / s. The films were dried after coating for one minute at 70 ° C in air on a precision hot plate of LHG.

Photoluminescence spectroscopy and TCSPC

Steady-state emission spectroscopy was performed with a Horiba Scientific FluoroMax-4 fluorescence spectrometer equipped with a 150 W xenon-arc lamp, excitation and emission monochromators and a Hamamatsu R928 photomultiplier tube, and a "time-correlated single-photon count" (Time -correlated single-photon counting, TCSPC) option. Emission and excitation spectra were corrected by standard correction curves.

Emission decay times were also measured on this system using the TCSPC method with the FM-2013 accessory and a TCSPC hub from Horiba Yvon Jobin. Excitation sources:
NanoLED 370 (wavelength: 371 nm, pulse duration: 1.1 ns)
NanoLED 290 (wavelength: 294 nm, pulse duration: <1 ns)
SpectraLED 310 (wavelength: 314 nm)
SpectraLED 355 (wavelength: 355 nm).

mit e_i: Durch den Fit vorhergesagte Größe und o_i: gemessenen Größe.The evaluation (exponential fitting) was carried out with the software package DataStation and the DAS 6 evaluation software. The fit was given by the chi-square method

with e _i : size predicted by the fit and o _i : measured size.

Quantum efficiency determination

The photoluminescence quantum yield (PLQY) was measured by Hamamatsu Photonics Absolute PL Quantum Yield Measurement C9920-03G system. This consists of a 150 W xenon gas discharge lamp, automatically adjustable Czerny-Turner monochromators (250-950 nm) and an Ulbricht sphere with highly reflecting Spektralon coating (a teflon derivative), which is connected via a fiber optic cable with a PMA-12 multichannel detector BT (back thinned) CCD chip with 1024 × 122 pixels (size 24 × 24 microns) is connected. The evaluation of the quantum efficiency and the CIE coordinates took place with the help of the software U6039-05 version 3.6.0. The emission maximum is given in nm, the quantum yield Φ in% and the CIE color coordinates as x, y values.

The photoluminescence quantum yield was determined according to the following protocol:

1) Implementation of quality assurance:

The reference material is anthracenes in ethanol of known concentration.

2) Determining the excitation wavelength:

First, the absorbance maximum of the organic molecule was determined and excited with it.

3) Execution of the sample measurement:

mit der Photonenzahl n_photon und der Intensität Int.The absolute quantum yield was determined for degassed solutions and films under a nitrogen atmosphere. The calculation was carried out system-internally according to the following equation:

with the photon number n _photon and the intensity int.

Preparation and characterization of organic electroluminescent devices from the gas phase

With the organic molecules according to the invention, OLED devices can be created by means of vacuum sublimation technology. If a layer contains several components, the ratio of these is given in percentage by mass. These not yet optimized OLEDs can be characterized by default; For this purpose, the electroluminescence spectra, the external quantum efficiency (measured in%) as a function of the brightness, calculated from the light detected by the photodiode, and the current are recorded. The lifetime of the OLEDs can be determined from the time course of the electroluminescence spectra. The specified LT50 value corresponds to the time at which the luminance has fallen to 50% of the starting value. Analogously, the LT70 value corresponds to the time at which the luminance has fallen to 70% of the starting value. The values given result from the average of the different pixels of an OLED. The spectra shown each show a measurement series of a pixel.

HPLC-MS:

HPLC-MS spectroscopy was measured on an Agilent HPLC system (1100 series) with a connected MS detector (Thermo LTQ XL). For HPLC, an Agilent Eclipse Plus C18 column having a particle size of 3.5 μm, a length of 150 mm and an internal diameter of 4.6 mm was used. It was worked without precolumn and at room temperature with the solvents acetonitrile, water and tetrahydrofuran in these concentrations: Solvent A: H ₂ O (90%) MeCN (10%) Solvent B: H ₂ O (10%) MeCN (90%) Solvent C: THF (100%)

An injection volume of 15 μL and a concentration of 10 μg / mL was used with this gradient: Flow [ml / min] Time [min] A [%] B [%] C [%] Pressure [bar] 0.3 0 80 20 - 115 0.3 5 80 20 - 115 0.3 14 0 90 10 65 0.3 25 0 90 10 65 0.3 26 80 20 - 115 0.3 33 80 20 - 115

The ionization of the sample is carried out by APCI (atmospheric pressure chemical ionization). example 1

Example 1 was prepared according to AAV1 (yield 93%) and AAV3 (yield 78%).
MS (HPLC-MS), m / z (retention time): 593, (21.73 min)
R _f = 0.76 (cyclohexane / ethyl acetate 5: 1). 1 shows the emission spectrum of Example 1 (10% in PMMA). The emission maximum is 462 nm. The photoluminescence quantum yield (PLQY) is 81% and the half-width is 0.47 eV. Example 2

Example 2 was prepared according to AAV1 (yield 93%) and AAV7 (yield 67%).
MS (HPLC-MS), m / z (retention time): 508, (18.04 min)
R _f = 0.67 (cyclohexane / ethyl acetate 5: 1). 2 shows the emission spectrum of Example 2 (10% in PMMA). The emission maximum is 467 nm. The photoluminescence quantum yield (PLQY) is 77% and the half-width is 0.47 eV. Example 3

Example 3 was prepared according to AAV1 (yield 93%) and AAV7 (yield 84%).
MS (HPLC-MS), m / z (retention time): 540, (14.45 min)
R _f = 0.33 (cyclohexane / ethyl acetate 5: 1) 3 shows the emission spectrum of Example 3 (10% in PMMA). The emission maximum is 497 nm. The photoluminescence quantum yield (PLQY) is 49% and the half-width is 0.49 eV.

characters

Show it:

1 Emission spectrum of Example 1 in 10% PMMA.

2 Emission spectrum of Example 2 in 10% PMMA.

3 Emission spectrum of Example 3 in 10% PMMA.

Claims (14)

Organic molecule comprising - a first chemical entity comprising or consisting of a structure according to formula I.

and - a second chemical entity D comprising one or consisting of a structure according to formula II,

wherein the first chemical entity is linked to the second chemical entity D via a single bond; where X is H or the point of attachment of the single bond between the first chemical entity and the second chemical entity D; Y is H or point of attachment of the single bond between the first chemical entity and the second chemical entity D; W is CN or CF ₃ ; # denotes the point of attachment of the single bond between the second chemical entity D and the first chemical entity; Z is each time the same or different a direct bond or selected from the group consisting of CR ³ R ⁴ , C = CR ³ R ⁴ , C = O, C = NR ³ , NR ³ , O, SiR ³ R ⁴ , S , S (O) and S (O) ₂ ; R ¹ and R ² are each the same or different H, deuterium, a linear alkyl group having 1 to 5 C atoms, a linear alkenyl or alkynyl group having 2 to 8 C atoms, a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms, wherein one or more H atoms may be replaced by deuterium, or an aromatic or heteroaromatic ring system having 5 to 15 aromatic ring atoms, each of which may be substituted by one or more R ⁶ ; R ^a , R ³ and R ⁴ are each the same or different at each occurrence H, deuterium, N (R ⁵ ) ₂ , OH, Si (R ⁵ ) ₃ , B (OR ⁵ ) ₂ , OSO ₂ R ⁵ , CF ₃ , CN, F, Br, I, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl -, alkoxy or Thioalkoxygruppe having 3 to 40 carbon atoms, each of which may be substituted with one or more radicals R ⁵ , wherein one or more non-adjacent CH ₂ groups by R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R ⁵ , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R ⁵ or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R ⁵ ; R ⁵ is the same or different H, deuterium, N (R ⁶ ) ₂ , OH, Si (R ⁶ ) ₃ , B (OR ⁶ ) ₂ , OSO ₂ R ⁶ , CF ₃ , CN, F, Br at each occurrence. I, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having from 3 to 40 carbon atoms, each of which may be substituted by one or more R ⁶ radicals, one or more non-adjacent CH ₂ groups represented by R ⁶ C = CR ⁶ , C≡C, Si (R ⁶ ) ₂ , Ge (R ⁶ ) ₂ , Sn (R ⁶ ) ₂ , C = O, C = S, C = Se, C = NR ⁶ , P (= O) (R ⁶ ), SO, SO ₂ , NR ⁶ , O , S or CONR ⁶ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each by one or more R ⁶ may be substituted, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms which may be substituted by one or more R ⁶ , or a Diarylaminogruppe, Diheteroarylaminogruppe or Arylheteroarylaminogruppe having 10 to 40 aromatic ring atoms, which by one or several radicals R ⁶ may be substituted; R ⁶ is the same or different H, Deuterium, OH, CF ₃ , CN, F, a linear alkyl, alkoxy or thioalkoxy group having 1 to 5 C atoms or a linear alkenyl or alkynyl group having 2 to 5 C at each occurrence Atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 5 C atoms, wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms or a Diarylaminogruppe, Diheteroarylaminogruppe or Arylheteroarylaminogruppe with 10 to 40 aromatic ring atoms; where each of the radicals R ^a , R ³ , R ⁴ or R ^{5 can} also form with one or more further radicals R ^a , R ³ , R ⁴ or R ⁵ a mono- or polycyclic, aliphatic, aromatic and / or benzoanelliertes ring system; wherein exactly one radical selected from the group consisting of X and Y is equal to the point of attachment of the single bond between the first chemical entity and the second chemical entity D. An organic molecule according to claim 1, wherein R ¹ and R ^{2 are the} same or different at each occurrence, being H, methyl or phenyl. An organic molecule according to claim 1 or 2, wherein W is CN. Organic molecule according to claim 1 to 3, wherein the second chemical entity D has a structure of the formula IIa or consists of:

wherein for # and R ^a the definitions given in claim 1 apply. Organic molecule according to claim 1 to 4, wherein the second chemical entity D has a structure of the formula IIb or consists of:

wherein R ^b is a linear at each occurrence the same or different N (R ⁵⁾ _2, OH, Si (R ⁵⁾ _3, B (OR ⁵⁾ _2, OSO ₂ R ^5, CF _3, CN, F, Br, I, Alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may each be substituted by one or more radicals R ⁵ , wherein one or more non-adjacent CH ₂ groups by R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R ⁵ , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R ⁵ or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms which may be substituted by one or more R ⁵ groups; and for # and R ⁵ the definitions given in claim 1 apply. Organic molecule according to claim 1 to 4, wherein the second chemical entity D has a structure of the formula IIc or consists of:

wherein R ^{b is} selected from the group consisting of N (R ⁵ ) ₂ , OH, Si (R ⁵ ) ₃ , B (OR ⁵ ) ₂ , OSO ₂ R ⁵ , CF ₃ , CN, F, Br, I, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more R ⁵ radicals, wherein one or more non-adjacent CH ₂ groups is replaced by R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ can be replaced and wherein one or more H atoms can be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R ⁵ , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R ⁵ or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R ⁵ ; and, moreover, the definitions given in claim 1 apply. Organic molecule according to claim 5 or 6, wherein R ^b at each occurrence, identically or differently, Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph, which in each case by one or more groups selected from Me, ⁱ Pr, ^Bu, CN , CF ₃ or Ph may be substituted pyridinyl by one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted, pyrimidinyl which is selected by one or more radicals selected from Me , ⁱ Pr, Bu, CN, CF ₃ or Ph may be substituted, triazinyl which is selected by one or more radicals selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted, carbazolyl, which in each case by one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted, or N (Ph) _2. A method for producing an organic molecule of claim 1 to 7, wherein an R ¹ -substituted 3,5-bis phenylboronic acid or 2,4,6-position (trifluoromethyl), a corresponding in 2,4,6-position, R ¹ - substituted 3,5-bis (trifluoromethyl) -phenylboronsäureester is used as starting material.  Use of an organic molecule according to claims 1 to 7 as a luminescent emitter 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 organic optoelectronic device.  Use according to claim 9, wherein the organic optoelectronic device is selected from the group consisting of: Organic light-emitting diodes (OLEDs), Light-emitting electrochemical cells, OLED sensors, especially in non-hermetically shielded gas and vapor sensors, Organic diodes, • organic solar cells, Organic transistors, Organic field effect transistors, • organic lasers and • Down conversion elements.  Composition comprising or consisting of: (A) at least one organic molecule according to any one of claims 1 to 7, in particular in the form of an emitter and / or host, and (b) one or more emitter and / or host materials other than the molecule of claims 1 to 7, and (c) optionally one or more dyes and / or one or more solvents. Organic optoelectronic device comprising an organic molecule according to claim 1 to 7 or a composition according to claim 11, in particular formed as a device selected from the group consisting of organic light emitting diode (OLED), light emitting electrochemical cell, OLED sensor, in particular non-hermetically externally shielded gas and vapor sensors, organic diode, organic solar cell, organic transistor, organic field effect transistor, organic laser and down-conversion element. An organic optoelectronic device according to claim 12, comprising A substrate, An anode and A cathode, wherein the anode or the cathode are applied to the substrate, and At least one light emitting layer disposed between the anode and the cathode and comprising an organic molecule according to claims 1 to 7 or a composition according to claim 11.  A method for producing an optoelectronic component, wherein an organic molecule according to claim 1 to 7 is used, in particular comprising the processing of the organic molecule by means of a vacuum evaporation method or from a solution.

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