Compound and organic electroluminescent device comprising the compound

Abstract

The present invention relates to specific compounds, materials for organic electroluminescent devices comprising the compounds, preferably emitter materials, organic electroluminescent devices comprising the specific compounds, electronic devices comprising the organic electroluminescent devices, a light-emitting layer comprising at least one host and at least one dopant, wherein the dopant comprises at least one of the specific compounds, and use of the compounds in organic electroluminescent devices.

Description

Technical Field

[0001] The present invention relates to a specific compound, a material for an organic electroluminescent device comprising the specific compound, preferably an emitter material, an organic electroluminescent device comprising the specific compound, an electronic device comprising the organic electroluminescent device, a light-emitting layer comprising at least one host and at least one dopant, wherein the dopant comprises at least one of the specific compounds, and use of the compound in an organic electroluminescent device.

[0002] When voltage is applied to an organic electroluminescent device (hereinafter may be referred to as an organic EL device), holes are injected from the anode into the emission layer, and electrons are injected from the cathode into the emission layer. In the emission layer, the injected holes and electrons recombine and form excitons.

[0003] The organic EL device includes an emission layer between an anode and a cathode. In addition, there may be a case where it has a stacked layer structure including organic layers such as a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and the like. Background Art

[0004] WO2019132040 A1 relates to a compound of the following formula (1) and an organic electroluminescent device using the same.

[0005] Provided that at least one of R1 to R8 is a group represented by the following formula (2)

[0006] -L1-HAr (2)

[0007] In formula (2), L1 represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic ring having 5 to 30 ring atoms, and HAr is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0008] WO2021020931 A1 relates to a compound represented by formula (1) and an organic light-emitting device comprising the same.

[0009] Wherein the substituents of A and B and one or more of R1-R3 are groups represented by formula (2)

[0010]

[0011] WO2019132028 A1 relates to a compound represented by formula (1) and an organic electroluminescent device using the same.

[0012]

[0013] JP2021014446 A relates to a polymer of a polycyclic aromatic compound represented by the following general formula (1) or a polycyclic aromatic compound having a plurality of structures represented by the following general formula (1).

[0014] wherein at least one hydrogen in at least one ring of the C ring is replaced by a group represented by the above formula (Am)

[0015]

[0016] wherein Ar1 and Ar2 are independently aryl or heteroatom.

[0017] KR102225908 B1 relates to a heterocyclic compound of the following formula (1) and an organic light-emitting device comprising the same.

[0018] Among them, 11 To R 14 , R 21 To R 24 , R 31 To R 35 , R 41 To R 43 , and R 51 To R 55 In the substituted or unsubstituted ring formed by bonding of adjacent substituents, at least one of the two adjacent substituents is represented by the formula (2):

[0019]

[0020] The specific structure and substitution pattern of polycyclic compounds have a significant impact on the performance of polycyclic compounds in organic electronic devices.

[0021] Citation List

[0022] Patent Literature

[0023] WO2019132040 A1

[0024] WO2021020931 A1

[0025] WO2019132028 A1

[0026] JP2021014446 A

[0027] KR102225908 B1 SUMMARY OF THE INVENTION

[0029] Technical issues

[0030] Despite the above developments, there is still a need for organic electroluminescent devices comprising new materials, in particular dopant (=emitter) materials, in order to provide improved properties of the electroluminescent devices.

[0031] Therefore, with respect to the above-mentioned related art, an object of the present invention is to provide materials suitable for providing organic electroluminescent devices, which ensure good performance of the organic electroluminescent device, especially good EQE and / or long lifetime. More particularly, it should be possible to provide dopant (= emitter) materials, especially blue light emitting dopant materials with narrow spectrum (smaller FWHM), i.e. good color purity when used as dopant in organic electroluminescent devices.

[0032] Solutions to the Problem

[0033] The object is solved according to a first aspect of the present invention by a compound represented by formula (I):

[0034]

[0035] in

[0036] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms; unsubstituted or substituted aralkyl having 7 to 60 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted haloalkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 20 SR 21 ; C(=O)R 22 ;COOR 23 ;SiR 24 R 25 R 26 ; NAr2Ar3 or halogen;

[0037] or

[0038] Two adjacent residues together form an unsubstituted or substituted ring structure;

[0039] Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 At least one, preferably R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 At least one of represents an amino group NAr2Ar3;

[0040] Ar2 and Ar3 each independently represent an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 60 ring atoms;

[0041] R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms; unsubstituted or substituted aralkyl having 7 to 60 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted haloalkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 20 SR 21 ; C(=O)R 22 ;COOR 23 ;SiR 24 R 25 R 26 or halogen;

[0042] or

[0043] Two adjacent residues come together to form an unsubstituted or substituted ring structure:

[0044] Where R 12 , R 13 , R 14 , R15 , R 16 , R 17 , R 18 and R 19 One is the bonding site with L2;

[0045] R a and R b each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms or unsubstituted or substituted alkyl having 1 to 20 carbon atoms;

[0046] or

[0047] R a and R b together form an unsubstituted or substituted aromatic ring structure having 3 to 13 ring atoms or an unsubstituted or substituted aliphatic ring structure having 3 to 9 ring atoms;

[0048] L1 represents a direct bond, an unsubstituted or substituted divalent aromatic hydrocarbon group containing 6 to 30 ring atoms, an unsubstituted or substituted divalent alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted divalent heteroaromatic group containing 3 to 30 ring atoms;

[0049] L2 represents a direct bond, an unsubstituted or substituted divalent aromatic hydrocarbon group containing 6 to 30 ring atoms, an unsubstituted or substituted divalent alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted divalent heteroaromatic group containing 3 to 30 ring atoms;

[0050] Ar1 represents an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 60 ring atoms or an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms;

[0051] R 20 , R 21 , R 22 and R 23 each independently represents an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 60 ring atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms;

[0052] R 24 , R 25 and R 26Each independently represents an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 60 ring atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms.

[0053] Advantageous Effects of the Invention

[0054] The compounds of formula (I) can in principle be used in any layer of an EL device. Preferably, the compounds of formula (I) are dopants (=emitters) in an organic EL element, especially in the emitting layer, more preferably fluorescent dopants. In particular, the compounds of formula (I) are used as fluorescent dopants in organic EL devices, especially in the emitting layer. BRIEF DESCRIPTION OF THE DRAWINGS

[0056] Figure 1 A schematic configuration of one example of the organic EL device of the present invention is shown.

[0057] Description of the implementation plan

[0058] The term organic EL device (organic electroluminescent device) is used interchangeably with the term organic light emitting diode (OLED) in this application.

[0059] It has been found that the specific compounds of formula (I) exhibit narrow emission characteristics, preferably narrow fluorescence, more preferably narrow blue fluorescence. Such narrow emission characteristics are suitable for preventing the energy loss caused by coupling out. The compound of formula (I) according to the present invention preferably has a full width at half maximum (FWHM) lower than 30nm, more preferably lower than 25nm.

[0060] It has further been found that organic EL devices comprising the compounds of the present invention are generally characterized by high external quantum efficiency (EQE) and long lifetime, especially when the specific compounds of formula (I) are used as dopants (luminescent materials), especially fluorescent dopants, in organic electroluminescent devices.

[0061] Examples of optional substituents represented by "substituted or unsubstituted" and "possibly substituted" as mentioned above or below include aryl having 6 to 60, preferably 6 to 30, more preferably 6 to 18 ring carbon atoms, which in turn is unsubstituted or substituted, heteroaryl having 5 to 60, preferably 5 to 30, more preferably 5 to 18 ring atoms, which in turn is unsubstituted or substituted, alkyl having 1 to 20, preferably 1 to 8 carbon atoms, cycloalkyl having 3 to 20, preferably 3 to 6 carbon atoms, the group OR 20 , a haloalkyl group having 1 to 20, preferably 1 to 8, carbon atoms, a halogen atom (fluorine, chlorine, bromine, iodine), CN, C(═O)R 22 、COOR 23, carboxamidoalkyl, silyl SiR having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms 24 R 25 R 26 , B(R 21 )2. Group SR 21 , NO2 and carboxamide aryl having 6 to 18 ring carbon atoms in the aryl residue;

[0062] or

[0063] Two adjacent substituents together form a ring structure, which in turn is unsubstituted or substituted;

[0064] R 20 , R 21 , R 22 , R 23 , R 24 , R 25 and R 26 As defined above.

[0065] The terms hydrogen, halogen, unsubstituted or substituted alkyl having 1 to 20 carbon atoms, unsubstituted or substituted haloalkyl having 1 to 20 carbon atoms, unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 60, preferably 6 to 30, more preferably 6 to 18 ring carbon atoms; substituted or unsubstituted heteroaryl having 5 to 60, preferably 5 to 30, more preferably 5 to 18 ring atoms, C(═O)R 22 , carboxamidoalkyl having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms, carboxamidoaryl having 6 to 18 ring carbon atoms in the aryl residue, OR 20 , SR 21 、C(=O)R 22 、COOR 23 、SiR 24 R 25 R 26 , unsubstituted or substituted aralkyl having 7 to 60 carbon atoms, unsubstituted or substituted alkenyl having 2 to 20 carbon atoms and unsubstituted or substituted alkynyl having 2 to 20 carbon atoms are known in the art and generally have the following meanings if the groups are not further specified in the specific embodiments mentioned below:

[0066] In the present invention, hydrogen includes isotopes having different neutron numbers, namely, protium, deuterium and tritium.

[0067] In the present specification, at a bondable position in a chemical formula in which a symbol representing a deuterium atom such as “R” or “D” is not indicated, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is bonded.

[0068] The presence of deuterium atoms in the compound is confirmed by mass spectrometry or 1H-NMR spectroscopy. The position of the deuterium atom bonded to the compound is determined by 1H-NMR analysis. Specifically, the following method can be used.

[0069] The compound to be measured is subjected to mass spectrometry. If the molecular weight increases by 1 compared to the molecular weight of the corresponding compound in which all hydrogen atoms are protium atoms, it can be confirmed that the compound contains one deuterium atom. In addition, the number of deuterium atoms in the molecule can be confirmed by the integral value obtained by 1H-NMR analysis of the compound to be measured, because deuterium atoms do not give signals in 1H-NMR analysis. In addition, the deuterium atom bonding position in the compound can be confirmed by performing 1H-NMR analysis of the compound to be measured and assigning the obtained signal.

[0070] The substituted or unsubstituted aryl group having 6 to 60, preferably 6 to 30, more preferably 6 to 18, and most preferably 6 to 13 ring carbon atoms may be a non-condensed aromatic group or a condensed aromatic group. Specific examples thereof include phenyl, naphthyl, phenanthrenyl, biphenyl, terphenyl, fluoranthenyl, triphenylenyl, phenanthrenyl, fluorenyl, indenyl, anthracenyl, phenyl, 1-naphthyl, 2-naphthyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, phenanthren-9-yl, phenanthren-3-yl, phenanthren-2-yl, phenanthren-2-yl, fluoren-2-yl, especially 9,9-di-C 1-20 Alkylfluoren-2-yl, such as 9,9-dimethylfluoren-2-yl, 9,9-di-C 6-18 Arylfluoren-2-yl, such as 9,9-diphenylfluoren-2-yl, or 9,9-di-C 5-18 The heteroaryl fluoren-2-yl, 1,1-dimethylindenyl, fluoranthene-3-yl, fluoranthene-2-yl and fluoranthene-8-yl groups are more preferred, and phenyl is most preferred.

[0071] The substituted or unsubstituted heteroaryl group having 5 to 60, preferably 5 to 30, more preferably 5 to 18 ring atoms, most preferably 5 to 13 ring atoms may be a non-fused heteroaromatic group or a fused heteroaromatic group. Specific examples thereof include a pyrrole ring, an isoindole ring, a benzofuran ring, an isobenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, a phenanthridine ring, a phenanthroline ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an indole ring, a quinoline ring, an acridine ring, a carbazole ring, a furan ring, a thiophene ring, a benzoxazole ring, a benzothiazole ring, a benzimidazole ring, a dibenzofuran ring, a triazine ring, an oxazole ring, an oxadiazole ring, a thiazole ring, a thiadiazole ring, a triazole ring, an imidazole ring, an indolidine ring, an imidazopyridine ring, 4-imidazo[1,2-a]benzimidazolyl, 5-benzimidazol[1,2-a] The residues of benzimidazolyl and benzimidazolo[2,1-b][1,3]benzothiazolyl, among which the residues of benzofuran ring, indole ring, benzothiophene ring, dibenzofuran ring, carbazole ring and dibenzothiophene ring are preferred, and the residues of benzofuran ring, 1-phenylindole ring, benzothiophene ring, dibenzofuran-1-yl, dibenzofuran-3-yl, dibenzofuran-2-yl, dibenzofuran-4-yl, 9-phenylcarbazole-3-yl, 9-phenylcarbazole-2-yl, 9-phenylcarbazole-4-yl, dibenzothiophene-2-yl and dibenzothiophene-4-yl, dibenzothiophene-1-yl and dibenzothiophene-3-yl are more preferred.

[0072] Examples of unsubstituted or substituted alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, wherein methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl are preferred. Preferably, there is an alkyl group having 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms. Suitable examples of alkyl groups having 1 to 8 carbon atoms or 1 to 4 carbon atoms are mentioned above.

[0073] Examples of unsubstituted or substituted haloalkyl groups having 1 to 20 carbon atoms include those disclosed as alkyl groups in which their hydrogen atoms are partially or completely replaced by halogen atoms. Preferred haloalkyl groups are fluoroalkyl groups having 1 to 20 carbon atoms including the alkyl groups mentioned above in which their hydrogen atoms are partially or completely replaced by fluorine atoms, such as CF3.

[0074] The example of the alkenyl with 2 to 20 carbon atoms that is unsubstituted or replaced comprises vinyl group, n-propylene group, isopropylene group, n-butylene group, isobutylene group, n-pentene group, n-hexene group, n-heptene group, n-octene group, n-nonene group, n-decene group, n-undecene group, n-dodecene group, n-tridecene group, n-tetradecene group, n-pentadecenyl group, n-hexadecene group, n-heptadecene group, n-octadecene group, n-octadecene group, wherein vinyl group, n-propylene group, isopropylene group, n-butylene group, isobutylene group are preferred.Preferably there is 2 to 8 carbon atoms, more preferably the alkenyl of 2 to 4 carbon atoms.The above mentioned suitable example of the alkenyl with 2 to 8 carbon atoms or 2 to 4 carbon atoms.

[0075] Examples of unsubstituted or substituted alkynyl groups having 2 to 20 carbon atoms include ethynyl, n-propynyl, n-butynyl, n-pentynyl, n-hexynyl, n-heptynyl, n-octynyl, of which ethynyl, n-propynyl, n-butynyl are preferred. Preferred are alkynyl groups having 2 to 8 carbon atoms, more preferably 2 to 4 carbon atoms. Suitable examples of alkynyl groups having 2 to 8 carbon atoms or 2 to 4 carbon atoms are mentioned above.

[0076] Examples of unsubstituted or substituted cycloalkyl groups having 3 to 20 ring carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and adamantyl, with cyclopentyl and cyclohexyl being preferred. Preferred are cycloalkyl groups having 3 to 6 carbon atoms. Suitable examples of cycloalkyl groups having 3 to 6 carbon atoms are mentioned above.

[0077] One example of the unsubstituted or substituted aralkyl group having 7 to 60 carbon atoms includes a benzyl group.

[0078] Examples of the halogen atom include fluorine, chlorine, bromine and iodine, among which fluorine is preferred.

[0079] Group OR 20 C is preferred 1-20 Alkoxy or C 6-18 Aryloxy. Examples of alkoxy groups having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms, include those having an alkyl moiety selected from the alkyl groups mentioned above. Examples of aryloxy groups having 6 to 18 ring carbon atoms include those having an aryl moiety selected from the aryl groups mentioned above, for example -OPh.

[0080] Group SR 21 C is preferred 1-20 Alkylthio or C 6-18Arylthio. Examples of alkylthio groups having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms, include those having an alkyl moiety selected from the alkyl groups mentioned above. Examples of arylthio groups having 6 to 18 ring carbon atoms include those having an aryl moiety selected from the aryl groups mentioned above, such as -SPh.

[0081] SiR 24 R 25 R 26 C is preferred 1-20 Alkyl and / or C 6-18 Aryl substituted silyl. 1-20 Alkyl and / or C 6-18 Preferred examples of aryl-substituted silyl groups include alkylsilyl groups having 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms, in each alkyl residue, including trimethylsilyl, triethylsilyl, tributylsilyl, dimethylethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, dimethylisopropylsilyl, dimethylpropylsilyl, dimethylbutylsilyl, dimethyltert-butylsilyl, diethylisopropylsilyl, and arylsilyl groups having 6 to 18 ring carbon atoms in each aryl residue, preferably triphenylsilyl, and alkyl / arylsilyl groups, preferably phenyldimethylsilyl, diphenylmethylsilyl and diphenyltert-butylsilyl, of which diphenyltert-butylsilyl and tert-butyldimethylsilyl are preferred.

[0082] Examples of the carboxamidoalkyl group (alkyl-substituted amide group) having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms include those having an alkyl moiety selected from the alkyl groups mentioned above.

[0083] Examples of the carboxamide aryl group (aryl-substituted amide group) having 6 to 18 carbon atoms, preferably 6 to 13 carbon atoms include those having an aryl moiety selected from the aryl groups mentioned above.

[0084] The optional substituents preferably each independently represent unsubstituted or substituted aryl having 6 to 18 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 18 ring atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; SiR 24 R 25 R 26 , SR 21 OR 20 ;

[0085] or

[0086] Two adjacent substituents together form a ring structure, which in turn is unsubstituted or substituted.

[0087] More preferably, the optional substituents each independently represent an unsubstituted or substituted aryl group having 6 to 18 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 18 ring atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms; or CN;

[0088] or

[0089] Two adjacent substituents together form a ring structure, which in turn is unsubstituted or substituted.

[0090] Most preferably, the optional substituents each independently represent unsubstituted or substituted alkyl having 1 to 4 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 6 ring carbon atoms; unsubstituted or substituted aryl having 6 to 13 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 13 ring atoms; or CN.

[0091] R 20 , R 21 and R 22 Each independently represents an unsubstituted or substituted aryl group having 6 to 18 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 18 ring atoms which is connected to N or O or S via a carbon atom; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms, preferably an unsubstituted or substituted aryl group having 6 to 18 ring carbon atoms; or an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms.

[0092] R 24 , R 25 and R 26 represents an unsubstituted or substituted aryl group having 6 to 18 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 18 ring atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms.

[0093] The above-mentioned optional substituents may be further substituted with one or more of the above-mentioned optional substituents.

[0094] The number of optional substituents depends on the number of groups substituted by the substituents. The maximum number of possible substituents is defined by the number of hydrogen atoms present. Preferably, each substituted group has 1, 2, 3, 5, 6, 7, 8 or 9 optional substituents, more preferably 1, 2, 3, 5, 5, 6 or 7 optional substituents, most preferably 1, 2, 3, 4 or 5 optional substituents, further most preferably 1, 2, 3, 4 or 5 optional substituents, further most preferably 1, 2, 3 or 4 optional substituents, further most preferably 1 or 2 optional substituents for each substituted group. In further preferred embodiments, some or all of the above groups are unsubstituted.

[0095] In a further preferred embodiment, the total number of substituents in the compounds of formula (I) is 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3, 4, 5 or 6, ie the remaining residues are hydrogen.

[0096] The "carbon number of a to b" in the expression "a substituted or unsubstituted X group having a to b carbon atoms" is the carbon number of the unsubstituted X group and does not include carbon atoms of the optional substituent.

[0097] The term "unsubstituted" referred to by "unsubstituted or substituted" means that the hydrogen atom is not replaced by one of the above mentioned groups.

[0098] The index 0 in the definitions in any of the formulae mentioned above and below means that a hydrogen atom is present at the position defined by said index.

[0099] An example of a ring structure formed by two adjacent substituents is shown below:

[0100] For example

[0101] For example

[0102] For example

[0103] For example

[0104] For example like

[0105] For example

[0106] For example

[0107] in

[0108] X stands for O, S or CR 68 R 69 ;

[0109] R 42 , R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 , R 54 , R 55 , R 56 , R 57 , R 58 , R 59 , R 60 , R 61 , R 62 , R 63 , R 64 , R 65 , R 66 and R 67 , R 70 , R 71 , R 72 , R 73 , R 74 , R 75 , R 76 , R 77 and R 78 Each independently represents hydrogen, unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms;

[0110] or

[0111] Two adjacent residues together form an unsubstituted or substituted ring structure,

[0112] The dashed lines are bonding sites;

[0113] R 68 and R 69 each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms or unsubstituted or substituted alkyl having 1 to 20 carbon atoms;

[0114] or

[0115] R68 and R 69 together form an unsubstituted or substituted aromatic ring structure having 3 to 13 ring atoms or an unsubstituted or substituted aliphatic ring structure having 3 to 9 ring atoms;

[0116] X" and Y" independently represent O, CR c R d , S, BR e or NR e ,

[0117] R c and R d Each independently represents a C1 to C8 alkyl group or a substituted or unsubstituted C6 to C 18 Aryl, preferably C1 to C4 alkyl or substituted or unsubstituted C6 to C 10 Aryl, more preferably methyl or unsubstituted or substituted phenyl,

[0118] R e represents a C1 to C8 alkyl group, preferably a C1 to C4 alkyl group, or a substituted or unsubstituted C6 to C 10 Aryl, preferably unsubstituted or substituted phenyl,

[0119] and

[0120] Dashed lines are bonding sites.

[0121] Preferred examples of the ring structure formed by two adjacent substituents are the ring structures (A), (D) and (G), and a more preferred ring structure formed by two adjacent substituents is

[0122]

[0123] Compounds of formula (I)

[0124] In the heterocyclic compound represented by formula (I)

[0125] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 At least one, preferably R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8At least one of represents an amino group NAr2Ar3. More preferably, R 2 and R 7 At least one of them represents an amino group NAr2Ar3, most preferably R 2 and / or R 7 represents amino group NAr2Ar3 and R 1 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 , R 10 and R 11 It does not represent amino group NAr2Ar3.

[0126] In amino NAr2Ar3:

[0127] Ar2 and Ar3 each independently represent an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 60 ring atoms. Preferably, Ar2 and Ar3 each independently represent an unsubstituted or substituted aryl group having 6 to 18 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 18 ring atoms.

[0128] More preferably, the amino group NAr2Ar3 is represented by the following formula (II):

[0129]

[0130] in

[0131] R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 each independently represents hydrogen, unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms,

[0132] or

[0133] Two adjacent residues R 27 , R 28 , R 29 , R 30 and R 31 and / or two adjacent residues R 32 , R 33 , R 34 , R35 and R 36 together to form an unsubstituted or substituted ring structure,

[0134] Preferably

[0135] R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 each independently represents hydrogen, unsubstituted or substituted aryl having 6 to 10 ring carbon atoms,

[0136] or

[0137] Two adjacent residues R 27 , R 28 , R 29 , R 30 and R 31 and / or two adjacent residues R 32 , R 33 , R 34 , R 35 and R 36 Together they form a ring structure of the following formula (A) or (D), preferably a ring structure of the following formula (A):

[0138]

[0139] in

[0140] X stands for O, S or CR 68 R 69 ;

[0141] R 42 , R 43 , R 44 , R 45 , R 60 , R 61 , R 62 and R 63 Each independently represents hydrogen, unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms;

[0142] or

[0143] Two adjacent residues together form an unsubstituted or substituted ring structure,

[0144] The dashed lines are bonding sites;

[0145] R 46 and R 47 each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms or unsubstituted or substituted alkyl having 1 to 20 carbon atoms;

[0146] or

[0147] R 68 and R 69 Together they form an unsubstituted or substituted aromatic ring structure having 3 to 13 ring atoms or an unsubstituted or substituted aliphatic ring structure having 3 to 9 ring atoms.

[0148] Preferably, R 27 , R 28 , R 29 , R 30 and R 31 0, 1 or 2 and / or R 32 , R 33 , R 34 , R 35 and R 36 0, 1 or 2 of each independently represent an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 60 ring atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, preferably an unsubstituted or substituted aryl group having 6 to 10 ring carbon atoms or an alkyl group having 1 to 4 carbon atoms,

[0149] or

[0150] Two adjacent residues R 27 , R 28 , R 29 , R 30 and R 31 and / or two adjacent residues R 32 , R 33 , R 34 , R 35 and R 36 Together they form an unsubstituted or substituted ring structure, preferably a ring structure of the following formula (A) or (D), more preferably a ring structure of the following formula (A)

[0151]

[0152] X stands for O, S or CR 68 R 69 , preferably O;

[0153] R 42 , R 43 , R 44 , R 45, R 60 , R 61 , R 62 and R 63 Each independently represents hydrogen, unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; preferably hydrogen, unsubstituted or substituted aryl having 6 to 13 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 13 ring atoms; unsubstituted or substituted alkyl having 1 to 4 carbon atoms; more preferably, R 42 , R 43 , R 44 and R 45 is hydrogen; and

[0154] R 68 and R 69 each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 13 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 13 ring atoms or unsubstituted or substituted alkyl having 1 to 4 carbon atoms;

[0155] and

[0156] R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 The remaining residues of are hydrogen, unsubstituted or substituted aryl having 6 to 10 ring carbon atoms or alkyl having 1 to 4 carbon atoms,

[0157] or

[0158] Two adjacent residues R 27 , R 28 , R 29 , R 30 and R 31 and / or two adjacent residues R 32 , R 33 , R 34 , R 35 and R 36 Together they form a ring structure of the above formula (A) or (D), more preferably a ring structure of the following formula (A).

[0159] More preferably, R 27 , R 28 , R 29 , R 30 , R 31 , R32 , R 33 , R 34 , R 35 and R 36 is hydrogen, unsubstituted or substituted aryl having 6 to 10 ring carbon atoms or alkyl having 1 to 4 carbon atoms,

[0160] or

[0161] Two adjacent residues R 27 , R 28 , R 29 , R 30 and R 31 and / or two adjacent residues R 32 , R 33 , R 34 , R 35 and R 36 Together they form a ring structure of the above formula (A) or (D), more preferably a ring structure of formula (A).

[0162] L1 represents a direct bond, an unsubstituted or substituted divalent aromatic hydrocarbon group containing 6 to 30 ring atoms, an unsubstituted or substituted divalent alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted divalent heteroaromatic group containing 3 to 30 ring atoms;

[0163] Preferably, L1 represents a direct bond, an unsubstituted or substituted divalent aromatic hydrocarbon group containing 6 to 30 ring atoms, an unsubstituted or substituted divalent heteroaromatic group containing 3 to 30 ring atoms;

[0164] More preferably, L1 represents a direct bond, an unsubstituted or substituted divalent aromatic hydrocarbon group containing 6 to 24 ring atoms, preferably 6 to 18 ring atoms, or an unsubstituted or substituted divalent heteroaromatic group containing 3 to 24 ring atoms, preferably 3 to 18 ring atoms;

[0165] Still more preferably, L1 represents a direct bond, an unsubstituted or substituted divalent phenyl group, an unsubstituted or substituted divalent naphthyl group, an unsubstituted or substituted divalent anthracenyl group, an unsubstituted or substituted phenanthrenyl group, an unsubstituted or substituted triphenylenyl group, a 9,9-dimethylfluorenyl group, an unsubstituted or substituted 9,9-diphenylfluorenyl group or an unsubstituted or substituted divalent heteroaromatic group containing 3 to 24 ring atoms, preferably 3 to 14 ring atoms;

[0166] Most preferably, L1 represents a direct bond, unsubstituted 1,4-phenylene, unsubstituted 1,3-phenylene, 1,4-phenylene substituted by phenyl, naphthyl or phenanthryl, 1,3-phenylene substituted by phenyl, naphthyl or phenanthryl, unsubstituted 1,4-naphthalene, unsubstituted 1,5-naphthalene, unsubstituted 1,6-naphthalene, unsubstituted 2,6-naphthalene, unsubstituted 2,7-9,9-diphenyl-fluorene, unsubstituted 2,5-9,9-diphenyl-fluorene, unsubstituted 2,7-9,9-dimethyl-fluorene, unsubstituted 2,5-9,9-dimethyl-fluorene, unsubstituted 2,7-triphenylenyl, unsubstituted 9,10-anthryl, substituted 9,6-anthryl, substituted 9,7-anthryl or an unsubstituted divalent heteroaromatic group containing 3 to 24 ring atoms, preferably 3 to 14 ring atoms;

[0167] Further most preferably, L1 represents a direct bond.

[0168] Ar1 represents an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 60 ring atoms or an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; preferably an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms or an unsubstituted or substituted heteroaryl group having 5 to 60 ring atoms; more preferably an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms.

[0169] Most preferably, Ar1 represents a group of formula (III)

[0170]

[0171] in

[0172] R 37 , R 38 , R 39 , R 40 and R 41 each independently represents hydrogen, unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms,

[0173] or

[0174] Two adjacent residues together form an unsubstituted or substituted ring structure,

[0175] The dashed lines are bonding sites.

[0176] Preferably, R 37 , R 38 , R 39 , R 40 and R 41Each independently represents hydrogen, unsubstituted or substituted aryl having 6 to 13 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 13 ring atoms; unsubstituted or substituted alkyl having 1 to 8 carbon atoms.

[0177] In a preferred embodiment of the invention, the group --- L1-Ar1 is thus

[0178] wherein L1 is a direct bond, and Ar1 is a group of formula (III).

[0179] More preferably, 0, 1, 2 or 3, preferably 0, 1 or 2 residues R 37 , R 38 , R 39 , R 40 and R 41 represents an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 60 ring atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms,

[0180] or

[0181] Two adjacent residues together form an unsubstituted or substituted ring structure,

[0182] The dashed lines are bonding sites;

[0183] Preferably, unsubstituted or substituted aryl having 6 to 13 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 13 ring atoms; unsubstituted or substituted alkyl having 1 to 8 carbon atoms;

[0184] and the remaining residues are hydrogen.

[0185] Most preferably, Ar1 represents a group of formula (IIIA)

[0186]

[0187] in

[0188] R 39 represents hydrogen, unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms or unsubstituted or substituted alkyl having 1 to 20 carbon atoms; preferably unsubstituted or substituted aryl having 6 to 13 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 13 ring atoms; unsubstituted or substituted alkyl having 1 to 8 carbon atoms;

[0189] The dashed lines are bonding sites.

[0190] L2 represents a direct bond, an unsubstituted or substituted divalent aromatic hydrocarbon group containing 6 to 30 ring atoms, an unsubstituted or substituted divalent alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted divalent heteroaromatic group containing 3 to 30 ring atoms;

[0191] Preferably, L2 represents a direct bond, an unsubstituted or substituted divalent aromatic hydrocarbon group containing 6 to 30 ring atoms, an unsubstituted or substituted divalent heteroaromatic group containing 3 to 30 ring atoms;

[0192] More preferably, L2 represents a direct bond, an unsubstituted or substituted divalent aromatic hydrocarbon group containing 6 to 24 ring atoms, preferably 6 to 18 ring atoms, or an unsubstituted or substituted divalent heteroaromatic group containing 3 to 24 ring atoms, preferably 3 to 18 ring atoms;

[0193] Still more preferably, L2 represents a direct bond, an unsubstituted or substituted divalent phenyl group, an unsubstituted or substituted divalent naphthyl group, an unsubstituted or substituted divalent anthracenyl group, an unsubstituted or substituted phenanthrenyl group, an unsubstituted or substituted triphenylenyl group, a 9,9-dimethylfluorenyl group, an unsubstituted or substituted 9,9-diphenylfluorenyl group, or an unsubstituted or substituted divalent heteroaromatic group containing 3 to 24 ring atoms, preferably 3 to 14 ring atoms;

[0194] Most preferably, L2 represents a direct bond, unsubstituted or substituted 1,2-phenylene, unsubstituted or substituted 1,4-phenylene, unsubstituted or substituted 1,3-phenylene, unsubstituted or substituted 1,4-naphthalene, unsubstituted or substituted 1,5-naphthalene, unsubstituted or substituted 1,6-naphthalene, unsubstituted or substituted 2,6-naphthalene, unsubstituted 2,7-9,9-diphenyl-fluorene, unsubstituted 2,5-9,9-diphenyl-fluorene, unsubstituted 2,7-9,9-dimethyl-fluorene, unsubstituted 2,5-9,9-dimethyl-fluorene, unsubstituted 2,7-triphenylenyl or an unsubstituted or substituted divalent heteroaromatic group containing 3 to 24 ring atoms, preferably 3 to 14 ring atoms;

[0195] Further most preferably, L2 represents a direct bond, unsubstituted 1,2-phenylene, unsubstituted 1,4-phenylene, unsubstituted 1,3-phenylene, 1,2-phenylene substituted by phenyl, naphthyl or phenanthryl, 1,4-phenylene substituted by phenyl, naphthyl or phenanthryl, 1,3-phenylene substituted by phenyl, naphthyl or phenanthryl, unsubstituted 1,4-naphthalene, unsubstituted 1,5-naphthalene, unsubstituted 1,6-naphthalene, unsubstituted 2,6-naphthalene, unsubstituted 2,7-9,9-diphenyl-fluorene, unsubstituted 2,5-9,9-diphenyl-fluorene, unsubstituted 2,7-9,9-dimethyl-fluorene, unsubstituted 2,5-9,9-dimethyl-fluorene, unsubstituted 2,7-triphenylenyl or an unsubstituted divalent heteroaromatic group containing 3 to 24 ring atoms, preferably 3 to 14 ring atoms;

[0196] Still further most preferably, L2 represents a direct bond.

[0197] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms; unsubstituted or substituted aralkyl having 7 to 60 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted haloalkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 20 SR 21 ; C(=O)R 22 ;COOR 23 ;SiR 24 R 25 R 26 , NAr2Ar3 or halogen;

[0198] or

[0199] Two adjacent residues together form an unsubstituted or substituted ring structure;

[0200] Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 At least one, preferably R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 At least one of the amino groups NAr2Ar3 is mentioned above and below as the preferred groups for NAr2Ar3 and their positions and occurrences in the structure of formula (I).

[0201] Preferably, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 18 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 18 ring atoms; unsubstituted or substituted aralkyl having 7 to 19 carbon atoms; unsubstituted or substituted alkyl having 1 to 8 carbon atoms; unsubstituted or substituted haloalkyl having 1 to 8 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 18 ring carbon atoms; CN; OR 20 SR 21 ;SiR 24 R 25 R 26 , NAr2Ar3 or halogen;

[0202] or

[0203] Two adjacent residues together form an unsubstituted or substituted ring structure, preferably a ring structure of formula (A), (D) and (G), more preferably a ring structure of the above formula (G);

[0204] Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 At least one, preferably R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 At least one of the amino groups NAr2Ar3 is mentioned above and below as the preferred groups for NAr2Ar3 and their positions and occurrences in the structure of formula (I).

[0205] More preferably, R 1 , R 2 , R 3 , R 4 , R5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 18 ring carbon atoms; unsubstituted or substituted alkyl having 1 to 8 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 18 ring carbon atoms, NAr2Ar3 or SiR 24 R 25 R 26 ;

[0206] or

[0207] Two adjacent residues together form a ring structure of the above formula (G);

[0208] Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 At least one, preferably R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 At least one of the amino groups NAr2Ar3 is mentioned above and below as the preferred groups for NAr2Ar3 and their positions and occurrences in the structure of formula (I).

[0209] Preferably, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 110, 1, 2, 3 or 4, more preferably 0, 1 or 2, of which each independently represents an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 60 ring atoms; an unsubstituted or substituted aralkyl group having 7 to 60 carbon atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; an unsubstituted or substituted haloalkyl group having 1 to 20 carbon atoms; an unsubstituted or substituted alkenyl group having 2 to 20 carbon atoms; an unsubstituted or substituted alkynyl group having 2 to 20 carbon atoms; an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms; CN; NO2; OR 20 SR 20 ; C(=O)R 21 ;COOR 22 ;SiR 24 R 25 R 26 or halogen;

[0210] or

[0211] Two adjacent residues together form an unsubstituted or substituted ring structure,

[0212] And R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 The remaining residues are hydrogen. The preferred residues R which are not hydrogen are mentioned above 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 ,

[0213] Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 At least one, preferably R 1 , R2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 At least one of them represents an amino group NAr2Ar3.

[0214] In a preferred embodiment, R 6 and / or R 10 each independently represents hydrogen, unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms; unsubstituted or substituted aralkyl having 7 to 60 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted haloalkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 20 SR 20 ; C(=O)R 21 ;COOR 22 ;SiR 24 R 25 R 26 or halogen;

[0215] And R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 The remaining residues are hydrogen. The preferred residues R which are not hydrogen are mentioned above 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 ,

[0216] Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R7 , R 8 , R 9 , R 10 and R 11 At least one, preferably R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 At least one of them represents an amino group NAr2Ar3.

[0217] Most preferably, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 It is hydrogen,

[0218] Where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 At least one, preferably R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 At least one of them represents an amino group NAr2Ar3.

[0219] R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms; unsubstituted or substituted aralkyl having 7 to 60 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted haloalkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 20 SR 21 ; C(=O)R 22 ;COOR 23 ;SiR 24 R 25 R 26 or halogen;

[0220] or

[0221] Two adjacent residues together form an unsubstituted or substituted ring structure,

[0222] Where R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One of them is the bonding site to L2.

[0223] Preferably, R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 18 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 18 ring atoms; unsubstituted or substituted aralkyl having 7 to 19 carbon atoms; unsubstituted or substituted alkyl having 1 to 8 carbon atoms; unsubstituted or substituted haloalkyl having 1 to 8 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 18 ring carbon atoms; CN; OR 20 SR 21 ;SiR 24 R 25 R 26 or halogen;

[0224] or

[0225] Two adjacent residues together form an unsubstituted or substituted ring structure, preferably a ring structure of the above formula (A), (D) or (G);

[0226] Where R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One of them is the bonding site to L2.

[0227] More preferably, R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 18 ring carbon atoms; unsubstituted or substituted alkyl having 1 to 8 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 18 ring carbon atoms or SiR 24 R 25 R 26 ;

[0228] or

[0229] Two adjacent residues together form a ring structure of the above formula (A) or (D);

[0230] Where R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One of them is the bonding site to L2.

[0231] Preferably, R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 190, 1 or 2, more preferably 0 or 1, of which each independently represents an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 60 ring atoms; an unsubstituted or substituted aralkyl group having 7 to 60 carbon atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; an unsubstituted or substituted haloalkyl group having 1 to 20 carbon atoms; an unsubstituted or substituted alkenyl group having 2 to 20 carbon atoms; an unsubstituted or substituted alkynyl group having 2 to 20 carbon atoms; an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms; CN; NO2; OR 20 SR 20 ; C(=O)R 21 ;COOR 22 ;SiR 24 R 25 R 26 or halogen;

[0232] or

[0233] Two adjacent residues together form an unsubstituted or substituted ring structure,

[0234] And R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 The remaining residues are hydrogen. The preferred residues R which are not hydrogen are mentioned above 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 .

[0235] In a preferred embodiment, R 13 represents hydrogen, unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms; unsubstituted or substituted aralkyl having 7 to 60 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted haloalkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 20 SR 20 ; C(=O)R 21 ;COOR 22 ;SiR24 R 25 R 26 or halogen;

[0236] And R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 The remaining residues are hydrogen. The preferred residues R which are not hydrogen are mentioned above 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 .

[0237] Most preferably, R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 is hydrogen, where R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One, preferably R 16 , R 17 , R 18 and R 19 One of them is the bonding site to L2.

[0238] R a and R b Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms or unsubstituted or substituted alkyl having 1 to 20 carbon atoms; preferably unsubstituted or substituted aryl having 6 to 13 ring carbon atoms; or unsubstituted or substituted alkyl having 1 to 8 carbon atoms; more preferably methyl or phenyl;

[0239] or

[0240] R a and R bTogether they form an unsubstituted or substituted aromatic ring structure having 3 to 13 ring atoms or an unsubstituted or substituted aliphatic ring structure having 3 to 9 ring atoms; preferably one of the following ring structures

[0241]

[0242] The dashed lines are bonding sites.

[0243] The most preferred group Where R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One of them is the bonding site with L2, which is represented by the following formula

[0244]

[0245] in

[0246] R a and R b Each independently represents an unsubstituted or substituted aryl group having 6 to 13 ring carbon atoms or an unsubstituted or substituted alkyl group having 1 to 8 carbon atoms; preferably a methyl group or a phenyl group;

[0247] or

[0248] R a and R b Together they form one of the following ring structures

[0249]

[0250] The dashed lines are bonding sites.

[0251] Preferred compounds of formula (I) are shown below, wherein the residues are as defined above

[0252]

[0253]

[0254] More preferred compounds of formula (I) are compounds wherein the residues are as defined above

[0255]

[0256]

[0257] In one embodiment, the compound of formula (I) has at least one deuterium atom. For example, one or more hydrogen atoms selected from the following are deuterium atoms:

[0258] By R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 Or by R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 the hydrogen atoms possessed by the resulting unsubstituted or substituted ring structure;

[0259] By R a and R b hydrogen atoms possessed by an unsubstituted or substituted aromatic ring structure having 3 to 13 ring atoms or an unsubstituted or substituted aliphatic ring structure having 3 to 9 ring atoms;

[0260] When R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 , R a and R b each being a hydrogen atom;

[0261] When the groups are each substituents, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R8 , R 9 , R 10 and R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 , R a and R b the number of hydrogen atoms each possesses; and

[0262] A hydrogen atom possessed by each of Ar1, Ar2, Ar3, L1 and L2.

[0263] Any of the above compounds may have at least one deuterium atom.

[0264] In any of the above compounds, at least one hydrogen atom in Ar2 or Ar3 may be a deuterium atom.

[0265] In any of the above compounds, R 27 To R 36 At least one of may be a deuterium atom.

[0266] In any of the above compounds, R 27 To R 36 Both can be deuterium atoms.

[0267] Examples of compounds of formula (I) are given below. In the following specific examples, "D" represents a deuterium atom.

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300] Preparation of compounds of formula (I)

[0301] The compounds represented by formula (I) can be synthesized according to the reactions performed in the examples of the present application and by reactions and starting materials similar to those known in the art, using alternative reactions or starting materials suitable for the desired product.

[0302] The compound of formula (I) is prepared, for example, by the following steps:

[0303] BHal'3 is added to intermediate (IV), thereby obtaining a compound of formula (I):

[0304]

[0305] in

[0306] Hal represents halogen, preferably F, Cl, Br or I, more preferably Cl or Br, most preferably Br;

[0307] R-Li represents an alkyl lithium, for example, tert-butyl lithium, sec-butyl lithium or n-butyl lithium;

[0308] The boron reagent represents, for example, trimethyl borate, triethyl borate, triisopropyl borate, 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, BF3, BCl3, BBr3 or BI3;

[0309] The Lewis acid represents, for example, BCl 3 , BBr 3 , BI 3 , AlCl 3 , TiCl 4 , ZrCl 4 or BF 3 , preferably in the presence of an amine base, for example N-ethyl-N-isopropylpropan-2-amine, triethylamine, 2,6-lutidine, pyridine, 2,2,6,6-tetramethylpiperidine or 2,4,6-tri-tert-butylpyridine;

[0310] Z represents B(Rx)2;

[0311] R x represents halogen, preferably Cl or Br, or OR y ;

[0312] R y represents hydrogen, unsubstituted or substituted C1 to C10 alkyl, preferably methyl, ethyl, isopropyl, or

[0313] Two groups R y can form a ring together, preferably a 5- or 6-membered ring, thereby preferably forming one of the following groups

[0314]

[0315] All other residues and indices are as defined above.

[0316] Intermediate (IV) is prepared, for example, by the following steps:

[0317] (i)

[0318]

[0319] (ii)

[0320]

[0321] in

[0322] Hal a represents halogen, preferably F, Cl, Br or I, more preferably Cl or Br, most preferably Br;

[0323] Hal b represents halogen, preferably F, Cl, Br or I, more preferably I;

[0324] Base A and base B are each independently any suitable base; preferred bases are alkali metal tert-butoxides, such as KOtBu and NaOtBu);

[0325] Catalyst A and catalyst B are each independently any suitable catalyst; the preferred catalyst is a Pd catalyst;

[0326] All other residues and indices are as defined above.

[0327] Suitable Pd catalysts are, for example, Pd(0) complexes with bidentate ligands such as dba (dibenzylideneacetone), or in combination with bidentate phosphine ligands such as dppf ((diphenylphosphino)ferrocene), dppp ((diphenylphosphino)propane), BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl), Xantphos (4,5-bis(diphenylphosphino)-9,9-dimethylxanthene), DPEphos (bis[(2-diphenylphosphino)phenyl]ether) or Josiphos, or in combination with monodentate phosphine ligands such as di-tert-butyl-( Pd(II) salts such as PdCl2 or Pd(OAc)2 in combination with N-heterocyclic carbene such as 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr), 1,3-dimesityl imidazol-2-ylidene (Imes).

[0328] Josiphos:

[0329] wherein R and R' are typically substituted or unsubstituted phenyl.

[0330] Suitable reaction conditions are known to those skilled in the art.

[0331] Details of all reaction steps and process conditions are mentioned in the examples of this application.

[0332] Organic electroluminescent devices

[0333] According to one aspect of the present invention, there is provided a material for an organic electroluminescent device, comprising at least one compound of formula (I).

[0334] According to another aspect of the present invention, there is provided an organic electroluminescent device comprising at least one compound of formula (I).

[0335] According to another aspect of the present invention, the following organic electroluminescent device is provided: an organic electroluminescent device comprising a cathode, an anode and one or more organic thin film layers containing a light-emitting layer arranged between the cathode and the anode, wherein at least one layer of the organic thin film layer comprises at least one compound of formula (I).

[0336] According to another aspect of the present invention, an organic electroluminescent device is provided, wherein the light-emitting layer comprises at least one compound of formula (I).

[0337] According to another aspect of the present invention, an organic electroluminescent device is provided, wherein the light-emitting layer comprises at least one compound of formula (I) as a dopant material and an anthracene compound as a host material.

[0338] According to another aspect of the present invention, there is provided an electronic device having the organic electroluminescent device according to the present invention.

[0339] According to another aspect of the present invention, there is provided an emitter material comprising at least one compound of formula (I).

[0340] According to another aspect of the present invention, there is provided a light-emitting layer comprising at least one host and at least one dopant, wherein the dopant comprises at least one compound of formula (I).

[0341] According to another aspect of the present invention, there is provided use of the compound of formula (I) according to the present invention in an organic electroluminescent device.

[0342] In one embodiment, the organic EL device comprises a hole transport layer between the anode and the emissive layer.

[0343] In one embodiment, the organic EL device comprises an electron transport layer between the cathode and the emissive layer.

[0344] In this specification, with respect to "one or more organic thin film layers between the emission layer and the anode", if there is only one organic layer between the emission layer and the anode, it refers to that layer, and if there are multiple organic layers, it refers to at least one layer thereof. For example, if there are two or more organic layers between the emission layer and the anode, the organic layer closer to the emission layer is referred to as the "hole transport layer", and the organic layer closer to the anode is referred to as the "hole injection layer". The "hole transport layer" and the "hole injection layer" can each be a single layer or can be formed by two or more layers. One of these layers can be a single layer, and the other can be formed by two or more layers.

[0345] Similarly, with respect to “one or more organic thin film layers between the emission layer and the cathode”, if there is only one organic layer between the emission layer and the cathode, it refers to that layer, and if there are multiple organic layers, it refers to at least one layer thereof. For example, if there are two or more organic layers between the emission layer and the cathode, the organic layer closer to the emission layer is referred to as the “electron transport layer”, and the organic layer closer to the cathode is referred to as the “electron injection layer”. The “electron transport layer” and the “electron injection layer” can each be a single layer or can be formed of two or more layers. One of these layers can be a single layer, and the other can be formed of two or more layers.

[0346] The "one or more organic thin film layers comprising an emission layer" mentioned above, preferably an emission layer, comprises a compound represented by formula (I). The compound represented by formula (I) preferably acts as an emitter material, more preferably acts as a fluorescent emitter material, and most preferably acts as a blue fluorescent emitter material. The compound of formula (I) is present in an organic EL device, preferably in an emission layer, to provide an organic EL device characterized by high external quantum efficiency (EQE) and long life.

[0347] According to another aspect of the present invention, there is provided an emission layer of an organic electroluminescent device, comprising at least one compound of formula (I).

[0348] Preferably, the emissive layer comprises at least one emissive material (dopant material) and at least one host material, wherein the emissive material is at least one compound of formula (I).

[0349] In one embodiment, the host is not selected from CBP (4,4′-bis-(N-carbazolyl)-biphenyl), mCP, mCBPSif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophen-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, azole, 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).

[0350] Preferred host materials are substituted or unsubstituted polycyclic aromatic hydrocarbon (PAH) compounds, substituted or unsubstituted polycyclic heteroaromatic compounds, substituted or unsubstituted anthracene compounds, or substituted or unsubstituted pyrene compounds.

[0351] More preferably, the organic electroluminescent device according to the present invention comprises at least one compound of formula (I) as a dopant material and at least one host material selected from substituted or unsubstituted polycyclic aromatic hydrocarbon (PAH) compounds, substituted or unsubstituted polycyclic heteroaromatic compounds, substituted or unsubstituted anthracene compounds and substituted or unsubstituted pyrene compounds in the emission layer. Preferably, the at least one host is at least one substituted or unsubstituted anthracene compound.

[0352] In a further preferred embodiment, the organic electroluminescent device according to the present invention comprises at least one compound of formula (I) as a dopant material and at least one host material selected from substituted or unsubstituted polycyclic aromatic hydrocarbon (PAH) compounds, substituted or unsubstituted anthracene compounds and substituted or unsubstituted pyrene compounds in the emission layer. Preferably, the at least one host is at least one substituted or unsubstituted anthracene compound.

[0353] According to another aspect of the present invention, there is provided an emission layer of an organic electroluminescent device, comprising at least one compound of formula (I) as a dopant material and an anthracene compound as a host material.

[0354] Suitable anthracene compounds are represented by the following formula (10):

[0355]

[0356] in

[0357] Two or more adjacent R 101 To R 110 One or more pairs of may form a substituted or unsubstituted, saturated or unsaturated ring;

[0358] R does not form a substituted or unsubstituted, saturated or unsaturated ring 101 To R 110 independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylene group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, -Si(R 121 )(R 122 )(R 123 ), -C(=O)R 124 、-COOR 125 、-N(R 126 )(R 127 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or a group represented by the following formula (31);

[0359] R 121 To R 127 are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; when R 121 To R 127 When multiple R 121 To R 127 Each can be the same or different;

[0360] Provided that there is no R forming a substituted or unsubstituted, saturated or unsaturated ring 101 To R 110 At least one of the groups is a group represented by the following formula (31). If there are two or more groups represented by the formula (31), these groups may be the same or different;

[0361] -L 101 -Ar 101(31)

[0362] In formula (31),

[0363] L 101 is a single bond, a substituted or unsubstituted arylene group containing 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group containing 5 to 30 ring atoms;

[0364] Ar 101 is a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group comprising 5 to 50 ring atoms.

[0365] Each substituent in the compound (10), specific examples for the "substituted or unsubstituted" substituent and the halogen atom are the same as those mentioned above.

[0366] "Two or more adjacent R 101 To R 110 One or more pairs of them may form a substituted or unsubstituted, saturated or unsaturated ring”.

[0367] "Two or more adjacent R 101 To R 110 A pair of "is for example R 101 and R 102 , R 102 and R 103 , R 103 and R 104 , R 105 and R 106 , R 106 and R 107 , R 107 and R 108 , R 108 and R 109 , R 101 and R 102 and R 103 And so on.

[0368] The substituent in "substituted" in "substituted or unsubstituted" with respect to the saturated or unsaturated ring is the same as the substituent in "substituted or unsubstituted" mentioned in formula (10).

[0369] When R 101 and R 102 When forming a ring, a "saturated or unsaturated ring" refers to, for example, a ring consisting of 101 The carbon atom bonded to R 102 A ring formed by bonding carbon atoms and one or more arbitrary elements. Specifically, when the ring is composed of R 101 and R 102 When the unsaturated ring is formed by 101The carbon atom bonded to R 102 When the bonded carbon atom is formed with four carbon atoms, R 101 and R 102 The ring formed is a benzene ring.

[0370] The "arbitrary element" is preferably a C element, a N element, an O element or an S element. In the arbitrary element (for example, a C element or a N element), atomic bonds that do not form a ring may be terminated with a hydrogen atom or the like.

[0371] The “one or more arbitrary elements” are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, further preferably 3 or more and 5 or less arbitrary elements.

[0372] For example, R 101 and R 102 Can form a ring, at the same time, R 105 and R 106 In this case, the compound represented by formula (10) is, for example, a compound represented by the following formula (10A):

[0373]

[0374] In one embodiment, R 101 To R 110 It is independently a hydrogen atom, a substituted or unsubstituted alkyl group containing 1 to 50 carbon atoms, a substituted or unsubstituted aryl group containing 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group containing 5 to 50 ring atoms, or a group represented by formula (31).

[0375] Preferably, R 101 To R 110 It is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by formula (31).

[0376] More preferably, R 101 To R 110 It is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, or a group represented by formula (31).

[0377] Most preferably, R 109 and R 110 At least one of them is a group represented by formula (31).

[0378] More preferably, R 109 and R 110 are independently a group represented by formula (31).

[0379] In one embodiment, compound (10) is a compound represented by the following formula (10-1):

[0380]

[0381] In formula (10-1), R 101 To R 108 , L 101 and Ar 101 As defined in formula (10).

[0382] In one embodiment, compound (10) is a compound represented by the following formula (10-2):

[0383]

[0384] In formula (10-2), R 101 , R 103 To R 108 , L 101 and Ar 101 As defined in formula (10).

[0385] In one embodiment, compound (10) is a compound represented by the following formula (10-3):

[0386]

[0387] In formula (10-3),

[0388] R 101A To R 108A is independently a hydrogen atom or a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms;

[0389] L 101A is a single bond or a substituted or unsubstituted arylene group containing 6 to 30 ring carbon atoms, and two L 101A Can be the same or different;

[0390] Ar 101A is a substituted or unsubstituted aryl group containing 6 to 50 ring carbon atoms, and both Ar 101A Can be the same or different.

[0391] In one embodiment, compound (10) is a compound represented by the following formula (10-4):

[0392]

[0393] In formula (10-4),

[0394] L 101 and Ar101 As defined in formula (10);

[0395] R 101A To R 108A is independently a hydrogen atom or a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms;

[0396] X 11 is O, S or N (R 61’ );

[0397] R 61’ is a hydrogen atom, a substituted or unsubstituted alkyl group containing 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group containing 6 to 50 ring carbon atoms;

[0398] R 62’ To R 69’ One is with L 101 Bonding atoms bond;

[0399] No with L 101 Bonded adjacent R 62’ To R 69’ One or more pairs of may be bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring; and

[0400] No with L 101 R is bonded and does not form a substituted or unsubstituted, saturated or unsaturated ring 62’ To R 69’ are independently a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms.

[0401] In one embodiment, compound (10) is a compound represented by the following formula (10-4A):

[0402]

[0403] In formula (10-4A),

[0404] L 101 and Ar 101 As defined in formula (10);

[0405] R 101A To R 108A is independently a hydrogen atom or a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms;

[0406] X 11 is O, S or N (R 61 );

[0407] R 61is a hydrogen atom, a substituted or unsubstituted alkyl group containing 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group containing 6 to 50 ring carbon atoms;

[0408] Two or more adjacent R 62A To R 69A One or more pairs of may form a substituted or unsubstituted, saturated or unsaturated ring, and R 62A To R 69A Two adjacent ones of form a ring represented by the following formula (10-4A-1); and

[0409] R does not form a substituted or unsubstituted, saturated or unsaturated ring 62A To R 69A are independently a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms.

[0410]

[0411] In formula (10-4A-1),

[0412] Two atoms bond* each to R 62A To R 69A Two adjacent bonds;

[0413] R 70’ To R 73’ One is with L 101 bonding atoms; and

[0414] No with L 101 Bonded R 70’ To R 73’ are independently a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms.

[0415] In one embodiment, compound (10) is a compound represented by the following formula (10-6):

[0416]

[0417] In formula (10-6),

[0418] L 101 and Ar 101 As defined in formula (10);

[0419] R 101A To R 108A As defined in formula (10-4);

[0420] R 66’ To R 69’As defined in formula (10-4); and

[0421] X 12 It is O or S.

[0422] In one embodiment, the compound represented by formula (10-6) is a compound represented by the following formula (10-6H):

[0423]

[0424] Wherein in the formula (10-6H),

[0425] L 101 and Ar 101 As defined in formula (10);

[0426] R 66’ To R 69’ As defined in formula (10-4); and

[0427] X 12 It is O or S.

[0428] In one embodiment, the compound represented by formula (10-6) and (10-6H) is a compound represented by the following formula (10-6Ha):

[0429]

[0430] In the formula (10-6Ha),

[0431] L 101 and Ar 101 As defined in formula (10); and

[0432] X 12 It is O or S.

[0433] In one embodiment, the compound represented by formula (10-6), (10-6H) and (10-6Ha) is a compound represented by the following formula (10-6Ha-1) or (10-6Ha-2):

[0434]

[0435] Wherein in the formula (10-6Ha-1) and (10-6Ha-2),

[0436] L 101 and Ar 101 As defined in formula (10); and

[0437] X 12 It is O or S.

[0438] In one embodiment, compound (10) is a compound represented by the following formula (10-7):

[0439]

[0440] In formula (10-7),

[0441] L 101 and Ar 101 As defined in formula (10);

[0442] R 101A To R 108A As defined in formula (10-4);

[0443] X 11 As defined in formula (10-4); and

[0444] R 62’ To R 69’ As defined in formula (10-4), the condition is that R 66’ and R 67’ , R 67’ and R 68’ and R 68’ and R 69’ Any pair of is bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring.

[0445] In one embodiment, compound (10) is a compound represented by the following formula (10-7H):

[0446]

[0447] Wherein in formula (10-7H),

[0448] L 101 and Ar 101 As defined in formula (10);

[0449] X 11 As defined in formula (10-4); and

[0450] R 62’ To R 69’ As defined in formula (10-4), the condition is that R 66’ and R 67’ , R 67’ and R 68’ and R 68’ and R 69’ Any pair of is bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring.

[0451] In one embodiment, compound (10) is a compound represented by the following formula (10-8):

[0452]

[0453] In formula (10-8),

[0454] L 101 and Ar 101 As defined in formula (10);

[0455] R 101A To R 108A As defined in formula (10-4);

[0456] X 12 is O or S; and

[0457] R 66’ To R 69’ As defined in formula (10-4), the condition is that R 66’ and R 67’ , R 67’ and R 68’ and R 68’ and R 69’ Any pair of is bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring.

[0458] In one embodiment, the compound represented by formula (10-8) is a compound represented by the following formula (10-8H):

[0459]

[0460] In the formula (10-8H), L 101 and Ar 101 As defined in formula (10).

[0461] R 66’ To R 69’ As defined in formula (10-4), the condition is that R 66’ and R 67’ , R 67’ and R 68’ and R 68’ and R 69’ Any pair of R is bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring. 66’ and R 67’ , R 67’ and R 68’ and R 68’ and R 69’ Any pair of may preferably be bonded to each other to form an unsubstituted benzene ring; and

[0462] X 12 It is O or S.

[0463] In one embodiment, for the compound represented by formula (10-7), (10-8) or (10-8H), R 66’ and R 67’ , R 67’ and R 68’ and R 68’ and R 69’ Any pair of R is bonded to each other to form a ring represented by the following formula (10-8-1) or (10-8-2), and R does not form a ring represented by the following formula (10-8-1) or (10-8-2). 66’ To R 69’ No substituted or unsubstituted, saturated or unsaturated ring is formed.

[0464]

[0465] In formulas (10-8-1) and (10-8-2),

[0466] Two atoms bond* independently to R 66’ and R 67’ , R 67’ and R 68’ or R 68’ and R 69’ A pair of bonds;

[0467] R 80 To R 83 are independently a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms; and

[0468] X 13 It is O or S.

[0469] In one embodiment, compound (10) is a compound represented by the following formula (10-9):

[0470]

[0471] In formula (10-9),

[0472] L 101 and Ar 101 As defined in formula (10);

[0473] R 101A To R 108A As defined in formula (10-4);

[0474] R 66’ To R 69’ As defined in formula (10-4), the condition is that R 66’ and R 67’ , R 67’ and R68’ and R 68’ and R 69’ are not bonded to each other and do not form a substituted or unsubstituted, saturated or unsaturated ring; and

[0475] X 12 It is O or S.

[0476] In one embodiment, compound (10) is selected from the compounds represented by the following formulae (10-10-1) to (10-10-4).

[0477]

[0478] In formulas (10-10-1H) to (10-10-4H), L 101A and Ar 101A As defined in formula (10-3).

[0479] In one embodiment, in the compound represented by formula (10-1), at least one Ar 101 It is a monovalent group having a structure represented by the following formula (50).

[0480]

[0481] In formula (50),

[0482] X 151 is O, S or C (R 161 )(R 162 ).

[0483] R 151 To R 160 One is with L 101 Single bond bonding.

[0484] Not with L 101 One or more groups of two or more adjacent R 151 To R 154 and one or more groups of two or more adjacent R 155 To R 160 They form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or they do not form a substituted or unsubstituted, saturated or unsaturated ring.

[0485] R 161 and R 162 They form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or they do not form a substituted or unsubstituted, saturated or unsaturated ring.

[0486] R does not form a substituted or unsubstituted, saturated or unsaturated ring 161 and R 162, and not with L 101 R is a single bond bonded to the ring and does not form a substituted or unsubstituted, saturated or unsaturated ring 151 To R 160 The alkyl radicals are independently hydrogen atoms, substituted or unsubstituted alkyl radicals including 1 to 50 carbon atoms, substituted or unsubstituted haloalkyl radicals including 1 to 50 carbon atoms, substituted or unsubstituted alkenyl radicals including 2 to 50 carbon atoms, substituted or unsubstituted alkynyl radicals including 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl radicals including 3 to 50 ring carbon atoms, substituted or unsubstituted alkoxy radicals including 1 to 50 carbon atoms, substituted or unsubstituted alkylene radicals including 1 to 50 carbon atoms, substituted or unsubstituted alkylene radicals including 6 to 8 ... A substituted or unsubstituted aryloxy group having 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, -Si(R121)(R122)(R123), -C(=O)R124, -COOR125, -N(R126)(R127), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0487] Ar is not a monovalent group having a structure represented by formula (50) 101 is a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group comprising 5 to 50 ring atoms.

[0488] In equation (50), it will become 101 The position of the single bond is not particularly limited. In one embodiment, R in formula (50) 151 To R 160 One is with L 101 Single bond bonding.

[0489] In one embodiment, Ar 101 It is the following formula (50-R 152 )、(50-R 153 )、(50-R 154 )、(50-R 157 ) or (50-R 158 ) is a monovalent group represented by

[0490]

[0491] In the formula (50-R 152 )、(50-R 153 )、(50-R 154 )、(50-R 157 ) and (50-R 158 ), X151 , R 151 To R 160 As defined in formula (50).

[0492] * is with L 101 Single bond bonding.

[0493] As for the compound represented by formula (10), the following compounds can be given as specific examples. The compound represented by formula (10) is not limited to these specific examples. In the following specific examples, "D" represents a deuterium atom.

[0494]

[0495]

[0496]

[0497]

[0498]

[0499]

[0500]

[0501]

[0502]

[0503]

[0504]

[0505]

[0506]

[0507]

[0508] In the case where the emission layer comprises a compound represented by formula (I) as a dopant and at least one host (wherein the host is preferably as mentioned above, and the host is more preferably at least one compound represented by formula (10)), the content of the at least one compound represented by formula (I) is preferably 0.5% to 70% by mass, more preferably 0.5 to 30% by mass, further preferably 1 to 30% by mass, even further preferably 1 to 20% by mass, particularly preferably 1 to 10% by mass, and further particularly preferably 1 to 5% by mass, relative to the total mass of the emission layer.

[0509] Relative to the total mass of the emission layer, the content of the at least one host (wherein the preferred host is as mentioned above), preferably the at least one compound represented by formula (10), is preferably 30% to 99.9% by mass, more preferably 70 to 99.5% by mass, further preferably 70 to 99% by mass, further preferably 80 to 99% by mass, particularly preferably 90 to 99% by mass, and further particularly preferably 95 to 99% by mass.

[0510] An explanation will be given of the layer configuration of an organic EL device according to one aspect of the present invention.

[0511] The organic EL device according to one aspect of the present invention comprises a cathode, an anode and one or more organic thin film layers containing an emission layer arranged between the cathode and the anode. The organic layer comprises at least one layer composed of an organic compound. Alternatively, the organic layer is formed by laminating a plurality of layers composed of organic compounds. The organic layer may further comprise an inorganic compound in addition to the organic compound.

[0512] At least one organic layer is an emission layer. The organic layer may be configured, for example, as a single emission layer, or may include other layers that may be used in the layer structure of an organic EL device. The layers that may be used in the layer structure of an organic EL device are not particularly limited, but examples thereof include a hole transport region (comprising at least one hole transport layer, and preferably further comprising at least one of a hole injection layer, an electron blocking layer, an exciton blocking layer, etc.), an emission layer, a spacer layer, and an electron transport region (comprising at least one electron transport layer, and preferably further comprising at least one of an electron injection layer, a hole blocking layer, etc.) disposed between the cathode and the emission layer.

[0513] The organic EL device according to one aspect of the present invention can be, for example, a fluorescent or phosphorescent monochromatic light emitting device or a fluorescent / phosphorescent mixed white light emitting device. Preferably, the organic EL device is a fluorescent monochromatic light emitting device, more preferably a blue fluorescent monochromatic light emitting device or a fluorescent / phosphorescent mixed white light emitting device. Blue fluorescence refers to fluorescence at 400 to 500nm (peak maximum), preferably at 430nm to 490nm (peak maximum).

[0514] Furthermore, it may be a simple type device having a single emission unit or a series type device having a plurality of emission units.

[0515] An 'emission unit' in this specification is a minimum unit including organic layers, wherein at least one organic layer is an emission layer and emits light through recombination of injected holes and electrons.

[0516] In addition, the "emission layer" described in this specification is an organic layer having an emission function. The emission layer is, for example, a phosphorescent emission layer, a fluorescent emission layer, etc., preferably a fluorescent emission layer, more preferably a blue fluorescent emission layer, and can be a single layer or a stack of multiple layers.

[0517] The emission unit may be a stacked unit having a plurality of phosphorescent emission layers or fluorescent emission layers. In this case, for example, a spacer layer for preventing excitons generated in the phosphorescent emission layer from diffusing into the fluorescent emission layer may be provided between the respective emission layers.

[0518] As a simple type organic EL device, a device configuration such as anode / emitting element / cathode can be given.

[0519] An example of a representative layer structure of an emission unit is shown below. The layers in brackets are provided arbitrarily.

[0520] (a) (hole injection layer / ) hole transport layer / fluorescence emission layer ( / electron transport layer / electron injection layer)

[0521] (b) (hole injection layer / hole transport layer / phosphorescent emission layer / electron transport layer / electron injection layer)

[0522] (c) (hole injection layer / hole transport layer / first fluorescent emission layer / second fluorescent emission layer ( / electron transport layer / electron injection layer)

[0523] (d) (hole injection layer / hole transport layer / first phosphorescent layer / second phosphorescent layer ( / electron transport layer / electron injection layer)

[0524] (e) (hole injection layer / ) hole transport layer / phosphorescent emission layer / spacer layer / fluorescent emission layer ( / electron transport layer / electron injection layer)

[0525] (f) (hole injection layer / hole transport layer / first phosphorescent emission layer / second phosphorescent emission layer / spacer layer / fluorescent emission layer ( / electron transport layer / electron injection layer)

[0526] (g) (hole injection layer / hole transport layer / first phosphorescent layer / spacer layer / second phosphorescent emission layer / spacer layer / fluorescent emission layer ( / electron transport layer / electron injection layer)

[0527] (h) (hole injection layer / ) hole transport layer / phosphorescent emission layer / spacer layer / first fluorescent emission layer / second fluorescent emission layer ( / electron transport layer / electron injection layer)

[0528] (i) (hole injection layer / ) hole transport layer / electron blocking layer / fluorescence emission layer ( / electron transport layer / electron injection layer)

[0529] (j) (hole injection layer / ) hole transport layer / electron blocking layer / phosphorescent emission layer ( / electron transport layer / electron injection layer)

[0530] (k) (hole injection layer / ) hole transport layer / exciton blocking layer / fluorescence emission layer ( / electron transport layer / electron injection layer)

[0531] (l) (hole injection layer / hole transport layer / exciton blocking layer / phosphorescent emission layer / electron transport layer / electron injection layer)

[0532] (m) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescence emission layer ( / electron transport layer / electron injection layer)

[0533] (n) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescence emission layer ( / first electron transport layer / second electron transport layer / electron injection layer)

[0534] (o) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent emission layer ( / electron transport layer / electron injection layer)

[0535] (p) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent emission layer ( / first electron transport layer / second electron transport layer / electron injection layer)

[0536] (q) (hole injection layer / ) hole transport layer / fluorescence emission layer / hole blocking layer ( / electron transport layer / electron injection layer)

[0537] (r) (hole injection layer / ) hole transport layer / phosphorescent emission layer / hole blocking layer ( / electron transport layer / electron injection layer)

[0538] (s) (hole injection layer / ) hole transport layer / fluorescence emission layer / exciton blocking layer ( / electron transport layer / electron injection layer)

[0539] (t) (hole injection layer / ) hole transport layer / phosphorescent emission layer / exciton blocking layer ( / electron transport layer / electron injection layer)

[0540] The layer structure of the organic EL device according to one aspect of the present invention is not limited to the above-mentioned examples.

[0541] For example, when the organic EL device has a hole injection layer and a hole transport layer, the hole injection layer is preferably provided between the hole transport layer and the anode. In addition, when the organic EL device has an electron injection layer and an electron transport layer, the electron injection layer is preferably provided between the electron transport layer and the cathode. In addition, the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer can each be formed by a single layer or by a plurality of layers.

[0542] Multiple phosphorescent emission layers, and multiple phosphorescent emission layers and fluorescent emission layers can be emission layers that emit different colors from each other. For example, the emission unit (F) may include a hole transport layer / a first phosphorescent layer (red light emission) / a second phosphorescent emission layer (green light emission) / a spacer layer / a fluorescent emission layer (blue light emission) / an electron transport layer.

[0543] An electron blocking layer may be provided between each light-emitting layer and a hole transport layer or a spacer layer. In addition, a hole blocking layer may be provided between each emission layer and an electron transport layer. By providing an electron blocking layer or a hole blocking layer, it is possible to confine electrons or holes in the emission layer, thereby improving the probability of carrier recombination in the emission layer and improving the luminous efficiency.

[0544] As a representative device configuration of the tandem organic EL device, for example, a device configuration such as anode / first emission unit / intermediate layer / second emission unit / cathode can be given.

[0545] The first emitting unit and the second emitting unit are independently selected from, for example, the emitting units described above.

[0546] The intermediate layer is also generally referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron-withdrawing layer, a connecting layer, a connector layer, or an intermediate insulating layer. The intermediate layer is a layer that supplies electrons to the first emission unit and holes to the second emission unit, and can be formed of a known material.

[0547] Figure 1 A schematic configuration of an example of an organic EL device of the present invention is shown. The organic EL device 1 includes a substrate 2, an anode 3, a cathode 4, and an emission unit 10 disposed between the anode 3 and the cathode 4. The emission unit 10 includes an emission layer 5, which preferably includes a host material and a dopant. A hole injection and transport layer 6 and the like may be provided between the emission layer 5 and the anode 3, and an electron injection layer 8 and an electron transport layer 7 and the like (electron injection and transport unit 11) may be provided between the emission layer 5 and the cathode 4. An electron blocking layer may be provided on the anode 3 side of the emission layer 5, and a hole blocking layer may be provided on the cathode 4 side of the emission layer 5. Due to such a configuration, electrons or holes may be confined in the emission layer 5, thereby improving the possibility of generating excitons in the emission layer 5.

[0548] The functions, materials, and the like of the respective layers constituting the organic EL device described in this specification will be explained below.

[0549] (Substrate)

[0550] The substrate is used as a carrier of the organic EL device. The substrate preferably has a light transmittance of 50% or more in the visible light region with a wavelength of 400 to 700nm, and a smooth substrate is preferred. Examples of substrate materials include soda-lime glass, aluminosilicate glass, quartz glass, plastics, etc. As a substrate, a flexible substrate can be used. A flexible substrate refers to a substrate that can be bent (flexible), examples of which include plastic substrates, etc. Specific examples of materials for forming plastic substrates include polycarbonate, polyallylate, polyether sulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, polyethylene naphthalate, etc. Inorganic vapor deposition films can also be used.

[0551] (anode)

[0552] As the anode, for example, a metal having a high work function (specifically, 4.0 eV or more), an alloy, a conductive compound, a mixture thereof, etc. are preferably used. Specific examples of the anode material include indium oxide-tin oxide (ITO: indium tin oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide or zinc oxide, graphene, etc. In addition, it is also possible to use gold, silver, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, and nitrides of these metals (e.g., titanium oxide).

[0553] These materials are usually deposited on a substrate by sputtering to form an anode. For example, indium oxide-zinc oxide can be formed by sputtering using a target material to which 1 to 10% by mass of zinc oxide is added relative to indium oxide. In addition, indium oxide containing tungsten oxide or zinc oxide can be formed by sputtering using a target material to which 0.5 to 5% by mass of tungsten oxide or 0.1 to 1% by mass of zinc oxide is added relative to indium oxide.

[0554] As other methods for forming the anode, there can be given a vacuum deposition method, a coating method, an inkjet method, a spin coating method, etc. When a silver paste or the like is used, a coating method, an inkjet method, etc. can be used.

[0555] The hole injection layer formed in contact with the anode is formed by using a material that easily injects holes regardless of the work function of the anode. Therefore, in the anode, it is possible to use common electrode materials such as metals, alloys, conductive compounds and mixtures thereof. Specifically, materials with a small work function are used, such as alkali metals such as lithium and cesium; alkaline earth metals such as calcium and strontium; alloys containing these metals (such as magnesium-silver and aluminum-lithium); rare earth metals such as europium and ytterbium; and alloys containing rare earth metals.

[0556] (Hole transport layer) / (Hole injection layer)

[0557] The hole transport layer is an organic layer formed between the emission layer and the anode, and has the function of transporting holes from the anode to the emission layer. If the hole transport layer is composed of multiple layers, the organic layer closer to the anode can generally be defined as a hole injection layer. The hole injection layer has the function of effectively injecting holes from the anode into the organic layer unit. The hole injection layer is generally used to stabilize the hole injection from the anode to the hole transport layer generally composed of an organic material. An organic material having good contact with the anode or an organic material having p-type doping is preferably used for the hole injection layer.

[0558] P-type doping is usually composed of one or more p-type dopant materials and one or more host materials. The host material preferably has a shallower HOMO energy level, and the p-type dopant preferably has a deeper LUMO energy level to enhance the carrier density of the layer. The specific example of the p-type dopant is the acceptor material mentioned below. Suitable host materials are the hole transport materials mentioned below, preferably aromatic or heterocyclic amine compounds.

[0559] An acceptor material or a condensed aromatic hydrocarbon material or a condensed heterocyclic ring having high planarity is preferably used as the p-type dopant material of the hole injection layer.

[0560] Specific examples of acceptor materials are quinone compounds having one or more electron withdrawing groups, such as F4TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane) and 1,2,3-tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane; hexa-azatriphenylene compounds having one or more electron withdrawing groups, such as hexa-azatriphenylene-hexanenitrile; aromatic compounds having one or more electron withdrawing groups; and arylboron compounds having one or more electron withdrawing groups. Preferred p-type dopants are quinone compounds having one or more electron withdrawing groups, such as F4TCNQ, 1,2,3-tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane.

[0561] The ratio of the p-type dopant relative to the host material is preferably less than 20 mol%, more preferably less than 10%, such as 1%, 3% or 5%.

[0562] The hole transport layer generally serves to efficiently inject and transport holes, and preferably uses an aromatic or heterocyclic amine compound.

[0563] A specific example of the compound for the hole transport layer is represented by the general formula (H),

[0564]

[0565] in

[0566] Ar 1’ To Ar 3’Each independently represents a substituted or unsubstituted aryl group having 5 to 50 carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, a fluorenyl group, a spirobifluorenyl group, an indenofluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophene group, a carbazole-substituted aryl group, a dibenzofuran-substituted aryl group or a dibenzothiophene-substituted aryl group; selected from Ar 1’ To Ar 3’ Two or more substituents of may be bonded to each other to form a ring structure such as a carbazole ring structure or an acridine ring structure.

[0567] Preferably, Ar 1’ To Ar 3’ At least one of the substituents has another aromatic or heterocyclic amine substituent, more preferably Ar 1’ With an additional arylamino substituent, in this case Ar 1’ Preferably represents a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group. Specific examples of hole transport materials are

[0568]

[0569] wait

[0570] A second hole transport layer is preferably inserted between the first hole transport layer and the emission layer to enhance device performance by blocking excess electrons or excitons.

[0571] The specific examples of the second hole transport layer are the same as those of the first hole transport layer. Preferably, the second hole transport layer has a higher triplet energy to block triplet excitons, especially for phosphorescent devices, such as bicarbazole compounds, benzidine compounds, triphenylamine compounds, fluorenylamine compounds, carbazole-substituted arylamine compounds, dibenzofuran-substituted arylamine compounds, and dibenzothiophene-substituted arylamine compounds.

[0572] (Emission Layer)

[0573] The emission layer is a layer containing a substance (emitter material or dopant material) with high emission properties. As a dopant material, various materials can be used. For example, fluorescent emission compounds (fluorescent dopants), phosphorescent emission compounds (phosphorescent dopants), etc. can be used. The fluorescent emission compound is a compound that can emit light from a singlet excited state, and the emission layer containing the fluorescent emission compound is called a fluorescent emission layer. In addition, the phosphorescent emission compound is a compound that can emit light from a triplet excited state, and the emission layer containing the phosphorescent emission compound is called a phosphorescent emission layer.

[0574] Preferably, the emission layer in the organic EL device of the present application comprises the compound of formula (I) as a dopant material.

[0575] The emission layer preferably comprises at least one dopant material and at least one host material to enable it to emit light efficiently. In some documents, the dopant material is referred to as a guest material, an emitter or an emission material. In some documents, the host material is referred to as a matrix material.

[0576] A single emissive layer may contain multiple dopant materials and multiple host materials. Additionally, there may be multiple emissive layers.

[0577] In this specification, a host material combined with a fluorescent dopant is referred to as a "fluorescent host", and a host material combined with a phosphorescent dopant is referred to as a "phosphorescent host". Note that fluorescent hosts and phosphorescent hosts are not only classified by molecular structure. A phosphorescent host is a material for forming a phosphorescent emission layer containing a phosphorescent dopant, but it does not mean that it cannot be used as a material for forming a fluorescent emission layer. The same applies to fluorescent hosts.

[0578] In one embodiment, it is preferred that the emission layer contains the compound represented by formula (I) according to the present invention (hereinafter, these compounds may be referred to as "compound (I)"). More preferably, it is contained as a dopant material. In addition, it is preferred that compound (I) is contained in the emission layer as a fluorescent dopant. Further, it is preferred that compound (I) is contained in the emission layer as a blue fluorescent dopant.

[0579] In one embodiment, there is no particular restriction on the content of the compound (I) as a dopant material in the emission layer. In view of sufficient emission and concentration quenching, the content is preferably 0.5 to 70% by mass, more preferably 0.8 to 30% by mass, further preferably 1 to 30% by mass, further preferably 1 to 20% by mass, particularly preferably 1 to 10% by mass, further particularly preferably 1 to 5% by mass, and further particularly preferably 2 to 4% by mass, relative to the mass of the emission layer.

[0580] (Fluorescent dopant)

[0581] Examples of fluorescent dopants other than compound (I) include condensed polycyclic aromatic compounds, styrylamine compounds, condensed ring amine compounds, boron-containing compounds, pyrrole compounds, indole compounds, and carbazole compounds. Among them, condensed ring amine compounds, boron-containing compounds, and carbazole compounds are preferred.

[0582] As the fused ring amine compound, there can be given diaminopyrene compounds, diamino Compounds, diaminoanthracene compounds, diaminofluorene compounds, diaminofluorene compounds fused with one or more benzofuran skeletons, and the like.

[0583] As the boron-containing compound, a pyrromethene compound, a triphenylborane compound, and the like can be given.

[0584] As the blue fluorescent dopant, for example, pyrene compounds, styrylamine compounds, Compounds, fluoranthene compounds, fluorene compounds, diamine compounds, triarylamine compounds, etc. Specifically, N,N′-bis[4-(9H-carbazole-9-yl)phenyl]-N,N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S), 4-(9H-carbazole-9-yl)-4′-(10-phenyl-9-anthracenyl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthracenyl)-4′-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPA), etc. can be given.

[0585] As the green fluorescent dopant, for example, aromatic amine compounds and the like can be given. Specifically, for example, N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthracenyl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DP APA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), etc.

[0586] As the red fluorescent dopant, there can be given a tetracene compound, a diamine compound, etc. Specifically, there can be given N,N,N',N'-tetrakis (4-methylphenyl) tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis (4-methylphenyl) acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), etc.

[0587] (Phosphorescent Dopant)

[0588] As the phosphorescent dopant, a phosphorescent heavy metal complex and a phosphorescent rare earth metal complex can be given.

[0589] As the heavy metal complex, there can be given an iridium complex, an osmium complex, a platinum complex, etc. The heavy metal complex is, for example, an ortho-metalated complex of a metal selected from iridium, osmium, and platinum.

[0590] Examples of rare earth metal complexes include terbium complexes, europium complexes, etc. Specifically, terbium (III) tris(acetylacetonate) (monophenanthroline) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedione) (monophenanthroline) europium (III) (abbreviation: Eu(DBM)3(Phen)), tris[1-(2-thiophenoyl)-3,3,3-trifluoroacetone] (monophenanthroline) europium (III) (abbreviation: Eu(TTA)3(Phen)), etc. can be given. These rare earth metal complexes are preferred as phosphorescent dopants because rare earth metal ions emit light due to electron transitions between different multiplicities.

[0591] As the blue phosphorescent dopant, for example, iridium complexes, osmium complexes, platinum complexes, etc. can be given. Specifically, bis[2-(4', 6'-difluorophenyl) picolinato-N, C2'] iridium(III)tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4', 6'-difluorophenyl) picolinato-N, C2'] iridium(III) picolinate (abbreviation: Ir(CF3ppy)2(pic)), bis[2-(4', 6'-difluorophenyl) picolinato-N, C2'] iridium(III) acetylacetonate (abbreviation: FIracac), etc. can be given.

[0592] As green phosphorescent dopants, for example, iridium complexes can be given. Specifically, tris(2-phenylpicolinate-N, C2')iridium(III) (abbreviation: Ir(ppy)3), bis(1,2-diphenyl-1H-benzimidazole)acetylacetonate iridium(III) (abbreviation: Ir(pbi)2(acac)), bis(benzo[h]quinolinecarboxylate)acetylacetonate iridium(III) (abbreviation: Ir(bzq)2(acac)), and the like can be given.

[0593] As the red phosphorescent dopant, there can be given an iridium complex, a platinum complex, a terbium complex, a europium complex, etc. Specifically, there can be given bis[2-(2'-benzo[4,5-α]thienyl)picolinato-N,C3']acetylacetonate iridium(III) (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinecarboxylate-N,C2')acetylacetonate iridium(III) (abbreviation: Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxalinecarboxylate]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), etc.

[0594] As mentioned above, the emissive layer preferably comprises at least one compound (I) as dopant.

[0595] (Main material)

[0596] As the host material, for example, there can be given metal complexes such as aluminum complexes, beryllium complexes and zinc complexes; heterocyclic compounds such as indole compounds, pyridine compounds, pyrimidine compounds, triazine compounds, quinoline compounds, isoquinoline compounds, quinazoline compounds, dibenzofuran compounds, dibenzothiophene compounds, oxadiazole compounds, benzimidazole compounds, phenanthroline compounds; condensed polycyclic aromatic hydrocarbon (PAH) compounds such as naphthalene compounds, triphenylene compounds, carbazole compounds, anthracene compounds, phenanthrene compounds, pyrene compounds, compounds, tetracene compounds, fluoranthene compounds; and aromatic amine compounds such as triarylamine compounds and condensed polycyclic aromatic amine compounds. A plurality of types of host materials may be used in combination.

[0597] As the fluorescent host, a compound having a singlet energy level higher than that of the fluorescent dopant is preferred. For example, heterocyclic compounds, condensed aromatic compounds, etc. can be given. As the condensed aromatic compound, anthracene compounds, pyrene compounds, Compounds, tetracene compounds, etc. are preferred. Anthracene compounds are preferably used as a blue fluorescent host.

[0598] In the case of using compound (I) as at least one dopant material, the preferred host material is a substituted or unsubstituted polycyclic aromatic hydrocarbon (PAH) compound, a substituted or unsubstituted polycyclic heteroaromatic compound, a substituted or unsubstituted anthracene compound or a substituted or unsubstituted pyrene compound, preferably a substituted or unsubstituted anthracene compound or a substituted or unsubstituted pyrene compound, more preferably a substituted or unsubstituted anthracene compound, and most preferably an anthracene compound represented by formula (10) as mentioned above.

[0599] As the phosphorescent host, a compound having a triplet energy level higher than that of the phosphorescent dopant is preferred. For example, metal complexes, heterocyclic compounds, condensed aromatic compounds, etc. can be given. Among them, indole compounds, carbazole compounds, pyridine compounds, pyrimidine compounds, triazine compounds, quinolone compounds, isoquinoline compounds, quinazoline compounds, dibenzofuran compounds, dibenzothiophene compounds, naphthalene compounds, triphenylene compounds, phenanthrene compounds, fluoranthene compounds, etc. can be given.

[0600] (Electron transport layer) / (Electron injection layer)

[0601] The electron transport layer is an organic layer formed between the emission layer and the cathode and has the function of transporting electrons from the cathode to the emission layer. When the electron transport layer is formed of multiple layers, the organic layer or inorganic layer closer to the cathode is generally defined as the electron injection layer (see, for example Figure 1 The electron injection layer 8 and the electron transport layer 7 form an electron injection and transport unit 11). The electron injection layer has the function of effectively injecting electrons from the cathode into the organic layer unit. Preferred electron injection materials are alkali metals, alkali metal compounds, alkali metal complexes, alkaline earth metal complexes and rare earth metal complexes.

[0602] According to one embodiment, the electron transport layer preferably further comprises one or more layers, such as a second electron transport layer, an electron injection layer for enhancing the efficiency and lifetime of the device, a hole blocking layer, an exciton blocking layer or a triplet blocking layer.

[0603] According to one embodiment, an electron donating dopant is preferably included in the interface region between the cathode and the emission unit. Due to such a configuration, the organic EL device can have an improved brightness or a long life. Here, the electron donating dopant refers to a dopant of a metal having a work function of 3.8 Ev or less. As a specific example thereof, at least one selected from alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earth metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes and rare earth metal compounds can be mentioned.

[0604] As alkali metals, Li (work function: 2.9 eV), Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), Cs (work function: 1.95 eV) and the like can be given. Alkali metals having a work function of 2.9 eV or less are particularly preferred. Among them, K, Rb and Cs are preferred. Rb or Cs is further preferred. CS is most preferred. As alkaline earth metals, Ca (work function: 2.9 eV), Sr (work function: 2.0 eV to 2.5 eV), Ba (work function: 2.52 eV) and the like can be given. Alkaline earth metals having a work function of 2.9 eV or less are particularly preferred. As rare earth metals, Sc, Y, Ce, Tb, Yb and the like can be given. Rare earth metals having a work function of 2.9 eV or less are particularly preferred.

[0605] Examples of alkali metal compounds include alkali metal oxides such as Li2O, Cs2O or K2O, and alkali metal halides such as LiF, NaF, CsF and KF. Among them, LiF, Li2O and NaF are preferred. Examples of alkaline earth metal compounds include BaO, SrO, CaO and mixtures thereof, such as Ba x Sr 1-x O(0<x<1) and Ba x Ca 1-x O (0<x<1). Among them, BaO, SrO and CaO are preferred. Examples of rare earth metal compounds include YbF3, ScF3, 5cO3, Y2O3, Ce2O3, GdF3 and TbF3. Among them, YbF3, ScF3 and TbF3 are preferred.

[0606] There is no particular restriction on alkali metal complexes, alkaline earth metal complexes and rare earth metal complexes, as long as they contain at least one of alkali metal ions, alkaline earth metal ions and rare earth metal ions as metal ions. Meanwhile, preferred examples of the ligand include, but are not limited to, quinolinephenol, benzoquinolinephenol, acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, hydroxyfluborane, bipyridine, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, β-diketone and azomethine.

[0607] Regarding the addition form of the electron donating dopant, the electron donating dopant is preferably formed in the shape of a layer or an island in the interface region. A preferred method for forming is a method in which an organic compound (light emitting material or electron injecting material) for forming the interface region is deposited by a resistance heating deposition method while depositing the electron donating dopant, thereby dispersing the electron donating dopant in the organic compound.

[0608] In the case where the electron-donating dopant is formed into a layer shape, the light-emitting material or electron injection material acting as an organic layer in the interface is formed into a layer shape. Thereafter, the reductive dopant is deposited separately by a resistance heating deposition method to form a layer preferably having a thickness of 0.1nm to 15nm. In the case where the electron-donating dopant is formed into an island shape, the light-emitting material or electron injection material acting as an organic layer in the interface is formed into an island shape. Thereafter, the electron-donating dopant is deposited separately by a resistance heating deposition method to form an island preferably having a thickness of 0.05nm to 1nm. As an electron transport material other than the compound of formula (I) used in the electron transport layer, an aromatic heterocyclic compound having one or more heteroatoms in the molecule can be preferably used. In particular, nitrogen-containing heterocyclic compounds are preferred.

[0609] According to one embodiment, the electron transport layer preferably comprises a nitrogen-containing heterocyclic metal chelate.

[0610] According to another embodiment, the electron transport layer preferably contains a substituted or unsubstituted nitrogen-containing heterocyclic compound. Specific examples of preferred heterocyclic compounds for the electron transport layer are 6-membered azine compounds; such as pyridine compounds, pyrimidine compounds, triazine compounds, pyrazine compounds, preferably pyrimidine compounds or triazine compounds; 6-membered fused azine compounds, such as quinolone compounds, isoquinoline compounds, quinoxaline compounds, quinazoline compounds, phenanthroline compounds, benzoquinoline compounds, benzisoquinoline compounds, dibenzoquinoxaline compounds, preferably quinolone compounds, isoquinoline compounds, phenanthroline compounds; 5-membered heterocyclic compounds, such as imidazole compounds, oxazole compounds, oxadiazole compounds, triazole compounds, thiazole compounds, thiadiazole compounds; fused imidazole compounds, such as benzimidazole compounds, imidazopyridine compounds, naphthymidazole compounds, benzimidazole and phenanthridine compounds, benzimidazole and benzimidazole compounds, preferably benzimidazole compounds, imidazopyridine compounds or benzimidazole and phenanthridine compounds.

[0611] According to another embodiment, the electron transport layer preferably comprises p1 Ar p2 Ar P3 A phosphine oxide compound wherein P=O.

[0612] Ar p1 To Ar p3 are substituents of the phosphorus atom, and each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0613] According to another embodiment, the electron transport layer preferably comprises an aromatic compound. Specific examples of preferred aromatic compounds for the electron transport layer are oligophenylene compounds, naphthalene compounds, fluorene compounds, fluoranthenyl, anthracene compounds, phenanthrene compounds, pyrene compounds, triphenylene compounds, benzanthracene compounds, Compounds, triphenylene compounds, tetracene compounds and benzophenone Compounds, preferably anthracene compounds, pyrene compounds and fluoranthene compounds.

[0614] (cathode)

[0615] For the cathode, metals, alloys, conductive compounds, and mixtures thereof each having a small work function (specifically, a work function of 3.8 eV or less) are preferably used. Specific examples of materials for the cathode include alkali metals such as lithium and cesium; alkaline earth metals such as magnesium, calcium, and strontium; aluminum, alloys containing these metals (e.g., magnesium-silver, aluminum-lithium); rare earth metals such as europium and ytterbium; and alloys containing rare earth metals.

[0616] The cathode is usually formed by vacuum vapor deposition or sputtering. In addition, in the case of using silver paste or the like, a coating method, an inkjet method, or the like can be used.

[0617] In addition, the cathode can be formed using various conductive materials independently selected from the work function, such as silver, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, and these conductive materials can be made into films using sputtering, inkjet, spin coating, etc.

[0618] (Insulation layer)

[0619] In organic EL devices, due to the application of an electric field to the film, pixel defects based on leakage or short circuit are easily generated. In order to prevent this, it is preferred to insert an insulating thin layer between a pair of electrodes. Examples of materials for insulating layers include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide and vanadium oxide. Its mixture can be used for insulating layers, and laminates including multiple layers of these materials can also be used for insulating layers.

[0620] (Spacer layer)

[0621] The spacer layer is a layer disposed between the fluorescent emission layer and the phosphorescent emission layer when the fluorescent emission layer and the phosphorescent emission layer are stacked to prevent the excitons generated in the phosphorescent emission layer from diffusing to the fluorescent emission layer or to adjust the carrier balance. In addition, a spacer layer may be provided between multiple phosphorescent emission layers.

[0622] Since the spacer layer is disposed between the emission layers, the material for the spacer layer is preferably a material having both electron transport capability and hole transport capability. In order to prevent the triplet energy from diffusing in the adjacent phosphorescent emission layer, the spacer layer preferably has a triplet energy of 2.6 eV or more. As the material for the spacer layer, the same material as that used in the above-mentioned hole transport layer can be given.

[0623] (Electron blocking layer, hole blocking layer, exciton blocking layer)

[0624] An electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, or the like may be provided adjacent to the emission layer.

[0625] The electron blocking layer has the function of preventing electrons from leaking from the emission layer to the hole transport layer. The hole blocking layer has the function of preventing holes from leaking from the emission layer to the electron transport layer. In order to improve the hole blocking ability, it is preferred to use a material with a deep HOMO energy level. The exciton blocking layer has the function of preventing the excitons generated in the emission layer from diffusing to the adjacent layers and confining the excitons in the emission layer. In order to improve the triplet blocking ability, it is preferred to use a material with a high triplet energy level.

[0626] (Method of forming layers)

[0627] Unless otherwise specified, the method for forming each layer of the organic EL device of the present invention is not particularly limited. Known film forming methods such as dry film forming methods, wet film forming methods, etc. can be used. Specific examples of dry film forming methods include vacuum deposition methods, sputtering methods, plasma methods, ion plating methods, etc. Specific examples of wet film forming methods include various coating methods, such as spin coating, dipping methods, flow coating methods, inkjet methods, etc.

[0628] (Film thickness)

[0629] Unless otherwise specified, the film thickness of each layer of the organic EL device of the present invention is not particularly limited. If the film thickness is too small, defects such as pinholes are likely to occur, making it difficult to obtain sufficient brightness. If the film thickness is too large, a high driving voltage needs to be applied, so that the efficiency is reduced. In this regard, the film thickness is preferably 0.1nm to 10μm, more preferably 5nm to 0.2μm.

[0630] (Electronic device (electronic equipment))

[0631] The present invention further relates to electronic devices (electronic devices) comprising the organic electroluminescent device according to the present application. Examples of electronic devices include display components such as organic EL panel modules; display devices of televisions, mobile phones, smart phones, personal computers, etc.; and emitting devices of lighting equipment and vehicle lighting devices. Example

[0632] Next, the present invention is explained in more detail according to the following Synthesis Examples, Examples and Comparative Examples, which should not be construed as limiting the scope of the present invention.

[0633] Unless otherwise indicated, the percentages and ratios mentioned in the following examples are by weight % and by weight ratio.

[0634] I. Synthesis Example

[0635] All experiments were carried out in a protective gas atmosphere.

[0636] Compound 1

[0637] Intermediate 1-1

[0638]

[0639] 42.0 ml (249.0 mmol) of 2,2,6,6-tetramethylpiperidine was dissolved in 250 ml of THF, and the solution was cooled to -78°C, and then 100 ml (250 mmol) of 2.5M n-butyl lithium / hexane was added dropwise via a cannula for 30 minutes. The solution was stirred at -78°C for 30 minutes. 67.0 ml (290.5 mmol) of triisopropyl borate was slowly added over 30 minutes, and the mixture was stirred at -78°C for 1 hour, and then 24.24 g (83.0 mmol) of 1,2-dibromo-4-(tert-butyl) benzene in 50 ml of THF was added dropwise at -78°C for 45 minutes. Then, the mixture was warmed to room temperature overnight. The reaction mixture was poured into 300 ml of ice-cold 1N HCl, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product was used for the next reaction without purification.

[0640] LC-MS: 335[M-1] -

[0641] Intermediate 1-2

[0642]

[0643] 27.86 grams (82.96 mmoles) of intermediate 1-1 and 1.63 grams (16.59 mmoles) of potassium acetate are suspended in 332 milliliters of acetonitrile. Then, at room temperature, 22.4 grams (99.55 mmoles) of N-iodosuccinimide are added to the suspension, and the mixture is stirred overnight. The reaction mixture is quenched with 300 milliliters of 10% sodium sulfite. The water layer is extracted with toluene, and the organic layer is washed with salt water, dried over magnesium sulfate, filtered and concentrated. The crude product is purified by silica gel column chromatography using heptane as eluent to obtain 22.1 grams (61% yield) of intermediate 1-2 as a white solid.

[0644] 1 H-NMR (300MHz, CD2Cl2) δ7.84 (d, J=2.2Hz, 1H), 7.63 (d, J=2.2Hz, 1H), 1.28 (s, 9H).

[0645] Intermediate 1-3

[0646]

[0647] 12.41 g (29.70 mmol) of intermediate 1-2, 7.96 g (28.28 mmol) of bis(4-(tert-butyl)phenylamine and 3.81 g (39.60 mmol) of sodium tert-butoxide were added to 190 ml of toluene. The suspension was degassed using 3 freeze-pump-thaw cycles, and 777 mg (0.85 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 982 mg (1.70 mmol) of xantphos were added to the reaction mixture. After two additional freeze-pump-thaw cycles followed by replacement with argon, the reaction mixture was heated to 90° C. for 19 hours. The reaction was cooled to room temperature and diluted with toluene and water. The organic extract was washed with water and dried over magnesium sulfate, filtered, and the solution was concentrated. The residue was purified by silica gel column chromatography using cyclohexane as the eluent to give 8.62 g (53% yield) of intermediate 1-3 as a white solid.

[0648] LC-MS: 572[M+1] +

[0649] Intermediate 1-4

[0650]

[0651] 9.5 g (16.62 mmol) of intermediate 1-3, 4.54 g (17.46 mmol) of N 1 , N 1 -diphenyl-1,3-phenylenediamine and 4.12 grams (41.6 mmoles) of sodium tert-butoxide are added in 190 milliliters of toluene. This suspension uses 3 freeze-pump-thaw cycles to deaerate, and 156 milligrams (0.17 mmoles) of tris (dibenzylideneacetone) dipalladium (0) and 423 milligrams (0.67 mmoles) of BINAP are added in the reaction mixture. After two other freeze-pump-thaw cycles are then replaced with argon, the reaction mixture is heated to 90 ℃ and continues for 2 hours. The reaction is cooled to room temperature and diluted with toluene and water. The organic extract is washed with water and dried over magnesium sulfate, filtered, and the solution is concentrated. Residue is purified by silica gel column chromatography using a mixed solvent of heptane and dichloromethane as eluent to obtain 11.8 grams (95% yield) of intermediate 1-4 as white foam.

[0652] LC-MS: 750[M+1] +

[0653] Intermediate 1-5

[0654]

[0655] 9.61 grams (12.80 mmoles) of intermediate 1-4, 4.60 grams (14.08 mmoles) of 2-iodo-9,9-dimethyl-9H-fluorene and 3.17 grams (32.0 mmoles) of sodium tert-butoxide are added to 128 milliliters of toluene. The suspension is degassed using 3 freeze-pump-thaw cycles, and 120 milligrams (0.13 mmoles) of tris(dibenzylideneacetone)dipalladium(0) and 152 milligrams (0.51 mmoles) of tri-tert-butylphosphonium tetrafluoroborate are added to the reaction mixture. After two other freeze-pump-thaw cycles are then replaced with argon, the reaction mixture is heated to 80°C for 2 hours. The reaction is cooled to room temperature and diluted with toluene and water. The organic extract is washed with water and dried over magnesium sulfate, filtered, and the solution is concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and dichloromethane as an eluent to obtain 10.36 g (86% yield) of Intermediate 1-5 as a white solid.

[0656] LC-MS: 942[M+1] +

[0657] Compound 1

[0658]

[0659] 2.06 grams (2.18 mmoles) of intermediate 1-5 are added to 62 milliliters of tert-butylbenzene, and the solution is bubbled with argon. 2.3 milliliters of 1.9M tert-butyl lithium / pentane are added dropwise to the solution at 0°C, and the reaction mixture is stirred at 0°C for 1 hour. The reaction mixture is then warmed to room temperature and stirred for 2 hours. The reaction mixture is cooled to -30°C, 0.41 milliliters (4.37 mmoles) of tribromoborane are added, and the reaction mixture is then stirred for 45 minutes. After the reaction mixture is warmed to 0°C, 1.9 milliliters (10.92 mmoles) of N-ethyl-N-isopropylpropane-2-amine are added, and the mixture is then heated to 145°C. After 45 minutes, the reaction mixture is cooled at room temperature and quenched with 10% sodium acetate aqueous solution. The mixture is diluted with ethyl acetate, and the water layer is extracted with ethyl acetate. The organic layer is washed with water and brine, and dried over magnesium sulfate. It is filtered and concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and dichloromethane as an eluent to obtain 0.67 g (35% yield) of Compound 1 as a yellow powder.

[0660] LC-MS: 872[M+1] +

[0661] Compound 2

[0662] Intermediate 2-1

[0663]

[0664] 27.86 grams (155.39 mmoles) of N-(phenyl-2,3,4,5,6-d5)benzene-2,3,4,5,6-d5-amine, 36.10 grams (178.70 mmoles) of 1-bromo-3-nitrobenzene and 20.91 grams (217.55 mmoles) of sodium tert-butoxide are added to 622 milliliters of toluene. The suspension is degassed using 3 freeze-pump-thaw cycles, and 2.85 grams (3.11 mmoles) of tris(dibenzylideneacetone)dipalladium(0) and 3.61 grams (12.43 mmoles) of tri-tert-butylphosphine tetrafluoroborate are added to the reaction mixture. After two other freeze-pump-thaw cycles, the reaction mixture is heated to 94 ℃ for 14 hours. The reaction mixture is cooled to room temperature, filtered through a diatomaceous earth pad, and washed with toluene. The solution is then concentrated. The residue was purified by silica gel column chromatography using cyclohexane as eluent to give 36.1 g (73% yield) of intermediate 2-1 as an orange oil.

[0665] LC-MS: 301.3[M+1] +

[0666] Intermediate 2-2

[0667]

[0668] 36.1 grams (120.18 mmoles) of intermediate 2-1 and 48.21 grams (901.36 mmoles) of ammonium chloride are suspended in 900 milliliters of 1,4-dioxane and 300 milliliters of ethanol. At room temperature, after 58.9 grams (901.36 mmoles) of zinc powder are added to the suspension, the mixture is refluxed for 14 hours. The reaction mixture is filtered through a diatomaceous earth pad, and washed with ethyl acetate. After the solution is concentrated, the crude product is purified by silica gel column chromatography using a mixed solvent of heptane and ethyl acetate as an eluent to obtain 29.5 grams (86% yield) of intermediate 2-2 as a beige solid.

[0669] LC-MS: 271.3[M+1] +

[0670] Intermediate 2-3

[0671]

[0672] 4.97 grams (18.38 mmoles) of intermediate 2-2, 10.0 grams (17.50 mmoles) of intermediate 1-3 and 3.36 grams (35.0 mmoles) of sodium tert-butoxide are added to 87 milliliters of toluene. The suspension is degassed using 3 freeze-pump-thaw cycles, and 240 milligrams (0.26 mmoles) of tris (dibenzylideneacetone) dipalladium (0) and 327 milligrams (0.33 mmoles) of BINAP are added to the reaction mixture. After two other freeze-pump-thaw cycles, the reaction mixture is heated to 80 ℃ and continues for 17.5 hours. The reaction is cooled to room temperature and diluted with toluene and water. The organic extract is washed with water and dried over magnesium sulfate. After filtering, the solution is concentrated. Residue is purified by silica gel column chromatography using a mixed solvent of toluene and cyclohexane as an eluent to obtain 13.6 grams (99% yield) of intermediate 2-3 as white foam.

[0673] LC-MS: 762.6[M+1] +

[0674] Intermediate 2-4

[0675]

[0676] 7.00 grams (9.20 mmoles) of intermediate 2-3, 3.24 grams (10.12 mmoles) of 2-iodo-9,9-dimethyl-9H-fluorene and 1.24 grams (12.88 mmoles) of sodium tert-butoxide are added to 92 milliliters of toluene. The suspension is degassed using 3 freeze-pump-thaw cycles, and 84 milligrams (0.09 mmoles) of tris(dibenzylideneacetone)dipalladium(0) and 110 milligrams (0.37 mmoles) of tri-tert-butylphosphonium tetrafluoroborate are added to the reaction mixture. After two other freeze-pump-thaw cycles, the reaction mixture is heated to 80 ℃ for 30 minutes. The reaction is cooled to room temperature and diluted with toluene and water. The organic extract is washed with water and dried over magnesium sulfate. After filtration, the solution is concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and toluene as an eluent to obtain 8.39 g (89% yield) of Intermediate 2-4 as a white solid.

[0677] LC-MS: 955[M+1] +

[0678] Compound 2

[0679]

[0680] 5.41 grams (5.68 mmoles) of intermediate 2-4 are added to 103 milliliters of tert-butylbenzenes, and the solution is bubbled with argon. 5.97 milliliters (11.35 mmoles) of 1.9M tert-butyl lithium / pentane are added dropwise to the solution at 5 ℃, and the reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is cooled at -65 ℃, and 1.08 milliliters (11.35 mmoles) of tribromoborane are added, and then the reaction mixture is stirred for 25 minutes after removing dry ice-acetone bath. Then, 5.0 milliliters (28.38 mmoles) of N-ethyl-N-isopropylpropane-2-amine are added, and the mixture is heated to 153 ℃. After being stirred for 2 hours, the reaction mixture is cooled at room temperature, and quenched with 10% sodium acetate aqueous solution. The mixture is diluted with toluene, and the water layer is extracted with toluene. The organic layer is washed with water and brine, and dried over magnesium sulfate. After filtering the solution, it is concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and dichloromethane as an eluent. Then, it was recrystallized from a mixed solvent of dichloromethane and heptane to obtain 1.17 g (23% yield) of Compound 2 as a yellow powder.

[0681] LC-MS: 881.7[M+1] +

[0682] Compound 3

[0683] Intermediate 3-1

[0684]

[0685] Intermediate 3-1 was synthesized from Intermediate 1-4 and 2-bromo-9,9-diphenyl-9H-fluorene according to the procedure of Intermediate 1-5 (89% yield).

[0686] LC-MS: 1066.6[M+1] +

[0687] Compound 3

[0688]

[0689] Compound 3 was synthesized from intermediate 3-1 according to the procedure of compound 1 (32% yield).

[0690] LC-MS: 997.0[M+1] +

[0691] Compound 4

[0692] Intermediate 4-1

[0693]

[0694] Intermediate 4-1 was synthesized according to the procedure of Intermediate 2-1 (59% yield) using bis(4-(tert-butyl)phenyl)amine instead of N-(phenyl-2,3,4,5,6-d5)benzene-2,3,4,5,6-d5-amine.

[0695] LC-MS: 403.2[M+1] +

[0696] Intermediate 4-2

[0697]

[0698] Intermediate 4-2 was synthesized from Intermediate 4-1 according to the procedure of Intermediate 2-2 (96% yield).

[0699] LC-MS: 373.6[M+1] +

[0700] Intermediate 4-3

[0701]

[0702] Intermediate 4-3 was synthesized from Intermediate 1-3 and Intermediate 4-2 according to the procedure of Intermediate 1-4 (94% yield).

[0703] LC-MS: 862.8[M+1] +

[0704] Intermediate 4-4

[0705]

[0706] Intermediate 4-4 was synthesized from Intermediate 4-3 and 4-bromo-9,9-dimethyl-9H-fluorene according to the procedure of Intermediate 1-5 (78% yield).

[0707] LC-MS: 1054.9[M+1] +

[0708] Compound 4

[0709]

[0710] Compound 4 was prepared from intermediate 4-4 according to the procedure of compound 1 (26% yield).

[0711] LC-MS: 984.9[M+1] +

[0712] Compound 5

[0713] Intermediate 5-1

[0714]

[0715] Intermediate 5-1 was synthesized from Intermediate 4-3 and 2-iodo-9,9-dimethyl-9H-fluorene according to the procedure of Intermediate 1-5 (93% yield).

[0716] LC-MS: 1055.0[M+1] +

[0717] Compound 5

[0718]

[0719] Compound 5 was prepared from intermediate 5-1 according to the procedure of compound 1 (17% yield).

[0720] LC-MS: 984.7[M+1] +

[0721] Compound 6

[0722] Intermediate 6-1

[0723]

[0724] Intermediate 6-1 was synthesized according to the procedure of Intermediate 2-1 using N-[4-(1,1-dimethylethyl)phenyl][1,1′-biphenyl]-2-amine instead of N-(phenyl-2,3,4,5,6-d5)benzene-2,3,4,5,6-d5-amine. The yield was 65%.

[0725] LC-MS: 423.2[M+1] +

[0726] Intermediate 6-2

[0727]

[0728] Intermediate 6-2 was synthesized from Intermediate 6-1 according to the procedure of Intermediate 2-2. The yield was 85%.

[0729] LC-MS: 393.3[M+1] +

[0730] Intermediate 6-3

[0731]

[0732] Intermediate 6-3 was synthesized from Intermediate 6-2 and Intermediate 1-3 according to the procedure of Intermediate 2-3. The yield was 93%.

[0733] LC-MS: 884.6[M+1] +

[0734] Intermediate 6-4

[0735]

[0736] Intermediate 6-4 was synthesized from Intermediate 6-3 and 2-iodo-9,9-dimethyl-9H-fluorene according to the procedure of Intermediate 2-4. The yield was 91%.

[0737] LC-MS: 1076.6[M+1] +

[0738] Compound 6

[0739]

[0740] Compound 6 was synthesized from intermediate 6-4 according to the procedure of compound 2. The yield was 19%.

[0741] LC-MS: 1004.7[M+1] +

[0742] Compound 7

[0743] Intermediate 7-1

[0744]

[0745] Intermediate 7-1 was synthesized according to the procedure of Intermediate 2-1 using 5-(tert-butyl)-N-phenyl-[1,1′-biphenyl]-2-amine instead of N-(phenyl-2,3,4,5,6-d5)benzene-2,3,4,5,6-d5-amine. The yield was 93%.

[0746] LC-MS: 423.3[M+1] +

[0747] Intermediate 7-2

[0748]

[0749] Intermediate 7-2 was synthesized from Intermediate 7-1 according to the procedure of Intermediate 2-2. The yield was 98%.

[0750] LC-MS: 393.3[M+1] +

[0751] Intermediate 7-3

[0752]

[0753] Intermediate 7-3 was synthesized from Intermediate 7-2 and Intermediate 1-3 according to the procedure of Intermediate 2-3. The yield was 88%.

[0754] LC-MS: 884.6[M+1]+

[0755] Intermediate 7-4

[0756]

[0757] Intermediate 7-4 was synthesized from Intermediate 7-3 and 2-iodo-9,9-dimethyl-9H-fluorene according to the procedure of Intermediate 2-4. The yield was 95%.

[0758] LC-MS: 1076.6[M+1] +

[0759] Compound 7

[0760]

[0761] Compound 7 was synthesized from intermediate 7-4 according to the procedure of compound 2. The yield was 21%.

[0762] LC-MS: 1004.7[M+1] +

[0763] Compound 8

[0764] Intermediate 8-1

[0765]

[0766] Intermediate 8-1 was synthesized according to the procedure of Intermediate 2-1 using 4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-2,6-dimethylaniline instead of N-(phenyl-2,3,4,5,6-d5)benzene-2,3,4,5,6-d5-amine. The yield was 85%.

[0767] LC-MS: 431.4[M+1] +

[0768] Intermediate 8-2

[0769]

[0770] Intermediate 8-2 was synthesized from Intermediate 8-1 according to the procedure of Intermediate 2-2. The yield was 94%.

[0771] LC-MS: 401.3[M+1] +

[0772] Intermediate 8-3

[0773]

[0774] Intermediate 8-3 was synthesized from Intermediate 8-2 and Intermediate 1-3 according to the procedure of Intermediate 2-3. The yield was 84%.

[0775] LC-MS: 892.6[M+1] +

[0776] Intermediate 8-4

[0777]

[0778] Intermediate 8-4 was synthesized from Intermediate 8-3 and 2-iodo-9,9-dimethyl-9H-fluorene according to the procedure of Intermediate 2-4. The yield was 91%. LC-MS: 1084.6 [M+1] +

[0779] Compound 8

[0780]

[0781] Compound 8 was synthesized from intermediate 8-4 according to the procedure of compound 2. The yield was 16%.

[0782] LC-MS: 1012.8[M+1] +

[0783] Compound 9

[0784] Intermediate 9-1

[0785]

[0786] Intermediate 9-1 was synthesized according to the procedure of Intermediate 2-1 using di([1,1′-biphenyl]-4-yl)amine instead of N-(phenyl-2,3,4,5,6-d5)benzene-2,3,4,5,6-d5-amine. The yield was 93%.

[0787] LC-MS: 443.3[M+1] +

[0788] Intermediate 9-2

[0789]

[0790] Intermediate 9-2 was synthesized from Intermediate 9-1 according to the procedure of Intermediate 2-2. The yield was 90%.

[0791] LC-MS: 413.4[M+1] +

[0792] Intermediate 9-3

[0793]

[0794] Intermediate 9-3 was synthesized from Intermediate 9-2 and Intermediate 1-3 according to the procedure of Intermediate 2-3. The yield was 87%.

[0795] LC-MS: 904.5[M+1] +

[0796] Intermediate 9-4

[0797]

[0798] Intermediate 9-4 was synthesized from Intermediate 9-3 and 2-iodo-9,9-dimethyl-9H-fluorene according to the procedure of Intermediate 2-4. The yield was 96%.

[0799] LC-MS: 1096.6[M+1] +

[0800] Compound 9

[0801]

[0802] Compound 9 was synthesized from intermediate 9-4 according to the procedure of compound 2. The yield was 24%.

[0803] LC-MS: 1024.7[M+1] +

[0804] Compound 10

[0805] Intermediate 10-1

[0806]

[0807] Intermediate 10-1 was synthesized according to the procedure of Intermediate 1-1 using 1,2-dibromo-4-methylbenzene instead of 1,2-dibromo-4-(tert-butyl)benzene.

[0808] Intermediate 10-2

[0809]

[0810] Intermediate 10-2 was synthesized from Intermediate 10-1 according to the procedure of Intermediate 1-2. The yield was 58%.

[0811] Intermediate 10-3

[0812]

[0813] 48.0 grams (110 mmoles) of 3-bromo-N, N-bis[4-(1,1-dimethylethyl) phenyl] aniline, 16.4 grams (110 mmoles) of 4-(tert-butyl) aniline and 26.4 grams (275 mmoles) of sodium tert-butoxide are added in 450 milliliters of toluene. This suspension uses 3 freeze-pump-thaw cycles to degas, and 504 milligrams (0.55 mmoles) of tris(dibenzylideneacetone) dipalladium (0) and 685 milligrams (1.1 mmoles) of BINAP are added in the reaction mixture. After two other freeze-pump-thaw cycles, the reaction mixture is heated to 80 ℃ and continues for 3 hours. The reaction is cooled to room temperature and diluted with toluene. The organic extract is washed with water and dried over magnesium sulfate, filtered, and the solution is concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and dichloromethane as an eluent to obtain 52.3 g (94% yield) of Intermediate 10-3 as a white foam.

[0814] LC-MS: 505.5[M+1] +

[0815] Intermediate 10-4

[0816]

[0817] Intermediate 10-4 was synthesized according to the procedure of Intermediate 1-3 using Intermediate 10-2 instead of Intermediate 1-2 and using Intermediate 10-3 instead of bis(4-(tert-butyl)phenylamine. The yield was 57%.

[0818] LC-MS: 753.4[M+1] +

[0819] Intermediate 10-5

[0820]

[0821] Intermediate 10-5 was synthesized from Intermediate 10-4 and 3-(tert-butyl)aniline according to the procedure of Intermediate 2-3. The yield was 89%.

[0822] LC-MS: 822.5[M+1] +

[0823] Intermediate 10-6

[0824]

[0825] Intermediate 10-6 was synthesized from Intermediate 10-5 and 2-iodo-9,9-dimethyl-9H-fluorene according to the procedure of Intermediate 2-4. The yield was 77%.

[0826] LC-MS: 1014.8[M+1] +

[0827] Compound 10

[0828]

[0829] Compound 10 was synthesized from intermediate 10-6 according to the procedure of compound 2. The yield was 30%.

[0830] LC-MS: 944.9[M+1] +

[0831] Compound 11

[0832] Intermediate 11-1

[0833]

[0834] Intermediate 11-1 was synthesized from Intermediate 10-2 and bis(4-(tert-butyl)phenylamine according to the procedure of Intermediate 1-3. The yield was 58%.

[0835] LC-MS: 530.2[M+1] +

[0836] Intermediate 11-2

[0837]

[0838] Intermediate 11-2 was synthesized from Intermediate 8-2 and Intermediate 11-1 according to the procedure of Intermediate 2-3. The yield was 81%.

[0839] LC-MS: 850.6[M+1] +

[0840] Intermediate 11-3

[0841]

[0842] Intermediate 11-3 was synthesized from Intermediate 11-2 and 2-iodo-9,9-dimethyl-9H-fluorene according to the procedure of Intermediate 2-4. The yield was 94%.

[0843] LC-MS: 1042.4[M+1] +

[0844] Compound 11

[0845]

[0846] Compound 11 was synthesized from intermediate 11-3 according to the procedure of compound 2. The yield was 21%.

[0847] LC-MS: 970.8[M+1] +

[0848] Compound 12

[0849] Intermediate 12-1

[0850]

[0851] Intermediate 12-1 was synthesized according to the procedure of Intermediate 2-1 using 4-methyl-N-(4-methyl[1,1′-biphenyl]-3-yl)[1,1′-biphenyl]-3-amine instead of N-(phenyl-2,3,4,5,6-d5)benzene-2,3,4,5,6-d5-amine. The yield was 93%.

[0852] LC-MS: 471.3[M+1] +

[0853] Intermediate 12-2

[0854]

[0855] Intermediate 12-2 was synthesized from Intermediate 12-1 according to the procedure of Intermediate 2-2. The yield was 96%.

[0856] LC-MS: 441.3[M+1] +

[0857] Intermediate 12-3

[0858]

[0859] Intermediate 12-3 was synthesized from Intermediate 12-2 and Intermediate 11-1 according to the procedure of Intermediate 2-3. The yield was 90%.

[0860] LC-MS: 880.5[M+1] +

[0861] Intermediate 12-4

[0862]

[0863] Intermediate 12-4 was synthesized from Intermediate 12-3 and 2-iodo-9,9-dimethyl-9H-fluorene according to the procedure of Intermediate 2-4. The yield was 87%.

[0864] LC-MS: 1082.6[M+1] +

[0865] Compound 12

[0866]

[0867] Compound 12 was synthesized from intermediate 12-4 according to the procedure of compound 2. The yield was 17%.

[0868] LC-MS: 1010.6[M+1] +

[0869] Compound 13

[0870] Intermediate 13-1

[0871]

[0872] 20.00 g (76 mmol) of methyl 2-iodobenzoate, 14.95 g (84 mmol) of (4-(tert-butyl) phenyl) boric acid and 24.27 g (229 mmol) of sodium carbonate were added to 270 ml of toluene, 108 ml of water and 270 ml of ethanol. Nitrogen was blasted into the reaction mixture for 10 minutes and 0.882 g (0.76 mmol) of tetrakis (triphenylphosphine) palladium (0) was added. The reaction mixture was heated to 80 ° C for 15 hours. The reaction was cooled to room temperature and diluted with toluene and water. The organic extract was washed with water and dried over magnesium sulfate. After filtering, the solution was concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and toluene as an eluent to obtain 15.41 g (75% yield) of intermediate 13-1 as a white solid.

[0873] 1 H NMR (300MHz, DMSO-d6) δ7.76-7.68 (m, 1H), 7.61 (td, J=7.5, 1.5Hz, 1H), 7.51-7.40 (m, 4H), 7.27-7.19 (m, 2H), 3.61 (s, 3H), 1.32 (s, 9H).

[0874] Intermediate 13-2

[0875]

[0876] 83.00 ml (133 mmol) of 1.6 molar diethyl ether solution of methyl lithium was diluted in 180 ml of dry THF, and the solution was cooled to 5°C with an ice-water bath. 13.9 g (51.6 mmol) of intermediate 13-1 was dissolved in 80 ml of dry THF and slowly added to the methyl lithium solution to keep the reaction temperature below 12°C. The reaction was stirred at room temperature for 1 hour and quenched with 40 ml of water. Volatiles were removed and the residue was extracted with dichloromethane. The organic phases were combined, dried over magnesium sulfate, filtered and evaporated to give 13.8 g (100% yield) of colorless oil, which was used without further purification.

[0877] Intermediate 13-3

[0878]

[0879] 13.8 g (51.6 mmol) of intermediate 13-2 was dissolved in 180 ml of acetic acid, 2.5 ml (26.6 mmol) of concentrated aqueous HCl solution was added and the reaction was stirred at 110° C. for 5.5 hours. After evaporation of the solvent, the residue was extracted with water and dichloromethane, the organic phases were combined, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and dichloromethane as eluent to obtain 10.02 g (73% yield) of intermediate 13-3 as a colorless glass.

[0880] 1 H NMR (300MHz, DMSO-d6) δ7.82-7.74 (m, 1H), 7.72 (dd, J=8.0, 0.6Hz, 1H), 7.60-7.54 (m, 1H), 7 .54-7.48(m, 1H), 7.38(dd, J=8.0, 1.8Hz, 1H), 7.35-7.21(m, 2H), 1.44(s, 6H), 1.35(s, 9H).

[0881] Intermediate 13-4

[0882]

[0883] 10.02 g (39.1 mmol) of intermediate 13-3 was dissolved in 390 ml of dichloromethane and cooled to 5 ° C in an ice-water bath. 1.91 ml (37.1 mmol) of bromine was dissolved in 20 ml of dichloromethane, placed in a dropping funnel and added to the solution of intermediate 13-3 over 10 minutes so that the reaction temperature does not exceed 10 ° C. The reaction was stirred at 5 ° C for 1.5 hours and then stirred at room temperature for another 2.5 hours. The reaction was quenched with an aqueous sodium thiosulfate solution and each phase was separated. The aqueous phase was extracted with dichloromethane, the organic phase was combined, washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and toluene as an eluent to obtain 7.90 g (61% yield) of intermediate 13-4 as a white solid.

[0884] 1 H NMR (300 MHz, chloroform-d) δ 7.63 (dd, J = 8.0, 0.7 Hz, 1H), 7.57 (dd, J = 6.3, 0.6 Hz, 1H), 7.55 (s, 1H), 7.50-7.43 (m, 2H), 7.41 (dd, J = 8.0, 1.8 Hz, 1H), 1.50 (s, 6H), 1.40 (s, 9H).

[0885] Intermediate 13-5

[0886]

[0887] Intermediate 13-5 was synthesized from Intermediate 13-4 and Intermediate 1-4 according to the procedure of Intermediate 2-4. The yield was 71%.

[0888] LC-MS: 998.5[M+1] +

[0889] Compound 13

[0890]

[0891] Compound 13 was synthesized from intermediate 13-5 according to the procedure of compound 2. The yield was 14%.

[0892] LC-MS: 928.6[M+1] +

[0893] Compound 14

[0894] Intermediate 14-1

[0895]

[0896] 14.08 g (115 mmoles) of phenylboronic acid, 21.00 g (105 mmoles) of 4-bromo-3,5-dimethylaniline and 89.00 g (420 mmoles) of tripotassium phosphate are added to 262 ml of toluene, 175 ml of dioxane and 87 ml of water. The suspension is degassed for 20 minutes by bubbling nitrogen, and 471 mg (2.10 mmoles) of palladium acetate (II) and 1.72 g (4.20 mmoles) of dicyclohexyl (2', 6'-dimethoxy [1,1'-biphenyl] -2-yl) phosphane are added to the reaction mixture, which is heated to 80° C. for 1.5 hours. The reaction is cooled to room temperature and diluted with toluene and water. The organic extract is washed with water and dried over magnesium sulfate, filtered, and the solution is concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and ethyl acetate as an eluent to obtain 19.75 g (95% yield) of Intermediate 14-1 as a white solid.

[0897] LC-MS: 198.1[M+1] +

[0898] Intermediate 14-2

[0899]

[0900] Intermediate 14-2 was synthesized from Intermediate 14-1 and 2,6-dimethyl-4-bromobiphenyl according to the procedure of Intermediate 1-5. The yield was 69%.

[0901] LC-MS: 378.2[M+1] +

[0902] Intermediate 14-3

[0903]

[0904] Intermediate 14-3 was synthesized from Intermediate 14-2 according to the procedure of Intermediate 2-1. The yield was 65%.

[0905] LC-MS: 499.2[M+1] +

[0906] Intermediate 14-4

[0907]

[0908] Intermediate 14-4 was synthesized from Intermediate 14-3 according to the procedure of Intermediate 2-2. The yield was 88%.

[0909] LC-MS: 469.3[M+1] +

[0910] Intermediate 14-5

[0911]

[0912] Intermediate 14-5 was synthesized from Intermediate 10-2 and bis(4-(tert-butyl)phenylamine according to the procedure of Intermediate 1-3. The yield was 55%.

[0913] LC-MS: 530.1[M+1] +

[0914] Intermediate 14-6

[0915]

[0916] Intermediate 14-6 was synthesized from Intermediate 14-5 and Intermediate 14-4 according to the procedure of Intermediate 1-4. The yield was 89%.

[0917] LC-MS: 916.4[M+1] +

[0918] Intermediate 14-7

[0919]

[0920] Intermediate 14-7 was synthesized from Intermediate 14-5 according to the procedure of Intermediate 1-5. The yield was 91%.

[0921] LC-MS: 1108.5[M+1]+

[0922] Compound 14

[0923]

[0924] Compound 14 was synthesized from intermediate 14-7 according to the procedure of compound 1. The yield was 28%.

[0925] LC-MS: 1038.6[M+1] +

[0926] Compound 15

[0927] Intermediate 15-1

[0928]

[0929] Intermediate 15-1 was synthesized from Intermediate 4-2 and 2-bromo-9,9-dimethyl-9H-fluorene according to the procedure of Intermediate 10-3. The yield was 91%.

[0930] LC-MS: 565.4[M+1] +

[0931] Intermediate 15-2

[0932]

[0933] Intermediate 15-2 was synthesized from Intermediate 15-1 and Intermediate 10-2 according to the procedure of Intermediate 1-3. The yield was 49%.

[0934] LC-MS: 813.2[M+1] +

[0935] Intermediate 15-3

[0936]

[0937] Intermediate 15-3 was synthesized from Intermediate 15-2 and 3-tert-butylaniline according to the procedure of Intermediate 1-4. The yield was 87%.

[0938] LC-MS: 880.4[M+1] +

[0939] Intermediate 15-4

[0940]

[0941] Intermediate 15-4 was synthesized from Intermediate 15-3 and 4-(tert-butyl)-4′-iodo-1,1′-biphenyl according to the procedure of Intermediate 1-5. The yield was 72%.

[0942] LC-MS: 1088.5[M+1] +

[0943] Compound 15

[0944]

[0945] Compound 15 was synthesized from intermediate 15-4 according to the procedure of compound 1. The yield was 11%.

[0946] LC-MS: 1018.6[M+1] +

[0947] Compound 16

[0948] Intermediate 16-1

[0949]

[0950] Intermediate 16-1 was synthesized from Intermediate 15-3 and 1-tert-butyl-4-iodobenzene according to the procedure of Intermediate 1-5. The yield was 83%.

[0951] LC-MS: 1012.5[M+1] +

[0952] Compound 16

[0953]

[0954] Compound 16 was synthesized from intermediate 16-1 according to the procedure of compound 1. The yield was 9%.

[0955] LC-MS: 942.6[M+1] +

[0956] Compound 17

[0957] Intermediate 17-1

[0958]

[0959] Intermediate 17-1 was synthesized from Intermediate 1-4 and 4-bromo-9,9-diphenyl-9H-fluorene according to the procedure of Intermediate 1-5. The yield was 25%.

[0960] LC-MS: 1067.6[M+1] +

[0961] Compound 17

[0962]

[0963] Compound 17 was synthesized from intermediate 17-1 according to the procedure of compound 1. The yield was 37%.

[0964] LC-MS: 881.7[M+1] +

[0965] Compound 18

[0966] Intermediate 18-1

[0967]

[0968] Intermediate 18-1 was synthesized from Intermediate 15-3 and 2-iodo-9,9-dimethyl-9H-fluorene according to the procedure of Intermediate 1-5. The yield was 67%.

[0969] LC-MS: 1072.5[M+1] +

[0970] Compound 18

[0971]

[0972] Compound 18 was synthesized from intermediate 18-1 according to the procedure of compound 1. The yield was 12%.

[0973] LC-MS: 942.6[M+1] +

[0974] Device (compounds of the invention as emitter dopants)

[0975] Preparation and evaluation of organic EL devices

[0976] Organic EL devices were prepared and evaluated as follows:

[0977] Application Example 1

[0978] A glass substrate with a 130 nm thick indium tin oxide (ITO) transparent electrode (manufactured by Geomatec Co., Ltd.) used as an anode was first treated with N2 plasma for 100 seconds. This treatment also improves the hole injection properties of ITO. The cleaned substrate was mounted on a substrate holder and loaded into a vacuum chamber. Thereafter, the organic materials specified below were added at about 10 -6 -10 -8 mbar below about The rate is applied to the ITO substrate by vapor deposition. As a hole injection layer, a mixture of 10nm thick compound HT-1 and 3 wt% compound HI is applied. Then 80nm thick compound HT-1 and 10nm compound HT-2 are applied as hole transport layer 1 and hole transport layer 2, respectively. Subsequently, a mixture of 2 wt% emitter compound 1 and 98 wt% host compound BH-1 is applied to form a 25nm thick fluorescent emission layer. On the emission layer, a 10nm thick compound ET-1 is applied as a hole blocking layer, and a 15nm compound ET-2 is applied as an electron transport layer. Finally, a 1nm thick LiF is deposited as an electron injection layer, and then an 80nm thick Al is deposited as a cathode to complete the device. In an inert nitrogen atmosphere with less than 1ppm water and oxygen, the device is sealed with a glass cover and a getter. In order to characterize the OLED, electroluminescence (EL) spectra are recorded at various currents and voltages. The EL peak maximum and half-peak full width (FWHM) are recorded at 10mA / cm2. In addition, the current-voltage characteristics were measured in combination with the brightness to determine the luminous efficiency and external quantum efficiency (EQE). 2 The driving voltage (V) is given at a current density of . The device results are shown in Table 1.

[0979]

[0980]

[0981] Table 1

[0982] Application Examples Voltage, V EQE, % EL max, nm FWHM, nm Application Example 1 3.68 10.2 461 24

[0983] These results demonstrate that Application Example 1 provides good EQE and narrow spectrum (smaller FWHM), ie, good color purity, when used as a fluorescent emission material in OLEDs.

[0984] Additional Application Examples

[0985] Example 1 was repeated except that comparative compound 1 and compounds 2-13 and 15-17 were used instead of compound 1 as the emitter in the fluorescent emission layer.

[0986]

[0987]

[0988]

[0989]

[0990] Table 2.

[0991] Application Examples Compound Voltage, V EQE, % EL max, nm FWHM, nm Comparative Application Example 1 Comparative Compound 1 3.66 7.5 467 24 Application Example 2 Compound 2 3.63 10.3 462 24 Application Example 3 Compound 3 3.64 9.7 462 26 Application Example 4 Compound 4 3.64 9.9 459 23 Application Example 5 Compound 5 3.68 10.6 459 24 Application Example 6 Compound 6 3.57 10.3 459 23 Application Example 7 Compound 7 3.62 10.2 459 24 Application Example 8 Compound 8 3.64 10.6 456 23 Application Example 9 Compound 9 3.65 10.6 462 23 Application Example 10 Compound 10 3.68 10.3 453 24 Application Example 11 Compound 11 3.71 10.1 454 24 Application Example 12 Compound 12 3.65 10.2 455 24 Application Example 13 Compound 13 3.64 10.3 461 24 Application Example 14 Compound 15 3.68 10.1 452 24 Application Example 15 Compound 16 3.68 9.8 452 24 Application Example 16 Compound 17 3.67 10.0 461 24

[0992] These results demonstrate that, when used as fluorescent emitting materials in OLEDs, the compounds of the present invention provide higher EQE than comparative compound 1 while maintaining a narrow spectrum (smaller FWHM), ie, good color purity.

Claims

1. Compound represented by formula (I) in R 1 , R 4 , R 5 , R 6 , R 8 , R 9 , and R 11 Each independently represents hydrogen; R 2 and R 7 Each independently represents hydrogen; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; or NAr2Ar3; R 3 and R 10 Each independently represents hydrogen; or an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; R 2 or R 7 At least one of them represents an amino group NAr2Ar3; Ar2 and Ar3 each independently represent an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms; R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 Each independently represents hydrogen; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; Where R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One is the bonding site with L2; R a and R b Each independently represents hydrogen; an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms; or an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; L1 represents a direct bond, or an unsubstituted or substituted divalent aromatic hydrocarbon group containing 6 to 30 ring atoms; L2 represents a direct bond; Ar1 represents an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms; or an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; The optional substituents represented by "unsubstituted or substituted" each independently represent an unsubstituted aryl group having 6 to 60 ring carbon atoms, an alkyl group having 1 to 20 carbon atoms.

2. The compound according to claim 1, wherein Ar2 and Ar3 in NAr2Ar3 representing an amino group each independently represent an unsubstituted or substituted aryl group having 6 to 18 ring carbon atoms.

3. A compound according to claim 2, wherein the amino group NAr2Ar3 is represented by the following formula (II): in R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 Each independently represents hydrogen; an unsubstituted aryl group having 6 to 60 ring carbon atoms; or an alkyl group having 1 to 20 carbon atoms.

4. A compound according to claim 3, wherein R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 Each independently represents hydrogen or an unsubstituted aryl group having 6 to 60 ring carbon atoms.

5. The compound according to claim 1, wherein L1 is a direct bond.

6. The compound according to claim 1, wherein Ar1 represents an unsubstituted or substituted aryl group having 6 to 60 ring carbon atoms.

7. The compound according to claim 1, wherein Ar1 is represented by the following formula (III): in R 37 , R 38 , R 39 , R 40 and R 41 Each independently represents hydrogen, unsubstituted aryl having 6 to 60 ring carbon atoms; or alkyl having 1 to 20 carbon atoms; wherein the dashed line is the bonding site.

8. A compound according to claim 7, wherein R 37 , R 38 , R 39 , R 40 and R 41 Each independently represents hydrogen; an unsubstituted aryl group having 6 to 13 ring carbon atoms; or an alkyl group having 1 to 8 carbon atoms.

9. The compound according to claim 1, wherein Ar1 is represented by the following formula (IIIA) in R 39 represents an unsubstituted aryl group having 6 to 60 ring carbon atoms; or an alkyl group having 1 to 20 carbon atoms, The dashed lines are bonding sites.

10. The compound according to claim 1, wherein R 16 and R 18 One of them is the bonding site to L2.

11. The compound according to claim 1, wherein the compound is represented by one of the following formulae (IA) and (IB) in R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 10 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R a and R b As mentioned above; R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 each independently represents hydrogen; an unsubstituted aryl group having 6 to 60 ring carbon atoms; or an alkyl group having 1 to 20 carbon atoms; R 37 , R 38 , R 39 , R 40 and R 41 Each independently represents hydrogen; an unsubstituted aryl group having 6 to 60 ring carbon atoms; or an alkyl group having 1 to 20 carbon atoms.

12. The compound according to claim 11, which is represented by one of the following formulae (IAa) and (IBa): in R 3 , R 6 , R 10 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R a and R b As mentioned above; R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 each independently represents hydrogen; an unsubstituted aryl group having 6 to 60 ring carbon atoms; or an alkyl group having 1 to 20 carbon atoms; and R 39 is an unsubstituted aryl group having 6 to 60 ring carbon atoms; or an alkyl group having 1 to 20 carbon atoms.

13. A compound according to claim 12, wherein R a and R b Each independently represents an unsubstituted or substituted aryl group having 6 to 13 ring carbon atoms; or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms.

14. A compound according to claim 12, wherein R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 Each independently represents hydrogen; an unsubstituted aryl group having 6 to 10 ring carbon atoms; or an alkyl group having 1 to 4 carbon atoms.

15. A compound according to claim 12, wherein R 39 represents an unsubstituted aryl group having 6 to 13 ring carbon atoms; or an alkyl group having 1 to 4 carbon atoms.

16. A compound according to claim 12, wherein R 3 and R 10 Each is independently an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms.

17. A compound according to claim 12, wherein R 3 and R 10 Each is independently an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms; R a and R b Each independently represents an unsubstituted or substituted aryl group having 6 to 13 ring carbon atoms; or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms; R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 each independently represents hydrogen; an unsubstituted aryl group having 6 to 10 ring carbon atoms; or an alkyl group having 1 to 4 carbon atoms; and R 39 represents an unsubstituted aryl group having 6 to 13 ring carbon atoms; or an alkyl group having 1 to 4 carbon atoms.

18. The compound according to claim 1, wherein the compound has at least one deuterium atom.

19. The compound according to claim 1, wherein at least one hydrogen atom in Ar2 or Ar3 is a deuterium atom.

20. The compound according to claim 3, wherein R 27 To R 36 At least one of them is a deuterium atom.

21. The compound according to claim 3, wherein R 27 To R 36 They are all deuterium atoms.

22. A material for an organic electroluminescent device, comprising at least one compound according to any one of claims 1 to 21, said at least one compound being represented by formula (I).

23. An organic electroluminescent device comprising at least one compound according to any one of claims 1 to 21, said at least one compound being represented by formula (I).

24. An organic electroluminescent device according to claim 23, comprising a cathode, an anode and one or more organic thin film layers including an emission layer arranged between the cathode and the anode, wherein at least one layer of the organic thin film layers comprises at least one compound represented by formula (I).

25. The organic electroluminescent device according to claim 24, wherein the light-emitting layer comprises at least one compound represented by formula (I).

26. The organic electroluminescent device according to claim 25, wherein the light-emitting layer comprises at least one host and at least one dopant, and the dopant comprises at least one compound represented by formula (I).

27. The organic electroluminescent device according to claim 26, wherein the host comprises at least one unsubstituted or substituted fused aromatic compound and / or at least one unsubstituted or substituted anthracene compound.

28. The organic electroluminescent device according to claim 27, wherein the anthracene compound is represented by the following formula (10): in Two or more adjacent R 101 To R 110 One or more pairs of may form an unsubstituted or substituted, saturated or unsaturated ring; R does not form an unsubstituted or substituted, saturated or unsaturated ring 101 To R 110 independently hydrogen, unsubstituted or substituted alkyl including 1 to 50 carbon atoms, unsubstituted or substituted haloalkyl including 1 to 50 carbon atoms, unsubstituted or substituted alkenyl including 2 to 50 carbon atoms, unsubstituted or substituted alkynyl including 2 to 50 carbon atoms, unsubstituted or substituted cycloalkyl including 3 to 50 ring carbon atoms, unsubstituted or substituted alkoxy including 1 to 50 carbon atoms, unsubstituted or substituted aryloxy including 6 to 50 ring carbon atoms, unsubstituted or substituted arylthio including 6 to 50 ring carbon atoms, unsubstituted or substituted aralkyl including 7 to 50 carbon atoms, -Si(R 121 )(R 122 )(R 123 ), -C(=O)R 124 、-COOR 125 、-N(R 126 )(R 127 ), a halogen atom, a cyano group, a nitro group, an unsubstituted or substituted aryl group having 6 to 50 ring carbon atoms, an unsubstituted or substituted monovalent heterocyclic group having 5 to 50 ring atoms, or a group represented by the following formula (31); R 121 To R 127 are independently hydrogen atoms, unsubstituted alkyl groups including 1 to 50 carbon atoms, unsubstituted cycloalkyl groups including 3 to 50 ring carbon atoms, unsubstituted aryl groups including 6 to 50 ring carbon atoms, or unsubstituted monovalent heterocyclic groups including 5 to 50 ring atoms; when R 121 To R 127 When multiple R 121 To R 127 Each can be the same or different; Provided that there is no unsubstituted or substituted, saturated or unsaturated ring R 101 To R 110 At least one of the following is a group represented by the following formula (31); if there are two or more groups represented by the following formula (31), these groups may be the same or different; -L 101 -On 101 (31) in, L 101 is a single bond, an unsubstituted or substituted arylene group containing 6 to 30 ring carbon atoms, or an unsubstituted or substituted divalent heterocyclic group containing 5 to 30 ring atoms; Ar 101 is an unsubstituted or substituted aryl group containing 6 to 50 ring carbon atoms or an unsubstituted or substituted monovalent heterocyclic group containing 5 to 50 ring atoms.

29. An electronic device comprising the organic electroluminescent device according to claim 23.

30. A light-emitting layer comprising at least one host and at least one dopant, wherein the dopant comprises at least one compound according to any one of claims 1 to 21, the at least one compound being represented by formula (I).

31. Use of the compound represented by formula (I) according to any one of claims 1 to 21 in an organic electroluminescent device.

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