Organic electroluminescence device and electronic apparatus using the same

An organic electroluminescence device comprising:

• a cathode,
• an anode, and
• an organic layer disposed between the cathode and the anode,
• wherein the organic layer comprises an emitting layer and an electron barrier layer,
• the electron barrier layer is disposed between the anode and the emitting layer and is directly adjacent to the emitting layer,
• the emitting layer comprises a first compound represented by the following formula (41),
• the electron barrier layer comprises a second compound which satisfies the following expression (M1), and
• the second compound is not a compound which has both a 9,9-dimethyl-2-fluorenyl group and a 2-biphenylyl group in the molecule at the same time:
• Ip(HT)≥5.67 eV (M1)
• wherein in the expression (M1), Ip(HT) is the ionization potential of the second compound;
• wherein in the formula (41),
• a ring a, a ring b, and a ring c are independently
• a substituted or unsubstituted aromatic hydrocarbon ring including 6 to 50 ring carbon atoms, or
• a substituted or unsubstituted heterocyclic ring including 5 to 50 ring atoms;
• R401 and R402 independently form a substituted or unsubstituted heterocyclic ring by bonding with the ring a, the ring b, or the ring c, or do not form a substituted or unsubstituted heterocyclic ring;
• and
• R401 and R402 which do not form the substituted or unsubstituted heterocyclic ring are independently
• a substituted or unsubstituted alkyl 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 aryl group including 6 to 50 ring carbon atoms, or
• a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms.

An organic electroluminescence device comprising:

• a cathode,
• an anode, and
• an organic layer disposed between the cathode and the anode,
• wherein the organic layer comprises an emitting layer and an electron barrier layer,
• the electron barrier layer is disposed between the anode and the emitting layer and is directly adjacent to the emitting layer,
• the emitting layer comprises a first compound represented by the following formula (21) or (51), and
• the electron barrier layer comprises a second compound represented by the following formula (C1) or (A):
• wherein in the formula (21),
• Z's are independently a CRa or a nitrogen atom;
• a ring A1 and a ring A2 are independently a substituted or unsubstituted aromatic hydrocarbon ring including 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring including 5 to 50 ring atoms;
• when a plurality of Ra's are present, one or more sets of adjacent two or more among the plurality of Ra's form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
• when a plurality of Rb's are present, one or more sets of adjacent two or more among the plurality of Rb's form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
• when a plurality of Rc's are present, one or more sets of adjacent two or more among the plurality of Rc's form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
• n21 and n22 are independently an integer of 0 to 4;
• Ra to Re which do not form the substituted or unsubstituted, saturated or unsaturated ring are independently
• a hydrogen atom,
• a substituted or unsubstituted alkyl 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,
• —Si(R901)(R902)(R903),
• —O—(R904),
• —S—(R905),
• —N(R906)(R907),
• a halogen atom, a cyano group, a nitro group,
• 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;
• R901 to R907 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;
• and
• when one or more of R901 to R907 are present in two or more, each of the two or more R901 to R907 are the same or different;
• p-q-r-s-t (51)
• wherein in the formula (51),
• a ring r is a ring represented by the formula (52) or the formula (53) which is fused with an adjacent ring at an arbitrary position;
• a ring q and a ring s are independently a ring represented by the formula (54) which is fused with an adjacent ring at an arbitrary position;
• a ring p and a ring t are independently a structure represented by the formula (55) or the formula (56) which is fused with an adjacent ring at an arbitrary position;
• when a plurality of R501's are present, the plurality of adjacent R501's form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
• X501 is an oxygen atom, a sulfur atom, or NR502;
• R501 which do not form the substituted or unsubstituted, saturated or unsaturated ring, and R502 are independently
• a hydrogen atom,
• a substituted or unsubstituted alkyl 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,
• —Si(R901)(R902)(R903),
• —O—(R904),
• —S—(R905),
• —N(R906)(R907),
• a halogen atom, a cyano group, a nitro group,
• 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;
• R901 to R907 are as defined in the formula (21);
• Ar501 and Ar502 are independently
• a substituted or unsubstituted alkyl 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 aryl group including 6 to 50 ring carbon atoms, or
• a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
• L501 is
• a single bond,
• a substituted or unsubstituted alkylene group including 1 to 50 carbon atoms,
• a substituted or unsubstituted alkenylene group including 2 to 50 carbon atoms,
• a substituted or unsubstituted alkynylene group including 2 to 50 carbon atoms,
• a substituted or unsubstituted cycloalkylene group including 3 to 50 ring carbon atoms,
• a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms, or
• a substituted or unsubstituted divalent heterocyclic group including 5 to 50 ring atoms;
• m1 is an integer of 0 to 2, m2 is an integer of 0 to 4, m3 is an integer of 0 to 3, and m4 is an integer of 0 to 5;
• and
• when a plurality of R501's are present, the plurality of R501's may be the same as or different from each other;
• wherein in the formula (C1),
• LA, LB, and LC are independently a single bond, a substituted or unsubstituted arylene group including 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group including 5 to 13 ring atoms;
• A, B, and C are independently
• a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms,
• a substituted or unsubstituted monovalent heterocyclic group including 5 to 30 ring atoms, or
• —Si(R908)(R909)(R910);
• R908 to R910 are independently a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms;
• and
• when one or more of R908 to R910 are present in two or more, each of the two or more R908 to R910 are the same or different;
• provided that when a 4-dibenzofuranyl structure is contained in the molecule of the compound represented by the formula (C1), the compound represented by the formula (C1) contains one 4-dibenzofuranyl structure;
• wherein in the formula (A),
• A1 and A2 are independently a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 30 ring atoms;
• one of Y5 to Y8 is a carbon atom which bonds with *1;
• one of Y9 to Y12 is a carbon atom which bonds with *2;
• Y1 to Y4, Y13 to Y16, Y5 to Y8 which are not a carbon atom which bonds with *1, and Y9 to Y12 which are not a carbon atom which bonds with *2 are independently CR;
• when a plurality of R's are present, one or more sets of adjacent two or more among the plurality of R's form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
• R which does not form the substituted or unsubstituted, saturated or unsaturated ring is
• a hydrogen atom,
• a substituted or unsubstituted alkyl 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,
• —Si(R901)(R902)(R903),
• —O—(R904),
• a halogen atom, a nitro group,
• 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;
• R901 to R904 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 one or more of R901 to R904 are present in two or more, each of the two or more R901 to R904 are the same or different;
• when a plurality of R's are present, the plurality of R's may be the same as or different from each other;
• and
• L1 and L2 are independently a single bond, a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group including 5 to 30 ring atoms.

An organic electroluminescence device comprising:

• a cathode,
• an anode, and
• an organic layer disposed between the cathode and the anode,
• wherein the organic layer comprises an emitting layer and an electron barrier layer,
• the electron barrier layer is disposed between the anode and the emitting layer and is directly adjacent to the emitting layer,
• the emitting layer comprises a first compound represented by the following formula (41), and
• the electron barrier layer comprises a second compound represented by the following formula (C1) or (A):
• wherein in the formula (41),
• a ring a, a ring b, and a ring c are independently
• a substituted or unsubstituted aromatic hydrocarbon ring including 6 to 50 ring carbon atoms, or
• a substituted or unsubstituted heterocyclic ring including 5 to 50 ring atoms;
• R401 and R402 independently form a substituted or unsubstituted heterocyclic ring by bonding with the ring a, the ring b, or the ring c, or do not form a substituted or unsubstituted heterocyclic ring;
• and
• R401 and R402 which do not form the substituted or unsubstituted heterocyclic ring are independently
• a substituted or unsubstituted alkyl 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 aryl group including 6 to 50 ring carbon atoms, or
• a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
• wherein in the formula (C1),
• LA, LB, and LC are independently a single bond, or a substituted or unsubstituted arylene group including 6 to 18 ring carbon atoms,
• A, B, and C are independently
• a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms,
• a group represented by any one of the following formulas (H1) to (H3) or
• —Si(R908)(R909)(R910);
• R908 to R910 are independently a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms;
• and
• when one or more of R908 to R910 are present in two or more, each of the two or more R908 to R910 are the same or different;
• provided that when a 4-dibenzofuranyl structure is contained in the molecule of the compound represented by the formula (C1), the compound represented by the formula (C1) contains one 4-dibenzofuranyl structure, and the compound represented by the formula (C1) is not a compound simultaneously having both a 9,9-dimethyl-2-fluorenyl group and a 2-biphenylyl group;
• wherein in the formula (H1),
• any one of W11 to W12, W14 to W15, and W17 to W19 is a single bond which is bonded with LA, Lb, or LC;
• W11 to W12, W14 to W15, and W17 to W19 which are not a single bond which is bonded with LA, LB, or LC, and W13 and W16 are independently
• a hydrogen atom,
• a substituted or unsubstituted alkyl 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,
• —Si(R911)(R912)(R913),
• —O—(R914),
• —S—(R915),
• —N(R916)(R917),
• a halogen atom, a cyano group, a nitro group,
• 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;
• R911 to R917 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;
• and
• when one or more of R911 to R917 are present in two or more, each of the two or more R911 to R917 are the same or different;
• wherein in the formula (H2),
• any one of W21 to W28 is a single bond which is bonded with LA, LB, or LC;
• W21 to W28 which are not a single bond which is bonded with LA, LB, or LC are independently
• a hydrogen atom,
• a substituted or unsubstituted alkyl 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,
• —Si(R911)(R912)(R913),
• —O—(R914),
• —S—(R915),
• —N(R916)(R917),
• a halogen atom, a cyano group, a nitro group,
• 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;
• R911 to R917 are as defined in the formula (H1);
• and
• when one or more of R911 to R917 are present in two or more, each of the two or more R911 to R917 are the same or different;
• wherein in the formula (H3),
• any one of W31 to W38 is a single bond which is bonded with a LA, LB or L0;
• W31 to W38 which are not a single bonds which is bonded with LA, LB, or LC are independently
• a hydrogen atom,
• a substituted or unsubstituted alkyl 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,
• —Si(R911)(R912)(R913),
• —O—(R914),
• —S—(R915),
• —N(R916)(R917),
• a halogen atom, a cyano group, a nitro group,
• 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;
• R911 to R917 are as defined in the formula (H1);
• and
• when one or more of R911 to R917 are present in two or more, each of the two or more R911 to R917 are the same or different;
• wherein in the formula (A),
• A1 and A2 are independently a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 30 ring atoms;
• one of Y5 to Y8 is a carbon atom which bonds with *1;
• one of Y9 to Y12 is a carbon atom which bonds with *2;
• Y1 to Y4, Y13 to Y16, Y5 to Y8 which are not a carbon atom which bonds with *1, and Y9 to Y12 which are not a carbon atom which bonds with *2 are independently CR;
• when a plurality of R's are present, one or more sets of adjacent two or more among the plurality of R's form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
• R which does not form the substituted or unsubstituted, saturated or unsaturated ring is
• a hydrogen atom,
• a substituted or unsubstituted alkyl 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,
• —Si(R901)(R902)(R903),
• —O—(R904),
• a halogen atom, a nitro group,
• 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;
• R901 to R904 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 one or more of R901 to R904 are present in two or more, each of the two or more R901 to R904 are the same or different;
• when a plurality of R's are present, the plurality of R's may be the same as or different from each other;
• and
• L1 and L2 are independently a single bond, a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group including 5 to 30 ring atoms.