Organic molecules for optoelectronic devices

Abstract

The present invention relates particularly to an organic molecule for application in optoelectronic devices. According to the present invention, the organic molecule has the structure of the following chemical formula I: Chemical formula I.

Description

Technology Field

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

[0002] The objective of the present invention is to provide a molecule suitable for use in optoelectronic devices. means of solving the problem

[0003] This objective is achieved by the present invention, which provides a new type of organic molecule.

[0004] According to the present invention, the organic molecule is a pure organic molecule, that is, it does not contain any metal ions, in contrast to metal complexes known to be used in optoelectronic devices. Effects of the invention

[0005] According to the present invention, the organic molecule exhibits maximum emission in the blue, sky blue, or green spectral range. The organic molecule exhibits maximum emission particularly at 420 nm to 520 nm, preferably 440 nm to 495 nm, and more preferably 450 nm to 470 nm. The photoluminescent quantum yield of the organic molecule according to the present invention is particularly 50% or higher. When the molecule according to the present invention is used in an optoelectronic device, for example, an organic light-emitting diode (OLED), the efficiency or color purity of the device is increased, which is expressed as the emission full width at half maximum (FWHM) of the device. The corresponding OLED has higher stability than OLEDs with known emitter materials and similar colors. Specific details for implementing the invention

[0006] The organic light-emitting molecule of the present invention comprises a first chemical moiety having the structure of the following chemical formula Ia and a second chemical moiety having the structure of the following Ib, or is composed of these:

[0007]

[0008] Chemical formula Ia

[0009]

[0010] Chemical formula Ib

[0011] Among chemical formulas Ia and Ib,

[0012] T is the bonding site of a single bond connecting the first chemical moiety to the second chemical moiety, or R 2 And;

[0013] V is the bonding site of a single bond connecting the first chemical moiety to the second chemical moiety, or R 2 And;

[0014] W is the bonding site of a single bond connecting the first chemical moiety to the second chemical moiety, or R 2 And;

[0015] X is the bonding site of a single bond connecting the first chemical moiety to the second chemical moiety, or R 2 And;

[0016] * indicates the binding site of the second chemical moiety to the first chemical moiety (i.e., T and V, V and W or W and X; for example, N of the second chemical moiety binds to T and B of the second chemical moiety binds to V. Or, B of the second chemical moiety binds to T and N of the second chemical moiety binds to V).

[0017] R 1 In each case, is selected independently from a group consisting of:

[0018] One or more substituents R 5 C1-C5-alkyl selectively substituted with;

[0019] One or more substituents R 5 C6-C optionally substituted 60 -aryl; and

[0020] One or more substituents R5 C2-C optionally substituted 57 -Heteroaryl;

[0021] R 2 is selected independently from a group consisting of in each case:

[0022] Hydrogen, deuterium,

[0023] C1-C5-alkyl,

[0024] Here, one or more hydrogen atoms are selectively substituted by deuterium;

[0025] C2-C8-Alkenyl,

[0026] Here, one or more hydrogen atoms are selectively substituted by deuterium;

[0027] C2-C8-alkynyl,

[0028] Here, one or more hydrogen atoms are selectively substituted by deuterium;

[0029] C6-C 18 -Aril;

[0030] Here, one or more hydrogen atoms are selectively substituted by deuterium; and

[0031] R a , R 3 , R 4 is independently selected from a group consisting of in each case:

[0032] Hydrogen, Deuterium, N(R 5 )2, OR 5 , Si(R 5 )3, B(OR 5 )2, B(R 5 )2, OSO2R 5 , CF3, CN, F, Br, I,

[0033] One or more substituents R 5 C1-C optionally substituted with 40 -alkyl,

[0034] Here, one or more non-adjacent CH2 groups are R 5 C=CR5 , 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 Optionally substituted by;

[0035] One or more substituents R 5 C1-C optionally substituted with 40 - Alkoxy,

[0036] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0037] One or more substituents R 5 C1-C optionally substituted with 40 -Thioalkoxy,

[0038] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0039] One or more substituents R 5 C2-C optionally substituted40 -Alkenil,

[0040] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0041] One or more substituents R 5 C2-C optionally substituted 40 -Alkinil,

[0042] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0043] One or more substituents R 5 C6-C optionally substituted 60 -aryl; and

[0044] One or more substituents R 5 C2-C optionally substituted 57 -Heteroaryl;

[0045] R 5 is selected independently from a group consisting of in each case:

[0046] Hydrogen, Deuterium, N(R 6 )2, OR 6 , Si(R 6)3, B(OR 6 )2, B(R 6 )2, OSO2R 6 , CF3, CN, F, Br, I,

[0047] One or more substituents R 6 C1-C optionally substituted with 40 -alkyl,

[0048] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0049] One or more substituents R 6 C1-C optionally substituted with 40 - Alkoxy,

[0050] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0051] One or more substituents R 6 C1-C optionally substituted with 40 -Thioalkoxy,

[0052] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0053] One or more substituents R 6 C2-C optionally substituted 40 -Alkenil,

[0054] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0055] One or more substituents R 6 C2-C optionally substituted 40 -Alkinil,

[0056] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0057] One or more substituents R 6 C6-C optionally substituted 60 -aryl; and

[0058] One or more substituents R 6 C2-C optionally substituted 57 -Heteroaryl;

[0059] R 6 In each case, is selected independently from a group consisting of:

[0060] Hydrogen, Deuterium, OPh (Ph = Phenyl), CF3, CN, F,

[0061] C1-C5-alkyl,

[0062] Here, optionally, one or more hydrogen atoms are independently substituted by deuterium, CN, CF3, or F;

[0063] C1-C5-alkoxy,

[0064] Here, optionally, one or more hydrogen atoms are independently substituted by deuterium, CN, CF3, or F;

[0065] C1-C5-thioalkoxy,

[0066] Here, optionally, one or more hydrogen atoms are independently substituted by deuterium, CN, CF3, or F;

[0067] C2-C5-alkenyl,

[0068] Here, optionally, one or more hydrogen atoms are independently substituted by deuterium, CN, CF3, or F;

[0069] C2-C5-alkynyl,

[0070] Here, optionally, one or more hydrogen atoms are independently substituted with deuterium, CN, CF3, or F;

[0071] C6-C 18 -Aril,

[0072] This is optionally substituted with one or more C1-C5-alkyl substituents;

[0073] C2-C 17 -Heteroaryl,

[0074] This is optionally substituted with one or more C1-C5-alkyl substituents;

[0075] N(C6-C 18 -Aril)2;

[0076] N(C2-C 17 -heteroaryl)2, and

[0077] N(C2-C 17 -heteroaryl)(C6-C 18 -Aril);

[0078] Here, substituent R a , R 3 , R 4 , R 5 are independently one or more substituents R a , R 3 , R 4 , R 5 Selectively forming monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo condensed ring systems together with; and

[0079] Here, exactly two adjacent substituents selected from the group of T, V, W, and X represent the bonding sites of a single bond connecting the first chemical moiety to the second chemical moiety to form a condensation ring, i.e.,

[0080] - If T and V represent the bonding sites of a single bond connecting the first chemical moiety to the second chemical moiety, then W and X are R 2 And;

[0081] - If V and W represent the bonding sites of a single bond connecting the first chemical moiety to the second chemical moiety, then T and X are R 2 And;

[0082] - If W and X represent the bonding sites of a single bond connecting the first chemical moiety to the second chemical moiety, then T and V are R 2 am.

[0083] Alternatively, the organic molecule according to the present invention comprises or is composed of the structure of the following chemical formula I:

[0084]

[0085] Chemical formula I.

[0086] The organic molecule according to the present invention comprises or consists of a structure selected from the group of the following chemical formulas II-VII:

[0087]

[0088] Chemical Formula II Chemical Formula III

[0089]

[0090] Chemical Formula IV Chemical Formula V

[0091]

[0092] Chemical Formula VI Chemical Formula VII.

[0093] In one embodiment, the organic molecule according to the present invention comprises or is composed of a structure selected from the group consisting of Formula II and Formula III.

[0094] In a further embodiment of the present invention, R a is selected independently from a group consisting of in each case:

[0095] hydrogen,

[0096] Me,

[0097] i Pr,

[0098] t Bu,

[0099] CN,

[0100] CF3,

[0101] Me, i Pr, tPh, which is optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0102] Me, i Pr, t Pyridinyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph,

[0103] Me, i Pr, t Pyrimidinyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0104] Me, i Pr, t Carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0105] Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0106] and N(Ph)2.

[0107] In a further embodiment of the present invention, R a is selected independently from a group consisting of in each case:

[0108] hydrogen,

[0109] Me,

[0110] i Pr,

[0111] t Bu,

[0112] CN,

[0113] CF3,

[0114] Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of Me, iPr, tBu, CN, CF3, and Ph,

[0115] Me, i Pr, t Pyridinyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph,

[0116] Me, i Pr, t Pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, and

[0117] Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0118] In a further embodiment of the present invention, the first chemical moiety comprises or is composed of the structure of the following formula Ia-1, the structure of formula Ia-2, or the structure of formula Ia-3:

[0119]

[0120] Chemical formula Ia-1 Chemical formula Ia-2 Chemical formula Ia-3

[0121] Here

[0122] R b is selected independently from a group consisting of in each case:

[0123] Hydrogen, Deuterium, N(R 5 )2, OR 5 , Si(R 5 )3, B(OR 5 )2, OSO2R 5 , CF3, CN, F, Br, I,

[0124] C1-C 40 -alkyl,

[0125] This is one or more substituents R 5 Optionally replaced with,

[0126] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0127] C1-C 40 - Alkoxy,

[0128] This is one or more substituents R 5 Optionally replaced with,

[0129] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0130] C1-C 40 -Thioalkoxy,

[0131] This is one or more substituents R 5 Optionally replaced with,

[0132] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0133] C2-C 40 -Alkenil,

[0134] This is one or more substituents R 5 Optionally replaced with,

[0135] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0136] C2-C 40 -Alkinil,

[0137] This is one or more substituents R 5 Optionally replaced with,

[0138] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0139] C6-C 60 -Aril,

[0140] This is one or more substituents R5 Optionally substituted as; and

[0141] C3-C 57 -Heteroaryl,

[0142] This is one or more substituents R 5 It is optionally replaced with.

[0143] In addition, the previously mentioned definition applies.

[0144] In a specific embodiment of the present invention, the first chemical moiety of the organic molecule comprises or consists of the structure of Formula Ia-4, the structure of Formula Ia-5, the structure of Formula Ia-6, the structure of Formula Ia-7, the structure of Formula Ia-8, the structure of Formula Ia-9, or the structure of Formula Ia-10:

[0145]

[0146] Chemical formula Ia-4 Chemical formula Ia-5 Chemical formula Ia-6

[0147]

[0148] Chemical formula Ia-7 Chemical formula Ia-8 Chemical formula Ia-9

[0149]

[0150] Chemical formula Ia-10

[0151] The previously mentioned definition applies here.

[0152] In a further embodiment of the present invention, the second chemical moiety of the organic molecule comprises or is composed of the structure of the following formula Ib-3, the structure of the formula Ib-4, or the structure of the formula Ib-5:

[0153]

[0154] Chemical formula Ib-3 Chemical formula Ib-4 Chemical formula Ib-5

[0155] Here

[0156] R bis selected independently from a group consisting of in each case:

[0157] Hydrogen, Deuterium, N(R 5 )2, OR 5 , Si(R 5 )3, B(OR 5 )2, OSO2R 5 , CF3, CN, F, Br, I,

[0158] One or more substituents R 5 C1-C selected as 40 -alkyl,

[0159] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0160] One or more substituents R 5 C1-C selected as 40 - Alkoxy,

[0161] This is one or more substituents R 5 Optionally replaced with,

[0162] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0163] One or more substituents R 5 C1-C selected as 40 -Thioalkoxy,

[0164] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0165] One or more substituents R 5 C2-C selected as 40 -Alkenil,

[0166] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0167] One or more substituents R 5 C2-C selected as 40 -Alkinil,

[0168] Here, one or more non-adjacent CH2 groups are 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 Optionally substituted by;

[0169] One or more substituents R 5 C6-C selected as 60 -aryl; and

[0170] One or more substituents R 5 C3-C selected as 57 -Heteroaryl.

[0171] In addition, the previously mentioned definition applies.

[0172] In a specific embodiment of the present invention, the second chemical moiety of the organic molecule comprises or consists of the structure of formula Ib-6, the structure of formula Ib-7, the structure of formula Ib-8, the structure of formula Ib-9, the structure of formula Ib-10, the structure of formula Ib-11, or the structure of formula Ib-12:

[0173]

[0174] Chemical formula Ib-6 Chemical formula Ib-7 Chemical formula Ib-8

[0175]

[0176] Chemical formula Ib-9 Chemical formula Ib-10 Chemical formula Ib-11

[0177]

[0178] Chemical formula Ib-12

[0179] The previously mentioned definition applies here.

[0180] In a further embodiment of the present invention, R b is selected independently from a group consisting of in each case:

[0181] hydrogen,

[0182] Me, iPr, tBu, CN, CF3,

[0183] Me, i Pr, tPh, which is optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0184] Me, i Pr, t Pyridinyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph,

[0185] Me, i Pr, t Carbazolyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0186] Me, i Pr, t Triazinyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0187] and N(Ph)2.

[0188] In a further embodiment of the present invention, R b is selected independently from a group consisting of in each case:

[0189] Me, iPr, tBu, CN, CF3,

[0190] Me, i Pr, t Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0191] Me, i Pr, t Pyridinyl selectively substituted with one or more mutually independent substituents selected from the group consisting of Bu, CN, CF3 and Ph,

[0192] Carbazolyl selectively substituted with one or more substituents independently selected from the group consisting of Me, iPr, tBu, CN, CF3, and Ph,

[0193] Me, i Pr, t Triazinyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0194] and N(Ph)2.

[0195] In a further embodiment of the present invention, R b is selected independently from a group consisting of in each case:

[0196] hydrogen,

[0197] Me,

[0198] iPr,

[0199] tBu,

[0200] CN,

[0201] CF3,

[0202] Me, i Pr, t Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0203] Me, i Pr, t Pyridinyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph,

[0204] Me, i Pr, t Pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, and

[0205] Me, i Pr, t Triazinyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0206] In a further embodiment of the present invention, Rb is selected independently from a group consisting of in each case:

[0207] Me,

[0208] i Pr,

[0209] t Bu,

[0210] CN,

[0211] CF3,

[0212] Me, i Pr, t Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0213] Me, i Pr, t Pyridinyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph,

[0214] Me, i Pr, t Pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, and

[0215] Me, i Pr, t Triazinyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0216] The following are examples of structures of the second chemical moiety corresponding to chemical formula Ib:

[0217]

[0218]

[0219]

[0220] All previously mentioned definitions apply here.

[0221] The following are examples of structures of the first chemical moiety corresponding to chemical formula Ia:

[0222]

[0223]

[0224]

[0225] All previously mentioned definitions apply here.

[0226] In a specific implementation example, R a and R 5 In each case, hydrogen (H), methyl (Me), and i-propyl (CH(CH3)2)( i It is independently selected from the group consisting of Pr), t-butyl (tBu), phenyl (Ph), CN, CF3 and diphenylamine (NPh2).

[0227] In a specific embodiment, the organic molecule according to the present invention comprises or is composed of a structure selected from the group consisting of the following formulas IIa and IIIa:

[0228]

[0229] Chemical formula IIa Chemical formula IIIa

[0230] In a specific embodiment, the organic molecule according to the present invention comprises or is composed of a structure selected from the group consisting of the following formulas IIb, IIIb, IIc and IIIc:

[0231]

[0232] Chemical formula IIb Chemical formula IIIb

[0233]

[0234] Chemical formula IIc Chemical formula IIIc

[0235] In one embodiment, R 2 In each case, they are independently selected from the group consisting of H, deuterium, C1-C5-alkyl and phenyl.

[0236] In one embodiment, R 2 In each case, they are independently selected from the group consisting of H, deuterium, methyl, and phenyl.

[0237] In one embodiment, R 2 In each case, they are independently selected from the group consisting of H, methyl, and phenyl.

[0238] In one embodiment, R 2 is phenyl in each case.

[0239] In a preferred embodiment, R 2 is H in each case.

[0240] In a specific implementation example, R 1 In each case, independently of each other

[0241] One or more substituents R 5 It is a C1-C5-alkyl selectively substituted.

[0242] In a specific implementation example, R 1 In each case, independently of each other

[0243] One or more substituents R 5 C2-C optionally substituted 57 - It is a heteroaryl.

[0244] In a specific implementation example, R 1 In each case, independently of each other

[0245] One or more substituents R 5 C6-C optionally substituted 60 - It is Aril.

[0246] In a specific implementation example, R 1 In each case, independently of each other

[0247] C6-C optionally substituted with one or more substituents selected from the group consisting of the following 60 -Arilida:

[0248] Hydrogen, Deuterium, N(R 6 )2, OR 6 , Si(R6 )3, B(OR 6 )2, B(R 6 )2, OSO2R 6 , CF3, CN, F, Br, I,

[0249] One or more substituents R 6 C1-C optionally substituted with 40 -alkyl;

[0250] One or more substituents R 6 C6-C optionally substituted with 60 -aryl; and

[0251] One or more substituents R 6 C2-C optionally substituted with 57 -Heteroaryl.

[0252] In one embodiment, R 1 In each case, independently of each other

[0253] C6-C optionally substituted with one or more substituents selected from the group consisting of the following 60 -Arilida:

[0254] Hydrogen, Deuterium, N(R 6 )2, Si(R 6 )3, B(R 6 )2, CF3, CN, F,

[0255] One or more substituents R 6 C1-C optionally substituted with 40 -alkyl;

[0256] One or more substituents R 6 C6-C optionally substituted with 60 -aryl; and

[0257] One or more substituents R 6 C2-C optionally substituted with 57 -Heteroaryl.

[0258] In one embodiment, R 1 In each case, independently of each other,

[0259] methyl; and

[0260] Selected from the group consisting of: phenyl optionally substituted with one or more substituents selected from the group consisting of:

[0261] Me, i Pr, t Bu, CN, CF3,

[0262] Me, i Pr, t Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0263] Me, i Pr, t Pyridinyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph,

[0264] Me, i Pr, t Carbazolyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0265] Me, i Pr, t Triazinyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0266] and N(Ph)2.

[0267] In a preferred embodiment, R 1 In each case, independently of each other

[0268] It is a phenyl selectively substituted with one or more substituents selected from the group consisting of:

[0269] Me, i Pr, t Bu, CN, CF3,

[0270] Me, i Pr, tPh, which is optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0271] Me, i Pr, t Pyridinyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph,

[0272] Me, i Pr, t Carbazolyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0273] Me, i Pr, t Triazinyl selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph,

[0274] and N(Ph)2.

[0275] In one embodiment, R 1 In each case, independently of each other

[0276] It is a phenyl selectively substituted with one or more substituents selected from the group consisting of:

[0277] Me, i Pr, t Bu, CN, CF3.

[0278] In one embodiment, R 1 In each case, independently of each other

[0279] It is a phenyl selectively substituted with one or more C1-C5-alkyl substituents.

[0280] As used throughout this application, the terms “aryl” and “aromatic” may 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. A heteroaryl group comprises 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. Nevertheless, throughout this specification, the number of aromatic ring atoms may be given as a subscript number in the definition of a specific substituent. In particular, a heteroaromatic ring comprises 1 to 3 heteroatoms. Additionally, the terms “heteroaryl” and “heteroaromatic” may be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic heteroaromatic moiety comprising at least one heteroatom. The heteroatom may be the same or different in each case and may be individually selected from the group consisting of N, O, and S. Accordingly, the term “arylene” refers to a divalent substituent that acts as a linker by possessing two bonding sites for other molecular structures. In exemplary embodiments, where a group is defined differently from the definition given herein, for example, where the number of aromatic ring atoms or heteroatoms is different from the given definition, the definition in the exemplary embodiments applies. According to the present invention, a condensed (ringed) aromatic or heteroaromatic polycyclic ring is composed of two or more single aromatic or heteroaromatic rings that form a polycyclic ring through a condensation reaction.

[0281] In particular, as used throughout this specification, the term “aryl group” or “heteroaryl group” refers to benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; Pyrrole, Indole, Isoindole, Carbazole, Pyridine, Quinoline, Isoquinoline, Acridine, Fenantridine, Benzo-5,6-quinoline, Benzo-6,7-quinoline, Benzo-7,8-quinoline, Phenothiazine, Fenoxazine, Pyrazol, Indazole, Imidazole, Benzimidazole, Naphthoimidazole, Fenantroimidazole, Pyridoidazole, Pyrazinoimidazole, Quinoxalinoimidazole, Oxazole, Benzooxazole, Naphthoxazole, Anthroxazole, Fenantroxazole, Isooxazole, 1,2-Thiaazole, 1,3-Thiaazole, Benzothiazole, Pyridazine, Benzopyridazine, Pyrimidine, Benzopyrimidine, 1,3,5-Triazine, Quinoxaline, Pyrazine, It includes a group that can be bonded through any position of an aromatic or heteroaromatic group derived from phenazine, naftiridine, carbolin, benzocarbolin, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3,4-tetrazine, purine, pteridine, indolizine and benzothiadiazole or a combination of the groups mentioned above.

[0282] As used throughout this specification, the term “annular group” may be understood in its broadest sense as any single-, double-, or multi-cyclic moiety.

[0283] As used throughout this specification, the term “biphenyl” as a substituent may be understood in the broadest sense as ortho-biphenyl, meta-biphenyl, or para-biphenyl, where ortho, meta, and para are defined in relation to the binding position to different chemical moiety.

[0284] As used throughout this specification, the term “alkyl group” may be understood in the broadest sense as any linear, branched, or cyclic alkyl substituent. In particular, the term “alkyl” refers to the substituents methyl (Me), ethyl (Et), and n-propyl ( n Pr), i-profile( i Pr), cyclopropyl, n-butyl ( n Bu), i-butyl ( i Bu), s-butyl( s Bu), t-butyl( t Bu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]-octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-hept-1-yl, 1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n-dec-1-yl, 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexadec-1-yl, 1,1-dimethyl-n-octadec-1-yl, 1,1-diethyl-n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct-1-yl, 1,1-diethyl-n-dec-1-yl, 1,1-diethyl-n-dodec-1-yl, 1,1-diethyl-n-tetradec-1-yl, Includes 1,1-diethyl-n-hexadec-1-yl, 1,1-diethyl-n-octadex-1-yl, 1-(n-propyl)-cyclohex-1-yl, 1-(n-butyl)-cyclohex-1-yl, 1-(n-hexyl)-cyclohex-1-yl, 1-(n-octyl)-cyclohex-1-yl, and 1-(n-decyl)-cyclohex-1-yl.

[0285] As used throughout this specification, the term “alkenyl” includes linear, branched, and cyclic alkenyl substituents. The term “alkenyl group” includes, for example, substituents such as ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, or cyclooctadienyl.

[0286] As used throughout this specification, the term “alkynyl” includes linear, branched, and cyclic alkynyl substituents. The term “alkynyl group” includes, for example, ethinyl, propynyl, butynyl, fentinyl, hexinyl, heptynyl, or octinyl.

[0287] As used throughout this specification, the term “alkoxy” includes linear, branched, and cyclic alkoxy substituents. The term “alkoxy group” includes, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, and 2-methylbutoxy.

[0288] As used throughout this specification, the term “thioalkoxy” comprises linear, branched, and cyclic thioalkoxy substituents, wherein the O of the exemplary alkoxy group is substituted with S.

[0289] The terms “halogen” and “halo” as used throughout this specification may be understood in the broadest sense as preferably fluorine, chlorine, bromine, or iodine.

[0290] Hydrogen (H) may also be substituted with deuterium in each case whenever mentioned in this specification.

[0291] When a molecular fragment is described as a substituent or attached to another moiety, it may be described as if it were a fragment (e.g., naphthyl, dibenzofuryl) or as if it were the whole molecule (e.g., naphthalene, dibenzofuran). As used herein, these different ways of referring to a substituent or an attached fragment are considered equivalent.

[0292] In one embodiment, in a PMMA (poly(methyl methacrylate)) film containing 2 weight% of organic molecules at room temperature, said organic molecules according to the present invention have an excited state lifetime of 5.0 μs or less, 2.5 μs or less, particularly 2.0 μs or less, more preferably 1.0 μs or less or 0.7 μs or less.

[0293] In a further embodiment of the present invention, in a PMMA (poly(methyl methacrylate)) film comprising 2 weight% of organic molecules at room temperature, said organic molecules according to the present invention have an emission peak in the visible light or near-ultraviolet range, i.e., a wavelength range of 380 to 800 nm, and have a full width at half maximum value of less than 0.25 eV, preferably less than 0.22 eV, more preferably less than 0.18 eV, even more preferably less than 0.15 eV or less than 0.12 eV.

[0294] Orbital and excited state energies can be determined through experimental methods. Molecular orbital energy E occupying the highest level HOMO is determined with an accuracy of 0.1 eV from cyclic amperometric measurements by methods known to those skilled in the art. Lowest level unoccupied molecular orbital energy E LUMO is E HOMO + E gap It is calculated as, where E gap is determined as follows: for the host compound, unless otherwise specified, the onset of the emission spectrum of a poly(methyl methacrylate) (PMMA) film containing 10 wt% of the host is E gap It is used as. In the case of an emitter molecule, E gap is determined as the energy at which the excitation and emission spectra of a PMMA film containing 2 wt% of an emitter intersect. In the case of the organic molecule according to the present invention, E gapThe excitation and emission spectra of a PMMA film containing 2 wt% emitter are determined as the energy at which they cross.

[0295] The energy of the first excited triplet state T1 is determined from the onset of the emission spectrum at a low temperature, typically 77 K. For a host compound in which the first excited singlet state and the lowest triplet state are energetically separated by > 0.4 eV, phosphorescence is generally observed in the steady-state spectrum within 2-Me-THF. Therefore, the triplet energy can be determined from the onset of the phosphorescence spectrum. For the TADF emitter molecule, the energy of the first excited triplet state T1 is determined from the onset of the delayed emission spectrum at 77 K and is measured in a PMMA film containing 2 wt% of the emitter unless otherwise specified. For the organic molecule according to the present invention, it is measured in a PMMA film containing 2 wt% of the organic molecule according to the present invention. For both the host and emitter compounds, the energy of the first excited singlet state S1 is determined from the beginning of the emission spectrum and, unless otherwise specified, is measured in a PMMA film containing 10 wt% of the host or emitter compound, and in the case of the organic molecule according to the present invention, is measured in a PMMA film containing 2 wt% of the organic molecule according to the present invention.

[0296] The start of the emission spectrum is determined by calculating the intersection point of the tangent to the emission spectrum and the x-axis. The tangent to the emission spectrum is set on the high-energy side of the emission band and at the point of maximum half the maximum intensity of the emission spectrum.

[0297] A further aspect of the present invention relates to the use of the organic molecules of the present invention as luminescent emitters or absorbers, and / or host materials and / or electron transport materials, and / or hole injection materials, and / or hole blocking materials in optoelectronic devices.

[0298] A preferred embodiment relates to the use of an organic molecule according to the present invention as a light-emitting emitter in a photoelectronic device.

[0299] Optoelectronic devices can be understood in the broadest sense as any device based on an organic material suitable for emitting light in the visible light or near-ultraviolet (UV) range, i.e., a wavelength range of 380 to 800 nm. More preferably, organic electroluminescent devices can emit light in the visible light range, i.e., a wavelength range of 400 nm to 800 nm.

[0300] In relation to these applications, optoelectronic devices are selected more specifically from the group consisting of:

[0301] - Organic Light-Emitting Diode (OLED),

[0302] - Luminescent electrochemical cell,

[0303] - OLED sensors, especially gas and vapor sensors that are not completely isolated from the outside,

[0304] - Organic diode,

[0305] - Organic solar cells,

[0306] - Organic transistor,

[0307] - Organic field-effect transistor,

[0308] - Organic lasers, and

[0309] - Down-conversion element.

[0310] In a preferred embodiment related to such applications, the organic electroluminescent device is a device selected from the group consisting of an organic light-emitting diode (OLED), a light-emitting electrochemical cell (LEC), and a light-emitting transistor.

[0311] For the above applications, the fraction of the organic molecule according to the present invention in the light-emitting layer of the optoelectronic device, more particularly in an OLED, is 0.1 wt% to 99 wt%, more particularly 1 wt% to 80 wt%. In another embodiment, the proportion of the organic molecule in the light-emitting layer is 100 wt%.

[0312] In one embodiment, the light-emitting layer further comprises the organic molecule according to the present invention as well as a host material having triplet (T1) and singlet (S1) energy levels higher than the triplet (T1) and singlet (S1) energy levels of the organic molecule.

[0313] A further aspect of the present invention relates to a composition comprising or made thereof of the following:

[0314] (a) one or more organic molecules according to the present invention, particularly in the form of an emitter and / or host,

[0315] (b) one or more emitter and / or host materials different from the organic molecule according to the present invention and

[0316] (c) Optionally, one or more dyes and / or one or more solvents.

[0317] In one embodiment, the light-emitting layer comprises or is essentially composed of a composition including or made of the following:

[0318] (a) one or more organic molecules according to the present invention, particularly in the form of an emitter and / or host,

[0319] (b) one or more emitter and / or host materials different from the organic molecule according to the present invention and

[0320] (c) Optionally, one or more dyes and / or one or more solvents.

[0321] In a specific embodiment, the light-emitting layer EML comprises or is essentially composed of a composition including or consisting of the following:

[0322] (i) 0.1-10 wt%, preferably 0.5-5 wt%, particularly 1-3 wt% of one or more organic molecules according to the present invention;

[0323] (ii) 5-99 wt%, preferably 15-85 wt%, particularly 20-75 wt% of one or more host compounds H;

[0324] (iii) one or more additional host compounds D having a structure different from the structure of the molecule according to the present invention, in an amount of 0.9-94.9 wt%, preferably 14.5-80 wt%, particularly 24-77 wt%; and

[0325] (iv) optionally, 0-94 wt%, preferably 0-65 wt%, particularly 0-50 wt% of solvent; and

[0326] (v) Optionally, at least one additional emitter molecule F having a structure different from the structure of the molecule according to the present invention in an amount of 0 to 30 weight%, particularly 0 to 20 weight%, preferably 0 to 5 weight%.

[0327] Preferably, energy can be transferred from a host compound H to one or more organic molecules according to the present invention, in particular 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 organic molecules E according to the present invention, 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 organic molecules E according to the present invention.

[0328] In one embodiment, the host compound H has an energy E in the range of -5 to -6.5 eV. HOMO Having a highest-level occupied molecular orbital HOMO (H) having (H), and at least one additional host compound D is E HOMO It has a highest-level occupied molecular orbital HOMO(D) having (D), where E HOMO (H) > E HOMO (D) is.

[0329] In an additional embodiment, the host compound H has energy E LUMO Having a lowest-level unoccupied molecular orbital LUMO(H) having (H), and at least one additional host compound D has energy E LUMO Having a lowest level unoccupied molecular orbital LUMO(D) having (D), where E LUMO (H) > E LUMO (D) is.

[0330] In one embodiment, the host compound H has energy E HOMO Highest level occupied molecular orbital HOMO(H) with (H) and energy E LUMO Having a lowest-level unoccupied molecular orbital LUMO(H) with (H),

[0331] At least one additional host compound D has energy E HOMO Highest level occupied molecular orbital HOMO(D) with (D) and energy E LUMO It has a lowest level unoccupied molecular orbital LUMO(D) having (D), and

[0332] The organic molecule E according to the present invention is energy E HOMO Highest level occupied molecular orbital HOMO(E) with (E) and energy E LUMO It has a lowest-level unoccupied molecular orbital LUMO(E) having (E), and

[0333] Here

[0334] E HOMO (H) > E HOMO(D) and the energy level (E) of the highest level occupied molecular orbital HOMO(E) of the organic molecule E according to the present invention HOMO (E)) and the highest level occupied molecular orbital HOMO(H) energy level of host compound H (E 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;

[0335] E LUMO (H) > E LUMO (D) and the energy level (E) of the lowest level unoccupied molecular orbital LUMO(E) of the organic molecule E according to the present invention LUMO The energy level (E) between the lowest level unoccupied molecular orbital LUMO (D) of (E) and at least one additional host compound D. LUMO (D)) The difference between is -0.5 eV to 0.5 eV, more preferably -0.3 eV to 0.3 eV, even more preferably -0.2 eV to 0.2 eV or even between -0.1 eV and 0.1 eV.

[0336] In one embodiment of the present invention, host compound D and / or host compound H are thermally activated delayed fluorescence (TADF) materials. The TADF material is 2500 cm⁻¹ -1 ΔE corresponding to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1) less than ST Indicates the value. Preferably, the TADF material is 3000 cm -1 Less than, more preferably 1500 cm -1 Less than, even more preferably 1000 cm -1 Less than or even 500 cm -1 ΔE less than ST Represents the value.

[0337] In one embodiment, host compound D is a TADF material, and host compound H is 2500 cm -1 Excess ΔE ST Indicates a value. In a specific embodiment, host compound D is a TADF material, and host compound H is selected from the group consisting of CBP, mCP, mCBP, furan 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.

[0338] In one embodiment, host compound H is a TADF material, and host compound D is 2500 cm -1 Excess ΔE ST Indicates a value. In a specific embodiment, host compound H is a TADF material, and host compound D is selected from the group consisting of 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'-spirobifluoren-2-yl)-1,3,5-triazine).

[0339] In a further aspect, the present invention relates to an optoelectronic device comprising an organic molecule or composition of the type described herein, more specifically to a device selected from the group consisting of an organic light-emitting diode (OLED), a light-emitting electrochemical cell, an OLED sensor, in particular a gas and vapor sensor that is not completely isolated from the outside, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser, and a down-conversion device.

[0340] In a preferred embodiment, the organic electroluminescent device is a device selected from the group consisting of an organic light-emitting diode (OLED), a light-emitting electrochemical cell (LEC), and a light-emitting transistor.

[0341] In one embodiment of the optoelectronic device of the present invention, the organic molecule E according to the present invention is used as a light-emitting material in the light-emitting layer EML.

[0342] In one embodiment of the optoelectronic device of the present invention, the light-emitting layer EML is composed of the composition according to the present invention as described herein.

[0343] If the organic electroluminescent device is an OLED, it may have a layer structure such as the following, for example.

[0344] 1. Substrate

[0345] 2. Anode Layer A

[0346] 3. Hole injection layer, HIL

[0347] 4. Hole Transport Layer, HTL

[0348] 5. Electron Blocking Layer, EBL

[0349] 6. Emitting layer, EML

[0350] 7. Hole Blocking Layer, HBL

[0351] 8. Electron Transport Layer, ETL

[0352] 9. Electron injection layer, EIL

[0353] 10. Cathode layer,

[0354] Here, the OLED may selectively include each layer selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL, different layers may be merged, and the OLED may include one or more layers of each layer type defined above.

[0355] Additionally, in one embodiment, the organic electroluminescent device may include at least one protective layer that protects the device from damaging exposure to harmful species in an environment, such as moisture, vapor, and / or gas.

[0356] In one embodiment of the present invention, the organic electroluminescent device is an OLED having the following inverted layer structure:

[0357] 1. Substrate

[0358] 2. Cathode layer

[0359] 3. Electron injection layer, EIL

[0360] 4. Electron Transport Layer, ETL

[0361] 5. Hole Blocking Layer, HBL

[0362] 6. Emitting layer, B

[0363] 7. Electron Blocking Layer, EBL

[0364] 8. Hole Transport Layer, HTL

[0365] 9. Hole injection layer, HIL

[0366] 10. Anode Layer A

[0367] Here, the OLED may selectively include each layer selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers may be merged, and the OLED may include one or more layers of each layer type defined above.

[0368] In one embodiment of the present invention, the organic electroluminescent device is an OLED that may have a stacked structure. In this structure, unlike a typical arrangement where OLEDs are placed side by side, individual units are stacked on top of each other. Mixed light may be generated by the OLED having the stacked structure, and in particular, white light may be generated by stacking blue, green, and red OLEDs. Additionally, the OLED having the stacked structure may include a charge generation layer (CGL), which is generally located between two OLED subunits and is generally composed of an n-doped layer and a p-doped layer, and generally the n-doped layer of one CGL is located closer to the anode layer.

[0369] In one embodiment of the present invention, the organic electroluminescent device is an OLED comprising two or more light-emitting layers between an anode and a cathode. In particular, such a so-called tandem OLED comprises three light-emitting layers, wherein one light-emitting layer emits red light, one light-emitting layer emits green light, and one light-emitting layer emits blue light, and optionally may include additional layers such as a charge generation layer, a charge blocking layer, or a charge transport layer between the individual light-emitting layers. In a further embodiment, the light-emitting layers are stacked adjacently. In a further embodiment, the tandem OLED comprises a charge generation layer between each of the two light-emitting layers. Additionally, light-emitting layers separated by adjacent light-emitting layers or charge generation layers may be combined.

[0370] The substrate may be formed from any material or a composition of materials. In most cases, a glass slide is used as the substrate. Alternatively, a thin metal layer (e.g., copper, gold, silver, or aluminum film) or a plastic film or slide may be used. This may allow for a higher level of flexibility. The anode layer A is composed of a material that allows for obtaining a mostly (essentially) transparent film. Since at least one of the two electrodes must be (essentially) transparent to allow light emission from the OLED, either the anode layer A or the cathode layer C is transparent. Preferably, the anode layer A contains a large amount of transparent conductive oxides (TCOs) or is even composed of them. This anode layer A may include, for example, indium tin oxide, aluminum zinc 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.

[0371] The anode layer A may be composed of (essentially) indium tin oxide (ITO) (e.g., (InO3)0.9(SnO2)0.1). The roughness of the anode layer (A) caused by the transparent conductive oxide (TCO) can be offset by using a hole injection layer (HIL). Additionally, the HIL can facilitate the injection of quasi-charge carriers (i.e., holes) in that it facilitates the transport of quasi-charge carriers (i.e., holes) from the TCO to the hole transport layer (HTL). The hole injection layer (HIL) may comprise poly-3,4-ethylenedioxythiophene (PEDOT), polystyrene sulfonate (PSS), MoO2, V2O5, CuPC, or CuI, particularly a mixture of PEDOT and PSS. The hole injection layer (HIL) can also prevent the diffusion of metal from the anode layer (A) to the hole transport layer (HTL). For example, HIL is 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'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene), DNTPD (N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine), NPB (N,N'-nis-(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine), It may be composed of NPNPB (N,N'-diphenyl-N,N'-di-[4-(N,N-diphenyl-amino) )phenyl]benzidine), MeO-TPD (N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine), HAT-CN (1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile) and / or spiro-NPD (N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine).

[0372] A hole transport layer (HTL) is typically located adjacent to the anode layer A or the hole injection layer (HIL). Here, any hole transport compound may be used. For example, electron-rich heteroaromatic compounds such as triarylamine and / or carbazole may be used as hole transport compounds. The HTL can reduce the energy barrier between the anode layer (A) and the emissive layer (EML). The hole transport layer (HTL) may also be an electron blocking layer (EBL). Preferably, the hole transport compound has a triplet state T1 at a relatively high energy level. For example, the hole transport layer (HTL) may comprise a star-shaped heterocyclic ring such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenyl-amine)), α-NPD (poly(4-butylphenyl-diphenyl-amine)), TAPC (4,4'-cyclohexylidene-bis[N,N-bis(4-methylphenyl)benzenamine]), 2-TNATA (4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN and / or TrisPcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazole-3-yl)-9H,9'H-3,3'-bicarbazole). Additionally, the HTL may include a p-doped layer that may consist of an inorganic or organic dopant in an organic hole-transport matrix. For example, transition metal oxides such as vanadium oxide, molybdenum oxide, or tungsten oxide may be used as inorganic dopants. For example, tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper-pentafluorobenzoate (Cu(I)pFBz), or transition metal complexes may be used as organic dopants.

[0373] EBL may include, for example, mCP (1,3-bis(carbazole-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazole-9-yl)biphenyl), tris-Pcz, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), and / or DCB (N,N'-dicarbazoleyl-1,4-dimethylbenzene).

[0374] An emitting layer (EML) is generally located adjacent to a hole transport layer (HTL). The emitting layer (EML) comprises at least one emitting molecule. In particular, the EML comprises one or more emitting molecules E according to the present invention. In one embodiment, the emitting layer comprises only organic molecules according to the present invention. Generally, the EML further comprises one or more host materials H. For example, host material H is CBP(4,4'-bis-(N-carbazoleyl)-biphenyl), mCP, mCBP Sif87(dibenzo[b,d]thiophene-2-yltriphenylsilane), CzSi, Sif88(dibenzo[b,d]thiophene-2-yl)diphenylsilane), DPEPO(bis[2-(diphenylphosphino)phenyl]ether oxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 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, 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'-spirobifluoren-2-yl)-1,3,5-triazine). The host substance H should generally be selected to exhibit first triplet (T1) and first singlet (S1) energy levels that are energetically higher than the first triplet (T1) and first singlet (S1) energy levels of the organic molecule.

[0375] In one embodiment of the present invention, the EML comprises a so-called mixed host system having at least one hole-dominant host and one electron-dominant host. In a specific embodiment, the EML comprises exactly one luminescent organic molecule according to the present invention and, as an electron-dominant host, T2T and as a hole-dominant host, one selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 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. In an additional embodiment, the EML comprises 50-80 wt%, preferably 60-75 wt%, of a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 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; 10-45 wt%, preferably 15-30 wt%, of T2T; and 5-40 wt%, preferably 10-30 wt%, of a luminescent molecule according to the present invention.

[0376] An electron transport layer (ETL) may be located adjacent to the emissive layer (EML). Here, any electron transporter may be used. For example, electron-deficient compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone may be used. The electron transporter may also be a star-shaped heterocyclic ring such as 1,3,5-tri(1-phenyl-1H-benzo[d]imidazole-2-yl)phenyl (TPBi). ETLs include NBphen(2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3(aluminum-tris(8-hydroxyquinoline)), TSPO1(diphenyl-4-triphenylsilylphenyl-phosphinoxide), BPyTP2(2,7-di(2,2'-bipyridine-5-yl)triphenyl), Sif87(dibenzo[b,d]thiophene-2-yltriphenylsilane), Sif88(dibenzo[b,d]thiophene-2-yl)diphenylsilane), BmPyPhB(1,3-bis[3,5-di(pyridine-3-yl)phenyl]benzene) and / or BTB(4,4'-bis-[2-(4),6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl). It may include. Optionally, the ETL may be doped with a material such as Liq. The electron transport layer (ETL) may also block holes, or a hole blocking layer (HBL) may be introduced.

[0377] HBL may include, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = batocuproin), BAlq (bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (aluminum-tris(8-hydroxyquinoline)), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphinoxide), T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine), It may include TST (2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine) and / or TCB / TCP (1,3,5-tris(N-carbazoleyl)benzol / 1,3,5-tris(carbazole)-9-yl)benzene).

[0378] A cathode layer C may be located adjacent to the electron transport layer (ETL). The cathode layer C may comprise, for example, a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy, or may be composed of these. For practical reasons, the cathode layer may be composed of (inherently) opaque metals such as Mg, Ca, or Al. Alternatively, or additionally, the cathode layer C may also comprise graphite and / or carbon nanotubes (CNT). Alternatively, the cathode layer C may also be composed of nanoscale silver wires.

[0379] The OLED may optionally further include a protective layer (which may be referred to 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(8-hydroxyquinolinolatol lithium), Li2O, BaF2, MgO, and / or NaF.

[0380] Optionally, the electron transport layer (ETL) and / or hole blocking layer (HBL) may also include one or more host compounds H.

[0381] To further adjust the emission spectrum and / or absorption spectrum of the emitting layer (EML), the emitting layer (EML) may further comprise one or more additional emitter molecules (F). These emitter molecules F may be any emitter molecules known in the art. Preferably, these emitter molecules F are molecules having a structure different from that of molecule E according to the present 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 spectrum and / or absorption spectrum of the emitting layer EML. For example, triplet and / or singlet excitons may be transferred from the organic emitter molecule according to the present invention to the emitter molecule F before relaxing to the ground state S0, thereby emitting light that is typically red-shifted compared to the light emitted by the organic molecule. Optionally, the emitter molecule F can also induce a two-photon effect (i.e., absorption of two photons at half the energy of the maximum absorption).

[0382] Optionally, the organic electroluminescent device (e.g., OLED) may be, for example, an essentially white organic electroluminescent device. For example, such a white organic electroluminescent device may comprise at least one (deep) blue emitter molecule and one or more emitter molecules that emit green and / or red light. Then, optionally, there may also be energy transfer between two or more molecules as described above.

[0383] As used herein, unless more specifically defined in a particular context, the color designation of emitted and / or absorbed light is as follows:

[0384] Purple: Wavelength range >380-420 nm;

[0385] Dark blue: wavelength range of >420-480 nm;

[0386] Sky blue: wavelength range of >480-500 nm;

[0387] Green: Wavelength range of >500-560 nm;

[0388] Yellow: Wavelength range >560-580 nm;

[0389] Orange: Wavelength range >580-620 nm;

[0390] Red: Wavelength range of >620-800 nm.

[0391] These colors represent maximum emission in relation to emitter molecules. Thus, for example, a deep blue emitter has maximum emission in the range of >420–480 nm, a sky blue emitter has maximum emission in the range of >480–500 nm, a green emitter has maximum emission in the range of >500–560 nm, and a red emitter has maximum emission in the range of >620–800 nm.

[0392] The deep blue emitter may preferably have a maximum emission of less than 480 nm, more preferably less than 470 nm, much more preferably less than 465 nm, or even less than 460 nm. This will typically be greater than 420 nm, preferably greater than 430 nm, more preferably greater than 440 nm, or even greater than 450 nm.

[0393] Accordingly, an additional aspect of the present invention is 1000 cd / m 2Exhibiting an external quantum efficiency of greater than 8%, more preferably greater than 10%, even more preferably greater than 13%, even more preferably greater than 15% or even greater than 20%, or exhibiting / exhibiting maximum emission at 420 nm to 500 nm, preferably 430 nm to 490 nm, more preferably 440 nm to 480 nm, much more preferably 450 nm to 470 nm, or 500 cd / m² 2 The present invention relates to an OLED exhibiting an LT80 value greater than 100h, preferably greater than 200h, more preferably greater than 400h, much more preferably greater than 750h, or even greater than 1000h. Accordingly, a further aspect of the present invention relates to an OLED exhibiting CIEy color coordinates of less than 0.45, preferably less than 0.30, more preferably less than 0.20, or much more preferably less than 0.15, or even less than 0.10.

[0394] Another aspect of the present invention relates to an OLED that emits light from distinct color points. According to the present invention, the OLED emits light having a narrow emission band (small full width at half maximum (FWHM)). In one aspect, the OLED according to the present invention emits light having a FWHM of the main emission peak of less than 0.25 eV, preferably less than 0.20 eV, more preferably less than 0.17 eV, much more preferably less than 0.15 eV, or even less than 0.13 eV.

[0395] Another aspect of the present invention relates to an OLED emitting light having color coordinates CIEx and CIEy close to the color coordinates CIEx (= 0.131) and CIEy (= 0.046) of the primary blue color (CIEx = 0.131 and CIEy = 0.046) as defined in the ITU-R Recommendation BT.2020 (Rec. 2020), which is suitable for use in ultra-high definition (UHD) displays, e.g., UHD-TVs. Accordingly, a further aspect of the present invention relates to an OLED that emits light in CIEx color coordinates of 0.02 to 0.30, preferably 0.03 to 0.25, more preferably 0.05 to 0.20, or even more preferably 0.08 to 0.18, or even 0.10 to 0.15 and / or CIEy color coordinates of 0.00 to 0.45, preferably 0.01 to 0.30, more preferably 0.02 to 0.20, or even more preferably 0.03 to 0.15, or even 0.04 to 0.10.

[0396] In a further aspect, the present invention relates to a method for manufacturing a photoelectronic component. In this case, the organic molecule of the present invention is used.

[0397] An organic electroluminescent device according to the present invention, particularly an OLED, can be manufactured by any means of vapor deposition and / or liquid phase processes. Accordingly, at least one layer is manufactured by the following process:

[0398] - Sublimation process,

[0399] - Organic vapor deposition process,

[0400] - Carrier gas sublimation process,

[0401] - Solution processing or printing.

[0402] Methods used to manufacture organic electroluminescent devices, particularly OLEDs according to the present invention, are known in the art. Different layers are deposited individually and sequentially on a suitable substrate by a subsequent deposition process. Individual layers may be deposited using the same or different deposition methods.

[0403] For example, vapor deposition processes include thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. For active matrix OLED displays, an AMOLED backplane is used as the substrate. Individual layers can be processed from solutions or dispersions using suitable solvents. For example, solution deposition processes include spin coating, dip coating, and jet printing. Liquid processing can optionally be performed in an inert atmosphere (e.g., a nitrogen atmosphere), and the solvent can be completely or partially removed by means known in the art.

[0404] [Example]

[0405] General Synthesis Method I:

[0406]

[0407] General procedure for synthesis:

[0408] AAVI :

[0409]

[0410] E-0 (1.00 equivalents), the corresponding donor molecule E-1 (2.00 equivalents), and tripotassium phosphate (CAS 7778-53-2, 4.00 equivalents) are suspended in DMSO under a nitrogen atmosphere and stirred at 120°C. After cooling to room temperature, the reaction mixture is poured into water to precipitate the organic matter. The precipitate is filtered (glass fiber filter) and then dissolved in dichloromethane. The resulting solution is added to brine, and the phases are separated. After drying on the MgSO4 phase, the crude product is purified by recrystallization or flash chromatography. Product I-1 is obtained as a solid.

[0411] AAV2 :

[0412]

[0413] Dissolve I-1 (1.00 equivalents) in tert-butylbenzene under a nitrogen atmosphere, and cool the solution to -30°C. tert-butyllithium ( t Dropwise add BuLi solution (4.20 equivalents, CAS: 594-19-4) and heat the reaction mixture to 0°C. After stirring at 0°C for 120 minutes, t The solvent and byproducts of the BuLi solution are removed under reduced pressure, and the reaction mixture is cooled back to -78°C. Dichloroarylborane (R 1A solution of BCl2 (4.00 equivalents) was added dropwise, the cooling bath was removed, and the reaction mixture was heated to 0°C. After stirring at 0°C for 30 minutes, a boron tribromide solution (BBr3, CAS: 10294-33-4, 3.00 equivalents) was added dropwise. The reaction mixture was heated to room temperature (rt) and then stirred at room temperature for 3 hours. Subsequently, the reaction mixture was poured into water, the resulting precipitate was filtered, and washed with water. The precipitate was filtered (glass fiber filter) and then dissolved in dichloromethane. The resulting solution was added to brine, and the phases were separated. After drying with MgSO4, the unrefined product was purified by recrystallization or flash chromatography.

[0414] General Synthesis Method II:

[0415]

[0416] AAV3 :

[0417]

[0418] E-0 (1.00 equivalents), the corresponding donor molecule E-1 (1.00 equivalents), and tripotassium phosphate (CAS 7778-53-2, 2.00 equivalents) are suspended in DMSO under a nitrogen atmosphere and stirred at 120°C. After cooling to room temperature, the reaction mixture is poured into water to precipitate the organic matter. The precipitate is filtered (glass fiber filter) and then dissolved in dichloromethane. The resulting solution is added to brine, and the phases are separated. After drying on the MgSO4 phase, the crude product is purified by recrystallization or flash chromatography. Product I-2 is obtained as a solid.

[0419] AAV4:

[0420]

[0421] I-2 (1.00 equivalents), the corresponding donor molecule E-2 (1.00 equivalents), and tripotassium phosphate (CAS 7778-53-2, 2.00 equivalents) are suspended in DMSO under a nitrogen atmosphere and stirred at 120°C. After cooling to room temperature, the reaction mixture is poured into water to precipitate the organic matter. The precipitate is filtered (glass fiber filter) and then dissolved in dichloromethane. The resulting solution is added to brine, and the phases are separated. After drying on the MgSO4 phase, the unrefined product is purified by recrystallization or flash chromatography. Product I-3 is obtained as a solid.

[0422] cyclic voltammetry

[0423] The cyclic voltammetry is such that the concentration of organic molecules in dichloromethane or a suitable solvent and suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate) is 10 -3 Measurements are taken in a mol / L solution. Measurements are performed at room temperature in a nitrogen atmosphere using a three-electrode assembly (working and counter electrodes: Pt wire, reference electrode: Pt wire), and FeCp2 / FeCp2 is used as an internal standard. + Correction is performed using [the method]. HOMO data was calibrated for the saturated calomel electrode (SCE) using ferrocene as an internal standard.

[0424] Density Functional Theory Calculation

[0425] The molecular structure is optimized using the BP86 function and the RI (Resolution of Identity) approach. Excitation energies are calculated using the (BP86) optimized structure and employing the Time-Dependent DFT (TD-DFT) method. Orbital and excited state energies are calculated using the B3LYP function. The Def2-SVP base set and m4-grid for numerical integration are used. The Turbomole program package is used for all calculations.

[0426] Optical physics measurement

[0427] Sample Pretreatment: Spin Coating

[0428] Device: Spin150, SPS euro.

[0429] The sample concentration is 10 mg / ml and is dissolved in a suitable solvent.

[0430] Program: 1) 3 seconds at 400 U / min; 20 seconds at 1000 U / min (1000 Upm / s). 3) 10 seconds at 4000 U / min (1000 Upm / s). After coating, dry the film at 70°C for 1 minute.

[0431] Photoluminescence Spectroscopy and Time-Correlated Single Photon Counting (TCSPC)

[0432] Steady-state emission spectroscopy is measured using a Horiba Scientific, Model FluoroMax-4 equipped with a 150 W Xenon-Arc lamp, excitation and emission monochromators, a Hamamatsu R928 photomultiplier tube, and a time-correlated single-photon counting option. The emission and excitation spectra are corrected using standard correction fits.

[0433] Here, the state lifespan is determined using the same system employing the TCSPC method with the FM-2013 equipment and the Horiba Yvon TCSPC hub.

[0434] Source here:

[0435] NanoLED 370 (Wavelength: 371 nm, Pulse duration: 1.1 ns)

[0436] NanoLED 290 (Wavelength: 294nm, Pulse duration: <1ns)

[0437] SpectraLED 310 (Wavelength: 314nm)

[0438] SpectraLED 355 (Wavelength: 355nm).

[0439] Data analysis (exponential fit) is performed using the DataStation software suite and DAS6 analysis software. The fit is determined using the chi-squared test.

[0440] Photoluminescence Quantum Yield Measurement

[0441] The Absolute PL Quantum Yield Measurement C9920-03G system (Hamamatsu Photonics) is used for the measurement of photoluminescence quantum yield (PLQY). Quantum yield and CIE coordinates are determined using software U6039-05 version 3.6.0.

[0442] Maximum emission is expressed in nm, quantum yield Φ in %, and CIE coordinates in x,y values.

[0443] PLQY is determined using the following protocol.

[0444] 1) Quality assurance: Anthracene in ethanol (known concentration) is used as a reference.

[0445] 2) Wavelength: The maximum absorption of the organic molecule is determined, and the molecule is excited using this wavelength.

[0446] 3) Measurement

[0447] Quantum yield is measured for solution or film samples in a nitrogen atmosphere. The yield is calculated using the following equation.

[0448]

[0449] Here, n 광자 represents the number of photons, and Int represents the intensity.

[0450] Fabrication and Characterization of Optoelectronic Devices

[0451] An optoelectronic device, particularly an OLED device, comprising an organic molecule according to the present invention can be manufactured through a vacuum deposition method. If a layer comprises more than one compound, the weight percentage of one or more compounds is expressed in %. Since the total weight percentage value becomes 100%, the fraction of the compound for which no value is specified is equal to the difference between the specified values ​​and 100%.

[0452] An OLED that is not fully optimized is characterized by measuring an external quantum efficiency (%) that depends on intensity and current, calculated using the electroluminescence spectrum and light detected by the photodiode using standard methods. The lifetime of the OLED device is derived from the change in luminance while operating at a constant current density. The LT50 value corresponds to the time when the measured luminance decreases to 50% of the initial luminance, similarly, LT80 corresponds to the time when the measured luminance decreases to 80% of the initial luminance, LT95 corresponds to the time when the measured luminance decreases to 95% of the initial luminance, and so on.

[0453] Accelerated life measurements are performed (e.g., increased current density is applied). For example, 500 cd / m 2 The LT80 value is determined using the following formula.

[0454]

[0455] Here, L0 represents the initial luminance at the applied current density.

[0456] The values ​​correspond to the average of several pixels (typically 2 to 8), and the standard deviation between these pixels is provided.

[0457] HPLC-MS

[0458] HPLC-MS analysis is performed on an Agilent HPLC (1100 series) equipped with an MS detector (Thermo LTQ XL).

[0459] An exemplary typical HPLC method is as follows. A reverse-phase column of 4.6 mm × 150 mm and a particle size of 3.5 μm from Agilent (ZORBAX Eclipse Plus 95Å C18, 4.6×150 mm, 3.5 μm HPLC column) are used for HPLC. HPLC-MS measurements are performed at room temperature (rt) according to the following gradient.

[0460] Flow rate [ml / min] Hours [minutes] A[%] B[%] C[%] 2.5 0 40 50 10 2.5 5 40 50 10 2.5 25 10 20 70 2.5 35 10 20 70 2.5 35.01 40 50 10 2.5 40.01 40 50 10 2.5 41.01 40 50 10

[0461] The following solvent mixture was used:

[0462] Solvent A: H2O(90%) MeCN(10%) Solvent B: H2O(10%) MeCN(90%) Solvent C: THF(50%) MeCN(50%)

[0463] Take an injection volume of 5 μL from an analyte solution at a concentration of 0.5 mg / mL for measurement.

[0464] Ionization of the probe is performed using an atmospheric pressure chemical ionization (APCI) source in positive (APCI+) or negative (APCI-) ionization mode.

[0465] Synthesis of Example 1:

[0466]

[0467]

[0468] 1,4-difluorobenzene (1.00 equivalents), 1-bromo-9H-carbazole (CAS 16807-11-7, 2.00 equivalents), and tripotassium phosphate (CAS 7778-53-2, 4.00 equivalents) are suspended in DMSO under a nitrogen atmosphere and stirred at 120°C. After cooling to room temperature, the reaction mixture is poured into water to precipitate the organic matter. The precipitate is filtered (glass fiber filter) and then dissolved in dichloromethane. The resulting solution is added to brine, and the phases are separated. After drying on the MgSO4 phase, the unrefined product is purified by recrystallization or flash chromatography. Product I-1 is obtained as a solid.

[0469]

[0470] Dissolve I-1 (1.00 equivalents) in tert-butylbenzene under a nitrogen atmosphere, and cool the solution to -30°C. tert-butyllithium ( t Dropwise add BuLi solution (4.20 equivalents, CAS: 594-19-4) and heat the reaction mixture to 0°C. After stirring at 0°C for 120 minutes, t The solvent and byproducts of the BuLi solution are removed under reduced pressure, and the reaction mixture is cooled back to -78°C. Dichlorophenylborane solution (PhBCl2, CAS: 873-51-8, 4.00 equivalents) is added dropwise, the cooling bath is removed, and the reaction mixture is heated to 0°C. After stirring for 30 minutes at 0°C, boron tribromide solution (BBr3, CAS: 10294-33-4, 3.00 equivalents) is added dropwise. The reaction mixture is heated to room temperature (rt) and then stirred at room temperature for 3 hours. Subsequently, the reaction mixture is poured into water, the resulting precipitate is filtered, and washed with water. The precipitate is filtered (glass fiber filter) and then dissolved in dichloromethane. The resulting solution is added to brine, and the phases are separated. After drying with MgSO4, the unrefined product is purified by recrystallization or flash chromatography.

[0471] Additional examples of organic molecules of the present invention

[0472]

[0473]

[0474]

[0475]

[0476]

[0477]

[0478]

Claims

Claim 1 Organic molecule having the structure of Chemical Formula III below: Chemical Formula III, among Chemical Formula III, R 1 is a phenyl selectively substituted with one or more C1-C5-alkyl substituents in each case; R 2 In each case, is independently selected from the group consisting of H, deuterium, C1-C5-alkyl and phenyl; R a is independently selected from the group consisting of: hydrogen, Me, in each case i Pr, t Bu, CN, CF3, Me; i Pr, t Ph,Me, which is optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, i Pr, t Pyridinyl,Me, selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, i Pr, t Pyrimidinyl,Me, optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, i Pr, t Carbazolyl, Me, optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, and N(Ph)2; where substituent R a are independently one or more substituents R a It selectively forms a monocyclic, polycyclic, aliphatic, aromatic, heteroaromatic, or benzo condensed ring system together with. Claim 2 delete Claim 3 delete Claim 4 delete Claim 5 In paragraph 1, R 2 An organic molecule that is H in each case. Claim 6 delete Claim 7 delete Claim 8 In claim 1, among the above chemical formula III Organic molecule in which the moiety represented by is the structure of the following chemical formula Ib-3, the structure of the following chemical formula Ib-4, or the structure of the following chemical formula Ib-5: Chemical formula Ib-3 Chemical formula Ib-4 Chemical formula Ib-5 where R b In each case, is selected independently from the group consisting of: hydrogen, Me, i Pr, t Bu, CN, CF3, Me; i Pr, t Ph,Me, which is optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, i Pr, t Pyridinyl,Me, selectively substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, i Pr, t Pyrimidinyl,Me, optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, i Pr, t Carbazolyl, Me, optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, and N(Ph)2;R 1 is identical to the definition described in paragraph 1, and * indicates a bonding site. Claim 9 In claim 1, an organic molecule having the structure of the following chemical formula IIIa: Chemical formula IIIa where R b In each case, is selected independently from the group consisting of: hydrogen, Me, i Pr, t Bu, CN, CF3, Me; i Pr, t Ph,Me, which is optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, i Pr, t Pyridinyl,Me, optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, i Pr, t Carbazolyl, Me, optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph, and N(Ph)2;R 1 and R 2 Each is identical to the definition stated in Paragraph 1. Claim 10 An organic molecule that is a light-emitting emitter in a photoelectronic device, in any one of claims 1, 5, 8 and 9. Claim 11 In claim 10, the above-mentioned optoelectronic device is an organic molecule selected from the group consisting of: - organic light-emitting diode (OLED), - light-emitting electrochemical cell, - OLED sensor, - organic diode, - organic solar cell, - organic transistor, - organic field-effect transistor, - organic laser, - down-conversion element. Claim 12 A composition comprising: (a) the organic molecule according to claim 1, (b) an emitter and / or host material different from the organic molecule, and (c) optionally, a dye and / or solvent. Claim 13 An optoelectronic device comprising the organic molecule according to any one of claims 1, 5, 8 and 9 or the composition according to claim 12, and having a device form selected from the group consisting of an organic light-emitting diode (OLED), a light-emitting electrochemical cell, an OLED sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser, and a down-conversion device. Claim 14 In claim 13, the optoelectronic device comprises a substrate, an anode, a cathode, and a light-emitting layer, wherein the anode or the cathode is disposed on the substrate, the light-emitting layer is disposed between the anode and the cathode, and the organic molecule or the composition. Claim 15 A method for manufacturing a photoelectronic device, wherein the organic molecule according to any one of claims 1, 5, 8 and 9 or the composition according to claim 12 is used, and the method comprises the step of treating the organic molecule by a vacuum evaporation method or treating the organic molecule from a solution.

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