Organic molecules for optoelectronic devices

Abstract

The invention relates to an organic molecule, in particular for use in optoelectronic devices. According to the invention, the organic molecule consists of a first chemical moiety having a structure of Formula I, and two second chemical moieties having a structure of Formula II, wherein # represents a binding site of a single bond connecting the first chemical moiety to the second chemical moiety; exactly one substituent selected from the group consisting of W, X and Y is a cyanophenyl group; exactly one substituent selected from the group consisting of T, V and W represents a binding site of a single bond connecting the first chemical moiety to one of the two second chemical moieties; exactly one substituent selected from the group consisting of W', X' and Y' is CN or CF3; and exactly one substituent selected from the group consisting of T', V' and W' represents a binding site of a single bond connecting the first chemical moiety to one of the two second chemical moieties.

Description

Technical Field

[0001] The invention relates to organic molecules and their use in organic light-emitting diodes (OLEDs) and other optoelectronic devices. Background Technology

[0002] We are actively developing applications of organic molecules in optoelectronic devices. Summary of the Invention

[0003] The purpose of this invention is to provide organic molecules suitable for use in optoelectronic devices.

[0004] This objective is achieved through the invention of a novel organic molecule.

[0005] The invented organic molecule is a pure organic molecule, that is, it does not contain any metal ions, unlike known metal complexes used in optoelectronic devices.

[0006] The organic molecules exhibit emission maxima in the sky-blue, green, or yellow spectral ranges. Specifically, the organic molecules exhibit emission maxima between 490 nm and 600 nm (more preferably between 510 nm and 560 nm, and even more preferably between 520 nm and 540 nm). Specifically, the photoluminescence quantum yield of the organic molecules according to the invention is 10% or greater. Specifically, the organic molecules of the invention exhibit thermally activated delayed fluorescence (TADF). The use of the organic molecules according to the invention in optoelectronic devices (e.g., organic light-emitting diodes (OLEDs)) results in higher efficiency of the optoelectronic devices. The corresponding OLEDs have higher stability than OLEDs with known emitter materials and comparable colors, and / or by employing the organic molecules according to the invention in OLED displays, more accurate reproduction of inherently visible colors is achieved, i.e., higher resolution of displayed images. Specifically, the organic molecules can be used in combination with fluorescent emitters to ensure so-called superfluorescence.

[0007] The organic molecule according to the invention comprises, or is composed of, a first chemical part and two second chemical parts, wherein the first chemical part comprises or is composed of a structure of Formula I.

[0008]

[0009] Both second chemical parts independently include or consist of the structure of Formula II.

[0010]

[0011] The first chemical part is connected to each of the second chemical parts via single bonds.

[0012] T is the binding site of a single bond that connects the first chemical moiety to one of the two second chemical moiety sites, or R I .

[0013] V is the bonding site of a single bond that connects the first chemical moiety to one of the two second chemical moiety sites, or R I .

[0014] W is the binding site of a single bond that connects the first chemical moiety to one of the two second chemical moiety sites, or is selected from R. I and R A A group that is formed.

[0015] X is selected from R I and R A A group that is formed.

[0016] Y is selected from R I and R A A group that is formed.

[0017] T' is the binding site of a single bond that connects the first chemical moiety to one of the two second chemical moiety assemblies, or R II .

[0018] V' is the bonding site of a single bond that connects the first chemical moiety to one of the two second chemical moiety assemblies, or R II .

[0019] W' is the binding site of a single bond that connects the first chemical moiety to one of the two second chemical moiety assemblies, or is selected from R. II The group consists of CN and CF3.

[0020] X' is selected from R II The group consists of CN and CF3.

[0021] Y' is selected from R II The group consists of CN and CF3.

[0022] Z is selected independently from direct connection key and CR each time it appears. 3 R 4 C = CR 3 R 4 C=O, C=NR 3 NR 3 O, SiR 3 R 4 The group consists of S, S(O) and S(O)2.

[0023] # represents the binding site between the first and second chemical parts.

[0024] RA Includes or is composed of the structure of formula BN-I.

[0025]

[0026] The structure of formula BN-I is combined with the structure of formula I via the positions marked by dashed lines, and in which exactly one R BN The group is CN, while the other two are R. BN All the groups are hydrogen, that is, R A Includes structures according to any one of formulas BN-Ia, BN-Ib, and BN-Ic, or consists of structures according to any one of formulas BN-Ia, BN-Ib, and BN-Ic:

[0027]

[0028] R I Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; C2-C8 alkenyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; C2-C8 alkynyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; and C6-C 18 Aryl.

[0029] R II Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; C2-C8 alkenyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; C2-C8 alkynyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; and C6-C 18 Aryl.

[0030] R 11 R 12 R 13 R 14 and R 15 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; CN; CF3; phenyl (Ph); C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; C2-C8 alkenyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; C2-C8 ynyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; and C6-C 18 Aryl.

[0031] R a R 3 and R 4 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R)5 )2; OR 5 ;Si(R) 5 )3;B(OR 5 )2; OSO2R 5 ;CF3;CN;F;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally 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, SO2, NR 5 O, S or CONR 5 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally 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, SO2, NR 5 O, S or CONR 5 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally 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, SO2, NR 5 O, S or CONR 5 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally R5 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, SO2, NR 5 O, S or CONR 5 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. 5 And wherein, one or more non-adjacent CH2 groups are optionally 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, SO2, NR 5 O, S or CONR 5 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 5 ; and C3-C 57 Heteroaryl, optionally substituted with one or more substituents R 5 .

[0032] R 5 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 6 )2; OR 6 ;Si(R) 6 )3;B(OR 6 )2; OSO2R 6 ;CF3;CN;F;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 6 And wherein, one or more non-adjacent CH2 groups are optionally 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, SO2, NR 6 O, S or CONR6 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 6 And wherein, one or more non-adjacent CH2 groups are optionally 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, SO2, NR 6 O, S or CONR 6 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R 6 And wherein, one or more non-adjacent CH2 groups are optionally 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, SO2, NR 6 O, S or CONR 6 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 6 And wherein, one or more non-adjacent CH2 groups are optionally 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, SO2, NR 6 O, S or CONR 6 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. 6 And wherein, one or more non-adjacent CH2 groups are optionally 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, SO2, NR 6 O, S or CONR 6 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 6 ; and C3-C 57 Heteroaryl, optionally substituted with one or more substituents R 6 .

[0033] R 6 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; OPh; CF3; CN; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C1-C5 alkoxy, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C1-C5 thioalkoxy, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C2-C5 alkenyl, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C2-C5 alkynyl, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C6-C 18 Aryl group, optionally substituted with one or more C1-C5 alkyl substituents; C3-C 17 Heteroaryl groups, optionally substituted with one or more C1-C5 alkyl substituents; N(C6-C 18 Aryl)2; N(C3-C 17 (heteroaryl)2; and N(C3-C) 17 (C6-C) 18 Aryl).

[0034] Optionally, the substituent R a R 3 R 4 and R 5 Any one of them independently with one or more other substituents R a R 3 R 4 or R 5 Forming monocyclic or polycyclic aliphatic, aromatic, and / or benzofused ring systems.

[0035] According to the invention, exactly one substituent selected from the group consisting of W, X, and Y is R. AAnd exactly one substituent selected from the group consisting of T, V and W represents the binding site of the single bond connecting the first chemical moiety to one of the two second chemical moiety.

[0036] Furthermore, according to the invention, exactly one substituent selected from the group consisting of W', X', and Y' is CN or CF3, and exactly one substituent selected from the group consisting of T', V', and W' represents the binding site of a single bond connecting the first chemical moiety to one of the two second chemical moiety.

[0037] In a particular embodiment of the invention, the two second chemical components are identical.

[0038] In one embodiment of the invention, W and W' are both binding sites of a single bond connecting the first chemical part to one of the two second chemical parts.

[0039] In one embodiment of the invention, W and W' are both binding sites of single bonds connecting the first chemical moiety to one of the two second chemical moiety, and X is R A X' is CN.

[0040] In one embodiment of the invention, W and W' are both binding sites of single bonds connecting the first chemical moiety to one of the two second chemical moiety, and X is R A X' is CF3.

[0041] In one embodiment of the invention, W and W' are both binding sites of single bonds connecting the first chemical moiety to one of the two second chemical moiety, and Y is R A Y' is CN.

[0042] In one embodiment of the invention, W and W' are both binding sites of single bonds connecting the first chemical moiety to one of the two second chemical moiety, and Y is R A Y' is CF3.

[0043] In one embodiment of the invention, V and V' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety.

[0044] In one embodiment of the invention, V and V' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and W is R A ,W' is CN.

[0045] In one embodiment of the invention, V and V' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and W is R A , W' is CF3.

[0046] In one embodiment of the invention, V and V' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and X is R A X' is CN.

[0047] In one embodiment of the invention, V and V' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and X is R A X' is CF3.

[0048] In one embodiment of the invention, V and V' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and Y is R A Y' is CN.

[0049] In one embodiment of the invention, V and V' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and Y is R A Y' is CF3.

[0050] In a preferred embodiment of the invention, T and T' are both binding sites of a single bond connecting the first chemical part to one of the two second chemical parts.

[0051] In one embodiment of the invention, T and T' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and W is R A ,W' is CN.

[0052] In one embodiment of the invention, T and T' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and W is R A , W' is CF3.

[0053] In a particularly preferred embodiment of the invention, T and T' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and X is R A X' is CN.

[0054] In one embodiment of the invention, T and T' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and X is R A X' is CF3.

[0055] In another particularly preferred embodiment of the invention, T and T' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and W is R A X' is CN.

[0056] In another embodiment of the invention, T and T' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and W is R AX' is CF3.

[0057] In one embodiment of the invention, T and T' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and X is R A ,W' is CN.

[0058] In another embodiment of the invention, T and T' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and X is R A , W' is CF3.

[0059] In one embodiment of the invention, T and T' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and Y is R A Y' is CN.

[0060] In one embodiment of the invention, T and T' are both binding sites of a single bond connecting the first chemical moiety to one of the two second chemical moiety, and Y is R A Y' is CF3.

[0061] In one embodiment of the invention, R I Each time it appears, it is independently selected from the group consisting of hydrogen, methyl, isopropyl, tert-butyl, mesitylyl, xylyl, tolyl, and phenyl.

[0062] In one embodiment of the invention, R I Each time it appears, it is independently selected from the group consisting of hydrogen, methyl, mesitylene, tolyl, and phenyl.

[0063] In another embodiment of the invention, R I It is hydrogen each time it appears.

[0064] In one embodiment of the invention, R II Each time it appears, it is independently selected from the group consisting of hydrogen, methyl, isopropyl, tert-butyl, mesitylyl, xylyl, tolyl, and phenyl.

[0065] In one embodiment of the invention, R II Each time it appears, it is independently selected from the group consisting of hydrogen, methyl, mesitylene, tolyl, and phenyl.

[0066] In another embodiment of the invention, R II It is hydrogen each time it appears.

[0067] In one embodiment of the invention, R A It is represented by the formula BN-Ia.

[0068] In one embodiment of the invention, R AIt is represented by the formula BN-Ib.

[0069] In one embodiment of the invention, R A It is represented by the formula BN-Ic.

[0070] In another embodiment of the invention, R 3 R 4 R 5 and R 6 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF3; SiMe3; SiPh3; and C6-C 18 Aryl group, wherein one or more hydrogen atoms may optionally be independently substituted by C1-C5 alkyl groups, CN, CF3, and Ph.

[0071] In another embodiment of the invention, R 3 R 4 R 5 and R 6 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF3; SiMe3; SiPh3; and phenyl (Ph), wherein one or more hydrogen atoms may optionally be independently substituted by C1-C5 alkyl, CN, CF3 and Ph.

[0072] In another embodiment of the invention, R 3 R 4 R 5 and R 6 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF3; SiMe3; SiPh3; and phenyl, wherein optionally one or more hydrogen atoms are independently separated by Me, i Pr, t Bu, CN, CF3 and Ph substitutions.

[0073] In one embodiment of the invention, the second chemical part comprises or is composed of a structure of formula IIa:

[0074]

[0075] In one embodiment of the invention, R a Each time it appears, it is independently selected from the group consisting of: hydrogen; Me; i Pr; tBu; CN; CF3; Ph, optionally replacing each other independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; a pyrimidinyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; carbazoyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph; and N(Ph)2.

[0076] In yet another embodiment of the invention, R a Each time it appears, it is independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF3; Ph, optionally replacing each other independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; a pyrimidinyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; and a triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph.

[0077] In another embodiment of the invention, the second chemical part includes the structure of formula IIb, the structure of formula IIb-2, the structure of formula IIb-3, or the structure of formula IIb-4, or is composed of the structure of formula IIb, the structure of formula IIb-2, the structure of formula IIb-3, or the structure of formula IIb-4:

[0078]

[0079] Among them,

[0080] R b Each occurrence is independently selected from the group consisting of: deuterium; N(R) 5 )2; OR 5 ;Si(R) 5 )3;B(OR 5 )2; OSO2R 5 ;CF3;CN;F;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally 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, SO2, NR 5 O, S or CONR 5 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally 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, SO2, NR 5 O, S or CONR 5 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally 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, SO2, NR 5O, S or CONR 5 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally 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, SO2, NR 5 O, S or CONR 5 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. 5 And wherein, one or more non-adjacent CH2 groups are optionally 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, SO2, NR 5 O, S or CONR 5 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 5 ; and C3-C 57 Heteroaryl, optionally substituted with one or more substituents R 5 .

[0081] In another embodiment of the invention, the second chemical part includes the structure of formula IIc, the structure of formula IIc-2, the structure of formula IIc-3, or the structure of formula IIc-4, or is composed of the structure of formula IIc, the structure of formula IIc-2, the structure of formula IIc-3, or the structure of formula IIc-4:

[0082]

[0083] In yet another embodiment of the invention, R b Each occurrence is independently selected from the group consisting of: Me; i Pr; t Bu; CN; CF3; Ph, optionally replacing each other independently selected from Me, i Pr, tOne or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; carbazoyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph; and N(Ph)2.

[0084] In yet another embodiment of the invention, R b Each occurrence is independently selected from the group consisting of: Me; i Pr; t Bu; CN; CF3; Ph, optionally replacing each other independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; a pyrimidinyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; and a triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph.

[0085] Below is an example from the second chemistry section:

[0086]

[0087]

[0088]

[0089] In one embodiment, R a and R 5 Each time it appears, it is independently selected from hydrogen (H), methyl (Me), and isopropyl (CH(CH3)2) i Pr), tert-butyl (t The group consists of Bu, phenyl (Ph), CN, CF3 and diphenylamino (NPh2).

[0090] In one embodiment of the invention, the organic molecule comprises a structure according to any one of Formula III, IV, V, VI, VII, VIII, IX, X, and XI, or is composed of a structure according to any one of Formula III, IV, V, VI, VII, VIII, IX, X, and XI:

[0091]

[0092]

[0093] Among them, R Z It is CN or CF3.

[0094] In one embodiment of the invention, the organic molecule comprises a structure according to any one of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, and Formula XI, or is composed of a structure according to any one of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, and Formula XI, wherein R Z It's CN.

[0095] In one embodiment of the invention, the organic molecule comprises a structure according to any one of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, and Formula XI, or is composed of a structure according to any one of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, and Formula XI, wherein R Z It's CF3.

[0096] In one embodiment of the invention, the organic molecule comprises a structure according to any one of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, and Formula XI, or is composed of a structure according to any one of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, and Formula XI, wherein R I and R II It is hydrogen each time it appears.

[0097] In one embodiment of the invention, the organic molecule comprises a structure according to any one of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, and Formula XI, or is composed of a structure according to any one of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, and Formula XI, wherein R11 R 12 R 13 R 14 and R 15 It is hydrogen.

[0098] In one embodiment of the invention, the organic molecule comprises a structure according to any one of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, and Formula XI, or is composed of a structure according to any one of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, and Formula XI, wherein R I R II R 11 R 12 R 13 R 14 and R 15 It is hydrogen each time it appears.

[0099] In one embodiment of the invention, the organic molecule comprises a structure according to any one of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, and Formula XI, or is composed of a structure according to any one of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, and Formula XI, wherein R A It is represented by the formula BN-Ia.

[0100] In a preferred embodiment of the invention, the organic molecule comprises a structure according to any one of Formula III, IV, V, VI, VII, VIII, IX, X, and XI, or is composed of a structure according to any one of Formula III, IV, V, VI, VII, VIII, IX, X, and XI, wherein R A It is represented by the formula BN-Ib.

[0101] In one embodiment of the invention, the organic molecule comprises a structure according to any one of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, and Formula XI, or is composed of a structure according to any one of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, Formula X, and Formula XI, wherein R A It is represented by the formula BN-Ic.

[0102] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to Formula III.

[0103] In even more preferred embodiments of the invention, the organic molecule comprises or is composed of a structure according to Formula III, wherein RZ It's CN.

[0104] In a particularly preferred embodiment of the invention, the organic molecule comprises or is composed of a structure according to Formula III, wherein R Z It is CN, and among them, R I R II R 11 R 12 R 13 R 14 and R 15 It is hydrogen each time it appears.

[0105] In another preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to formula VIII.

[0106] In even more preferred embodiments of the invention, the organic molecule comprises or is composed of a structure according to Formula VIII, wherein R Z It's CN.

[0107] In a particularly preferred embodiment of the invention, the organic molecule comprises or is composed of a structure according to formula VIII, wherein R Z It is CN, and among them, R I R II R 11 R 12 R 13 R 14 and R 15 It is hydrogen each time it appears.

[0108] In one embodiment of the invention, the organic molecule comprises a structure according to any one of formula IIIa, IIIb, VIIIa, and VIIIb, or is composed of a structure according to any one of formula IIIa, IIIb, VIIIa, and VIIIb:

[0109]

[0110] Among them, R Z It is CN or CF3, and

[0111] Among them, R c Each occurrence is independently selected from the group consisting of: Me; i Pr; t Bu; Ph, optionally replacing those independently selected from Me, i Pr, tOne or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; a pyrimidinyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; carbazoyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph; and N(Ph)2.

[0112] In one embodiment of the invention, the organic molecule includes, or is composed of, a structure according to formula IIIa, IIIb, VIIIa, or VIIIb.

[0113] Among them, R Z It is CN or CF3, and

[0114] Among them, R c Each occurrence is independently selected from the group consisting of: Me; i Pr; t Bu; CN; CF3; Ph, optionally replacing each other independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; a pyrimidinyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; and a triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph.

[0115] In a preferred embodiment of the invention, the organic molecule comprises, or is composed of, a structure according to formula IIIa, IIIb, VIIIa, or VIIIb, or a structure according to formula IIIa, IIIb, VIIIa, or VIIIb, wherein R Z It's CN.

[0116] In a particularly preferred embodiment of the invention, the organic molecule comprises a structure according to any one of formula IIIa, IIIb, VIIIa, and VIIIb, or is composed of a structure according to any one of formula IIIa, IIIb, VIIIa, and VIIIb, wherein R Z It is CN, and among them, R I R II R 11 R 12 R 13 R 14 and R 15 It is hydrogen each time it appears.

[0117] In one embodiment of the invention, the organic molecule comprises, or is composed of, a structure according to formula IIIa, IIIb, VIIIa, or VIIIb, or a structure according to formula IIIa, IIIb, VIIIa, or VIIIb, wherein R Z It's CF3.

[0118] In one embodiment of the invention, the organic molecule includes a structure according to any one of formula IIIa, IIIb, VIIIa, and VIIIb, or is composed of a structure according to any one of formula IIIa, IIIb, VIIIa, and VIIIb, wherein R A It is represented by the formula BN-Ia.

[0119] In one embodiment of the invention, the organic molecule includes a structure according to any one of formula IIIa, IIIb, VIIIa, and VIIIb, or is composed of a structure according to any one of formula IIIa, IIIb, VIIIa, and VIIIb, wherein R A It is represented by the formula BN-Ib.

[0120] In one embodiment of the invention, the organic molecule includes a structure according to any one of formula IIIa, IIIb, VIIIa, and VIIIb, or is composed of a structure according to any one of formula IIIa, IIIb, VIIIa, and VIIIb, wherein R A It is represented by the formula BN-Ic. Attached Figure Description

[0121] Figure 1 The emission spectrum is that of Example 1 (10 wt%) in PMMA.

[0122] Figure 2 The emission spectrum is for Example 2 (10 wt%) in PMMA.

[0123] Figure 3 The emission spectrum is for example 3 (10 wt%) in PMMA.

[0124] Figure 4 The emission spectrum is shown for Example 4 (10 wt%) in PMMA. Detailed Implementation

[0125] As used above and herein, the terms "aryl" and "aromatic" can be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic aromatic moiety. Thus, an aryl group comprises 6 to 60 aromatic ring atoms, and a heteroaryl group comprises 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. Nevertheless, throughout the application, the number of aromatic ring atoms may be given as a subscript number in the definitions of certain substituents. Specifically, a heteroaromatic ring comprises one to three heteroatoms. Similarly, the terms "heteroaryl" and "heteroaromatic" can be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic heteroaromatic moiety comprising at least one heteroatom. Heteratoms may be the same or different each time they appear and may be individually selected from the group consisting of N, O, and S. Thus, the term "arylene" refers to a divalent substituent having two binding sites with other molecular structures and thus serving as a linking group structure. Where the group in the exemplary embodiments is defined differently from the definitions given herein (e.g., the number of aromatic ring atoms or the number of heteroatoms differs from the given definitions), the definitions in the exemplary embodiments will apply. According to the invention, the condensed (cyclized) aromatic polycyclic or heteroaromatic polycyclic is composed of two or more monoaromatic or heteroaromatic rings that form a polycyclic structure via a condensation reaction.

[0126] Specifically, as used throughout this application, the term aryl or heteroaryl includes groups that can be linked at any position via an aromatic group or heteroaryl aromatic group, which are derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, etc. Perylene, fluoranthene, benzo[a]anthene, benzo[a]phenanthrene, tetraphenyl, pentaphenyl, benzo[a]pyrene, furan, benzo[a]furan, isobenzo[a]furan, dibenzo[a]furan, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenotoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthiamidazole, phenanthrenemidazole, pyridinium pyridimazole, pyrazinium pyridimazole, quinoxalineium pyridimazole, oxazole, benzene The following are examples of benzoxazole, naphthoxazole, anthraxazole, phenanthrenexaazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1,3,5-triazine, quinoxaline, pyrazine, phenazine, naphthidine, carboline, benzocarboline, phenanthrene, 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-tetraazine, purine, pteridine, indene, and benzothiadiazole, or combinations thereof.

[0127] As used throughout, the term cyclic group can be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic moiety.

[0128] As used above and herein, the term alkyl can be understood in the broadest sense as any straight-chain, branched, or cyclic alkyl substituent. Specifically, the term alkyl includes substituents such as methyl (Me), ethyl (Et), n-propyl (... n Pr), isopropyl ( i Pr), cyclopropyl, n-butyl ( n Bu), isobutyl ( i Bu), sec-butyl ( s Bu), tert-butyl ( tBu), cyclobutyl, 2-methylbutyl, n-pentyl, secondary pentyl, tert-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, secondary hexyl, tert-hexyl, 2-hexyl, 3-hexyl, neohexyl, 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-trifluoroethyl, 1,1-dimethyl-n-hexyl-1-yl, 1,1-dimethyl-n-heptyl-1-yl, 1,1-dimethyl-n-octyl-1-yl, 1,1-dimethyl-n-decyl-1-yl, 1,1-dimethyl-n-dodecane-1-yl, 1,1-dimethyl-n-tetradecane-1-yl, 1,1-dimethyl-n-hexadecane-1-yl, 1,1-dimethyl-n-octadecane-1-yl, 1,1-diethyl-n-hexyl-1-yl, 1,1-diethyl-n-heptyl-1-yl, 1,1-diethyl-n-octyl-1-yl, 1,1-diethyl-n-decane-1-yl, 1,1-diethyl-n- Dodecane-1-yl, 1,1-diethyl-n-tetradecane-1-yl, 1,1-diethyl-n-hexadecane-1-yl, 1,1-diethyl-n-octadecane-1-yl, 1-(n-propyl)-cyclohexyl-1-yl, 1-(n-butyl)-cyclohexyl-1-yl, 1-(n-hexyl)-cyclohexyl-1-yl, 1-(n-octyl)-cyclohexyl-1-yl and 1-(n-decyl)-cyclohexyl-1-yl.

[0129] As used above and herein, the term alkenyl includes straight-chain, branched, and cyclic alkenyl substituents. The term alkenyl includes, for example, substituents such as vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, or cyclooctadienyl.

[0130] As used above and herein, the term alkynyl includes straight-chain, branched, and cyclic alkynyl substituents. Examples of alkynyl substituents include ethynyl, propynyl, butynyl, pentyynyl, hexynyl, heptyynyl, or octyynyl.

[0131] As used above and herein, the term alkoxy includes straight-chain, branched, and cyclic alkoxy substituents. Examples of alkoxy terms include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, and 2-methylbutoxy.

[0132] As used above and herein, the term thioalkoxy includes straight-chain, branched, and cyclic thioalkoxy substituents in which, for example, the O of an alkoxy group is replaced by an S group.

[0133] As used above and herein, the terms “halogen” and “halogenated” can be understood in the broadest sense as preferably fluorine, chlorine, bromine or iodine.

[0134] Whenever hydrogen (H) is mentioned here, it can also be replaced by deuterium each time it appears.

[0135] It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another part, its name may be written as if it were a fragment (e.g., naphthyl, dibenzofuranyl) or as if it were a whole molecule (e.g., naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attached fragments are considered equivalent.

[0136] In one embodiment, the organic molecules according to the invention have an excited-state lifetime of no more than 25 μs, no more than 15 μs, specifically no more than 10 μs, more preferably no more than 8 μs, or no more than 6 μs, or even more preferably no more than 4 μs, in a poly(methyl methacrylate) (PMMA) film containing 10 wt% organic molecules at room temperature.

[0137] In one embodiment of the invention, the organic molecule according to the invention represents a thermally activated delayed fluorescence (TADF) emitter, which exhibits an emission frequency of less than 5000 cm⁻¹. -1 (Preferably less than 3000cm) -1 More preferably less than 1500cm -1 or even more preferably less than 1000cm -1 Or even less than 500cm -1 The energy difference ΔE between the first excited singlet state (S1) and the first excited triplet state (T1) corresponds to the energy difference between them. ST value.

[0138] In another embodiment of the invention, the organic molecules according to the invention have an emission peak in the visible or near-ultraviolet range (i.e., in the wavelength range of 380 nm to 800 nm) and a full width at half maximum (FWHM) of less than 0.50 eV (preferably less than 0.48 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV or even less than 0.40 eV) in a poly(methyl methacrylate) (PMMA) film containing 10% by weight of the organic molecules at room temperature.

[0139] Orbital and excited-state energies can be determined experimentally or through calculations using quantum chemical methods (specifically, density functional theory calculations). The highest occupied molecular orbital energy (E0) HOMO The lowest unoccupied molecular orbital energy (E0) was determined by cyclic voltammetry with an accuracy of 0.1 eV using methods known to those skilled in the art. LUMO) is calculated as E HOMO +E gap E gap The following determination was made: For the host compound, unless otherwise specified, the starting point of the emission spectrum of a pure film having a host of 10% by weight in poly(methyl methacrylate) (PMMA) was used as the E. gap For emitter molecules, E gap The energy at which the excitation and emission spectra of a film having 10% emitter in PMMA cross.

[0140] The energy of the first excited triplet state (T1) is determined by the starting point of the emission spectrum at low temperature (typically, 77 K). For host compounds where the energy difference between the first excited singlet state and the lowest triplet state is >0.4 eV, phosphorescence is usually visible in the steady-state spectrum in 2-Me-THF. Therefore, the triplet state energy can be determined as the starting point of the phosphorescence spectrum. For TADF emitter molecules, unless otherwise specified, the energy of the first excited triplet state (T1) is determined by the starting point of the delayed emission spectrum at 77 K, measured in a PMMA film containing 10 wt% emitter. For both host and emitter compounds, the energy of the first excited singlet state (S1) is determined by the starting point of the emission spectrum (measured as follows: TADF emitter: 10 wt% concentration in a PMMA film; host: pure film).

[0141] The starting point of the emission spectrum is determined by calculating the intersection of the tangent to the emission spectrum with the x-axis. The tangent to the emission spectrum is set at the high-energy side of the emission band and at the point of half maximum intensity of the emission spectrum.

[0142] Another aspect of the invention relates to a method for preparing the organic molecule of the invention (with optional subsequent reactions), wherein a substituted 2,4-dichloro-6-phenyltriazine is used as a reactant:

[0143]

[0144]

[0145] According to the invention, borate esters can be used instead of boric acid, and vice versa.

[0146] For the reaction of nitrogen heterocycles in nucleophilic aromatic substitutions with aryl halides (preferably aryl fluorides), typical conditions include, for example, the use of a base (such as tripotassium phosphate or sodium hydride) in a nonprotic polar solvent (such as dimethyl sulfoxide (DMSO) or N,N-dimethylformamide (DMF)).

[0147] Optional synthetic routes include introducing nitrogen heterocycles into aryl halides or aryl pseudohalides (preferably aryl bromides, aryl iodides, aryl trifluoromethanesulfonates, or aryl toluenesulfonates) via copper or palladium-catalyzed coupling.

[0148] Another aspect of the invention relates to the application of the organic molecules according to the invention in optoelectronic devices as light emitters or absorbers and / or as host materials and / or as electron transport materials and / or as hole injection materials and / or as hole blocking materials.

[0149] Optoelectronic devices can be understood in the broadest sense as any device based on organic materials suitable for emitting light in the visible light or closest to ultraviolet (UV) range (i.e., in the wavelength range of 380 nm to 800 nm). More preferably, optoelectronic devices can be capable of emitting light in the visible light range (i.e., 400 nm to 800 nm).

[0150] In this context, optoelectronic devices are more specifically selected from the group consisting of:

[0151] Organic light-emitting diodes (OLEDs);

[0152] • Photoluminescent electrochemical cells;

[0153] • OLED sensors, specifically, gas sensors and vapor sensors that are not externally sealed and isolated;

[0154] Organic diodes;

[0155] Organic solar cells;

[0156] Organic transistors;

[0157] • Organic field-effect transistors;

[0158] Organic lasers; and

[0159] Down-conversion element.

[0160] The luminescent electrochemical cell consists of three layers (i.e., cathode, anode, and active layer), with the active layer containing organic molecules according to the invention.

[0161] In a preferred embodiment within the context of this application, the optoelectronic device is selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), organic lasers, and light-emitting transistors.

[0162] In one embodiment, the light-emitting layer (or “emitting layer”) of the organic light-emitting diode includes not only the organic molecule according to the invention, but also a host material whose triplet (T1) and singlet (S1) energy levels are higher in energy than those of the organic molecule.

[0163] Another aspect of the invention relates to a composition comprising or consisting of the following components:

[0164] (a) The organic molecule of the invention, specifically in the form of an emitter and / or a host; and

[0165] (b) one or more emitters and / or host materials different from the organic molecule of the invention; and

[0166] (c) Optionally, one or more dyes and / or one or more solvents.

[0167] In another embodiment of the invention, the composition has a photoluminescence quantum yield (PLQY) of greater than 26% (preferably greater than 40%, more preferably greater than 60%, even more preferably greater than 80% or even greater than 90%) at room temperature.

[0168] Composition having at least one other emitter

[0169] One embodiment of the invention relates to a composition comprising or consisting of the following components:

[0170] (i) 1% to 50% by weight (preferably, 5% to 40% by weight, specifically, 10% to 30% by weight) of the organic molecule (E) according to the invention;

[0171] (ii) 5% to 98% by weight (preferably 30% to 93.9% by weight, specifically 40% to 88% by weight) of a main compound (H);

[0172] (iii) 1% to 30% by weight (specifically, 1% to 20% by weight, preferably, 1% to 5% by weight) of at least one other emitter molecule (F), the other emitter molecule (F) having a structure different from that of the organic molecule (E) according to the invention; and

[0173] (iv) Optionally, from 0% to 94% by weight (preferably, from 0.1% to 65% by weight, specifically, from 1% to 50% by weight) of at least one other main compound (D), the other main compound (D) having a structure different from that of the organic molecule (E) according to the invention; and

[0174] (v) Optionally, a solvent of 0% to 94% by weight (preferably 0% to 65% by weight, specifically 0% to 50% by weight).

[0175] Select ingredients or components such that the total weight of the ingredients equals 100%.

[0176] In another embodiment of the invention, the composition has an emission peak in the visible light or closest to ultraviolet light range (i.e., in the wavelength range of 380 nm to 800 nm).

[0177] In one embodiment of the invention, at least one other emitter molecule (F) is a purely organic emitter.

[0178] In one embodiment of the invention, at least one other emitter molecule (F) is a pure organic TADF emitter. Pure organic TADF emitters are known by prior art, for example, Wong and Zysman-Colman (“Purely Organic Thermally Activated Delayed Fluorescence Materials for Organic Light-Emitting Diodes”, Adv. Mater. 2017 Jun; 29(22)).

[0179] In one embodiment of the invention, at least one other emitter molecule (F) is a fluorescent emitter (specifically, a blue, green, or red fluorescent emitter).

[0180] In another embodiment of the invention, the composition comprising at least one other emitter molecule (F) exhibits an emission peak at room temperature in the visible or closest to ultraviolet range (i.e., in the wavelength range of 380 nm to 800 nm) and a full width at half maximum (FWHM) of less than 0.30 eV (specifically less than 0.25 eV, preferably less than 0.22 eV, more preferably less than 0.19 eV or even less than 0.17 eV), with a lower limit of 0.05 eV.

[0181] Emissive Layer (EML)

[0182] In one embodiment, the light-emitting layer (EML) of the organic light-emitting diode of the invention comprises (or is substantially composed of) a composition comprising or consisting of the following components:

[0183] (i) 1% to 50% by weight (preferably, 5% to 40% by weight, specifically, 10% to 30% by weight) of one or more organic molecules (E) according to the invention;

[0184] (ii) at least one host compound (H) of 5% to 99% by weight (preferably 30% to 94.9% by weight, specifically 40% to 89% by weight); and

[0185] (iii) Optionally, from 0% to 94% by weight (preferably, from 0.1% to 65% by weight, specifically, from 1% to 50% by weight) of at least one other main compound (D), the other main compound (D) having a structure different from that of the organic molecule (E) according to the invention; and

[0186] (iv) Optionally, a solvent of 0% to 94% by weight (preferably 0% to 65% by weight, specifically 0% to 50% by weight); and

[0187] (v) Optionally, 0% to 30% by weight (specifically, 0% to 20% by weight, preferably, 0% to 5% by weight) of at least one other emitter molecule (F), which has a structure different from that of the organic molecule (E) according to the invention.

[0188] Preferably, energy can be transferred from the host compound (H) to one or more of the inventive organic molecules (E). Specifically, energy can be transferred from the first excited triplet state (T1(H)) of the host compound (H) to the first excited triplet state (T1(E)) of one or more of the inventive organic molecules (E), and / or from the first excited singlet state (S1(H)) of the host compound (H) to the first excited singlet state (S1(E)) of one or more of the inventive organic molecules (E).

[0189] In one embodiment, the host compound (H) has an energy (E) in the range of -5 eV to -6.5 eV. HOMO The highest occupied molecular orbital (HOMO(H)) of an organic molecule (E) according to the invention possesses energy (E) HOMO The highest occupied molecular orbital (HOMO(E)) of E) is where E HOMO (H)>E HOMO (E).

[0190] In yet another embodiment, the host compound (H) possesses energy (E) LUMO The lowest unoccupied molecular orbital (LUMO(H)) of an organic molecule (E) according to the invention possesses energy (E) LUMO The lowest unoccupied molecular orbital (LUMO(E)) of (E), where E LUMO (H)>E LUMO (E).

[0191] An emissive layer (EML) comprising at least one other host compound (D).

[0192] In yet another embodiment, the light-emitting layer (EML) of the organic light-emitting diode of the invention comprises (or is substantially composed of) a composition comprising or consisting of the following components:

[0193] (i) 1% to 50% by weight (preferably, 5% to 40% by weight, specifically, 10% to 30% by weight) of an organic molecule (E) according to the invention;

[0194] (ii) 5% to 99% by weight (preferably 30% to 94.9% by weight, specifically 40% to 89% by weight) of a main compound (H); and

[0195] (iii) 0% to 94% by weight (preferably 0.1% to 65% by weight, specifically 1% to 50% by weight) of at least one other main compound (D), the other main compound (D) having a structure different from that of the organic molecule (E) according to the invention; and

[0196] (iv) Optionally, a solvent of 0% to 94% by weight (preferably 0% to 65% by weight, specifically 0% to 50% by weight); and

[0197] (v) Optionally, 0% to 30% by weight (specifically, 0% to 20% by weight, preferably, 0% to 5% by weight) of at least one other emitter molecule (F), which has a structure different from that of the organic molecule (E) according to the invention.

[0198] In one embodiment of the organic light-emitting diode of the invention, the host compound (H) has an energy (E) in the range of -5 eV to -6.5 eV. HOMO The highest occupied molecular orbital (HOMO(H)) of (H) and at least one other host compound (D) possesses the energy (E) HOMO The highest occupied molecular orbital (HOMO(D)) of E(D)) is where E(D) is located. HOMO (H)>E HOMO (D). Relationship E HOMO (H)>E HOMO (D) It facilitates efficient hole transport.

[0199] In yet another embodiment, the host compound (H) possesses energy (E) LUMO The lowest unoccupied molecular orbital (LUMO(H)) of (H), and at least one other host compound (D) possessing the energy (E)LUMO The lowest unoccupied molecular orbital (LUMO(D)) of E(D), where E LUMO (H)>E LUMO (D). Relationship E LUMO (H)>E LUMO (D) It facilitates efficient electronic transmission.

[0200] In one embodiment of the invented organic light-emitting diode, the host compound (H) possesses energy (E). HOMO The highest occupied molecular orbital (HOMO(H)) and the energy (E) of (H) LUMO The lowest unoccupied molecular orbital (LUMO(H)) of (H) and

[0201] At least one other main compound (D) possesses energy (E) HOMO The highest occupied molecular orbital (HOMO(D)) and the energy possessed (E) LUMO The lowest unoccupied molecular orbital (LUMO(D)) of (D)

[0202] The invented organic molecule (E) possesses energy (E) HOMO The highest occupied molecular orbital (HOMO(E)) and the energy possessed by (E) LUMO The lowest unoccupied molecular orbital (LUMO(E)) of (E),

[0203] in,

[0204] E HOMO (H)>E HOMO (D), and according to the energy level (E) of the highest occupied molecular orbital (HOMO(E)) of the invented organic molecule (E). HOMO The energy levels of the highest occupied molecular orbital (HOMO(H)) of the host compound (H) and (E) are related to the energy levels of the host compound (H). HOMO The difference between (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

[0205] E LUMO (H)>E LUMO (D), and according to the invention, the energy level (E) of the lowest unoccupied molecular orbital (LUMO(E)) of the organic molecule (E) LUMO (E)) and the energy level of the lowest unoccupied molecular orbital (LUMO(D)) of at least one other host compound (D) LUMOThe difference between (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).

[0206] An emissive layer (EML) comprising at least one other emitter molecule (F).

[0207] In yet another embodiment, the light-emitting layer (EML) comprises (or is substantially composed of) a composition comprising or consisting of the following components:

[0208] (i) 1% to 50% by weight (preferably, 5% to 40% by weight, specifically, 10% to 30% by weight) of an organic molecule (E) according to the invention;

[0209] (ii) 5% to 98% by weight (preferably 30% to 93.9% by weight, specifically 40% to 88% by weight) of a main compound (H);

[0210] (iii) 1% to 30% by weight (specifically, 1% to 20% by weight, preferably, 1% to 5% by weight) of at least one other emitter molecule (F), the other emitter molecule (F) having a structure different from that of the organic molecule (E) according to the invention; and

[0211] (iv) Optionally, from 0% to 94% by weight (preferably, from 0.1% to 65% by weight, specifically, from 1% to 50% by weight) of at least one other main compound (D), the other main compound (D) having a structure different from that of the organic molecule (E) according to the invention; and

[0212] (v) Optionally, a solvent of 0% to 94% by weight (preferably 0% to 65% by weight, specifically 0% to 50% by weight).

[0213] In another embodiment, the light-emitting layer (EML) comprises a composition as described in a composition having at least one other emitter and at least one other emitter molecule (F) as defined in a composition in which at least one other emitter molecule (F) is a blue fluorescent emitter (or (substantially) composed of a composition as described in a composition having at least one other emitter and at least one other emitter molecule (F) as defined in a composition in which at least one other emitter molecule (F) is a blue fluorescent emitter).

[0214] In yet another embodiment, the emissive layer (EML) comprises a composition as described in a composition having at least one other emitter and at least one other emitter molecule (F) as defined in a composition in which at least one other emitter molecule (F) is a triplet-triplet annihilation (TTA) fluorescent emitter (or (substantially) composed of a composition as described in a composition having at least one other emitter and at least one other emitter molecule (F) as defined in a composition in which at least one other emitter molecule (F) is a triplet-triplet annihilation (TTA) fluorescent emitter).

[0215] In another embodiment, the light-emitting layer (EML) comprises a composition as described in a composition having at least one other emitter and at least one other emitter molecule (F) as defined in a composition in which at least one other emitter molecule (F) is a green fluorescent emitter (or (substantially) composed of a composition as described in a composition having at least one other emitter and at least one other emitter molecule (F) as defined in a composition in which at least one other emitter molecule (F) is a green fluorescent emitter).

[0216] In another embodiment, the light-emitting layer (EML) comprises a composition as described in a composition having at least one other emitter and at least one other emitter molecule (F) as defined in a composition in which at least one other emitter molecule (F) is a red fluorescent emitter (or (substantially) composed of a composition as described in a composition having at least one other emitter and at least one other emitter molecule (F) as defined in a composition in which at least one other emitter molecule (F) is a red fluorescent emitter).

[0217] In one embodiment of the light-emitting layer (EML) including at least one other emitter molecule (F), energy can be transferred from one or more inventive organic molecules (E) to at least one other emitter molecule (F), specifically, energy can be transferred from the first excited singlet state (S1(E)) of one or more inventive organic molecules (E) to the first excited singlet state (S1(F)) of at least one other emitter molecule (F).

[0218] In one embodiment, the first excited singlet state (S1(H)) of a host compound (H) of the light-emitting layer is higher in energy than the first excited singlet state (S1(E)) of one or more of the organic molecules (E) of the invention: S1(H)>S1(E), and the first excited singlet state (S1(H)) of a host compound (H) is higher in energy than the first excited singlet state (S1(F)) of at least one emitter molecule (F): S1(H)>S1(F).

[0219] In one embodiment, the first excited triplet state (T1(H)) of a host compound (H) is higher in energy than the first excited triplet state (T1(E)) of one or more of the organic molecules (E) of the invention: T1(H)>T1(E), and the first excited triplet state (T1(H)) of a host compound (H) is higher in energy than the first excited triplet state (T1(F)) of at least one emitter molecule (F): T1(H)>T1(F).

[0220] In one embodiment, the first excited singlet state (S1(E)) of one or more of the invented organic molecules (E) is more energetic than the first excited singlet state (S1(F)) of at least one emitter molecule (F): S1(E)>S1(F).

[0221] In one embodiment, the first excited triplet state (T1(E)) of one or more of the invented organic molecules (E) is more energetic than the first excited singlet state (T1(F)) of at least one emitter molecule (F): T1(E)>T1(F).

[0222] In one embodiment, the first excited triplet state (T1(E)) of one or more of the invented organic molecules (E) is higher in energy than the first excited singlet state (T1(F)) of at least one emitter molecule (F): T1(E)>T1(F), wherein the absolute value of the energy difference between T1(E) and T1(F) is greater than 0.3 eV (preferably greater than 0.4 eV or even greater than 0.5 eV).

[0223] In one embodiment, the host compound (H) possesses energy (E) HOMO The highest occupied molecular orbital (HOMO(H)) and the energy (E) of (H) LUMO The lowest unoccupied molecular orbital (LUMO(H)) of (H) and

[0224] An organic molecule (E) according to the invention possesses energy (E) HOMO The highest occupied molecular orbital (HOMO(E)) and the energy possessed by (E) LUMO The lowest unoccupied molecular orbital (LUMO(E)) of (E),

[0225] At least one other emitter molecule (F) possesses energy (E) HOMO The highest occupied molecular orbital (HOMO(F)) and the energy (E) of (F) LUMO The lowest unoccupied molecular orbital (LUMO(F)) of (F),

[0226] in,

[0227] E HOMO (H)>EHOMO (E), the energy level of the highest occupied molecular orbital (HOMO(F)) of at least one other emitter molecule (F). HOMO (F) and the energy level (E) of the highest occupied molecular orbital (HOMO(H)) of the host compound (H). HOMO The difference between (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

[0228] E LUMO (H)>E LUMO (E), the energy level of the lowest unoccupied molecular orbital (LUMO(F)) of at least one other emitter molecule (F). LUMO (F)) and the energy level (E) of the lowest unoccupied molecular orbital (LUMO(E)) of an organic molecule (E) according to the invention. LUMO The difference between (E) 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).

[0229] Optoelectronic devices

[0230] In another aspect, the invention relates to an optoelectronic device comprising organic molecules or compositions as described herein, and more specifically, the optoelectronic device is in the form of a device selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells, OLED sensors (more specifically, gas sensors and vapor sensors that are not externally sealed and isolated), organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

[0231] In a preferred embodiment, the organic optoelectronic device is selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), and light-emitting transistors.

[0232] In one embodiment of the optoelectronic device of the invention, the organic molecule according to the invention is used as the emitting material in the light-emitting layer (EML).

[0233] In one embodiment of the optoelectronic device of the invention, the light-emitting layer (EML) is composed of the composition according to the invention described herein.

[0234] For example, when the organic optoelectronic device is an OLED, it can exhibit the following layer structure:

[0235] 1. Base

[0236] 2. Anode layer, A

[0237] 3. Hole injection layer, HIL

[0238] 4. Hole transport layer, HTL

[0239] 5. Electron blocking layer, EBL

[0240] 6. Emitting layer, EML

[0241] 7. Hole blocking layer, HBL

[0242] 8. Electron Transport Layer (ETL)

[0243] 9. Electron Injection Layer (EIL)

[0244] 10. Cathode layer, C,

[0245] OLEDs consist of each layer, and alternatively, different layers may be combined. An OLED may include more than one layer of each of the layer types defined above.

[0246] In addition, the optoelectronic device may optionally include one or more protective layers that protect the device from damage caused by exposure to harmful substances in the environment, including, for example, moisture, vapor and / or gases.

[0247] In one embodiment of the invention, the optoelectronic device is an OLED exhibiting the following inverted layer structure:

[0248] 1. Base

[0249] 2. Cathode layer, C

[0250] 3. Electron Injection Layer (EIL)

[0251] 4. Electron Transport Layer (ETL)

[0252] 5. Hole blocking layer, HBL

[0253] 6. Emitting layer, EML

[0254] 7. Electron blocking layer, EBL

[0255] 8. Hole Transport Layer (HTL)

[0256] 9. Hole injection layer, HIL

[0257] 10. Anode layer, A,

[0258] OLEDs with inverted layer structures include each layer, and alternatively, different layers may be combined. An OLED may include more than one layer of each of the layer types defined above.

[0259] In one embodiment of the invention, the optoelectronic device is an OLED that can exhibit a stacked architecture. In this architecture, contrary to a typical arrangement in which OLEDs are placed side by side, the individual units are stacked on top of each other. Mixed light can be generated using an OLED exhibiting a stacked architecture; specifically, white light can be generated by stacking blue OLEDs, green OLEDs, and red OLEDs. Furthermore, an OLED exhibiting a stacked architecture may optionally include a charge generation layer (CGL), which is typically located between two OLED sub-units and typically consists of an n-doped layer and a p-doped layer, with the n-doped layer of a CGL typically located close to the anode layer.

[0260] In one embodiment of the invention, the optoelectronic device is an OLED comprising two or more emitting layers between the anode and cathode. Specifically, this so-called tandem OLED comprises three emitting layers, wherein one emitting layer emits red light, one emitting green light, and one emitting blue light, and optionally, layers such as charge-generating layers, blocking layers, or transport layers may be further included between the respective emitting layers. In another embodiment, the emitting layers are stacked adjacent to each other. In yet another embodiment, the tandem OLED includes a charge-generating layer between every two emitting layers. Additionally, adjacent emitting layers or emitting layers separated by charge-generating layers may be merged.

[0261] The substrate can be formed from any material or combination of materials. Most commonly, a glass slide is used as the substrate. Alternatively, a thin metal layer (e.g., a copper, gold, silver, or aluminum film) or a plastic film or glass slide can be used. This allows for a higher degree of flexibility. The anode layer (A) is primarily composed of materials that allow for a (substantially) transparent film. Since at least one of the two electrodes should be (substantially) transparent to allow light emission from the OLED, the anode layer (A) or cathode layer (C) is transparent. Preferably, the anode layer (A) comprises a large amount of transparent conductive oxide (TCO), or is even composed of transparent conductive oxide (TCO). Such an anode layer (A) can, for example, include indium tin oxide, zinc aluminum oxide, fluorine-doped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole, and / or doped polythiophene.

[0262] Preferably, the anode layer (A) is (essentially) made of indium tin oxide (ITO) (e.g., (InO3)). 0.9 (SnO2) 0.1The anode layer (A) can be composed of a hole injection layer (HIL). The roughness of the anode layer (A) caused by the transparent conductive oxide (TCO) can be compensated by using a hole injection layer (HIL). Furthermore, the HIL can promote the injection of quasi-charge carriers (i.e., holes) because the transport of quasi-charge carriers from the TCO to the hole transport layer (HTL) is facilitated. The hole injection layer (HIL) can include poly(3,4-ethylenedioxythiophene) (PEDOT), polystyrene sulfonate (PSS), MoO2, V2O5, CuPC, or CuI (specifically, a mixture of PEDOT and PSS). The hole injection layer (HIL) also prevents metal from diffusing from the anode layer (A) into the hole transport layer (HTL). HIL can include PEDOT:PSS (poly(3,4-ethylenedioxythiophene):polystyrene sulfonate), PEDOT (poly(3,4-ethylenedioxythiophene)), mMTDATA (4,4',4”-tris[phenyl(m-tolyl)amino]triphenylamine), spiro-TAD (2,2',7,7'-tetra(n,n-diphenylamino)-9,9'-spirodifluorene), DNTPD (N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylphenyl-1,4-diamine)), NPB (N,N'-bis(1- Naphthyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine), NPNPB(N,N'-diphenyl-N,N'-di-[4-(N,N-diphenyl-amino)phenyl]benzidine), MeO-TPD(N,N,N',N'-tetra(4-methoxyphenyl)benzidine), HAT-CN(2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenyl) and / or spiro-NPD(N,N'-diphenyl-N,N'-bis(1-naphthyl)-9,9'-spirodifluorene-2,7-diamine).

[0263] Adjacent to the anode layer (A) or hole injection layer (HIL), a hole transport layer (HTL) is typically located. Any hole transport compound can be used here. Exemplarily, electron-rich heteroaromatic compounds such as triarylamines and / or carbazole can be used as hole transport compounds. The HTL can lower the energy barrier between the anode layer (A) and the light-emitting layer (EML). The hole transport layer (HTL) can also be an electron blocking layer (EBL). Preferably, the hole transport compound has a relatively high energy level of its triplet state (T1). For example, the hole transport layer (HTL) may include tris(4-carbazole-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenylamine)), α-NPD (2,2'-dimethyl-N,N'-di[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine), TAPC (4,4'-cyclohexyl-bis[N,N-bis(4-methylphenyl)aniline]), 2-TNATA (4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine), spiro-TAD, DNTPD, NPB, NP Star-shaped heterocycles of NPB, MeO-TPD, HAT-CN, and / or Tris-Pcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole). Additionally, HTLs may include p-doped layers composed of inorganic or organic dopants in an organic hole transport matrix. Transition metal oxides such as vanadium oxide, molybdenum oxide, or tungsten oxide can be used as inorganic dopants. Tetrafluorotetracyanoquinone dimethyl ether (F4-TCNQ), copper pentafluorobenzoate (Cu(I)pFBz), or transition metal complexes can be used as organic dopants.

[0264] EBLs may include mCP (1,3-bis(carbazole-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-bis(9H-carbazole-9-yl)biphenyl), Tris-Pcz, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole) and / or DCB (N,N'-dicarbazole-1,4-dimethylbenzene).

[0265] Adjacent to the hole transport layer (HTL), a light-emitting layer (EML) is typically positioned. The light-emitting layer (EML) comprises at least one organic molecule. Specifically, the EML comprises at least one organic molecule (E) 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-carbazolyl)biphenyl), mCP, mCBP, Sif87 (dibenzo[b,d]thiophene-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophene-2-yldiphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl] ether oxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophene- [2-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine) and / or TST (2,4,6-tris(9,9'-spirodifluorene-2-yl)-1,3,5-triazine). The host material should typically be selected to exhibit a first triplet (T1) energy level and a first singlet (S1) energy level that are higher in energy than those of the organic molecule.

[0266] In one embodiment of the invention, the EML comprises a so-called hybrid host system having at least one hole-dominant host and one electron-dominant host. In a specific embodiment, the EML comprises exactly one organic molecule and a hybrid host system according to the invention, the hybrid host system comprising T2T as the electron-dominant host and a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophene-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophene)phenyl]-9H-carbazole as the hole-dominant host. In another embodiment, the EML comprises 50% to 80% by weight (preferably 60% to 75% by weight) of a body, 10% to 45% by weight (preferably 15% to 30% by weight) of T2T, and 5% to 40% by weight (preferably 10% to 30% by weight) of an organic molecule according to the invention, the body being selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole.

[0267] Adjacent to the luminescent layer (EML), an electron transport layer (ETL) may be positioned. Any electron transporter can be used here. Exemplarily, electron-depleted compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone can be used. The electron transporter can also be a star-shaped heterocycle such as 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi). ETLs may include NBphen (2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (tris(8-hydroxyquinoline)aluminum), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphine oxide), BPyTP2 (2,7-bis(2,2'-bipyridin-5-yl)triphenylene), Sif87 (dibenzo[b,d]thiophene-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophene-2-yldiphenylsilane), BmPyPhB (1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene) and / or BTB (4,4'-bis[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl). Optionally, the ETL may be doped with materials such as Liq. Electron transport layer (ETL) can also block holes, or a hole blocking layer (HBL) can be introduced.

[0268] HBLs can include, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), BAlq (bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (tris(8-hydroxyquinoline)aluminum), and TSPO1 (diphenyl-4-triphenylsilyl) Phenylphosphine oxide), T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), TST (2,4,6-tris(9,9'-spirodifluorene-2-yl)-1,3,5-triazine) and / or TCB / TCP (1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazolyl-9-yl)benzene).

[0269] The cathode layer (C) can be positioned adjacent to the electron transport layer (ETL). For example, the cathode layer (C) can comprise a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, Li, Ca, Ba, Mg, In, W, or Pd) or a metal alloy, or can be composed of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, Li, Ca, Ba, Mg, In, W, or Pd) or a metal alloy. For practical reasons, the cathode layer can also be composed of a (substantially) opaque metal such as Mg, Ca, or Al. Optionally or additionally, the cathode layer (C) can also comprise graphite and / or carbon nanotubes (CNTs). Optionally, the cathode layer (C) can also be composed of nanoscale silver wires.

[0270] The OLED may optionally include a protective layer (which may be designated as an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer (C). This layer may include lithium fluoride, cesium fluoride, silver, Liq (lithium 8-hydroxyquinoline), Li2O, BaF2, MgO and / or NaF.

[0271] Optionally, the electron transport layer (ETL) and / or hole blocking layer (HBL) may also include one or more host compounds.

[0272] To further modify the emission and / or absorption spectra of the emissive layer (EML), the EML may further include one or more other emitter molecules (F). Such emitter molecules (F) can be any emitter molecule known in the art. Preferably, such emitter molecules (F) are molecules having a structure different from that of the organic molecule according to the invention. 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 capable of shifting the emission and / or absorption spectra of the EML. For example, by emitting light that is typically redshifted compared to light emitted by the organic molecule (E), triplet and / or singlet excitons can transfer from the organic molecule according to the invention to the emitter molecule (F) before relaxing to the ground state (S0). Optionally, the emitter molecule (F) may also induce a two-photon effect (i.e., absorption of half the energy of the maximum absorption value of the two photons).

[0273] Optionally, the optoelectronic device (e.g., OLED) can be, for example, a substantially white optoelectronic device. Exemplarily, such a white optoelectronic device may include at least one (deep) blue emitter molecule and one or more emitter molecules that emit green and / or red light. Then, energy transmittance may optionally exist between the two or more molecules as described above.

[0274] As used herein, unless otherwise defined in the specific context, the color of the emitted and / or absorbed light is specified as follows:

[0275] Purple: Wavelength range from >380nm to 420nm;

[0276] Deep blue: wavelength range >420nm to 480nm;

[0277] Sky blue: >480nm to 500nm wavelength range;

[0278] Green: Wavelength range >500nm to 560nm;

[0279] Yellow: Wavelength range >560nm to 580nm;

[0280] Orange: Wavelength range from >580nm to 620nm;

[0281] Red: Wavelength range from 620nm to 800nm.

[0282] For emitter molecules, this color refers to the emission maximum. Thus, for example, a dark blue emitter has an emission maximum in the range of >420 nm to 480 nm, a sky blue emitter has an emission maximum in the range of >480 nm to 500 nm, a green emitter has an emission maximum in the range of >500 nm to 560 nm, and a red emitter has an emission maximum in the range of >620 nm to 800 nm.

[0283] The green emitter can preferably have a maximum emission value between 500 and 560 nm, more preferably between 510 and 550 nm, and even more preferably between 520 and 540 nm.

[0284] Another embodiment of the invention relates to an OLED that emits light having CIEx and CIEy color coordinates (CIEx = 0.170, CIEy = 0.797) (these CIEx and CIEy color coordinates (CIEx = 0.170, CIEy = 0.797) are close to the CIEx (= 0.170), CIEy (= 0.797) color coordinates of the primary color green as defined by ITU-R Recommendation BT.2020 (Rec.2020), and is therefore suitable for use in ultra-high definition (UHD) displays (e.g., UHD-TV). In this context, the term "close to" refers to the range of CIEx and CIEy coordinates provided at the end of this paragraph. In commercial applications, top-emitting (top electrode is transparent) devices are typically used, while the test device used throughout this application represents a bottom-emitting device (bottom electrode and substrate are transparent). Therefore, another aspect of the present invention relates to an OLED whose emission exhibits CIEx color coordinates between 0.06 and 0.34 (preferably between 0.07 and 0.29, more preferably between 0.09 and 0.24, or even more preferably between 0.12 and 0.22, or even more preferably between 0.14 and 0.19) and / or CIEy color coordinates between 0.44 and 0.84 (preferably between 0.55 and 0.83, more preferably between 0.65 and 0.82, or even more preferably between 0.70 and 0.81, or even more preferably between 0.75 and 0.8).

[0285] Therefore, another aspect of the present invention relates to an OLED that has a density of 14500 cd / m². 2It exhibits an external quantum efficiency greater than 10% (more preferably greater than 13%, more preferably greater than 15%, even more preferably greater than 17%, or even greater than 20%), and / or exhibits a maximum emission value between 495 nm and 580 nm (preferably between 500 nm and 560 nm, more preferably between 510 nm and 550 nm, even more preferably between 510 nm and 540 nm), and / or at 14500 cd / m². 2 The LT97 value exhibits a value greater than 100 hours (preferably greater than 250 hours, more preferably greater than 500 hours, even more preferably greater than 750 hours, or even greater than 1000 hours).

[0286] Another aspect of the invention relates to an OLED that emits light at different color points. According to the invention, the OLED emits light having a narrow emission band (small half-peak full width (FWHM)). In one aspect, the OLED according to the invention emits light with an FWHM of a main emission peak of less than 0.50 eV (preferably less than 0.48 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV or even less than 0.40 eV).

[0287] In another aspect, the invention relates to a method for manufacturing optoelectronic components. In this case, the organic molecules of the invention are used.

[0288] Organic optoelectronic devices (specifically, OLEDs) according to the invention can be fabricated by any method of vapor deposition and / or liquid processing. Therefore, at least one layer:

[0289] -Prepared via sublimation process.

[0290] -Prepared using an organic vapor deposition process.

[0291] -Prepared via carrier gas sublimation process.

[0292] - Solution treatment or printing.

[0293] The method for manufacturing organic electroluminescent devices (specifically, OLEDs) according to the present invention is known in the art. Different layers are deposited individually and continuously on a suitable substrate via subsequent deposition processes. The individual layers can be deposited using the same or different deposition methods.

[0294] Vapor deposition processes can include thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. For active-matrix OLED displays, an AMOLED backplane serves as the substrate. Individual layers can be processed from a solution or dispersion using a suitable solvent. Solution deposition processes exemplarily include spin coating, dip coating, and jet printing. Liquid processing can optionally be performed in an inert atmosphere (e.g., in a nitrogen atmosphere), and the solvent can optionally be completely or partially removed by means known in the art.

[0295] Example

[0296] General Synthesis Scheme I

[0297] General Synthesis Scheme I provides a synthesis scheme for the organic molecule according to the invention.

[0298]

[0299] General Synthesis Scheme II

[0300] General Synthesis Scheme II provides an alternative synthesis scheme for the organic molecules according to the invention.

[0301]

[0302] General steps for synthesizing AAV1-1

[0303]

[0304] Under a nitrogen atmosphere, a mixture of THF and water (4:1 ratio) was added to 4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborphane-2-yl)benzyl nitrile (1.00 equivalent, CAS 863868-29-5), 2,4-dichloro-6-phenyl-1,3,5-triazine (1.50 equivalent, CAS 1700-02-3), potassium carbonate (2.00 equivalent), and tetra(triphenylphosphine)palladium(0) (0.03 equivalent, CAS 14221-01-3), followed by nitrogen bubbling for 15 minutes. The reaction mixture was stirred at 60°C until complete conversion of pinacol borate was achieved as determined by GC and TLC. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and brine. The organic extract was concentrated under reduced pressure. The crude product was heated in ethanol to reflux for 20 minutes, then hot filtered and the solids were washed with ethanol. The product was purified by MPLC using cyclohexane and dichloromethane (1:1 ratio) to obtain a solid product.

[0305] General steps for synthesizing AAV2-1

[0306]

[0307] Under a nitrogen atmosphere, a mixture of dioxane and water (10:1 ratio; pre-degassed by nitrogen bubbling for 15 minutes) was added to (5-chloro-2-fluorophenyl)boronic acid (1.00 equivalent, CAS 352535-83-2), 3-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-4-fluorobenzyl nitrile (1.10 equivalent, product of AAV1-1), potassium acetate (3.00 equivalent), and [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloride (0.03 equivalent, CAS 72287-26-4). The reaction mixture was stirred under reflux (heating plate set to 110°C) for 4 hours. After cooling to room temperature, water was added, followed by extraction with ethyl acetate. The combined organic layers were concentrated under reduced pressure. The crude product was heated in ethanol to reflux for 3 hours, and washed with ethanol during hot filtration. The product was obtained as a solid.

[0308] General steps for synthesizing AAV2-2

[0309]

[0310] The reaction conditions were similar to those of AAV2-1, but (4-chloro-2-fluorophenyl)boronic acid (1.00 equivalent, CAS160591-91-3) was used as the reactant. After the reaction was complete (heated for 4 hours) and cooled to ambient temperature, the reaction mixture was poured into water. The resulting precipitate was filtered off and washed with water and cold ethanol. The crude product was heated to reflux for 1 hour in a mixture of toluene and cyclohexane (3:1 ratio). The product was washed with cold ethanol during hot filtration. It was obtained as a solid.

[0311] General steps for synthesizing AAV3-1

[0312]

[0313] 3-(4-(5-chloro-2-fluorophenyl)-6-phenyl-1,3,5-triazin-2-yl)-4-fluorobenzyl nitrile (1.00 equivalent, product of AAV2-1), the corresponding donor molecule DH (2.20 equivalent), and tripotassium phosphate (3.00 equivalent) were suspended in anhydrous DMSO under a nitrogen atmosphere and stirred at 80 °C for 72 h. The reaction mixture was then poured into a stirred mixture of water and ice. The resulting precipitate was filtered off and washed with water and n-hexane. The crude product was purified by MPLC using cyclohexane and dichloromethane (1:1 ratio), followed by heating to reflux in ethanol for 2 h. The product was washed with ethanol during hot filtration. It was obtained as a solid.

[0314] General steps for synthesizing AAV3-2

[0315]

[0316] The reaction conditions were similar to those of AAV3-1, but 3-(4-(4-chloro-2-fluorophenyl)-6-phenyl-1,3,5-triazin-2-yl)-4-fluorobenzyl nitrile (1.00 equivalent, the product of AAV2-2) was used as the reactant. Filtration was performed using toluene through an Alox column. The crude product was heated in acetonitrile to reflux for 2 hours. The product was washed with acetonitrile during hot filtration. Recrystallization from the mixture of toluene and acetonitrile (3:2 ratio) gave the product as a solid.

[0317] General steps for synthesizing AAV4-1

[0318]

[0319] Under a nitrogen atmosphere, a mixture of dioxane and water (20:3 ratio) was added to the product of AAV3-1 (1.0 equivalent), (2-cyanophenyl)boronic acid (1.25 equivalent, CAS150255-96-2), tris(dibenzylacetone)dipalladium(0) (0.04 equivalent, CAS 51364-51-3), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (X-Phos, 0.16 equivalent, CAS564483-18-7), and potassium carbonate (2.50 equivalent), followed by nitrogen bubbling for 10 minutes. The reaction mixture was refluxed and stirred for 2 hours (reaction monitored by TLC), then cooled to ambient temperature and poured into ice water. The precipitate was filtered and washed with water. The crude product was recrystallized from n-hexane and ethyl acetate, and then purified by MPLC using cyclohexane and dichloromethane in a 1:1 ratio. To obtain a product that is a solid.

[0320] General steps for synthesizing AAV4-2

[0321]

[0322] The reaction conditions are similar to those of AAV4-1, but the product of AAV3-2 is used as the reactant.

[0323] General steps for synthesizing AAV5-1

[0324]

[0325] Anhydrous toluene was added to 3'-chloro-4'-fluoro-[1,1'-biphenyl]-3-carboxynitrile (1.00 equivalent) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborhecyclopentane) (1.30 equivalent, CAS 73183-34-3) under a nitrogen atmosphere, followed by nitrogen bubbling for 15 minutes. The reaction mixture was stirred at 110 °C for 3 hours (monitored by TLC) and then cooled to 70 °C. Diatomaceous earth and charcoal were added, and the suspension was stirred at 70 °C for 20 minutes. The mixture was filtered, and the filtrate was extracted with ethyl acetate and brine. The combined organic layers were concentrated under reduced pressure, and the crude product was recrystallized from n-hexane. The product was given as a solid.

[0326] General steps for synthesizing AAV6-1

[0327]

[0328] Under a nitrogen atmosphere, a mixture of THF and water (4:1 ratio) was added to 4'-fluoro-3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborhexacyclopentan-2-yl)-[1,1'-biphenyl]-3-carboxynitrile (1.00 equivalent, product of AAV5-1), 2,4-dichloro-6-phenyl-1,3,5-triazine (1.50 equivalent, CAS1700-02-3), potassium carbonate (2.00 equivalent), and tetra(triphenylphosphine)palladium(0) (0.03 equivalent, CAS14221-01-3), followed by nitrogen bubbling for 10 minutes. The reaction mixture was stirred at 60°C for 16 hours. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and brine. The organic extract was concentrated under reduced pressure. The product was purified by MPLC using cyclohexane and dichloromethane (1:1 ratio) to give a solid product.

[0329] General steps for synthesizing AAV7-1

[0330]

[0331] Under a nitrogen atmosphere, a mixture of THF and water (25:3 ratio) was added to 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-4'-fluoro-[1,1'-biphenyl]-3-carboxynitrile (1.00 equivalent, product of AAV6-1), 4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborhecyclopentan-2-yl)benzylnitrile (1.20 equivalent, CAS863868-29-5), potassium carbonate (2.00 equivalent), and tetra(triphenylphosphine)palladium(0) (0.03 equivalent, CAS14221-01-3), followed by nitrogen bubbling for 15 minutes. The reaction mixture was stirred at 60°C for 16 hours. After cooling to room temperature, a mixture of water and THF (1:1 ratio) was added. The precipitate was filtered off and dissolved in dichloromethane. After washing with water, dichloromethane was removed under reduced pressure to obtain the product as a solid.

[0332] General steps for synthesizing AAV8-1

[0333]

[0334] 3'-(4-(5-cyano-2-fluorophenyl)-6-phenyl-1,3,5-triazin-2-yl)-4'-fluoro-[1,1'-biphenyl]-3-carboxynitrile (1.00 equivalent, product of AAV7-1), the corresponding donor molecule DH (2.20 equivalent), and tripotassium phosphate (3.00 equivalent) were suspended in anhydrous DMSO under a nitrogen atmosphere and stirred at 90 °C for 11 h. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and water, followed by extraction of the organic layer with water. Dichloromethane was removed under reduced pressure to give the crude product. The crude product was filtered through a silica stencil using dichloromethane, and the filtrate was concentrated under vacuum. Acetonitrile was added, and the mixture was treated in an ultrasonic bath for 15 min and stored at -18 °C. The precipitate formed was filtered off and washed with acetonitrile. The product was obtained as a solid.

[0335] Specifically, the donor molecule DH is 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).

[0336] For example, halogen-substituted carbazole (specifically, 3-bromocarbazole) can be used as DH.

[0337] In the subsequent reaction, boronic acid ester functional groups or borate functional groups can be introduced, for example, via reaction with bis(pinacolyl)diboron (CAS No. 73183-34-3) at the positions of one or more halogen substituents to obtain the corresponding carbazole-3-ylboronic acid esters or carbazole-3-ylboronic acids, wherein the one or more halogen substituents are introduced via DH. Subsequently, the reaction with the corresponding halogenated reactant R... a -Hal(preferably, R) a -Cl and R a The coupling reaction of -Br) introduces one or more substituents R. a Replaces borate ester groups or boric acid groups.

[0338] Optionally, the reaction can be performed at the positions of one or more halogen substituents via a reaction with substituent R. a Boric acid [R] a -B(OH)2] or the corresponding borate ester reaction introduces one or more substituents R. a The one or more halogen substituents are introduced via DH.

[0339] HPLC-MS:

[0340] HPLC-MS analysis was performed on an Agilent (1100 series) HPLC system equipped with an MS detector (Thermo LTQ XL).

[0341] For example, a typical HPLC method is as follows: A 4.6 mm × 150 mm reversed-phase column with a particle size of 3.5 μm (ZORBAX Eclipse Plus) from Agilent is used in the HPLC. (C18, 4.6 mm × 150 mm, 3.5 μm HPLC column). HPLC-MS measurements were performed at room temperature (rt) according to a gradient.

[0342]

[0343] Use the following solvent mixture:

[0344] Solvent A: <![CDATA[H2O(90%)]]> MeCN (10%) Solvent B: <![CDATA[H2O(10%)]]> MeCN (90%) Solvent C: THF (50%) MeCN (50%)

[0345] A 5 μL sample was taken from a solution with a concentration of 0.5 mg / mL for measurement.

[0346] The probe is ionized using an APCI (Atmospheric Pressure Chemical Ionization) source in either positive (APCI+) or negative (APCI-) ionization mode.

[0347] Cyclic voltammetry

[0348] Cyclic voltammograms are obtained by reacting a sample in dichloromethane or a suitable solvent with a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate) at a concentration of 10... -3 Measurements were taken in solutions containing mol / L organic molecules. Measurements were performed at room temperature under a nitrogen atmosphere using a three-electrode assembly (working and counter electrodes: Pt wires, reference electrode: Pt wires), and using FeCp2 / FeCp2... + Calibration was performed using ferrocene as an internal standard. HOMO data were corrected for the saturated calomel electrode (SCE) using ferrocene as an internal standard.

[0349] Density functional theory calculations

[0350] The molecular structure was optimized using the BP86 functional and the resolution of identity approach (RI). Excitation energies were calculated using the BP86-optimized structure via time-dependent DFT (TD-DFT). Orbital and excited-state energies were calculated using the B3LYP functional. The Def2-SVP basis set and an m4 grid were used for numerical integration. The Turbomole step package was used for all calculations.

[0351] Optical physical measurement

[0352] Sample pretreatment: spin coating.

[0353] Instruments: Spin150, SPS euro.

[0354] The sample concentration was 10 mg / mL, and it was dissolved in a suitable solvent.

[0355] Steps: 1) Apply at 400 U / min for 3 seconds. 2) Apply at 1000 Upm / s at 1000 U / min for 20 seconds. 3) Apply at 1000 Upm / s at 4000 U / min for 10 seconds. After coating, dry the film at 70°C for 1 minute.

[0356] Photoluminescence spectroscopy and TCSPC (Time-Correlated Single Photon Counting)

[0357] Steady-state emission spectra were measured using a Horiba Scientific Modell FluoroMax-4 equipped with a 150W xenon arc lamp, excitation and emission monochromators, a Hamamatsu R928 photomultiplier tube, and a time-correlated single-photon counting option. Emission and excitation spectra were corrected using standard calibration fitting.

[0358] The excited-state lifetime was determined using the same system as the FM-2013 device and the Horiba Yvon TCSPC hub, employing the TCSPC method.

[0359] Excitation source:

[0360] Nano LED 370 (wavelength: 371nm, pulse duration: 1.1ns)

[0361] Nano LED 290 (wavelength: 294nm, pulse duration: <1ns)

[0362] Spectral LED 310 (wavelength: 314nm)

[0363] Spectral LED 355 (wavelength: 355nm).

[0364] Perform data analysis (exponential fit) using the DataStation and DAS6 software suite. Specify the fit using the chi-square test.

[0365] Photoluminescence quantum yield measurement

[0366] For photoluminescent quantum yield (PLQY) measurements, an absolute PL quantum yield measurement system (Hamamatsu Photonics) C9920-03G was used. Quantum yield and CIE coordinates were determined using software version U6039-05 3.6.0.

[0367] The maximum emission value is given in nm, the quantum yield Φ is given in % and the CIE coordinates are given as x and y values.

[0368] PLQY is determined using the following protocol:

[0369] 1) Quality Assurance: Anthracene (known concentration) in ethanol is used as a reference.

[0370] 2) Excitation wavelength: Determine the maximum absorption value of organic molecules and use this wavelength to excite the organic molecules.

[0371] 3) Measurement

[0372] Quantum yield was measured for samples in solution or film under a nitrogen atmosphere. The yield was calculated using the equation:

[0373]

[0374] Where, n 光子 Indicates photon count, and Int. indicates intensity.

[0375] Fabrication and characterization of organic optoelectronic devices

[0376] Optoelectronic devices (such as OLED devices) comprising organic molecules according to the invention can be fabricated via vacuum deposition. If the layer contains more than one compound, the weight percentage of one or more compounds is given as %. The total weight percentage value totals 100%, so if no value is given, the fraction of the compound is equal to the difference between the given value and 100%.

[0377] The (not fully optimized) OLED was characterized using standard methods and measurements of electroluminescence spectra. External quantum efficiency (in percentage) depends on intensity and is calculated using light and current detected by a photodiode. OLED device lifetime was extracted from changes in brightness during operation at a constant current density. The LT50 value corresponds to the time point when the measured brightness decreases to 50% of the initial brightness; similarly, the LT80 value corresponds to the time point when the measured brightness decreases to 80% of the initial brightness, and the LT95 value corresponds to the time point when the measured brightness decreases to 95% of the initial brightness, and so on.

[0378] (For example, by applying an increased current density) Perform accelerated lifetime measurements. For example, determine 500 cd / m using the following equation. 2 The following LT80 value:

[0379]

[0380] Where L0 represents the initial brightness at the applied current density.

[0381] The values ​​correspond to the average of several (typically two to eight) pixels, giving the standard deviation among these pixels. The attached figure illustrates the data series for a single OLED pixel.

[0382] Example 1

[0383]

[0384] Example 1 was synthesized based on AAV1-1 (yield 45%), AAV2-1 (yield 74%), AAV3-1 (yield 29%) and AAV4-1 (yield 29%).

[0385] MS (HPLC-MS), m / z (retention time): 1070.0 (5.79 min).

[0386] Figure 1 The emission spectrum of Example 1 (in 10 wt% PMMA) is depicted. The emission maximum value (λ) is... max At 508 nm, the photoluminescence quantum yield (PLQY) was 70%, the full width at half maximum (FWHM) was 0.41 eV, and the emission lifetime was 8.9 μs. The obtained CIE... x The coordinates are determined to be at 0.28, and CIE...y The coordinates are determined to be at 0.53.

[0387] Example 2

[0388]

[0389] Example 2 was synthesized based on AAV1-1 (yield 41%), AAV2-2 (yield 63%), AAV3-2 (yield 63%) and AAV4-2 (yield 44%).

[0390] MS (HPLC-MS), m / z (retention time): 1070.6 (5.80 min).

[0391] Figure 2 The emission spectrum of Example 2 (in 10 wt% PMMA) is depicted. The emission maximum value (λ) is... max At 515 nm, the photoluminescence quantum yield (PLQY) was 66%, the full width at half maximum (FWHM) was 0.41 eV, and the emission lifetime was 9.2 μs. The obtained CIE... x The coordinates are determined to be at 0.31, and CIE... y The coordinates are determined to be at 0.56.

[0392] Example 3

[0393]

[0394] Example 3 was synthesized based on AAV5-1 (yield 86%), AAV6-1 (yield 51%), AAV7-1 (yield 79%) and AAV8-1 (yield 10%).

[0395] MS (HPLC-MS), m / z (retention time): 1070.8 (5.92 min).

[0396] Figure 3 The emission spectrum of Example 3 (10 wt% in PMMA) is depicted. The emission maximum value (λ) is... max At 509 nm, the photoluminescence quantum yield (PLQY) was 71%, the full width at half maximum (FWHM) was 0.41 eV, and the emission lifetime was 10.2 μs. The obtained CIE... x The coordinates are determined to be at 0.28, and CIE... y The coordinates are determined to be at 0.53.

[0397] Example 4

[0398]

[0399] Example 4 was synthesized by replacing 2-cyanophenolic acid with 4-cyanophenolic acid (CAS126747-14-6) according to AAV1-1 (yield 52%), AAV2-1 (yield 74%), AAV3-1 (yield 59%) and AAV4-1 (yield 65%).

[0400] MS (HPLC-MS), m / z (retention time): 1072.1 (5.92 min).

[0401] Figure 3 The emission spectrum of Example 4 (10 wt% in PMMA) is depicted. The maximum emission value (λ) is... max At 509 nm, the photoluminescence quantum yield (PLQY) was 74%, the full width at half maximum (FWHM) was 0.41 eV, and the emission lifetime was 15.2 μs. The obtained CIE... x The coordinates are determined to be at 0.28, and CIE... y The coordinates are determined to be at 0.53.

[0402] Example D1

[0403] Example 1 was tested in an optoelectronic device in the form of an OLED D1 with the following layer structure:

[0404]

[0405]

[0406]

[0407] OLED D1 at 1000cd / m 2 An external quantum efficiency (EQE) of 18.4% was achieved. The emission peak at 7.0 V was 512 nm with an FWHM of 76 nm. The corresponding CIEx value was 0.28 and CIEy value was 0.59. This was determined at 1200 cd / m². 2 The LT95 value is 220 hours.

[0408] Example D2

[0409] Example 2 was tested in an OLED D2 that was manufactured with the following layer structure:

[0410] Floor number thickness D2 10 100nm Al 9 2nm Liq 8 20nm NBPhen 7 10nm MAT1 6 50nm MAT2 (85%): Example 2 (15%) 5 10nm MAT2 4 10nm TCTA 3 50nm NPB 2 5nm HAT-CN 1 50nm ITO base Glass

[0411] OLED D2 at 1000cd / m 2 An external quantum efficiency (EQE) of 16.7% was achieved. The maximum emission at 7.0 V was 508 nm with an FWHM of 76 nm. The corresponding CIEx value was 0.26 and CIEy value was 0.58.

[0412] Example D3

[0413] Example 3 was tested in an OLED D3 that was manufactured with the following layer structure:

[0414]

[0415]

[0416] OLED D3 at 1000cd / m 2 An external quantum efficiency (EQE) of 18.3% was achieved. The maximum emission at 5.5V was 532nm with an FWHM of 36nm. The corresponding CIEx value was 0.31, and the CIEy value was 0.65.

[0417] Example D4

[0418] Example 4 was tested in an OLED D4 that was manufactured with the following layer structure:

[0419] Floor number thickness D4 10 100nm Al 9 2nm Liq 8 20nm NBPhen 7 10nm MAT1 6 50nm MAT2 (80%): Example 4 (20%) 5 10nm MAT2 4 10nm TCTA 3 50nm NPB 2 5nm HAT-CN 1 50nm ITO base Glass

[0420] OLED D4 at 1000cd / m 2 An external quantum efficiency (EQE) of 19.3% was achieved. The emission peak at 6.4 V was 514 nm with an FWHM of 78 nm. The corresponding CIEx value was 0.28 and CIEy value was 0.59. This was determined at 1200 cd / m². 2 The LT95 value is 245 hours.

[0421] Additional examples of the invented organic molecules

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

Claims

1. An organic molecule, said organic molecule comprising: The first chemical part includes or is composed of the structure of Formula I. Formula I, And two second chemical parts, each independently comprising or consisting of a structure of formula IIb, Formula IIb, The first chemical portion is connected to each of the second chemical portions via single bonds; in, T is the binding site of a single bond that connects the first chemical moiety to one of the two second chemical moiety components; V is R I ; W is selected from R I and R A The group formed; X is selected from the group consisting of R I and R A ; Y is R I ; T' is the binding site of a single bond that connects the first chemical moiety to one of the two second chemical moiety; V is R II ; W' is R II ; X' is selected from the group consisting of CN and CF3; Y' is R II ; # represents the binding site between the first chemical part and the second chemical part; R A comprises or consists of the structure of Formula BN-I, Formula BN-I, the structure of formula BN-I is bound to the structure of formula I via the position marked by a dotted line, and wherein exactly one R BN group is CN, while the other two R BN groups are hydrogen; R I at each occurrence is independently selected from the group consisting of hydrogen; deuterium; and C1-C5alkyl, wherein one or more hydrogen atoms are optionally replaced by deuterium; R II Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; and C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; R 11 , R 12 , R 13 , R 14 , and R 15 are independently selected from the group consisting of hydrogen; deuterium; and C1-C5alkyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; R b independently from each other in each occurrence are: Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr and t Bu; And among them, The exact one substituent selected from the group consisting of W and X is R. A .

2. The organic molecule according to claim 1, wherein, R I R II R 11 R 12 R 13 R 14 and R 15 Each time it appears, it is independently selected from the group consisting of hydrogen, methyl, isopropyl and tert-butyl.

3. An organic molecule, said organic molecule being selected from the following compounds: 。 4. The application of an organic molecule according to any one of claims 1 to 3 in optoelectronic devices as a light-emitting emitter and / or a host material and / or an electron transport material and / or a hole transport material and / or a hole injection material and / or a hole blocking material.

5. Use according to claim 4, wherein, The optoelectronic device is selected from the group consisting of: • Organic light-emitting diode; • Photoluminescent electrochemical cells; • Organic light-emitting diode (OLED) sensor; • Organic diodes; • Organic solar cells; • Organic transistors; • Organic field-effect transistors; • Organic lasers; and • Down-conversion element.

6. A composition comprising the following components: (a) An organic molecule according to one or more of claims 1 to 3, in the form of an emitter and / or a host; and (b) an emitter and / or host material different from the organic molecule; and (c) Optionally, one or more dyes and / or one or more solvents.

7. The composition according to claim 6, wherein the composition comprises the following components: (i) 1% to 50% by weight of an organic molecule according to any one of claims 1 to 3; (ii) 5% to 98% by weight of a main compound; (iii) 1% to 30% by weight of at least one other emitter molecule, said other emitter molecule having a structure different from that of the organic molecule according to any one of claims 1 to 3; and (iv) 0% to 94% by weight of at least one other main compound, said other main compound having a structure different from that of the organic molecule according to any one of claims 1 to 3; and (v) 0% to 94% by weight of solvent.

8. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 3 or a composition according to claim 6 or 7, wherein the optoelectronic device is in the form of a device selected from the group consisting of organic light-emitting diodes, light-emitting electrochemical cells, organic light-emitting diode sensors, organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

9. The optoelectronic device according to claim 8, wherein the optoelectronic device comprises: Base; anode; and cathode, wherein the anode or the cathode is disposed on the substrate; as well as A light-emitting layer is disposed between the anode and the cathode and includes the organic molecules or the composition.

10. A method for fabricating an optoelectronic device, wherein, The method, using an organic molecule according to any one of claims 1 to 3 or a composition according to claim 6 or 7, includes the step of using vacuum evaporation or treating the organic molecule from solution.

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